Grit

Guest: Mark McLaughlin, chairman of the board at Qualcomm 

When he was 24, Mark McLaughlin thought his career was over. Since childhood, he had dreamed of attending West Point and joining the Army, but a helicopter crash left him unable to serve, with a medical discharge. However, the crash also let him stay closer to his then-girlfriend Karen. They married and raised three children, and Mark found success in his new career, serving as CEO of Palo Alto Networks and now chairman of the board at Qualcomm. “In hindsight,” he says, “I would tell you the worst thing that ever happened in my life was the best thing that ever happened in my life.”

In this episode, Mark and Joubin discuss semi-retirement, Palo Alto Networks, identity crises, West Point, homeschooling, self-awareness, working on the plane, Walter Reed Hospital, Nikesh Arora, Cristiano Amon, non-founder CEOs, Paul Jacobs, Verisign, reference interviews, rising to the occasion, and fortitude.

Chapters:

• (00:57) - Mark’s reputation and family
• (09:40) - “What am I doing?”
• (14:58) - Deciding to step away
• (16:55) - Overcoming work addiction
• (22:15) - Mandatory sacrifice
• (24:25) - Carl Eschenbach
• (27:12) - The people who matter
• (32:11) - Energy vs. adrenaline
• (37:31) - The helicopter crash
• (44:02) - Leaving Palo Alto Networks
• (50:05) - Bungled CEO transitions
• (54:24) - “Detox” time off
• (57:32) - Waiting for the right pitch
• (01:04:48) - The at-home interview
• (01:08:59) - Work in perspective
• (01:12:10) - What “grit” means to Mark

Links:

Connect with Mark

• LinkedIn

Connect with Joubin

• Twitter
• LinkedIn
• Email: [email protected] 

Learn more about Kleiner Perkins

This episode was edited by Eric Johnson from LightningPod.fm

Guest: David Risher, CEO of Lyft

David Risher can measure his career in phone calls, from the one that introduced him to Jeff Bezos in 1995, to the call from the Lyft board in 2023, asking him to vie for the CEO job. But initially, he believed his life’s legacy might be the nonprofit Worldreader, which has brought books to more than 22 million readers around the globe; he had to convince himself that turning Lyft around during one of its most difficult eras was also a call worth answering.

In this episode, David and Joubin discuss reliable exercise, pickleball, Sean Aggarwal, John Zimmer and Logan Green, return to office, Women+ Connect, reference checks, Bill Gates and Steve Ballmer, Adam Bosworth, interracial marriages, children of divorce, powdered wigs, Barnes & Noble, the University of Washington, Barcelona, the Galapagos Islands, Amazon’s Kindle, Steve Kessel, expat talent, Bucky Moore, rideshare insurance, robo-taxis, Elon Musk, and data science.

Chapters:

• (00:45) - Biking to work — and across the US
• (03:44) - Lyft Bikes
• (07:35) - How David became CEO
• (12:18) - 14 months later...
• (15:28) - Customer obsession
• (17:40) - Jeff Bezos
• (21:00) - Leaving Microsoft
• (24:28) - Drive + empathy
• (27:39) - David’s parents
• (30:38) - Being straightforward
• (36:20) - Loving the Work
• (38:42) - Amazon’s early days
• (40:49) - Bezos’ farewell easter egg
• (43:44) - “What else is out there?”
• (48:36) - Ariel Cohen
• (49:56) - Living overseas
• (53:06) - Starting Worldreader
• (58:15) - The lifelong journey
• (01:00:40) - Growing profitably
• (01:04:09) - Waymo and driverless cars
• (01:10:45) - Physical businesses at scale
• (01:14:03) - Who Lyft is hiring
• (01:15:19) - What “grit” means to David

Links:

Connect with David

• Twitter
• LinkedIn
• The Amazon easter egg

Connect with Joubin

• Twitter
• LinkedIn
• Email: [email protected] 

Learn more about Kleiner Perkins

This episode was edited by Eric Johnson from LightningPod.fm

Guests: Vipul Ved Prakash, CEO and co-founder of Together AI; and Bucky Moore, partner at Kleiner Perkins

No one knows for sure whether the future of AI will be driven more by research labs and AI-native companies, or by enterprises applying the technology to their own data sets. But one thing is for sure, says Together AI CEO and co-founder Vipul Ved Prakash: It’s going to be a lot bigger. “If you look at the next 10 years or the next 20 years, we are doing maybe 0.1 percent of [the] AI that we’ll be doing 10 years from now.” 

In this episode, Vipul, Bucky, and Joubin discuss startup table stakes, Tri Dao, tentpole features, open-source AI, non-financial investors, Meta Llama, deep learning researchers, WeWork, “Attention is All You Need,” create vs. capture, Databricks, Docker, scaling laws, Ilya Sutskever, IRC, and Jordan Ritter and Napster.

Chapters:

• (00:53) - Executive hiring
• (04:40) - How Vipul and Bucky met
• (06:54) - Six years at Apple
• (08:19) - Together and the AI landscape
• (12:47) - Apple’s deal with OpenAI
• (14:27) - Open vs. closed AI
• (17:32) - Nvidia GPUs and capital expenditures
• (22:48) - Fame and reputation
• (24:17) - Planning for an uncertain future
• (27:00) - Stress and attention
• (30:18) - AI research
• (34:58) - Challenges for AI businesses
• (39:02) - Frequent disagreements
• (43:05) - Vipul’s first startups, Cloudmark and Topsy
• (47:55) - Taking time off
• (50:09) - The crypto-AI connection
• (53:20) - Who Together AI is hiring
• (54:37) - What “grit” means to Vipul

Links:

Connect with Vipul

• Twitter
• LinkedIn

Connect with Bucky

• Twitter
• LinkedIn

Connect with Joubin

• Twitter
• LinkedIn
• Email: [email protected] 

Learn more about Kleiner Perkins

This episode was edited by Eric Johnson from LightningPod.fm

Guest: Andrew Bialecki, CEO of Klaviyo

Whenever the marketing platform Klaviyo is hiring, says CEO Andrew Bialecki, “we sort of don't care so much what skills you have.” Instead, the company looks for “high slope” individuals who are curious and able to continually learn new things. “A big turnoff for me is [when] somebody says, ‘Oh, well, I was never good at that when I was growing up,’” Andrew explains. “You know, ‘I'm not a good writer’ or ‘I'm not good with numbers.’ And it's like, well, OK, but anybody can learn anything.”

In this episode, Andrew and Joubin discuss WeCrashed, Paul Graham, vertical integration, automating sales, Ed Hallen, The Talent Code by Daniel Coyle, child prodigies, interview questions, public speaking and decompression, taking ownership, hiring engineers, burnout, and productivity habits.

Chapters:

• (00:51) - Klaviyo's office
• (02:36) - Attention to detail
• (06:32) - Big decisions
• (12:23) - What Klaviyo does
• (14:50) - Its 2023 IPO
• (20:35) - The founding story
• (25:06) - Nature or nurture?
• (28:47) - Science and hockey
• (31:02) - Hiring for slope
• (33:57) - Extroversion
• (37:00) - Culture as product
• (39:53) - Owning your success
• (46:24) - “The algorithms of humanity”
• (50:55) - Why Andrew runs
• (52:35) - Sports psychology for startups
• (55:34) - Richard Feynman
• (58:27) - Who Klaviyo is hiring
• (59:20) - What “grit” means to Andrew

Links:

Connect with Andrew

• Twitter
• LinkedIn

Connect with Joubin

• Twitter
• LinkedIn
• Email: [email protected] 

Learn more about Kleiner Perkins

This episode was edited by Eric Johnson from LightningPod.fm

Guest: Niraj Shah, CEO and co-founder of Wayfair

Wayfair CEO Niraj Shah caught the entrepreneurship bug in his mid-20s, when he and his longtime co-founder Steve Conine sold their first company just a few years out of college. They left the acquirer and independently realized “we absolutely wanted to start something else,” Niraj recalls. “Once you’ve done that, if you enjoy that, it’s very hard to pursue something more traditional.” But the “if you enjoy that” bit really matters: Whenever he’s counseling younger people, Niraj tells them to pursue something they’re genuinely excited about. Otherwise, “it’s going to be very hard for you to do your best work.”

In this episode, Niraj and Joubin discuss shopping malls, employee discounts, working in Boston, family time, Jay Chaudhry, Cornell University, pursuing what you enjoy, fostering trust, family vacations, over-hiring corporate staff, taking market share, the power of ecommerce, ownership mentality, setting priorities, and rapid hiring.

Chapters:

• (00:51) - Wayfair’s first retail stores
• (05:35) - Buying from other stores
• (08:59) - Immigrant entrepreneurship and Niraj’s dad
• (12:57) - Building the flywheel
• (15:32) - Structuring your calendar
• (17:59) - Success and attention
• (21:47) - Niraj’s first business
• (25:54) - His co-founder, Steve Conine
• (29:58) - Wayfair’s operations and the COVID surge
• (33:52) - The home goods market
• (37:50) - Optimizing SKUs
• (41:21) - Specializing, focusing, and problem-solving
• (44:42) - Sustainable work ethic
• (48:05) - AI and personalization
• (52:42) - Who Wayfair is hiring
• (53:56) - What “grit” means to Niraj

Links:

Connect with Niraj

• LinkedIn
• Watch the Cornell talk

Connect with Joubin

• Twitter
• LinkedIn
• Email: [email protected] 

Learn more about Kleiner Perkins

This episode was edited by Eric Johnson from LightningPod.fm

Guest: Jay Chaudhry, CEO, chairman, and founder of Zscaler

Much of the media coverage of Zscaler CEO Jay Chaudhry is quick to identify him as the wealthiest Indian-American person, with a net worth of $10.8 billion. But to hear Jay himself tell it, that number has never been very important to him: “My family had no money,” he says of his childhood in India. “I had no attachment for money. There was no feeling of ‘I must buy this, buy this.’ ... And it hasn’t changed a bit.” Perhaps surprisingly, he says not caring about money is one of the big reasons for his financial success: With no attachment to money, “I could take risks.”

In this episode, Jay and Joubin discuss startup “gambling,” Jay’s wife Jyoti, scarcity and risk, wasting time, “bonding walks,” family vacations, self-confidence and self-criticism, gardening, seven-minute aerobics, Marc Andreessen and Netscape, and IBM.

Chapters:

• (01:54) - Selling SecureIT to Verisign
• (06:49) - Jay’s humble beginnings
• (09:12) - The worst way to describe him
• (11:42) - Working harder than ever
• (14:15) - Authenticity and selflessness
• (16:36) - Family time
• (18:53) - Happy childhood
• (21:33) - Setting an example
• (24:48) - Customer meetings
• (27:30) - Conviction and execution
• (31:07) - Do your best
• (33:16) - Turning off your brain
• (38:23) - Getting experience
• (40:17) - Who Zscaler is hiring
• (41:12) - What “grit” means to Jay

Links:

Connect with Jay

• LinkedIn

Connect with Joubin

• Twitter
• LinkedIn
• Email: [email protected] 

Learn more about Kleiner Perkins

This episode was edited by Eric Johnson from LightningPod.fm

Guest: Bill Magnuson, CEO and co-founder of Braze

The deployment of smartphones around the world was more impactful than any other technology to date, says Braze CEO Bill Magnuson — and that has big implications for emerging fields like generative AI. “If we get to the point where they [LLMs] really can be useful, human-like companions ... they will be usable by everyone that has smartphone technology.” In other words, the question is not business opportunity or scale: It’s capability.

In this episode, Bill and Joubin discuss earnings days, Aaron Levie, MIT, customer churn, shower thoughts, technical co-founders, lacking context, AGI, “hands on keyboard,” the T-Mobile G1, app marketing, the 2008 financial crisis, Bob Iger, World War II, Peter Reinhardt, Watershed, and international offices.

Chapters:

• (00:51) - Morning people
• (05:09) - What Braze does
• (06:59) - From CTO to CEO
• (08:17) - Waking up and commuting
• (10:49) - Leading vs. engineering
• (12:35) - Cognizant of believability
• (19:52) - LLMs and the human brain
• (25:46) - The AI ceiling
• (28:43) - The historic deployment of smartphones
• (37:58) - The benefits of youth
• (40:18) - Taking the leap
• (43:35) - Read more sci-fi
• (46:38) - Survivor bias
• (48:55) - Big risks at scale
• (52:30) - Who Braze is hiring around the world
• (55:32) - What “grit” means to Bill

Links:

Connect with Bill

• Twitter
• LinkedIn

Connect with Joubin

• Twitter
• LinkedIn
• Email: [email protected] 

Learn more about Kleiner Perkins

This episode was edited by Eric Johnson from LightningPod.fm

Guest: Clara Shih, CEO of Salesforce AI

In 2020, Clara Shih quit Hearsay, the company she founded and ran for 11 years; in hindsight, she says “I probably should have quit a little bit sooner.” But at the time, she cared a lot — too much — about what everyone else thought. “There's a lot of guilt around leaving initially and feeling bad for feeling bad,” Clara says. But her worries subsided when her replacement and former COO, Mike Boese, guided the company with “class and grace” to an exit: A $125 million+ acquisition just this week by Yext.

In this episode, Clara meets Joubin on the top level of Salesforce Tower to discuss Sarah Friar, AI “frenemies,” practice and discipline, quantifying hard work, burnout, turning off, Intercom, elite operators, “Serviceforce,” ChatGPT, hiring for hunger, kids and achivement, Thomas “TK” Kurian, Slack, David Schmeier, Juan Perez, Nvidia GPUs, Silvio Savarese and Frontier AI, Starbucks, and Sheryl Sandberg.

Chapters:

• (01:04) - Apple’s OpenAI partnership
• (03:18) - Organizing your life
• (04:45) - Working smarter
• (07:49) - Hindsight
• (08:58) - Hearsay’s acquisition by Yext
• (11:23) - What everyone else thinks
• (14:25) - Productive worry
• (17:27) - Coming (back) to Salesforce
• (20:47) - Paranoia and immigrant hustle
• (25:42) - Quitting
• (26:39) - Meetings and infusing AI
• (29:38) - Internal time savings
• (31:48) - The Matthew McConaughey ads
• (33:48) - Different horizons
• (37:35) - France and sovereign AI
• (38:46) - How Clara uses AI to keep up
• (40:33) - Dis-intermediating Netflix
• (41:27) - Who Salesforce AI is hiring
• (42:05) - Advice from Howard Schultz and Marc Benioff

Links:

• Connect with Clara
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Marissa Mayer, CEO and Founder of Sunshine and former CEO of Yahoo

When Marissa Mayer was first hired as the CEO of Yahoo, the company had lost nearly a quarter of its workforce in the preceding six months. Early on, she was chatting with employees in the cafeteria and one of them got her attention by smacking her tray. “Is it go time?” he asked. He was asking if the board and C-suite were ready to lead the company forward, but Marissa thought he had one foot out the door. “I had just come out of this meeting where they were like, ‘Everyone’s leaving!’” she recalled. “And I was like, ‘Oh no, please don’t go, I’ve only been here for four days!’”

In this episode, Marissa and Joubin discuss the number 12, contacts and photo sharing, fear of AI, soccer moms, maternity as a “disability,” mothers’ rooms, Jim Citrin, Project Cardinal, HTML5 vs. native apps, Ross Levinsohn, Lori Puccinelli Stern, Joe Montana, David Karp, Mark Zuckerberg, Taylor Swift, hiring at Google, Amit Patel, Hamilton, John Doerr, and the Google APM program.

Chapters:

• (00:52) - Reading your own press
• (04:55) - Marissa’s lucky number
• (07:19) - Her latest startup, Sunshine
• (15:03) - Burnout, resentment, and rhythm
• (21:46) - The opportunity to become CEO of Yahoo
• (27:00) - Inverting maternity leave
• (31:14) - The big interview
• (36:44) - An epic dinner party
• (42:51) - The voicemail
• (47:18) - Farzad “Zod” Nazem and David Philo
• (50:25) - Last day at Google
• (53:52) - “Is it go time?”
• (59:03) - Buying Tumblr
• (01:04:46) - Alibaba and Verizon
• (01:06:24) - Larry and Sergey bucks
• (01:11:05) - Eric Schmidt’s advice
• (01:12:59) - In the room at Google
• (01:18:36) - Teaching and identifying talent
• (01:24:32) - Who Sunshine is hiring

Links:

• Connect with Marissa
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Sarah Friar, former CEO of Nextdoor

Sarah Friar has worked with some of the top leaders in Silicon Valley, including Salesforce CEO Marc Benioff, Walmart CEO Doug McMillon, Block CEO Jack Dorsey, and most recently Nextdoor founder Nirav Tolia, who just replaced her as CEO in May. And one of the things that sets top performers apart from the rest, she argues, is their compassion and their responsiveness. When her former EA’s husband was diagnosed with cancer, Sarah texted Benioff — who she had just left behind to work at Square — for help. Within seconds, she recalls, he arranged an appointment at UCSF. “That is an amazing moment of compassion,” she says, “where he did not need to take that time.” 

In this episode, Sarah and Joubin discuss public markets vs. VC, George Floyd, working with the board, singular focus, Goldman Sachs, being in “flow,” the freedom of not getting the thing you want, Walmart, Steph Curry, Graham Smith, Charlie Rose and Donald Trump, ugly babies, Elon Musk, Ladies Who Lunch, CNBC, commuting from home, white noise, “frequent Friars,” @TechEmails on Twitter, and the “zone of gratefulness.”

Chapters:

• (02:04) - Why Sarah left Nextdoor
• (08:18) - The stock market and success
• (10:21) - Going through hell
• (14:48) - Life is not an A/B test
• (16:09) - Multiple tours of duty
• (19:21) - Ikigai
• (22:02) - Perfectionism and drive
• (25:54) - Sarah’s next operating role
• (28:35) - Big transitions
• (30:35) - Personal burn rate
• (35:34) - “Are people gonna take my call?”
• (38:40) - Leaving Salesforce for Square
• (41:27) - Loyalty
• (45:33) - Leaving the right way
• (47:44) - Square and Swiss cheese companies
• (50:03) - Growth companies
• (52:38) - Apolitical workplaces
• (53:42) - Leaving Square
• (55:38) - Loneliness
• (57:18) - Daily routines
• (01:05:03) - Working on weekends
• (01:08:30) - Hyper-responsiveness
• (01:11:47) - Resumé virtues and eulogy virtues
• (01:15:33) - What “grit” means to Sarah

Links:

• Connect with Sarah
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Stanislav Vishnevskiy, CTO and co-founder of Discord

For many years, the conventional wisdom was the gaming was not social because it was something you usually did at home. “But people who play games are often the most social,” says Discord CTO Stanislav Vishnevskiy. “They’re spending 10, 20 hours with other people online, hanging out.” As a teenager, Stanislav logged more than 1,000 days playing his favorite video game and socializing with friends around the world, but with 200 million monthly active users, the social platform is appealing to a lot more than hardcore gamers. “People online who need to get together and collaborate ... [want] tp have control and create a place,” he says. “That’s not just a gaming need, right? That’s pretty much any community.”

In this episode, Stanislav and Joubin discuss “Discord moments,” hanging out online, IRC and AIM, Fates Forever, good and bad stress, leadership coaches, Claire Hughes Johnson, socializing online, heart surgery, Slack, Jason Citron, in-browser voice chat, Reddit, authentic CX, hiring slowly, Mitch Lasky, “playing moneyball,” React, content moderation, deprecation plans, and collaborative projects.

Chapters:

• (02:09) - Discord’s scale and importance
• (07:35) - What is Discord?
• (09:43) - Hammer and Chisel
• (13:18) - How Stanislav’s role has changed
• (15:17) - Imposter syndrome
• (17:47) - Doing stuff for the first time
• (21:22) - Final Fantasy XI and Stanislav’s parents
• (25:12) - YOLO
• (27:02) - Games as social networks
• (30:49) - The evolution of Discord
• (35:58) - Inherent virality
• (39:04) - Building the company
• (41:39) - The COVID effect
• (43:08) - Hiring for slope
• (46:43) - Pivoting back to gaming
• (51:27) - The Discord Store and Nitro
• (54:30) - Emotional stakes
• (56:09) - Midjourney and AI art
• (59:58) - Virtual worlds
• (01:01:30) - Who Discord is hiring and what “grit” means to Stanislav

Links:

• Connect with Stanislav
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Eoghan McCabe, CEO, Chairman, and Co-Founder of Intercom

“We are not ready for the degree to which our world is going to change,” says Intercom CEO Eoghan McCabe, “in insane and incredible ways.” When he co-founded the company in 2011, the Irish-born entrepreneur was making it easier for companies to offer human customer service to their customers. But Eoghan believes “every single type of knowledge work” will soon be done by AI, and Intercom is well on its way to that destination: 45 percent of all tickets are being answered by bots now, and he expects that number to climb to 70 percent by 2026. “The agents no longer have to do the repetitive, painful, boring work,” Eoghan says. “They can focus on the more human, creative, interesting work that requires their empathy and creativity.”

In this episode, Eoghan and Joubin discuss fitting in, Archana Agrawal, authentic comms, taking risks, returning to the company you founded, politics at work, celebrating innovation, therapy for founders, and Ram Dass.

Chapters:

• (01:04) - Insecurity and success
• (06:16) - What Intercom does
• (08:20) - Reinvention and “big company values”
• (15:50) - Becoming an AI company
• (16:53) - 2011 vs. 2024 in San Francisco
• (21:03) - AI for customer service — and more
• (25:07) - “The shitty gift that being attacked brings”
• (30:25) - Expectations vs. reality, part one
• (33:16) - What success means now
• (36:08) - Running away
• (39:56) - Coming back
• (41:58) - Being busy is BS
• (44:10) - Expectations vs. reality, part two
• (45:44) - Self-mastery
• (50:38) - Sanding off the rough edges
• (55:08) - Who Intercom is hiring and what “grit” means to Eoghan

Links:

• Connect with Eoghan
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Mark Cuban, co-founder of Cost Plus Drugs and costar, Shark Tank

“I just love to compete,” says Mark Cuban. “And the day I stop is the day I’m dead.” Previously the co-founder of MicroSolutions and Broadcast.com, Cuban is probably best known to the public today for competing with the likes of Daymond John and Barbara Corcoran on the reality TV show Shark Tank. But his real focus — and his real enemy — these days is the pharmaceutical industry. His latest company, Cost Plus Drugs, aims to be far more transparent than established PBMs, or Pharmacy Benefit Managers, and Mark clearly relishes eating their margin. “Everybody talks about disrupting healthcare,” he says. “This is the easiest motherf**king industry I've ever tried to disrupt because it is so opaque, and everybody is so captured by the scale of these big companies.”

In this episode, Mark and Joubin discuss Luka Dončić, Synthesia, the Sony hack, the American Dream, TikTok propaganda, MicroSolutions, throwing away watches, keeping kids grounded, Black Mirror, keeping up, Ali Ghodsi, the NBA, MGM, gambling in Dallas, the Adelson family, CES, transparency, and Alex Oshmyansky.

Chapters:

• (00:55) - Game day and superstitions
• (03:08) - Email responsiveness
• (05:48) - Shark Tank
• (09:21) - Retiring young
• (10:57) - American Airlines’ lifetime pass
• (12:55) - Sports and blue-collar work
• (16:02) - Compete or die
• (17:43) - Why Mark hates meetings
• (19:57) - Immortality through AI
• (23:05) - The new AI wave
• (25:07) - Startup founders and low-hanging fruit
• (29:24) - Selling Broadcast.com to Yahoo
• (31:35) - The Dallas Mavericks
• (34:52) - Selling his majority stake
• (37:08) - The missing link in pharma
• (41:27) - Disrupting a huge industry
• (43:57) - The problem with debt
• (44:59) - What “grit” means to Mark

Links:

• Connect with Mark
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Taylor Francis, co-founder of Watershed

One day when he was 13, Taylor Francis walked out of the movie theater, and he was pissed off. He had just seen Al Gore’s documentary An Inconvenient Truth and internalized a “generational call to arms, that my parents had screwed our generation” by causing the climate crisis, he says. 14 years later, he was working at Stripe and felt another call to arms: The 2020s would be a crucial decade for slashing carbon emissions and combating global warming. So, he and his co-founders Avi Itskovich and Christian Anderson all left Stripe to start Watershed, which helps companies measure and reduce their emissions.

In this episode, Taylor and Joubin discuss Patrick Collison, Dan Miller-Smith, hiring challenges, Jonathan Neman, “golden age syndrome,” John Doerr and Mike Moritz, the Climate Reality Project, steady partnerships, DRI cultures, shared context, social distancing, information sprawl, and the founders’ “woe is me” narrative.

Chapters:

• (01:02) - Magnetic missions
• (06:40) - How enterprise sustainability works
• (08:40) - Watershed’s first client, Sweetgreen
• (11:04) - Reflecting on the early days
• (16:36) - Al Gore and An Inconvenient Truth
• (18:53) - Mobilizing teenagers
• (22:16) - The origins of Watershed
• (27:04) - Leaving Stripe and raising money
• (31:41) - Interchangeable co-founders
• (33:06) - The ground truth
• (35:25) - The Dunbar Number
• (38:22) - Watershed’s operating principles
• (41:56) - Intensity, priorities, and sacrifice
• (47:37) - Moving faster
• (50:26) - Sustainability is a part of business
• (52:21) - The topology of emissions
• (58:08) - Who Watershed is hiring

Links:

• Connect with Taylor
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guests: Victor Riparbelli, CEO and co-founder of Synthesia; and Josh Coyne, partner at Kleiner Perkins

When Victor Riparbelli wants to learn something, he’ll start with a YouTube video or a podcast: “I maybe buy the book on Amazon as like the fifth step,” the Synthesia CEO says. His company is trying to change the text-first (or text-only) way information is conveyed at work, making AI avatar-narrated videos to replace documents like customer profiles and HR manuals. Victor says that as the technology improves over many years, it could replace text entirely. “I think for most people, if they had a choice, they would probably prefer to watch video and listen to audio.”

In this episode, Victor, Josh, and Joubin discuss Seedcamp, Annie Case, Rubik’s Cubes, AI video dubbing, Instagram filters, emotive avatars, Ilya Fushman, Atlassian, Grammarly, the Gutenberg Parenthesis, European startups, email responsiveness, acqui-hires, and being “lonely at the top.”

Chapters:

• (01:33) - Loose screws
• (02:45) - How Victor and Josh met
• (04:35) - AI hype cycles
• (06:57) - What Synthesia does
• (08:22) - Copycats and competition
• (14:34) - Winner take all
• (16:38) - Synthesia’s origin story
• (21:36) - Category creation
• (23:41) - The next era of AI video
• (28:51) - The uncanny valley
• (30:07) - Watching videos at work
• (33:17) - Scaling video and audio content
• (37:45) - Emailing with Mark Cuban
• (45:15) - Battle scars
• (48:47) - Customer obsession
• (50:54) - Pressure to succeed
• (54:41) - Deep passion
• (57:16) - Who Synthesia is hiring

• Connect with Victor
  • Twitter
  • LinkedIn
• Connect with Josh
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Kat Cole, COO of Athletic Greens

You can’t make smart decisions if you don’t know the truth — the “true truth,” as Athletic Greens COO Kat Cole puts it. “As you get bigger and you have success, innovator’s dilemma, you end up talking to yourself instead of really being rooted in what’s going on.” That’s why she has embraced the anxiety of the unknown, channeling what she doesn’t know about the market into productive questions for her team and her customers. Anxiety can be harmful, she concedes, but “there’s a healthy version of believing you never really know what’s going on, and you never really know the true truth, because things change so quickly.”

In this episode, Kat and Joubin discuss Huberman Lab, ultra-endurance athletes, Chris Ashenden, founder-owned businesses, “fancy jobs,” international trips, unplanned succession, private equity, the Atkins diet, inheriting a bad situation, omni-channel marketing, working with franchisees, fully remote companies, “if not for...,” and why Athletic Greens has only one SKU.

Chapters:

• (01:04) - Podcast superfans
• (06:54) - AG1 and Kat’s professional journey
• (11:14) - Her “Jerry Springer childhood”
• (14:31) - Learning, moving, thriving
• (16:18) - The Hooters business school
• (24:05) - Leaving Hooters and joining Rourke Capital
• (28:46) - Cinnabon’s dark years
• (35:55) - The three questions
• (41:11) - MiniBons
• (45:37) - Anxiety and uncertainty
• (48:40) - The wad of paper story
• (50:26) - Favorite interview questions
• (54:49) - The temptation to do more

• Connect with Kat
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Anne Raimondi, COO and Head of Business at Asana

Asana COO Anne Raimondi feels pressure to perform in her job “every day, all the time.” But that pressure doesn’t come from her fellow executives; she imposes it on herself, trying to think carefully about how much each of her decisions will impact her team. “I have a lot of privilege and choice,” Anne says, “of how I spend my time, the resources available to me, and am I doing enough? ... Am I doing the most with the opportunities I have, and making as positive an impact as I can?”

In this episode, Anne and Joubin discuss returning to the office, Scott McNealy, the dotcom bust, Myers-Briggs, Star Trek: The Next Generation, empowering leaders, Blue Nile, Robert, Chatwani, tech leaders with children, Bain Capital, time management, being “in the moment,” Dave Goldberg, Dustin Moskovitz, staying curious, and being prescriptive.

Chapters:

• (01:05) - Hybrid remote policies
• (05:34) - Employees’ emotional journey
• (09:39) - Thoughtful answers and betazoids
• (13:17) - Anne’s immigrant parents
• (14:50) - Regrettable feedback
• (17:46) - Leaders who cast a shadow
• (19:36) - Company-hopping
• (24:14) - Startups and stability
• (28:42) - Pressure to perform
• (31:08) - Insecurity and parenthood
• (37:12) - Allocating your time
• (39:43) - Co-founding One Jackson
• (45:36) - Amanda Kleha
• (47:01) - Great founders
• (52:18) - “It is not glamorous”
• (54:03) - From board to operating at Asana
• (57:10) - Feedback for founders
• (01:00:25) - Recurring meetings
• (01:03:07) - Who Asana is hiring

Links:

• Connect with Anne
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Sanjay Beri, CEO and Founder of Netskope

“You can be waiting your whole life to do something, and then your life’s over,” says Sanjay Beri. After nine years at Juniper Networks, he left his comfortable job, moved his family to a house with a pricier mortgage, and launched the cloud security firm Netskope. His entrepreneurial story would make anyone stressed, he acknowledges, but “at some level, you have to be wired to enjoy it… that's why I tell everybody who joins, ‘It's not for the faint of heart.’”

In this episode, Sanjay and Joubin discuss Reddit, banker friends, professional legacies, the wrong way to raise capital, authenticity, Ponzi schemes, “fool’s gold,” high-risk hiring, hitting pause, your “other family,” and changing roles.

Chapters:

• (00:54) - 2024 IPOs
• (05:43) - Long on cybersecurity
• (07:59) - Netskope’s mission
• (10:22) - Sanjay’s first company, Ingrian
• (12:07) - The writing on the wall
• (15:02) - Mamoon Hamid
• (20:21) - Stress and perspective
• (24:53) - Sanjay’s mother
• (28:41) - The trenches vs. the clouds
• (30:53) - Guts, Resolve, Integrity, Tenacity
• (32:10) - Hiring for grit
• (38:06) - The lowest point
• (41:18) - “Always on”
• (43:49) - The hot desk office
• (46:13) - Scaling people
• (49:30) - Politics and integrity
• (53:03) - Who Netskope is hiring

• Connect with Sanjay
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Scott McNealy, former CEO and co-founder of Sun Microsystems & co-founder of Curriki

Scott McNealy never wanted to be CEO of Sun, and in his 22-year tenure before selling to Oracle, he knows there were times he failed to execute, or to rein in the once-iconic Silicon Valley firm’s worst impulses. But like his pro golfer son, Maverick, Scott doesn’t like to look back: “Golfers will always look back and blame the wind, a divot that wasn't repaired, a bad rake job, a mower cut that wasn't done properly, a gust of wind,” he explains. “If you blame yourself for all of the mistakes you make. You will hate yourself ... I look forward.”

In this episode, Scott and Joubin discuss Scott Cook, Maverick McNealy, why big companies are riskier than startups, Al Gore, Marc Andreessen, Mark Zuckerberg, Kodak, Dick Kleinhans, Harvard University, “bozo invasions,” Myers-Briggs, making an example, Motorola car phones, the Moscone Center, Elon Musk, Jeff Bezos, NVIDIA’s valuation, farewell letters, “you have no privacy,” open-source education, and toothpaste.com.

In this episode, we cover:

• (01:00) - John Doerr
• (02:47) - Fathers, sons, and sports
• (07:29) - Living in the piñata
• (10:48) - Why Scott left Sun
• (13:49) - The heyday of Sun Microsystems
• (18:24) - Vinod Khosla and founding Sun
• (21:24) - How Scott became CEO
• (27:21) - Profitable in three months
• (30:02) - Inferiority complex
• (32:20) - Executive exits and fun at work
• (35:49) - Managers and recognition
• (38:18) - “HR hero” Crawford Beveridge
• (40:35) - How Carol Bartz became VP of marketing
• (43:07) - Sharing in success
• (45:25) - Scott’s love life & meeting Susan
• (50:54) - The dotcom boom and crash
• (53:45) - Unicorn CEOs and IBM’s offer
• (55:49) - Competitors and hindsight
• (58:20) - “The planet system”
• (01:00:13) - Too many employees
• (01:04:06) - Larry Ellison and selling to Oracle
• (01:07:01) - Blaming yourself and looking forward
• (01:10:11) - Curriki
• (01:12:12) - The AI boom
• (01:14:42) - “Grit” and insecurity

Links:

• Connect with Scott
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Jyoti Bansal, CEO and co-founder of Harness

Cisco bought Jyoti Bansal’s first company AppDynamics for $3.7 billion, making him a very wealthy man. But after two African safaris, a week of Michelin-starred meals in Tokyo, and more adventures all around the world, he realized that spending his money didn’t truly make him happy. After some soul-searching, he realized what he really enjoyed: “I liked to build companies. That is my craft ... If someone enjoys playing gold for six hours, I would enjoy working on a startup for six hours.”

In this episode, Jyoti and Joubin discuss the evolution of Grit, Carlos Delatorre, Tom Mendoza, Glean, growing up in India, traveling the world, three-star restaurants, soul-searching, automating gruntwork, paying for nice hotels, red-eye flights, product-market fit, Jeff Bezos, the “three-layered cake,” Frank Slootman, raising the bar for distribution, technical debt, structural efficiency, and taking pride in your work. 

In this episode, we cover:

• (00:59) - Top-tier CROs
• (04:18) - The video game levels of startups
• (07:24) - Selling AppDynamics to Cisco
• (09:16) - Keeping up with high-growth companies
• (12:10) - The chip on Jyoti’s shoulder
• (16:15) - How he thinks about money
• (18:02) - Do what you enjoy every day
• (22:32) - “What would make me happy?”
• (24:56) - Starting BIG Labs and Harness
• (29:16) - Adjusting to a new reality
• (34:13) - Work-life balance
• (36:30) - What gets easier — and harder — over time
• (41:44) - Product vs. distribution
• (46:46) - Paying it forward
• (48:29) - The next level
• (50:24) - The four lists
• (53:45) - Assigning clear responsibilities
• (56:06) - Jyoti’s favorite interview question
• (57:41) - Who Harness is hiring

Links:

• Connect with Jyoti
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Clint Sharp, CEO and co-founder of Cribl

New employees are joining the remote data platform Cribl every week, and as the staff grows, CEO Clint Sharp has noticed a problem: He can’t file a bug report without a lot of caveats. When there were a handful of users, no one would bat an eye at the CEO posting a bug on Slack, but now he has had to learn how to phrase things because people assume he’s “irate and we should change everything we’re doing,” Clint says. “I’ll post something and there’s a flurry of DMs that are happening in the background, like ‘Oh my God.’” Unless the tone of his bug report is clear, workers with more experience at Cribl then have to reassure the newbies: “Calm down. When he does this, he’s not upset. He’s one of the power users of the product.” 

In this episode, Clint and Joubin discuss being on the road, niche audiences, top-of-funnel problems, “come to Jesus” meetings, moving the goalposts, building for building’s sake, “down and to the right,” mediating re-orgs, flat organizations, filing bugs as the CEO, setting the example, Henry Schuck, Baldur’s Gate III, legal narratives, Hacker News, Cisco, Doug Merritt, Gary Steele, Rippling, and dead trends.

In this episode, we cover:

• (01:08) - Running a remote company
• (02:57) - Cribl’s management meetings
• (05:56) - Looking back and recognition
• (08:08) - Growing quickly and what Cribl does
• (11:21) - Traction
• (14:53) - Solving a new problem
• (17:56) - Friends and family funding
• (21:45) - Why not shut it all down?
• (24:36) - Healthy arrogance and control
• (31:02) - Serial entrepreneurs and founder-CEOs
• (33:38) - What Clint loves about the job
• (35:31) - The hardest parts
• (38:41) - Core values
• (41:43) - Favorite interview questions
• (44:26) - Drawing boundaries
• (47:18) - Vacation and work-life balance
• (52:53) - Splunk’s lawsuit against Clint
• (56:26) - “Their brand is synonymous with expensive”
• (58:41) - Who owns the data?
• (01:01:59) - Building platforms
• (01:07:35) - “I’m so sick of AI”
• (01:11:25) - Who Cribl is hiring

• Connect with Clint
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Glen Tullman, CEO of Transcarent

Before he was CEO of Transcarent, Glen Tullman presided over the biggest digital health merger of all time: His previous company Livongo was acquired in 2020 by Teledoc for $18.5 billion. Over his decades of experience in health tech, he has developed saying: Hire low, fire high. When one of his friends was offered a job and said he wanted to consider another offer, Glen withdrew Transcarent’s offer because he didn’t want to be the highest bidder — in other words, hire low. But whenever he has to let someone go, he sees it as his responsibility to “help them go off and do something else that’s great, and be successful.” Firing and replacing executives, he said, is “just part of growing ... it doesn’t have to be ugly.”

In this episode, Glen and Joubin discuss conservative values, John Doerr, Teledoc, failures of leadership, Steve Case, Bill Gates, changing expectations, Travis Kalanick, incentive bonuses, Bucknell University, massive layoffs, criticizing in public, anonymous charity, cycling events, Michael Jordan, Bill McDermott, Barack Obama, private jets, and hiring without titles.

In this episode, we cover:

• (01:11) - How Glen splits his time
• (03:55) - Looking back and leaving Livongo
• (09:03) - Would he do it again differently?
• (13:42) - Energy at work
• (18:00) - Failure and starting over
• (21:16) - What Transcarent does
• (25:29) - Taking on the system and stress
• (30:33) - Turning Allscripts around
• (33:48) - “We educated you to make a difference”
• (38:06) - The birth of electronic prescriptions
• (42:52) - Hire low, fire high
• (47:47) - Radical honesty
• (53:04) - Charitable efforts
• (57:55) - Glen’s competitive childhood
• (01:00:55) - His family and priorities
• (01:08:24) - Would Glen go into politics?
• (01:12:32) - “I hate to sleep”
• (01:15:06) - Peloton meetings
• (01:17:32) - Trading money for time
• (01:24:11) - Sharing credit
• (01:25:54) - Who Transcarent is hiring
• (01:28:05) - What “grit” means to Glen

Links:

• Connect with Glen
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Filip Kaliszan, CEO and co-founder of Verkada

Great founders try to grow personally at least as fast as their companies do — but sometimes, says Verkada CEO Filip Kaliszan, that’s just not possible. By the time the company had about 200 employees, he says, “the scale of the business and the rate of the growth of the business ... outpaced my rate of learning, or my ability to consult the right people.” But over time, he has worked to fix past errors and earn everyone’s trust: “I can be only as good as the rate at which I fix my mistakes,” Filip says.

In this episode, Filip and Joubin discuss “the good old days,” first principle thinking, the business impact of the COVID-19 pandemic, the Bay Area bubble, going public, Aaron Levie, going down rabbit holes, power dynamics, idea validation, Brian Long, Hans Robertson, DIY entrepreneurship, commercial kitchens, cash efficiency, VR headsets, zeitgeist-y platform shifts, Mark Zuckerberg, and John Doerr.

In this episode, we cover:

• (00:50) - Verkada’s office culture
• (04:37) - The loss of community
• (10:37) - Not going remote during COVID
• (16:37) - Palo Alto Networks
• (22:15) - Does Filip like being CEO?
• (26:02) - Time management and flow state
• (29:47) - The problem with huge meetings
• (31:59) - Fundraising for Verkada
• (34:02) - Building a “camera company”
• (37:29) - Zero to one
• (41:17) - The first 10 people
• (42:48) - Allocating capital wisely
• (46:19) - Hiring in-house
• (51:17) - Biggest screw-ups
• (54:00) - The feeling of failure
• (55:05) - Customer therapy
• (56:39) - Divide and conquer
• (01:00:47) - The Apple Vision Pro
• (01:05:05) - Mark Zuckerberg’s response
• (01:09:25) - Who Verkada is hiring and what “grit” means to Filip

• Connect with Filip
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Wade Foster, CEO and co-founder of Zapier

When Wade Foster and his co-founders launched Zapier, he was 24, and doubted himself constantly. He consulted mentors like Paul Graham and Jay Simons, studied entrepreneurs like Jeff Bezos and Steve Jobs, and also took inspiration from an unlikely source: Actor and martial artist Bruce Lee. “[He] had this fighting style, ‘The Way of No Way,’” Wade says. “He would study all the different fighting styles, and he would say, ‘None of them is the best or the worst ... My job was to take the best of each and then discard the rest, and make it my own.’”

In this episode, Wade and Joubin discuss fully remote companies, long-term thinking, hyperscaling, product-market fit, broken products, secondary offerings, “delocation packages,” interview questions, mind-breaking growth, doubting yourself, LLMs, hackathons, and adding a sales team (eventually).

In this episode, we cover:

• (01:10) - Living in central Missouri
• (04:15) - Will Wade do this forever?
• (10:23) - Startup envy
• (13:09) - “Do people actually want this?”
• (18:44) - What Zapier does
• (20:15) - Taking outside capital
• (22:43) - Why Zapier is fully remote
• (28:01) - The pace of hiring
• (30:35) - Why résumés can be a trap
• (37:09) - When to promote from within
• (41:06) - Scaling problems
• (43:47) - Self-confidence and mentors
• (47:37) - Reacting to ChatGPT
• (53:43) - How Zapier’s team uses AI
• (58:12) - Who Zapier is hiring

• Connect with Wade
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Kim Scott, author of Radical Candor: Be a Kickass Boss Without Losing Your Humanity and Radical Respect: How To Work Together Better

After her first management book Radical Candor became a worldwide bestseller, Kim Scott found herself giving talks to all kinds of companies about how they could apply her advice and build a stronger, kinder culture. But then, after one such talk, the CEO — a longtime friend and former coworker — came up to Kim with an asterisk. As a Black woman, she explained, “as soon as I offer anyone even the most compassionate, gentle criticism, I get assigned the ‘angry Black woman’ stereotype.” Kim realized in that moment that her book needed a prequel of sorts, explaining what you need to have before you can create radical candor: “You're not going to care about people who you don't respect,” she says.

In this episode, Kim and Joubin discuss regret minimization, Juice Software, Sheryl Sandberg, saying “um,” moments of connection, Dick Costolo, negative truths, James March, snobbery, Charles Ferguson, Shona Brown, Fred Kofman, Christa Quarles, Jason Rosoff, Andy Grove, founders as outliers, Jack Dorsey, Steve Jobs, glows and grows, the Post Ranch Inn, failing your colleagues, sexual harassment, DEI, and intellectual honesty.

In this episode, we cover:

• (01:04) - Loud voices
• (03:59) - Writing a bestseller
• (07:48) - Why Kim wrote Radical Candor
• (14:21) - How to show you care
• (18:04) - Coaching tech CEOs
• (21:24) - Ruinous empathy and obnoxious aggression
• (25:40) - Leaving things unsaid
• (30:30) - Not an academic
• (35:21) - Learning from failed startups
• (38:55) - Performance reviews
• (42:30) - Why feedback feels risky
• (49:21) - How to reject feedback
• (53:11) - Creating space for feedback at home
• (56:08) - Running and sleeping
• (59:45) - Radical Respect and Kim’s other books
• (01:04:27) - The hardest story to share
• (01:06:44) - Optimism about the future

Links:

• Connect with Kim
  • Buy Radical Candor: Be a Kickass Boss Without Losing Your Humanity
  • Pre-order Radical Respect: How To Work Together Better
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Daniela Amodei, President and co-founder of Anthropic

With a reported valuation of as much as $18 billion, Anthropic has the resources to be one of the dominant AI companies in Silicon Valley; however, it was conceived as a public benefit corporation and always tries to strike a balance between hypergrowth and responsibility. Anthropic’s flagship LLM, Claude, must adhere to a “constitution” of values that prioritize the good of humanity. And even though every company wants to “do AI” right now, President Daniela Amodei says some of them should slow down. “I keep coming back to this idea of, ‘How much are you buying the hype?’” she says. “’How grounded are you in the reality of what's actually happening?’ And sometimes in business conversations, we tell a potential customer, ‘We don't think we're right for you.’”

In this episode, Daniela and Joubin discuss her brother Dario, staying grounded, hypergrowth startups, Claire Hughes Johnson, mechanistic interpretability, Paul Graham, AI training, what AI companies can learn from social media, Stripe, the pool of venture capital in the Bay Area, leading people, giving feedback to all your coworkers, interview questions, and Sheryl Sandberg.

In this episode, we cover:

• Holidays with the Amodei family (01:15)
• The tech industry bubble (05:35)
• Inside the AI hurricane (09:53)
• Scaling as a superpower (14:39)
• Complementary abilities (16:39)
• Claude 2 and constitutional AI (20:05)
• Making AI trustworthy, safe, and powerful (28:58)
• Generative AI’s high cost (31:03)
• Anthropic and OpenAI’s massive responsibility (37:50)
• The impact of new technology (42:32)
• Public benefit companies (46:55)
• Extremely lean go to market (53:36)
• AI as a business-led industry  (01:00:37)
• Customer obsession (01:06:58)
• Where do you want to use your innovation? (01:11:31)
• Who shouldn’t use AI? (01:14:33)
• “Everything to everyone” (01:18:15)
• Working with Daniela (01:22:26)
• Interviews at Anthropic (01:25:38)
• Intense performance reviews (01:29:47)
• Middle managers are underrated (01:35:46)
• “Tell me about yourself” (01:39:47)
• Who Anthropic is hiring (01:42:33)

Links:

• Connect with Daniela
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Dev Ittycheria, CEO and President of MongoDB

When you think about who you were and the decisions you made two, or four, or eight years ago ... how do you feel? Dev Ittycheria, the President and CEO of MongoDB, says he’s embarrassed about certain things he did — and that’s a good thing. “If you’re not [embarrassed], that means you’re not really growing that fast,” he says. He recalled one of his mentors, former BladeLogic chairman Steve Walske, explaining that everyone has an overinflated opinion of themselves, and the great leaders keep the gap between that opinion and reality narrow. One of the hallmarks of such a leader, Dev says, is that they have the intellectually honesty to recognize their own strengths and weaknesses, which others perceive.

In this episode, Dev and Joubin discuss looking for bad news, chips on your shoulder, Ivy League schools, being an outsider, highly educated parents, “aging out,” Bruce Springsteen, Chief People Officers, Frank Slootman and John McMahon, passive aggression, vulnerability as strength, imposter syndrome, open-source licenses, introverts, and time management.

In this episode, we cover:

• Shlomo Kramer and the “burden of persona” (00:59)
• Why BladeLogic started in Boston (04:30)
• The psychological edge (07:08)
• Dev’s family and education (08:56)
• “Am I good enough?” (13:11)
• “Do not squander this opportunity” (16:22)
• Dev’s wife (19:32)
• Fear of irrelevance (21:23)
• Relevance after retirement (26:06)
• Why CEO is a lonely job (28:14)
• Trusting your team (31:43)
• The meaning of life (35:16)
• Judgment and introspection (38:16)
• Taking people to the woodshed (40:54)
• What matters to other people (44:39)
• Taking risks at MongoDB (51:08)
• Founder-led businesses (53:26)
• What type of company is MongoDB? (57:39)
• Work-life harmony (01:00:20)
• Who MongoDB is hiring (01:03:17)

Links:

• Connect with Dev
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Frank Slootman, CEO and Chairman of Snowflake and author of Amp It Up

Snowflake CEO Frank Slootman doesn’t recall a time in his childhood where new achievements were celebrated — because, according to his father, putting everything into your work and “leaving it all on the field” was the only choice. “The problem with it,” Frank says, is that “it becomes a ‘never enough’ dynamic, because when is it enough?” To this day, he comes home on Friday night and asks himself, “Did it mater that I was there? ... If I’m just a passenger on the ship, that’s my nightmare.”

In this episode, Frank and Joubin discuss acting with urgency, Shlomo Kramer, negative role models, Elon Musk, Teddy Roosevelt’s “Man in the Arena” speech, aptitudes and weaknesses, ServiceNow, and the life spark of business.

In this episode, we cover:

• Being tough on yourself (00:59)
• Sailing and inner peace (03:00)
• Confronting your demons (09:07)
• Scaling Data Domain (11:15)
• Judging talent (15:20)
• That gnawing feeling (18:16)
• Daring greatly and rejecting pride (21:04)
• “Did it matter that I was there?” (25:02)
• How you play the game (27:59)
• The best version of yourself (29:59)
• Learning from the best (34:06)
• Sales as inspiration (37:52)
• Retirement and Tom Brady (39:09)
• The fog of war (41:16)
• Snowflake vs. Data Domain (44:31)
• Respect for luck (48:48)
• Who Snowflake is hiring (50:42)

Links:

• Connect with Frank
  • LinkedIn
  • Buy Frank’s book, Amp It Up: Leading for Hypergrowth by Raising Expectations, Increasing Urgency, and Elevating Intensity
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Jason Kelly, CEO and co-founder of Ginkgo Bioworks

Almost everyone in the second generation of biotechnology entrepreneurs, says Ginkgo Bioworks CEO Jason Kelly, works in that field because of one thing: Jurassic Park. The Michael Crichton novel-turned-Steven Spielberg movie captured both the wonder and beauty of bioengineering, and the challenges of bending DNA to your own ends. “You didn’t invent biology,” Jason says. “You need to have humility in the face of it ... because life will find a way. It will do things you don’t expect. It’s not a computer.” 

In this episode, Jason and Joubin discuss the Wall Street rollercoaster, designer cells, the history of biotech, Herbert Boyer and Genentech, ChatGPT, extinct flowers, Sam Altman and YCombinator, first principles thinking, compounding risk, Patrick Collison, super-voting shares, capital intensive businesses, Pets.com, and why biology is like “freakishly powerful alien technology.”

In this episode, we cover:

• Being private vs. being public (00:58)
• How bioengineering works (04:27)
• Jurassic Park (08:51)
• Biotech breakthroughs (12:15)
• Why this field is not well-known yet (16:57)
• “The ChatGPT moment for biotech” (22:05)
• Meaningful stuff takes forever (26:23)
• Ginkgo’s first five years (29:02)
• Why the company went public (36:20)
• Short sellers, Warren Buffett, and Elon Musk (42:08)
• Applying AI to DNA engineering (47:57)
• The long-term future (55:57)
• Who Ginkgo is hiring (58:39)

Links:

• Connect with Jason
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: John McMahon, author of The Qualified Sales Leader: Proven Lessons from a Five Time CRO

A hell of a lot of people work in sales. But until recently, says five-time CRO and The Qualified Sales Leader author John McMahon, it was rare for colleges and universities to offer a sales degree. Salespeople had to learn on the job from experienced coaches, and adapt. And their bosses, John explains, had to themselves as agents of transformation. “If somebody’s really smart, they’re going to pick up the knowledge,” he says. “If they have what I call a PHD — persistence, heart, and desire — they’re going to learn the skills ... You’re going to have to do thousands and thousands of repetitions before you’re going to get good.”

In this episode, John and Joubin discuss lazy LinkedIn cold calls, Tom Brady’s retirement, being “married to your job,” Carl Eschenbach, crying, sales as a calling, corporate culture vs. coaching culture, adaptable workers, opportunity vs. title, Bob Muglia, transactional leaders, sad rich people, cookie-cutter advice, handshake evaluations, and David Cancel.

In this episode, we cover:

• CRO to CEO? (02:21)
• Ego and relevance (04:25)
• Escaping the 90-day grind (06:25)
• Persistence and physical discipline (09:05)
• Daily habits and positive energy (14:12)
• Why John quit BMC (17:09)
• Poor communication (21:17)
• Was there another way? (24:37)
• Identifying sales talent (28:36)
• Showing that you care (32:58)
• Sales leaders as hockey coaches (39:46)
• Firing people (44:25)
• Interviewing the right type of salesperson (49:14)
• Snowflake and Chris Degnan (51:22)
• “What’s the book on you?” (56:03)
• Managing from a position of power (58:01)
• The three “whys” (01:00:31)
• Why John never went VC (01:04:33)
• Is he really done? (01:07:17)
• Shlomo Kramer (01:10:20)
• Having impact (01:13:11)
• Bad advice (01:16:19)
• Working with marketing (01:19:32)
• Sizing people up (01:21:26)
• Can CEOs give up? (01:26:51)
• Coaching sales “artists” (01:28:29)
• What “grit” means to John (01:30:48)

Links:

• Connect with John
  • LinkedIn
  • Buy The Qualified Sales Leader: Proven Lessons from a Five Time CRO
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Angela Duckworth, professor at the University of Pennsylvania and author of Grit: The Power of Passion and Perseverance

“There’s got to be a cost” when you pursue your passions, says University of Pennsylvania professor Angela Duckworth; in fact, the word “passion” comes from the Latin word for “suffering.” But that doesn’t mean that gritty people are unhappy. After the time needed for sleep, daily exercise, friends, and family, Dr. Duckworth explains, “what’s left is more than 40 hours.” Informed by her research and her own happiness, she tries to discourage her students from settling for a 9 to 5 life: “There’s so many people that exemplify a life of dedication, and hard work, and of happiness, and humor, and friends, and family, that I think we should tell young people, ‘Look, don't assume that's not possible.’”

In this episode, Angela and Joubin discuss being punctual, Danny Kahneman, AP Calculus, moving the finish line, teaching grit to children, Arthur Ashe, Diana Nyad, passion and sacrifice, hiring gritty people, “change your situation,” Marc Leder and Rodger Krouse, Invictus, ChatGPT, neural autopilot, and Steve Jobs.

In this episode, we cover:

• “I have a thing with time” (01:36)
• Being the GOAT (06:37)
• Mr. Yom (09:27)
• Chef Marc Vetri (14:15)
• The Devil Wears Prada (16:03)
• Talking about grit (18:12)
• Satisfaction, loneliness, and happiness (20:24)
• Success as a journey (28:23)
• The cost of hard work (32:52)
• Angela’s 70-hour work week (36:31)
• Charisma and loving what you do (40:55)
• Why high achievers have supportive partners (47:07)
• The next book (55:25)
• Pick the right market (57:45)
• Therapy questions (59:53)
• The Incredible Hulk vs. James Bond (01:02:45)
• Automating decisions (01:05:43)
• What “grit” means to Angela (01:09:39)

Links:

• Connect with Angela
  • Twitter
  • LinkedIn
• Additional reading:
  • Redefining Success: Adopt the Journey Mindset to Move Forward
  • Buy Grit: The Power of Passion and Perseverance
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: David Cancel, founder and former CEO of Drift; founder of Rey

After HubSpot acquired his company Performable in 2011, David Cancel became his acquirer’s Chief Product Officer — and didn’t give any thought to how long he’d be in that role. When he started eyeing the exit a few years later, he was told that wasn’t an option: HubSpot had already filed to go public, and an officer of the company leaving in the first 18 months would raise major red flags. “Maybe this is what’s led me to be an entrepreneur,” David recalls. “I can never feel trapped … Someone telling me, ‘you can’t leave,’ I was like, boom. Switch went off in my head … and I was like, ‘I’m out.’” The filing was ultimately delayed and David was able to quit just before the IPO; one day later, he started his next company, Drift.

In this episode, David and Joubin discuss the accountability of doing something, creating constraints, the Whitney Museum, imposter syndrome, Tony Hawk, John Romero, wandering without a map, conservative spending, Brian Halligan and Dharmesh Shah, Phil Jackson, the voices in your head, Shlomo Kramer, righteous independence, cancel culture and diversity, gut vs. data, and killing ideas with discipline.

In this episode, we cover:

• Action and distractions (00:50)
• Observer and outsider (05:36)
• Advising entrepreneurs (11:18)
• “It has to be bigger” (13:23)
• David’s new company, Rey (16:38)
• Remote vs. in-person work (21:24)
• Who David will hire first (25:39)
• Fundraising and bootstrapping (27:39)
• The timeline for Rey (31:48)
• Rebuilding Hubspot’s code base (33:36)
• Leaving HubSpot at the IPO (42:54)
• “You’re not done” (48:19)
• HubSpot’s infamous exec meetings (54:44)
• David’s hardest year and selling Drift (59:26)
• The upmarket mistake (01:03:13)
• Saying no to good ideas (01:08:12)
• What “grit” means to David (01:11:52)

Links:

• Connect with David
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: John Doerr, chairman of Kleiner Perkins

After Kleiner Perkins chairman John Doerr first invested in Google — $12.8 million for 13 percent of the company — he told co-founders Larry Page and Sergey Brin that they needed to hire a CEO to help them build the business. After they took meetings with a variety of successful tech execs, they came back to Doerr and told him “We’ve got some good news and some bad news.” The good news was that they agreed on the need for a CEO; the bad news, Doerr recalls, is that they believed there was only one person qualified for the role: The then-CEO of Pixar and interim CEO of Apple, Steve Jobs. 

In this encore presentation of the 100th episode of Grit, John and Joubin discuss the urgent need to act on the climate crisis, getting turned down by Kleiner Perkins, CEOs as sales leaders, the microprocessor revolution, balancing between work and family, the opportunity of AI and sustainability, what makes Jeff Bezos special, Bing Gordon and the invention of Amazon Prime, the Google CEO search, how the iPhone nearly killed Apple, Steve Jobs’ greatest gift, Bill Gates’ philanthropy, and how Doerr divides his time.

In this episode, we cover:

• John’s two books — Measure What Matters and Speed & Scale — and applying OKRs to the climate crisis (02:39)
• How John got to Silicon Valley and what he learned from his entrepreneurial father, Lou (08:55)
• “I didn’t want to be in venture capital” (16:27)
• Joining Kleiner Perkins at the dawn of personal computing (20:03)
• The internet, cloud computing, smartphones, and the next big tech wave: AI (24:41)
• How John met Amazon founder Jeff Bezos (29:46)
• Google co-founders Larry Page and Sergey Brin, and teaming up with Mike Moritz from Sequoia (38:26)
• John’s friendship with Steve Jobs and the creation of the $100 million iFund for iPhone apps (45:12)
• “Family first” and setting personal OKRs (50:10)
• Working with Bill Gates outside of Kleiner Perkins (52:51)
• Brian Roberts, Comcast, and hustling to make at-home broadband nationwide (59:28)

Links:

• Connect with John
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Shlomo Kramer, founder and CEO of Cato Networks

Shlomo Kramer has founded three companies to date — Check Point, Imperva, and most recently Cato Networks — and taken the first two public, with plans to do the same with Cato. By any measure, he is a successful entrepreneur, but he defines “success” as “a burden you need to shake off every day.” And the easiest way to do that he’s found is to keep moving, keep failing, and keep creating. The material wealth he’s created, he explains, was never the goal: “It was never about things. It was about ideas and making them real.”

In this episode, Shlomo and Joubin discuss the contexts of our actions, the IDF, taking three companies public, ideas vs. things, kibbutzes, Gong, Sumo Logic, serial entrepreneurs, leading by example, consumer cybersecurity, trusting others, Albert Einstein, “making it to the pass before winter,” and Israeli directness.

In this episode, we cover:

• The delta between micro and macro (00:54)
• Working in wartime Israel (03:18)
• The burden of persona (06:37)
• Shlomo’s family (13:19)
• The time between startups (16:30)
• Self-fulfillment (18:31)
• “What am I going to do next?” (21:14)
• Rebelliousness (24:58)
• Palo Alto Networks (29:42)
• Loyalty and competition (31:32)
• Building trust relationships (35:02)
• “The last one” (37:41)
• Shaq, Tom Brady, and Carl Eschenbach (42:15)
• Tough feedback (46:50)
• Shlomo’s friends (48:18)
• Intellectual honesty (50:14)
• What Cato does (52:37)
• Hiring and work culture (55:23)
• Ignoring startup advice (58:15)
• Ideation and being present (59:22)

Links:

• Connect with Shlomo
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Arvind Jain, Founder and CEO of Glean, and Mamoon Hamid, partner at Kleiner Perkins

“I’m an engineer, so I have doubts about everything,” says Glean founder and CEO Arvind Jain. Well ... almost everything. Since launching Glean in 2019, he has held to the belief that “all of us are going to have really powerful AI assistants” in the future. With a several-year lead on generative AI tools like ChatGPT, Glean has built a growing club of CIO fans. With the broad acceptance of AI over the past year, Arvind says, “the level of confidence is higher than ever before.”

In this episode, Arvind, Mamoon, and Joubin discuss golfer hats, ideas vs. execution, X1, energy audits, small towns in India, IIT, proving yourself, Rubrik, rejecting product-led growth, “workplace assistants,” CIO fans, internet ’94, Parker Conrad, and work as a hobby.

In this episode, we cover:

• Arvind’s newfound fame (01:08)
• The state of the AI business (03:42)
• “Why now?” (06:05)
• Building great products (09:16)
• Company-building (11:27)
• Arvind’s childhood (14:37)
• Competition and hard work (16:44)
• Leaving Google (18:46)
• Glean vs. Rubrik (20:53)
• The future of work (27:22)
• “Holy shit” moments (29:25)
• Finding positivity (32:51)
• AI hype (34:31)
• How to pick a venture capitalist (38:55)
• Turning off (42:24)
• Hiring and the meaning of “grit” (44:41)

Links:

• Connect with Arvind
  • LinkedIn
• Connect with Mamoon
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Scott Cutler, CEO of StockX

What’s the point of climbing a mountain, or heli-skiing in the Swiss Alps, or biking in the Tour de France? StockX CEO Scott Cutler has done all three, and for him, the answer is momentary perspective. “When you’re descending, you don’t see, but you know what is above,” he says. “You have experienced and have seen what you saw at the peak and you take that with you into the next experience.” He stressed that the pleasure of being at the top is a fleeting incentive to do it again, not the destination; in life, and in our careers, he argues, the journey is about continually facing new challenges and getting brief glimpses from the top.

In this episode, Scott and Joubin discuss out-of-touch VCs, the challenges of marketplaces, Josh Luber, Dan Gilbert, almost missing flights, gaining perspective, scary blackberry bushes, work-family balance, daily workouts, sleeping on planes, e-commerce in the U.S. vs. China, and digital ownership.

In this episode, we cover:

• Special shoes (01:07)
• Scott’s past jobs at the NYSE, StubHub, and eBay (05:47)
• Detroit and frequent flying (10:02)
• Over-optimizing your time (15:25)
• Why do you climb a mountain? (18:00)
• Scott’s childhood and his own kids (22:39)
• Routines and energy (30:15)
• StockX and the future of e-commerce (36:52)
• Going public (43:24)
• SPACs and NFTs (46:21)
• What’s next? (50:11)
• Persistence (52:06)
• Who StockX is hiring (54:34)

Links:

• Connect with Scott
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Brian Long, former CEO of Attentive and author of Problem Hunting: The Tech Startup Textbook

Brian Long’s most recent company, Attentive, was originally designed to help clients communicate with their distributed workforce — but about six months in, he and his co-founder realized that that business would not grow as quickly as they had hoped. So, they decided to pivot to SMS marketing, at the cost of a few dubious employees and a well-known Fortune 500 client. The successful pivot confirmed Brian’s belief that it’s possible to over-commit to one solution, when in fact there may be bigger and better problems to solve. “I’ve just seen so many entrepreneurs spend years of their life building something being stuck with it,” he says, “and then trying to figure out how to fit it into something that doesn’t work.” 

In this episode, Brian and Joubin discuss zero to one building, the problem with how entrepreneurs solve problems, How to Win Friends and Influence People, Matt Mochary, Tom Mendoza, transactional relationships, the dangers of ego, optimists and realists, best man speeches, defining a unique culture, reverse selling, Lunar Holdings, Peter Reinhardt, marketing conservatively, and business book sales.

In this episode, we cover:

• New York vs LA (00:54)
• How Brian feels, six months after stepping away from the CEO role (02:37)
• Product-market fit and TAM modeling (06:07)
  Build last (09:05)
• The qualities of great entrepreneurs (13:24)
• Tap Commerce and starting in sales (15:49)
• Listening and remembering names (20:40)
• The day after selling Tap Commerce (23:32)
• Starting another company, Attentive (25:07)
• Resilience and optimism (29:21)
• Fear, doubt, and the worst-case outcome (32:50)
• What Brian would tell his 29 year old self (37:13)
• Hiring and pivoting at Attentive (41:17)
• Text message marketing (45:49)
• How Brian interviews people (50:12)
• His new holding company, Lunar and its first startup (51:52)
• Don’t go social (55:21)
• What Brian is personally excited about and what “grit” means to him (01:01:57)

Links:

• Connect with Brian
  • LinkedIn
  • Buy Brian’s book, Problem Hunting: The Tech Startup Textbook
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Spencer Rascoff, co-founder and former CEO of Zillow + co-founder and general partner at 75 & Sunny 

When terrorists attacked the US on 9/11, Hotwire co-founder Spencer Rascoff and his colleagues had to put their own trauma aside and “spring into action” — the travel site had sold tens of millions of dollars’ worth of non-refundable flights and hotel rooms and customers who wouldn’t be traveling wanted their money back. Now a visiting professor at Harvard Business School, Spencer teaches this case to his students because this dilemma was not unique to 2001: “What the hell do you do when you’re running a company ... and all of a sudden, a pandemic happens? Or SVB shuts down?”

In this episode, Spencer and Joubin discuss Zestimates, context switching, Tom Brady, reinvention, Shaq, the live music business, beating pain, personal connection to tragedies, the structure of rounds, Juul, the qualities of success, Stewart Butterfield, Travis Kalanick, second homes, two-way doors, overstating risk, “Dad, I Have a Question,” management by walking around, and Carl Eschenbach.

In this episode, we cover:

• Spencer’s post-Zillow life (00:57)
• From player to coach (03:47)
• “The Forrest Gump of technology” (08:21)
• Joseph Rascoff and the Rolling Stones (10:56)
• Teaching grit to kids (14:43)
• Spencer’s brother (18:55)
• Channeling pain into achievement (21:35)
• Co-founding Hotwire (24:37)
• The impact of 9/11 (27:51)
• Re-capitalization and selling to Expedia (35:17)
• “Let’s build a real estate website” (38:05)
• Office Hours and founder-product fit (45:12)
• How Pacaso works (53:22)
• Career mirrors and leaving big companies (57:01)
• Staying organized (01:04:20)
• Dinner with the family (01:07:43)
• What “grit” means to him (01:09:14)

Links:

• Connect with Spencer
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Luis von Ahn, CEO and co-founder of Duolingo

When Luis von Ahn wanted to go to college in the United States, he had to take a standardized test called the TOEFL, or Test of English as a Foreign Language. But there was nowhere in his home country of Guatemala that could accommodate another test-taker, so he flew to war-torn El Salvador, just to take the TOEFL. Many years later, as the co-founder and CEO of Duolingo, Luis and his team “decided this type of thing, we could do a lot better.” Today, more than 4,500 universities accept the results of the online Duolingo English Test — a boon for the estimated 2 billion people currently learning English around the world.

In this episode, Luis and Joubin discuss returning to the office, Carnegie Mellon, identifying strivers, the “Luis dashboard,” ignoring Reddit, pre-meetings, the hardest part of learning, sounding dumb, private security, the job of a professor, digitizing books, 
working out every day, April Fools’ campaigns, Duo the owl, and hiring nice people.

In this episode, we cover:

• Working in Pittsburgh, in-person (00:57)
• How Duolingo hires (06:48)
• Growing up in Guatemala (10:29)
• Luis’ parents, intelligence, and drive (12:09)
• His morning routine (16:56)
• Ground truth (19:39)
• “The smaller the team, the better” (22:29)
• Language education and human behavior (24:32)
• Learning English (28:53)
• Back to Guatemala (32:03)
• CAPTCHA and reCAPTCHA (36:10)
• Money vs. impact (41:26)
• Luis’ TEDx Talk and public speaking tips (44:46)
• Love Language and nontraditional marketing (48:46)
• Doubling down on what works (53:27)
• Slow hiring (56:44)
• Would Luis ever start something new? (59:28)
• Who Duolingo is hiring and what “grit” means to Luis (01:01:46)

Links:

• Connect with Luis
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: René Lacerte, CEO of Bill

René Lacerte co-founded the online payroll firm PayCycle in 1999, and led it for six years until he was asked by the board to step down. Today, with 17 years as the CEO of Bill under his belt, he’s able to look back on that time with clearer eyes. “The title on my card is ‘CEO and Founder,’” he says. “At Paycycle, it was ‘Co-Founder and CEO.’” The order matters, because once you’ve become a founder or co-founder, you are one no matter what — and in hindsight, René believes he failed to keep up with how PayCycle was changing. “My job as a CEO, it changes every freaking day,” he says of Bill. “We’ve 10x’d in four years. My job today has far more responsibilities and requirements than it had four years ago. So how do you get ready for that?”

In this episode, René and Joubin discuss Silicon Valley OGs, the office environment, taking care of yourself, memorizing acronyms, Christmas presents, 11-finger jazz, intentionality and spontaneity, ordering your job titles, problem-solving at night, understanding insecurities, and measuring success.

In this episode, we cover:

• Why René did not want a corner office (02:22)
• The weight of being CEO (04:40)
• Dinner with the kids (08:50)
• Prioritizing, energy, and fitness (11:05)
• Music and René’s parents (17:31)
• His father and pride (23:13)
• Empathy for small businesses (28:00)
• Family values (32:46)
• “Legacy, I don’t care about that” (36:15)
• Stepping down from PayCycle (41:16) 
• Starting Bill (46:58)
• Leading in hyper-growth (50:10)
• The early years (53:07)
• Conventional wisdom (56:08)
• Who Bill is hiring and what “grit” means to René (01:01:02)

Links:

• Connect with René
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guests: Parker Conrad, CEO of Rippling, and Mamoon Hamid, partner at Kleiner Perkins

How long did it take for Parker Conrad to stop wanting revenge? “I’ll let you know when it switches over,” the Rippling CEO and co-founder jokes. He resigned from his last company, the buzzy HR unicorn Zenefits, in 2016 and then quickly realized that the company’s new leaders would never return it to its former glory. He still loved the problems he had been trying to solve, and launched Rippling because “there was an opportunity there, [and] if it works ... it’s going to be fundamentally and foundationally better as a product.” It worked. As of March, Rippling has been valued at more than $11 billion, more than double Zenefits’ peak.

In this episode, Parker, Mamoon, and Joubin discuss what happened at Zenefits, avoiding press coverage, FOMO and expectations, Paul Graham, fixing corporate insurance, Ryan Peterson’s “revenge portfolio,” CEO coaches, Mike Vernal, approving expenses, anecdata, and the Costco of SaaS. 

In this episode, we cover:

• How Parker and Mamoon met (00:56)
• The Zenefits Series B (06:29) 
• “Stuck in a nightmare” (09:20) 
• Entrepreneurship is “soul-destroying” (12:46) 
• Parker’s first company, SigFig (17:17) 
• Starting a company for the right reasons (21:02) 
• Starting over after Zenefits (27:06) 
• Avenging Zenefits (31:57) 
• Rippling’s unusual Series A (38:40) 
• What it does well (43:13) 
• “Go and see” (46:35) 
• The compound startup (51:44)
• Who Rippling is hiring and what “grit” means to Parker (01:00:39) 

Links:

• Connect with Parker
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Evan Goldberg, founder and EVP of Oracle Netsuite

In the late 1980s and early 1990s, Evan Goldberg working at Oracle, helping to bring its database software to the Mac. He left in 1995 because “I always wanted to do my own thing” and — with Larry Ellison’s support — launched his first startup, Embed. When it failed, he told Larry that he wanted another bite of the apple. “It’s the most exciting, it’s the most satisfying,” Evan said of startups. “It’s the highest risk, but ... even though I did just get married and we were going to have a kid, I still had this real appetite for risk.” The gamble paid off: In 2016, Oracle bought Netsuite for $9.3 billion, and he’s been back “home” ever since.

In this episode, Evan and Joubin discuss overestimating and underestimating, rose-colored glasses, collaborative partnerships, Marc Benioff, Larry Ellison’s superpowers, AI skepticism, Rise of the Resistance, energy vs. focus, supportive partners, Zach Nelson and Jim McGeever, and building the cloud.

In this episode, we cover:

• Eighteen years to $9.3 billion (00:47)
• Startups and failure (03:36)
• CEO vs. CTO vs. technical founder (06:38)
• Growing up and moving to California (10:08)
• Eight years at Oracle (12:30)
• Introversion (16:12)
• AI is the new internet (17:38)
• The incumbents’ advantage in AI (23:30)
• Inspiration to start something new (25:30)
• Leaving Oracle in 1995 & starting Embed (28:17)
• When to cut and run (32:16)
• Evan’s wife, Cindy (36:05)
• Starting NetSuite (40:18)
• Going public and the stock rollercoaster (43:46)
• OneWorld and fighter jets (47:17)
• Oracle’s acquisition of NetSuite (50:48)
• Co-founder and family cohesion (56:58)
• Do-overs (59:25)
• What would Evan do if not Netsuite? (01:02:29)
• Who Netsuite is hiring and what “grit” means to him (01:03:41)

Links:

• Connect with Evan
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Rahul Roy-Chowdhury, CEO of Grammarly

Driven by generative tools like ChatGPT, artificial intelligence is hot — but Grammarly CEO Rahul Roy-Chowdhury wishes that “AI” stood for something else: “Augmented Intelligence.” A longtime Googler and lifelong believer in using technology to make peoples’ lives better at scale, Roy-Chowdhury now leads a company well-positioned to do exactly that. “In the early days, Grammarly was all about the rules of language,” he says. “Now, with generative AI, we can actually help people across a much broader swath of communication tasks.”

In this episode, Rahul and Joubin discuss digital distraction, responsible AI, John Oliver, Ali Ghodsi, the hype cycle, fragmentation, being kind to yourself, Amp It Up, intentional strategy, candid dialogue, Google Chrome, and Dancing with the Butterfly.

In this episode, we cover:

• Growing up in India (01:05)
• Meaningful, impactful work (07:12)
• The potential of AI (13:09)
• Invisible AI (19:53)
• Would Grammarly go public? (23:51)
• What drives the business (28:19)
• Too many emails (31:05)
• Being an introvert CEO (35:11)
• How Rahul got the top job (37:36)
• Insecurity (39:48)
• Snowflake CEO Frank Slootman (41:57)
• Rahul’s decision-making framework (45:40)
• “I deprecated the thing I built” (54:12)
• The dino game (56:28)
• The book on Rahul’s desk (59:49)
• Who Grammarly is hiring and what “grit” means to Rahul (01:01:06)

Links:

• Connect with Rahul
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Jeff Shiner, CEO of 1Password

Far from the Silicon Valley bubble, in Waterloo, Ontario, they try to do things a bit differently, says 1Password CEO Jeff Shiner. “Our mantra has been, build a good product, support the heck out of your customers,” he says. Some businesses and VCs in the Valley, he argues, don’t draw enough of a distinction between customers and users, spending all their time chasing the latter. For many years, the whole team at 1Password — including the co-founders — would try to empty out the customer support queue every day. If the company hadn’t waited 14 years to raise outside funding, Jeff says, it would have been a lot harder to listen to them and build the best product.

In this episode, Jeff and Joubin discuss PowerPoint slides, LEGO sorting, early computers, artificial general intelligence, e-commerce, users vs. customers, loss of control, outsourcing, managers and team leads, OKRs, password schemes, Polish food, Ryan Reynolds, and live TV hits.

In this episode, we cover:

• Abnormal sleeping patterns (02:39) 
• “Playing farmer” (05:00)
• Running and competition (07:05)
• Fear of failure & the speed of technology (10:14)
• Jeff’s pre-1Password jobs (14:46)
• The Silicon Valley bubble (17:05)
• Raising $920 million (19:47)
• Hiring after the signals (23:44)
• Chief Eliminator of Obstacles (30:52)
• “We need to do less” (33:32)
• Could 1Password have grown differently? (38:22)
• 1Password vs. the competition (41:43)
• Customer Support Monday (43:57)
• Hiring by doubling (46:23)
• Thinking about exits (49:16)
• Imposter syndrome (54:29)
• “Do I have any real skills left?” (57:04)
• Speed and confidence (59:26)
• Who 1Password is hiring and what “grit” means to Jeff (01:03:02)

Links:

• Connect with Jeff
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Matt Steckman, CRO of Anduril Industries

Walk into one of Anduril Industries’ offices and it might take a minute for you to realize: This is a defense contractor. “It feels like a tech company, stylistically,” says CRO Matt Steckman, “because we know we have to recruit the best software talent in the world.” Matt says the executive team spends a “comical” amount of time on recruiting, one of his personal passions, and especially works to minimize the number of people who turn down offers. “That’s something that a lot of companies, both tech and non-tech, miss ... Are you losing candidates at the very end, where you spent a tremendous amount of time and resources getting to that decision?”

In this episode, Matt and Joubin discuss security clearance, Lockheed Martin and Boeing, politics vs. technology, Palantir, consensus building, border security, command and control technology, the qualities of great defense tech workers, and long-term thinking. 

In this episode, we cover:

• The importance of defense tech (02:37)
• What Anduril does (04:33)
• Barriers to entry (07:58)
• How the government picks winners (11:56)
• Matt’s path to the defense industry (17:04)
• Why he left Palantir (19:57)
• Low moments and self-awareness (22:17)
• What you can control (27:36)
• Joining Anduril (30:14)
• Surveillance towers (33:26)
• Dive Technologies (37:30)
• Risk mitigation (39:24)
• Kinetic warfare (42:43)
• Recruiting top talent (45:26)
• Performance against expectations (48:34)
• Caring and empathy (51:25)
• Hitting revenue goals (52:31)
• How Matt manages his calendar (54:38)
• The economics of defense (56:26)
• Who Anduril is hiring and what “grit” means to Matt (58:11)

Links:

• Connect with Matt
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Greg Brown, CEO of Udemy

Every night before he goes to bed, Greg Brown makes a to-do list. He has to because, as the CEO of the online learning platform Udemy, setting his priorities helps ensure that he makes the most of the scarce time on his calendar. “If I’m meeting with employees, what’s the message I want them to walk away with?” he asks. He also wants to make sure his team isn’t getting distracted by Udemy’s stock price. “Where it be sports, or life, or in business, you’ve got to be able to block out the noise,” Greg says. “Focus on what you can control and maniacally execute against those objectives.”

In this episode, Greg and Joubin discuss fitness routines, VO₂ max, multi-athletes, Webex, the dotcom bust, Gregg Coccari, streamlining, setting priorities, listening to analysts, and being intentional with family.

In this episode, we cover:

• Cold plunges and healthspan (00:42)
• Finding time for fitness (07:48)
• Greg’s father (10:04)
• From sports to business (15:55)
• Two-year investments in companies (18:15)
• Achievers and motivation data (22:57)
• Becoming CEO of Reflektive (26:07)
• Why Greg joined Udemy and what it does (28:40)
• The distraction of a stock price (34:54)
• Daily to-do lists (39:20)
• Back to growth (41:45)
• Go to market CEOs (48:25)
• Coachability (50:49)
• Applying AI to customer solutions (52:16)
• At-home office hours (56:09)
• Who Udemy is hiring and what “grit” means to Greg (58:12)

Links:

• Connect with Greg
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Chris Degnan, CRO of Snowflake

Chris Degnan was a teenager when his world got turned upside-down: His stockbroker father was revealed to be a serial liar & fraudster and was sent to prison; the wealth he thought his family had evaporated; and their house was foreclosed on by the IRS. The traumatic experience gave him both an “insane drive” and a slew of anxieties, which shaped the person he became as an adult ... and led him, eventually, to the C-Suite of Snowflake. “Those things have built character,” Chris says. “I’m super proud of the person I am… That’s what matters to me.” 

In this episode, Chris and Joubin discuss adjusting to tech fame, holding onto perspective, detecting lies, being the monster, paranoia,  talking about anxiety, fear of flying, living your values, Mike Scarpelli, trimming down meeting sizes, sales calls, being abrasive, Mike Speiser, succession plans, and Mark McLaughlin.

In this episode, we cover:

• Defining yourself by your job (01:04)
• The origin of Chris’ insecurities (06:25)
• Passion for the sport (11:11)
• Dinner-table conversation (15:41)
• “If I stop working, I’m going to die” (17:22)
• Changing history (20:34)
• Snowflake and its competitors (24:29)
• Bob Muglia and hiring big-company people (27:10)
• Snowflake CEO Frank Slootman (31:53)
• Getting the truth (37:42)
• Denise Persson (41:58)
• Therapy and support systems (48:37)
• Bringing your friends (51:52)

Links:

• Connect with Chris
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Jim Lanzone, CEO of Yahoo

Jim Lanzone doesn’t waste time thinking about what other people think of him ... or the companies he has run. After helping to rejuvenate Ask.com in the early 2000s, he has more recently served as CEO of Tinder, and now Yahoo. As an expert in brand turnarounds, he says, “don’t worry about what the world thinks ... worry about your growth versus yourself.” With a focus on people and product, Jim believes, “not only can you accomplish a lot, you’re going to make a lot of money at doing it.”

In this episode, Jim and Joubin discuss being bicoastal, downtown San Francisco, supportive partners, Garret Camp and StumbleUpon, “co-opetition,” Walt Mossberg, Redpoint Ventures, Dave Goldberg, Clicker, taking punches, Apollo Global Management, loyalty to the cause, high-EQ people, and user goals vs. company goals.

In this episode, we cover:

• Growing up in Silicon Valley (00:53)
• Long-lasting marriages (07:26)
• Jim’s first company, eTour (13:18)
• The Web 1.0 boom (17:33)
• Joining Ask.com & partnering with Google (20:40)
• Rejuvenating a brand (24:11)
• Back in the mud with Clicker (28:05)
• CBS All Access (34:02)
• 14 months at Tinder (37:25)
• What people get wrong about Jim (39:05)
• Becoming the CEO of Yahoo (42:45)
• How Jim hires great teams (49:54)
• Top priorities and Yahoo’s verticals (55:10)
• First principles & making decisions (01:02:26)
• Hiring & what “grit” means to Jim (01:05:02)

Links:

• Connect with Jim
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

In this special episode of Grit, Joubin looks back at what five past guests had to say about building a sales operation inside rapidly-growing companies:

• Intro (00:30)
• Stripe’s Mike Clayville on first principles & “tornado companies” (01:02)
• Former Paypal VP Marcy Campbell on establishing a successful sales motion (11:37)
• LinkedIn COO Dan Shapero on effective sales leadership during hypergrowth (20:16) 
• Herbold Consulting CEO Jim Herbold on “unicorn meat” (32:32)
• CRO Chris Degnan on the pivotal moments in Snowflake’s history (50:02)

Links:

• Connect with the guests
  • Mike’s LinkedIn
  • Marcy’s LinkedIn
  • Dan’s LinkedIn
  • Jim’s LinkedIn
  • Chris’ LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Yan-David Erlich, COO and CRO of Weights & Biases

After starting four companies, Yan-David Erlich had found happiness and success as a GP in Coatue’s venture fund — but then, after investing in the AI developer platform Weights & Biases, he realized the time was right to get back into operating. That was not a decision he made lightly, consulting with his wife before he became the startup’s COO. The challenges of entrepreneurship get easier, he explains, when you have a supportive partner in your corner. That’s why he believes he could roll with the loss of his home or his job or his money — but not her. 

In this episode, Yan-David and Joubin discuss Snowflake vs. Amazon, Slack vs. Microsoft Teams, Donald Trump, charting your own destiny, regret minimization, alternate selves, Michael Dearing, chips on your shoulder, Google Glass, industrial sales, the AI & ML window, hairball problems, fixing giant messes, and fighting a bear.

In this episode, we cover:

• The advantage of speed (01:06)
• Competing against a massive business (05:24)
• Idiocy and secrets (09:45)
• Yan-David’s past companies (12:34)
• His philosophy on life (17:17)
• Leaving LinkedIn (22:14)
• Anxiety and regret (26:27)
• The failure of Happiness Engines (34:43)
• Why Yan-David left Parsable after five years (38:05)
• Coatue’s venture fund (46:13)
• Weights & Biases and the ML moment (48:08)
• Why AI is still underhyped (51:05)
• From investor to board member to COO to CRO (55:20)
• Being a good lieutenant (58:51)
• The hidden costs of operating (01:01:33)
• Successful entrepreneurs and happy relationships (01:05:55)
• Who Weights & Biases is hiring & what “grit” means to Yan-David (01:10:26)

Links:

• Connect with Yan-David
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Nick Mehta, CEO of Gainsight

Gainsight CEO Nick Mehta describes himself as “the person who goes all in, on whatever.” So when he had a personally difficult year, he didn’t just go to therapy — he also talked to a professional coach, and read about religion, and experimented with (legal) ketamine therapy. All of that led to him “better understanding the inner self ... [and] helping to find ways to suppress the exterior.” In other words, even though Gainsight’s culture is suffused with Nick’s values, he is consciously trying to unpack a “new version of myself” that is greater than his company: “There’s a lot more to me than I realized,” he says.

In this episode, Nick and Joubin discuss Mike Moritz, golf clubs, Don Valentine, eclectic fashion, loneliness, Enneagram types, setting the tone, moments of vulnerability, Vista Equity Partners, talking to customers, Jack Dorsey, building others’ brands, startups as kids, Marc Benioff, and the ship of Theseus.

In this episode, we cover:

• The mystique of Sand Hill Road (00:58)
• Un-measurable marketing (05:07) 
• Launching Chipshot.com (09:17)
• I-banking culture and fitting in (13:14)
• Getting help after a rough year (19:48)
• Immigrant achievers and the meaning of work (21:32)
• Fueling success and belief in institutions (24:44)
• Winning while being human-first (30:19)
• Founder-defined values and culture (3 5:41)
• What happened to Chipshot? (40:46)
• Empathy for all entrepreneurs (44:11)
• Growing & selling LiveOffice (46:03)
• The new Nick (48:53)
• Selling Gainsight for $1.1 billion (51:56)
• Coda and time management (55:20)
• Ghost notes (59:01)
• When the spotlight goes away (01:02:17)
• Philosophy and science books (01:05:45)
• Deleting work apps every weekend (01:09:23)
• Who Gainsight is hiring and what “grit” means to Nick (01:10:26)

Links:

• Connect with Nick
  • Twitter
  • LinkedIn
  • Coda
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Manny Medina, CEO of Outreach

In its Seattle headquarters, the sales execution platform Outreach has at least one wall covered in AI diagrams and architectural flows. CEO Manny Medina says that’s because he believes “there’s no world in which reps don’t have an assistant the way that coders do.” The AI revolution has also given Manny — who got his M.A. in computer science at Penn — a chance to be more hands-on than your average CEO of a $4 billion company. “I try not to think myself as a CEO,” he says. “I try to think myself as a team member that is doing something useful.”

In this episode, Manny and Joubin discuss northern New Jersey, American opportunity, going to the future, crossing the chasm, jujitsu, Tony Robbins, winning on your own terms, shifting motivations, inspiration through transparency, Moonwalking with Einstein, Lululemon, hands-on CEOs, and “been there, done that.”

In this episode, we cover:

• Leaving Ecuador for the US (02:21)
• Would Manny do it all again? (07:45)
• Finding product-market fit (10:09) 
• Scaling, scarcity, and stability (14:41)
• AI-assisted sales reps (18:59)
• Winner takes most (24:20)
• Placing long-term bets (26:42)
• Imposter syndrome and chips on your shoulder (32:59)
• “Ten million or die” (35:15)
• Irrational forces (42:33)
• Manny’s weekly internal emails (44:17)
• Memorizing names and making sacrifices (48:00)
• Personal and professional goals (52:23)
• “All the other jobs were taken” (56:53)
• Do-overs (01:00:18)
• Bad and good startup advice (01:03:24)
• Who Outreach is hiring and what “grit” means to Manny (01:05:58)

Links:

• Connect with Manny
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Aaron Levie, CEO of Box, and Mamoon Hamid, partner at Kleiner Perkins

When he was a newly minted venture capitalist at USVP, Mamoon Hamid got a tip that he should meet a young entrepreneur named Aaron Levie, and fought for the right to invest in his cloud storage startup, Box. For years after that initial investment, the two men say, Box’s fate was precarious: “We could have died any day,” Mamoon says, and Aaron recalled several times he had to be talked “down from a ledge.” Today, they tell us how Box established itself as “open for business” — a concept Mamoon hounded Aaron with in the early years — and grew into success.

In this episode, Aaron, Mamoon, and Joubin discuss Box socks, authenticity at work, Josh Stein, living in the office, over-diligence, Google Platypus, the 2008 crash, nostalgia, everything is personal, the ten-person test, burnout, Dan Levin, ChatGPT, Parker Conrad, and Silicon Valley as “technology town.” 

In this episode, we cover:

• “Make mom proud, unless she’s evil” (01:59)
• How Mamoon and Aaron met (04:38)
• Mamoon’s first investment in Box (11:15) 
• Pausing the term sheet (16:08)
• “We could have died any day” (19:01)
• What is company-building? (23:23)
• Open For Business (25:27)
• Getting to cash flow positive (27:52) 
• Slow growth with no burn vs. fast growth, high burn (31:15)
• Tough feedback (34:31)
• Overcoming challenges around the Box IPO (36:31) 
• Growing as CEO (38:35) 
• The Apple Vision Pro and AI (44:15)
• Investing in cutting-edge companies (49:15)
• Using AI to re-juice growth (51:48)
• How Aaron educates himself (54:22)
• Business as a sport (57:14)
• Who Box is hiring and what “grit” means to Aaron (01:00:44)

Links:

• Connect with Aaron
  • Twitter
  • LinkedIn
• Connect with Mamoon
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Carl Eschenbach, co-CEO of Workday

When Carl Eschenbach decided to leave VMWare after more than 14 years as COO, no one believed it: Not chairman Joe Tucci, not CEO Pat Gelsinger, and maybe not Carl himself. But he needed a more predictable work-life balance to help raise his teenage children. For the next seven years, he served as a partner at Sequoia Capital. And every day, he thought — and to his wife’s chagrin, talked — about going back: “It was always on the back of my mind,” he says. After the kids were out of the house, in late 2022, he jumped back into operating and became co-CEO of Workday. “It’s what I love to do,” he says. “I feel like I’ve been called to do it.”

In this episode, Carl and Joubin discuss jumping rope, Mike Clayville, the Flowbee, focusing on the family, wrestling, commuting cross-country, servant leadership, Sequoia Capital, Aneel Bhusri, co-CEOs, and Palo Alto Networks.

In this episode, we cover:

• Working on Sand Hill Road (00:55)
• Carl’s workout routine (03:15)
• Staying humble and grounded (08:04)
• Carl’s family and dinner table conversation (11:41)
• Drive and ambition (16:08)
• College vs. trade school (19:53)
• 3Com, Inktomi, and EMC (24:33)
• Deciding to join VMware (28:02)
• Virtualizing the data center (31:48)
• The pressure of an incredible ride (35:54)
• The infamous CFO story (40:14)
• Eyeing the CEO job (46:00)
• Carl’s one “big regret” (47:40)
• Refocusing after a tragedy (52:05)
• A left turn into venture (55:37)
• The “itch” to go back to operating (01:00:17)
• Joining the Workday board (01:04:37)
• Building an enduring business (01:07:15)
• “End[ing] my career in an operating role” (01:09:09)
• Transitioning out of venture (01:15:56)
• Who Workday is hiring and what “grit” means to Carl (01:18:01)

Links:

• Connect with Carl
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Bob Muglia, “The Datapreneurs” Co-Author and Former Snowflake CEO

Longtime Microsoft executive and former Snowflake CEO Bob Muglia was done with his book about using data to drive the digital economy — and then ChatGPT came out. “The timeline for artificial intelligence moved in by 50 years in my head,” he recalls. Bob then told his co-author Steve Hamm that they needed to update “The Datapreneurs” to focus more on AI. “For the first time, we have intelligence in a computer,” he says. “English has become the primary programming interface of 2023!”

In this episode, Bob and Joubin discuss weekly meetings, Amazon’s values, the tech industry’s Yoda, antitrust lawsuits, the media and Bill Gates, tangling with Andy Jassy, gold rush times, FoundationDB, executive coaches, firing people faster, leaders vs. managers, deepfakes, and the zeroth law of robotics.

In this episode, we cover:

• Bob’s post-Snowflake career (00:57) 
• How he advises startup CEOs (04:12) 
• Getting fired by Steve Ballmer, twice (09:36) 
• Why didn’t he quit? (14:09)
• Satya Nadella (16:09)
• Immigrant families and early jobs (17:21)
• United States v. Microsoft Corp. (21:14)
• “It may be shit, but it’s compliant shit” (25:26) 
• Antitrust is not about the law (29:18) 
• Rose-colored memories (33:01)
• Competing with Microsoft and Amazon (34:41)
• Two years at Juniper (37:45)
• Transitioning into Snowflake (39:38)
• Earning credibility (42:32)
• Chris Degnan, Snowflake’s first sales rep (45:07)
• Near-death experiences (50:05)
• Finding traction & taking off (55:33)
• Surprising challenges (01:00:55)
• Fired, again (01:02:16)
• Tough feedback (01:07:01)
• “The Datapreneurs” and the AI acceleration (01:09:19)
• Optimism about the future (01:13:36)
• The Terminator and Isaac Asimov (01:17:48)

Links:

• Connect with Bob
  • Twitter
  • LinkedIn
  • Buy “The Datapreneurs”
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Noam Bardin, founder of Post News

One of the “aha” moments that could sway a dubious Waze user, recalls former CEO Noam Bardin, was navigating around “all those idiots sitting in traffic... and you’re like, ‘I’m a genius.’” Now, at the social news app Post, Noam says the “aha” is avoiding partisan gridlock and paywalls. Social incumbents boost engagement by making users angry, while Post just wants you to read. “If we can remove friction and give you the right articles at the right time, so you feel smarter when you walk away,” he says, “that’s the aha moment.”

In this episode, Noam and Joubin discuss stories vs. execution, ROFRs, culture clash, timing an acquisition, corporate tags, fear of going bigger, joining big companies, mobile app retention, big tech monopolies, competing against Foursquare, and not optimizing for “culture warriors.”

In this episode, we cover:

• Putting your opinions out there (01:15)
• Waze almost sold to Facebook (06:10)
• Getting in the room with Google (13:04)
• How the first Google deal fell apart (15:10)
• Back to Facebook — briefly (17:15)
• The news begins to leak, and Google returns (20:26)
• Grinding for five years at a startup (23:57)
• “Hockey sticks” are never smooth (28:32)
• The personal impact of volatility (31:37)
• “Everything is a mess in startups” (34:38)
• The worst day of Noam’s life (38:22)
• How Waze started, and how Noam joined (42:22)
• The failure of Intercast Networks (45:07)
• Brave faces and “corp-speak” (48:33)
• Integrating into Google’s culture (53:13)
• No constraints and too much money (01:01:08)
• Defining metrics that matter (01:04:11)
• Maps and social (01:06:46)
• Silicon Valley’s worst invention: “Pivoting” (01:09:56)
• The social news problem Post solves (01:14:51)
• Misinformation and authoritarianism (01:18:42)
• Post’s microtransactions (01:21:08)
• Being misunderstood and the “aha” moment (01:23:58)
• Who Post is hiring and what “grit” means to Noam (01:27:09)

Links:

• Connect with Noam
  • Twitter
  • Post
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Bipul Sinha, co-founder and CEO of Rubrik

When Bipul Sinha graduated from the Indian Insitute of Technology and came to America to work in tech, his mother told him: Don’t start a company. His ambitious father was a failed pharma entrepreneur, and Bipul was content for most of a decade to hold a steady job at Oracle. But in his early 30s, he began to shed his risk aversion, pursuing a part-time MBA and more difficult jobs, and by the time he co-founded the data security firm Rubrik in 2014, he had gone through an epiphany: “Only make decisions that you truly believe is the right thing to do,” he says. “If you are here, at the moment of truth, you want to succeed or lose based on your own terms, not what others feel.”

In this episode, Bipul and Joubin discuss how debate moves business forward, companies as living systems, growing up poor, refusing to compromise, risk aversion, finding your own potential, paying tuition, context matters, psychological safety, and smelling the roses.

In this episode, we cover:

• Joubin’s interview with Ali Ghodsi (00:51)
• The importance of authenticity (02:33)
• Extreme voices (05:10)
• Being yourself at work (08:14)
• Reducing blind spots (11:08)
• Tough feedback (13:09)
• Learning entrepreneurship through osmosis (14:41)
• IIT or bust (19:40)
• Setbacks and reorienting (23:35)
• Leaving India for America (26:53)
• From Oracle to Blumberg Capital (30:21)
• Prioritizing his own happiness (34:36)
• “This is a career” (37:08)
• Dissatisfaction and the next thing (40:37)
• Creating an enduring institution (45:02)
• No one knows what they’re doing (49:32)
• Open board meetings (53:39)
• Hiring and firing (55:37)
• Good and bad startup advice (57:58)
• Working forever (01:01:16)
• Positive feedback and empathy (01:04:19)
• Who Rubrik is hiring and what “grit” means to Bipul (01:08:55)

Links:

• Connect with Bipul
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Ted Purcell, CRO of Tealium

The biggest difference between small companies and big companies, says Tealium CRO Ted Purcell, is that at untested early-stage firms, you have to convince workers “to truly believe in what they believe... It’s not just ‘do this’ or ‘do that.’” To unlock high performers, Ted explains, you need to give them a “religious level” of belief in the company and the value it delivers to customers, which will carry over into every aspect of their jobs. And this is even more important in a market downturn: “That becomes the main job because the winning is not as evenly spread,” he says. 

In this episode, Ted and Joubin discuss empty-nesters, resisting leadership, liking to win vs. hating to lose, complete commitment, commitment to culture, hardcore accountability, Israeli conversations, Day-Timers, and endurance battles.

In this episode, we cover:

• Growing up and raising kids in Silicon Valley (00:56)
• From individual contributor to management (05:03)
• The appreciation for the grind (08:45)
• Ted’s father and his sudden passing (10:33)
• Stepping up to take care of the family (14:40)
• The Purcell family dinner table conversation (18:22)
• Working with Bill McDermott at SAP (20:50)
• Ted’s favorite Bill story (26:00)
• Getting comfortable as a leader (28:35)
• (Over-) Optimizing for lifestyle (34:02)
• How to spot greatness in interviews (37:25)
• A startup guy at big companies (39:48)
• Clarizen and corporate culture in Israel (42:10)
• Tealium and the “pressure cooker” environment (47:36)
• Believing in the “why” (51:13)
• Tough feedback and misconceptions (53:47)
• Recording ideas and daily habits (55:33)
• Pushing to achieve your potential (57:38)
• Gaining perspective (01:02:05)
• Who Tealium is hiring and what “grit” means to Ted (01:05:55)

Links:

• Connect with Ted
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Jay Parikh, CEO of Lacework

Jay Parikh describes himself as a “stickler” for meetings that start and end on time, and holds himself to the same expectations as his workers. “It’s just really important as a leader to set the standard for how everybody else should be respected,” the Lacework CEO says. “Too often in our industry, executives think that they can show up late, hold a meeting late, and everybody will adjust.” No one will complain, he says, to the person on top of the org chart when they are 10 minutes late, but they should: “I’m like, no, I disrespected 10 minutes of your time. So I take that really seriously.”

In this episode, Jay and Joubin discuss non-traditional CEOs, surviving Facebook’s early days, disrupting yourself, Akamai co-founder Danny Lewin, cultivating culture, applying restless energy, the loneliness of leaders, brushing your teeth, the love of the game, and being approachable.

In this episode, we cover:

• The “S-curve of learning” (01:04)
• Finding new challenges (05:10)
• “Is this too big of a job?” (07:33)
• Intensity and zen (11:00)
• Jay’s first jobs (15:07)
• Akamai’s post-IPO pop and crash (16:31)
• 9/11 and Danny Lewin’s legacy (19:56)
• Facebook’s pivot to mobile (24:58)
• Managing morale when the share price drops (27:16)
• Learning from Mark Zuckerberg (30:13)
• Being on time (34:44)
• Security in the cloud (37:58)
• Leaving Facebook (40:01)
• What has surprised Jay about becoming a CEO (45:00)
• Hiring, onboarding, and unlocking people (49:34)
• Jay’s favorite interview questions (54:34)
• Refusing to compromise on greatness (01:00:44)
• Balancing work and family (01:07:02)
• Who Lacework is hiring and what “grit” means to Jay (01:09:06)

Links:

• Connect with Jay
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Dave McJannet, CEO of HashiCorp

To scale a company effectively, says HashiCorp CEO Dave McJannet, you will have to make something like 10 decisions every single day. “There’s generally one that really needs to be right, but there are eight that if you get them wrong, you will cause real damage to yourself,” he says. “It won’t be fatal, and a lot of times, it’s cultural damage.” Sometimes, he adds, these decisions can seem innocuous, like deciding how to run internal town halls with workers. But even small choices can create a “cultural crater” that you’ll have to dig yourself out of three months later.

In this episode, Dave and Joubin discuss returning to the office, the sales data flow, unstructured problem-solving, why companies grow like trees, anonymous town halls entrepreneurs-in-residence, go to market vs. product, committing to the job, the executive “CPU tax,” and the 30-to-100 phase shift. 

In this episode, we cover:

• In-person vs. remote collaboration (00:43)
• How to build any kind of business (05:26)
• The value of being in the sales motion (07:30)
• Thinking like a venture capitalist (11:51)
• Commiserating with other CEOs (13:28)
• Systems-based thinking (17:37)
• Administrators vs. builders (20:25)
• The daily 10 decisions (22:29)
• Staving off decision fatigue (24:17)
• Dave’s past jobs and the path to CEO (26:01)
• The reluctant CEO (28:46)
• Rapid change vs. high-profile maintenance (32:20)
• The pressure of being at the top (35:12)
• The state of HashiCorp when Dave arrived (37:39)
• How he got the CEO job (40:38)
• Product-building POV (45:50)
• The first “oh shit” moment (48:48)
• Being motivated by competition (50:47)
• Laddered time horizons (53:47)
• Paul Moritz and empathy (55:17)
• Misconceptions about CEOs (57:10)
• Deciding to go public (59:45)
• Time and energy management (01:03:10)
• Anticipating phase shifts (01:06:12)
• Fierce independence (01:08:12)
• Getting the right feedback (01:09:13)
• Who HashiCorp is hiring and what “grit” means to Dave (01:12:30)

Links:

• Connect with Dave
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Robert Chatwani, President and General Manager of Growth at DocuSign

Robert Chatwani’s first reinvention was in his early 20s, when he left McKinsey & Company to start a people-powered commerce startup called MonkeyBin. And in the ensuing decades, his entrepreneurial energy hasn’t slowed down, with hops to eBay, Spring, Atlassian, and now DocuSign, where he is the President and General Manager of Growth. He cites a “healthy anxiety” that comes from getting too comfortable in any role, where he finds himself solving the same problems over and over again; but when you’re in a little bit over your head, Robert explains, “that’s a good place to be, because that’s where the best learning comes from.”

In this episode, Robert and Joubin discuss trusting your intuition, reinventing yourself, personal boards of advisors, people-powered commerce, betting on people, career coaching, taking time for family, being the same person in every room, bone marrow donors, energy takers vs. creators, and leading with empathy.

In this episode, we cover:

• Networking through venture capitalists (02:18)
• Leaving high-profile jobs (04:29)
• How to know when it’s time to leave (07:55)
• 12 years at eBay (11:05)
• The seeds of doubt (15:10)
• Finding purpose in company-building (17:51)
• Robert’s personal mission statement (21:01)
• Growing up in Chicago and his parents (24:40)
• Losing a parent (27:16)
• True North by Bill George (29:35)
• Finding ways to be human (32:45)
• What accomplishment Robert is most proud of (34:35)
• MonkeyBin and meeting eBay (36:08)
• Sameer Bhatia’s battle with leukemia (38:30)
• Building a global bone marrow campaign (42:38)
• “You can’t control every outcome” (48:07)
• Unexpected side effects (52:56)
• Business is a force for good (56:26)
• Working at Spring, and then Atlassian (01:00:01)
• Self-doubt and leaving Atlassian (01:06:29)
• Making tough calls with IQ & EQ (01:10:24)
• Who DocuSign is hiring, and what “grit” means to Robert (01:13:48)

Links:

• Connect with Robert
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Ariel Cohen, CEO and co-founder of Navan

As a business travel-focused startup, Navan (previously known as TripActions) was heavily impacted by the coronavirus pandemic in 2020; after laying off 24% of the staff, CEO Ariel Cohen says he became a “wartime CEO,” spending three months in “complete denial and just executing.” By June, employees were leaving and he was depressed — but he still believed that business travel would come back. “You cannot just look at a moment and say that it will change everything,” he says. “... I disconnected from the news and from some of our investors and from ... negativity and started to lead the company again.” In a way, he explains, it was like a reset to the earliest days of the business, because the only people left were long-term believers like him.

In this episode, Ariel and Joubin discuss “tier one” VCs, developing goodwill, company money vs. employee money, wartime CEOs, putting handcuffs on founders, staying dynamic, returning to the office, scuba diving, shared values, Macallan whisky, believing in startups, losing employees, in-person connections, secondary liquidity, and “deposits and withdrawals.”

In this episode, we cover:

• Picking the right investors (01:22)
• Connecting to the Matrix (04:04)
• Obsessing over failure (10:29)
• Reflecting on an eight-year journey (14:56)
• The benefits of naïveté (17:50)
• Ariel’s entrepreneur father and early jobs (20:45)
• Older startup founders (23:03)
• Getting out of large companies (25:35)
• Personal burn rate (28:03)
• Becoming the big company (30:11)
• Pivoting into AI (32:44)
• Project Reset and personally resetting (34:12)
• Making controversial decisions (39:55)
• “What could I have done better?” (45:43)
• Ariel’s co-founder Ilan Twig (47:04)
• What makes a co-founder relationship work? (48:50)
• Running out of cash (51:18)
• Being a travel startup during COVID (55:53)
• The depression quarter (01:00:12)
• Long-term believers (01:02:54)
• Why Navan would go public (01:07:55)
• Startup advice and hard-charging CEOs (01:11:27)
• What “grit” means to Ariel and who Navan is hiring (01:15:24)

Links:

• Connect with Ariel
  • LinkedIn
  • Email: [email protected]
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Seth Dallaire, CRO at Walmart

When Seth Dallaire was approached by Walmart about joining their team as CRO, he had one question: Are they serious? Seth knew that Walmart wanted him for his digital experience, having worked at Instacart and Amazon, but he also knew that building alternative revenue streams at a traditional retailer could be an uphill battle. “I knew I was gonna have to [fight the fight], it was just whether I’d have the air cover from up top to say, ‘This is strategic,’” Seth recalls. “And they obviously convinced me of that and we’re making really good progress.”

In this episode, Seth and Joubin discuss startup success, advertising attribution, “maintenance mode,” online grocery shopping, “the ultimate tailwind,” over-buying, digital vs. traditional retail, founder-led businesses, John Furner and Doug McMillon, sentiment vs. data, getting told “no,” the theory of constraints, and why you should visit Bentonville.

In this episode, we cover:

• Seth’s unique career path (00:59)
• Amazon’s elite team in 2000 (05:24)
• Growing up & dinner table conversations (08:25)
• Work-life balance (10:53)
• Ambition and achievement (12:08)
• Investing in yourself (16:04)
• Recommitting to a role (17:38)
• Leaving Amazon for Instacart (20:14)
• Grocery stores are underrated (23:56)
• Transitioning to a much smaller company (25:33)
• How COVID accelerated Instacart’s business (27:54)
• Advertising is a full-contact industry (32:03)
• Getting recruited by Walmart (34:06)
• Visiting Walmart stores with other execs (40:08)
• A leadership lesson from Doug McMillon (43:10)
• Product orientation (45:40)
• Compounding knowledge capital (47:57)
• Tough feedback (50:19)
• Leaving a team behind (54:34)
• Hand-written notes (56:04)
• The Goal and On the Shortness of Life (57:35)
• Relocating and refueling (01:00:40)
• Who Seth is hiring and what “grit” means to him (01:02:25)

Links:

• Connect with Seth
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Matt Mochary, CEO of Mochary Method

Matt Mochary was only 31 when he sold the company he co-founded, Totality, to Verizon, “and I made enough money that that was it,” he recalls. “I didn’t have to make more money anymore.” Instead, he decided to pursue projects that in one way or another would help other people, including a documentary about the slums of Rio de Janeiro and a program to train ex-convicts in the skills of legitimate work. Today, he coaches tech and finance leaders such as Brian Armstrong (CEO Coinbase), Bastian Lehmann (CEO Postmates), Sam Altman (CEO OpenAI), and Steve Huffman (CEO Reddit). All the money earned from that work, he says, bypasses his bank account and is funding the development of software that will teach tech workers the “Mochary Method.”

In this episode, Matt and Joubin discuss information asymmetry, GPT-4, focusing on fun, coaching software, saving people, the slums of Rio and the South Bronx, surfing vs. friends, the merits of crappy solutions, why companies fail, shadowing the CEO, feedback and resentment, pissing people off, the danger of “excellence,” and energy audits.

In this episode, we cover:

• Putting in effort, finding value (01:11)
• OpenAI CEO Sam Altman (05:43)
• Immediate responsiveness (09:48)
• “Mount Rushmore” referrals (11:54)
• When Matt’s coaching was free (15:08)
• His Hungarian grandfather and World War II (19:56)
• The hero complex (25:12)
• Stepping away from the game (31:30)
• Billionaires and inner peace (38:45)
• The phases of company-building (40:54)
• The problems Matt helps leaders solve (47:48)
• “It’s fun to be a founder!” (54:35)
• Craving feedback (56:48)
• The zones of excellence and genius (01:02:19)
• “Today, what went right?” (01:09:12)
• Growing too early (01:12:32)
• Who Matt is hiring and what “grit” means to him (01:15:00)

Links:

• Connect with Matt
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Shoaib Makani, CEO of Motive

“When we fail,” says Shoaib Makani, “it is because we have not understood the customer problem deeply and allowed them to guide us.” This wisdom is hard-won: Motive’s first product, an app for fleet management of trucks, idled for four years before becoming a runaway success story. Emboldened by this, the CEO tried to make an orthogonal push into all kinds of freight, “guns blazing,” only to realize six months in that he had way overestimated Motive’s competitive advantage. Retreating from freight was “painful,” Shoaib recalls, but helped the company extend its existing lead in trucking — and may have saved the whole business. 

In this episode — joined by special guest Ilya Fushman from Kleiner Perkins — Shoaib and Joubin discuss curiosity for the world, first impressions, reorienting yourself, electronic logging devices, directly connecting with customers, growing up as a CEO, waiting for the market, having a “low discount rate on the future,” the physical economy TAM, AI dash cams, and pricing in risk, and running out of runway.

In this episode, we cover:

• Shoaib’s Pakistani parents and doing extra homework (01:17)
• Explaining and experiencing startups (04:26)
• “High standards are infectious” (08:15)
• What Motive does (10:08)
• How Shoaib and Ilya met (10:54)
• The origins of Motive as “Keep Truckin’” (14:06)
• Working with friends (17:27)
• First-time founders (21:56)
• Deep empathy for users (24:01)
• Monetization and second-guessing (25:48)
• Sudden success and scale (29:12)
• Recruiting top talent (31:04)
• Shoaib and Ilya’s personal-professional relationship (32:07)
• “I knew the board I wanted” (34:32)
• Motive’s failed expansion into freight (36:21)
• Realizing and correcting the error (39:26)
• How to make smarter future bets (44:09)
• Second and third products (47:29)
• Back to the core mission (50:36)
• Autonomous driving vs. AI assistants (52:17)
• Thinking about competition (55:05)
• A tough conversation about runway (58:52)
• Sticking your neck out for your partner (01:04:09)
• Losing Ilya as a board member (01:06:23)
• Who Motive is hiring (01:08:32)
• What “grit” means to Shoaib (01:09:32)

Links:

• Connect with Shoaib
  • Twitter
  • LinkedIn
• Connect with Ilya
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Tom Hale, CEO of Oura

When he was growing up, Tom Hale’s family had pretty ordinary dinner-table conversations: What happened today, how was school, etc. But every day after dinner, Tom and his father would play backgammon, an experience that indirectly taught him a lot about business. Now the CEO of wearable health company Oura, he recalls that the game helped him understand risk-taking, strategy, pattern recognition, and more. Tom’s father also insisted they play for money: “If I could win 20 bucks, I could go down to the store and get something. But when I lost, I felt the sting of it. That’s the best teacher, because you’re learning the preciousness of the decisions you make.”

In this episode, Tom and Joubin discuss Tom’s radio voice, games of chance and skill, vacation rentals pre- and post-Airbnb, “irritant” service fees, health tracking, the psychology of rebranding, the consumerization of healthcare, personalized medicine, the myth of the founder-hero, rowing machines, and the meaning of work.

In this episode, we cover:

• Returning to the office (00:50)
• John Doerr and Macromedia (05:15)
• Post-dinner backgammon (08:01)
• Tom’s past jobs and HomeAway (11:31)
• Competing against private startups (16:09)
• How Airbnb captured demand (18:55)
• Being acquired by Expedia (24:26)
• What Oura’s smart rings do (26:13)
• Rebranding SurveyMonkey to Momentive (29:55)
• Leaving Momentive for Oura (31:54)
• Making the case for himself (34:59)
• The future of public health, data, and wearables (37:10)
• “Sleep is strategic” (42:32)
• Why Oura is an AI company (44:48)
• The health impact of a taxing job (47:16)
• Being a non-founder CEO (49:39)
• Working with people (53:38)
• What would be in a “working with Tom” doc? (54:52)
• Managing the psychology of a 10-year-old startup (56:48)
• Being there for family & colleagues (59:18)
• Who Oura is hiring, and what “grit” means to Tom (01:02:54)

Links:

• Connect with Tom
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Rachel Pike, COO at Modern Treasury

Payment operations startup Modern Treasury is not afraid to do things in “our own weird way,” says COO Rachel Pike. Its values statement is a 150 word essay, it has gone viral by writing about nerdy ACH payments minutiae, and it has an unusual rule for quarterly internal reviews: No slides. Instead, departments have to write one to two page essay, which are packaged together and then shared company-wide, and with the board. In previous jobs, Rachel laments, she and her coworkers would waste time “pushing pixels” around 50-slide decks. “It [the essay] actually takes more thinking and less hours to put together a summary of, ‘where have we been?’” she says.

In this episode, Rachel and Joubin discuss the state of San Francisco, the value of tradition, hunger to learn, the Draper Fisher Jurvetson split, the opportunity cost of staying put, HIPAA and startups, two-entrepreneur households, career transition coaching, “try before you buy” hiring, learning to be remote, the downside of grasping, and fixing inequalities in compensation.

In this episode, we cover:

• Why Rachel doesn’t like talking about herself (01:20)
• Job-hopping and the Bay Area (02:38)
• Early adopters vs. brilliant innovators (05:16)
• Why Rachel left academia (07:44)
• “I got a phD in startups” (10:24)
• The “nights and weekends” gig at AngelList (14:05)
• Describing startups to aliens (16:50)
• Four years at Grand Rounds (18:28)
• What makes Modern Treasury “modern” (21:51)
• How she got hired as employee #1 (24:16)
• Advice for wannabe early-stage startup workers (30:18)
• “Wonder is contagious” (32:00)
• “Do it right the first time” (35:09)
• Hacker News and other growth levers (38:20)
• The excitement of scaling (40:49)
• Advisors and quarterly planning essays (44:02)
• Forced prioritization (49:20)
• Hard feedback (51:50)
• The working with Rachel doc (54:19)
• How Modern Treasury does comp and bonuses (57:21)
• What’s past is prologue (59:43)
• Who Modern Treasury is hiring and what “Grit” means to Rachel (01:02:00)

Links:

• Connect with Rachel
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Ashley Kramer, CMO & CSO of GitLab

One day, when Ashley Kramer was an SVP at Alteryx, one of her direct reports hit her with a dose of reality: “She said, ‘I think you are trying to put me on a path to be you, and to have your job. I don’t want any of that.’” Now the CMO and CSO of GitLab, Kramer — who has been a perfectionist since childhood — used to hold her team to the same high bar. But as she’s learned over time, “Not everybody’s gonna have your same ambition. Not everybody’s gonna work as hard as you. It doesn’t mean they’re not good at their job. It just means different things are important to them.”

In this episode, Ashley and Joubin discuss what companies get wrong in CEO interviews, “the three P’s” of company values, loosely held disasters, thinking about the future, “everybody does not want to be like me”, how GitLab does meetings, pre-speech nervousness, context switching, skip-level meetings, credibility with the customer, setting the bar too high, and Naval Ravikant.

In this episode, we cover:

• People, Passion, and Product (04:36)
• Joining companies right after they IPO (07:16)
• Scaling questions (10:28)
• Job-hoppers and ambition (12:06)
• Parents and dinner-table conversations (16:35)
• Coping with perfectionism (19:17)
• Coaching and demotivators (21:36)
• Confident public speaking (26:21)
• How Ashley got out of engineering (32:08)
• Being CPO and CMO of Sisense at the same time (35:49)
• Representing “two constituencies” (38:54)
• Why Ashley has two titles again (44:59)
• The radical transparency of GitLab (47:20)
• Growing pains and becoming interim CTO (51:28)
• Working with founder-CEOs (56:08)
• Tough feedback (58:20)
• Personal and professional OKRs (01:01:15)
• Work-life balance (01:03:33)
• How to network (01:06:10)
• Who GitLab is hiring and the meaning of “Grit” (01:08:58)

Links:

• Connect with Ashley
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Jen Vescio, Chief Business Development Officer at Uber and founder of Awestruck Ventures

If you were to look at Jen Vescio’s calendar, it might look like a pack of Skittles: Every single one of her meetings is color-coded according to the Insights Color Focus system, which assigns the colors red, blue, yellow, and green based on what methods they emphasize in their work. As the chief business development officer of Uber, Jen has to work with people across that spectrum, and preps for each meeting accordingly.

In this episode, Jen and Joubin discuss the pros and cons of media training, Malcolm Gladwell’s Outliers, “semi-pro” soccer, how to ruin your Uber rating, the “fluorescent light” journey, working at “it” companies before they were disrupted, the art and science of business development, self-awareness vs. understanding others, Sean Bratches, what is your motive?, side letter PTSD, “speed and silence are your two worst enemies,” forced time off, getting buy-in, and why “Uber is wired for trauma.”

In this episode, we cover:

• “Dancing in the moment” (00:54)
• The Olympic Development Program (03:22)
• Jen’s parents (08:15)
• DJing and music in Ubers (10:40)
• Talking to Uber drivers (12:48)
• Retiring from soccer (15:04)
• “The big transition” (17:22)
• The dotcom boom and Jen’s first jobs (20:04)
• Innovation and disruption (22:15)
• Buy, build, or partner (27:24)
• Understanding the “color” of others (35:27)
• How to talk to a “double red” (38:38)
• Insights Color Focus and the color of companies (41:16)
• The Trust Quotient (46:45)
• The biggest deal Jen has brokered (50:17)
• The pressure of big deals (51:46)
• The $350 million deal she botched (55:14)
• Getting burned out on corporate jobs (58:22)
• Big, shiny brands like Uber (01:00:38)
• Mental contracts and taking time off (01:05:07)
• Tough feedback (01:08:24)
• Developing trust internally vs. externally (01:09:48)
• How COVID impacted Uber (01:13:08)
• Where Uber is hiring and what Jen thinks of when she hears the word “Grit” (01:18:16) 

Links:

• Connect with Jen
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Nikesh Arora, CEO and Chairman of Palo Alto Networks

Nikesh Arora has been in the C-Suite for more than two decades, including a 10-year stint as Google’s chief business officer and — most recently — five years as Palo Alto Networks’ CEO. But the COVID-19 pandemic made him radically reconsider the gap between the executive floor and the rest of the company. “There was a tremendous amount of anxiety and fear and uncertainty,” he says, “and this person I was talking to says, ‘Listen, your job as a leader is to create certainty.’ [...] It’s simple: Tell your employees you have their back.” That’s why, for the past 30 months, Nikesh has been making time to virtually meet thousands of Palo Alto Networks employees on Zoom; he gets candid feedback, communicates company goals, and provides a safe space for everyone to bond.

In this episode, Nikesh and Joubin discuss honest CEOs, not having a career plan, process vs. outcomes, remaining independent inside Google, organizational superpowers, understanding your competitors, “evergreen companies,” the ChatGPT disruption, integrating product and sales, blindfolded communication, Evian water, cloud vs. on-prem security, and problem solvers vs. problem representers.

In this episode, we cover:

• Amazing people at Google (02:15)
• T-Motion and T-Mobile (04:05)
• “You cannot control the outcome” (07:36)
• Growing up in India (11:12)
• 400+ rejection letters (14:38)
• Loving what you do (18:26)
• Joining Google (19:55)
• Sergey Brin and Eric Schmidt (24:16)
• Relocating to “the mothership” (27:01)
• “He’s not Googly enough” (28:26)
• Profit, innovation, and paranoia (31:12)
• Cybersecurity and AI (34:04)
• SoftBank CEO Masa Son (38:54)
• Joining Palo Alto Networks (43:04)
• Hiring as home-building (47:04)
• “Nobody comes to work to screw up” (50:25)
• Product and the power of marketing (53:28)
• Cybersecurity “swim lanes” (56:36)
• M&A strategy (01:01:14)
• The two schools of due diligence (01:05:05)
• Moving past problems (01:07:42)
• Creating certainty for employees (01:10:59)

Links:

• Connect with Nikesh
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guests: Alex Smith and Shaun Livingston, former players for the San Francisco 49ers and Golden State Warriors

“I just thought, the best of my life is behind me.” That’s what former NFL quarterback Alex Smith recalls of a devastating leg fracture in 2018 that threatened to end his football career forever. Former NBA guard Shaun Livingston suffered a similar injury early in his career, and both men were told the only way forward might be leg amputation & retirement. They endured through depression, surgeries, and painful physical therapy, and both of them found their way back to pro sports. “I hopped on a bike,” Shaun says. “’Oh, I can do this!’ All right, I hopped on a treadmill. ‘Okay, I can do this.’ You give yourself these small victories that, over time, end up adding up.”

In this episode, Alex, Shaun, and Joubin discuss going pro out of high school, the pressure of expectations, talking about emotions, Joe Namath, gratitude for life, military medical care and “group suck”, the D-League, competing against yourself, losing well, “rah-rah guys,” no-look slants, Tom Brady, Kevin Garnett, and the difference between winning and losing.

In this episode, we cover:

• Alex Smith’s background (01:15)
• Shaun Livingston’s background (02:07)
• Alex on the fear of failure (03:23)
• Shaun on “the opportunity of a lifetime” (07:03)
• Imposter syndrome and burying emotions (10:44)
• Anxiety as motivation (13:41)
• Dysfunctional early seasons (16:10)
• Alex and Shaun’s leg injuries (18:57)
• Depression vs. “small victories” (23:51)
• Alex’s recovery process (25:45)
• Shaun’s stint in the NBA Development League (29:51)
• Teaching yourself to walk (31:58)
• Steph Curry and great leadership (36:19)
• Pat Mahomes and the “final shot” (41:05)
• Tough feedback (44:32)
• Recharging in the off-season (47:09)
• Daily consistency (49:41)
• Who Alex and Shaun think of when they hear the word “grit” (54:05)

Links:

• Connect with Shaun
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Andre Iguodala, forward for the Golden State Warriors

The average professional basketball career lasts around four years. By the first time Andre Iguodala came to play for the Golden State Warriors, in 2013, he was already on year 10 in the NBA. “All I wanted to do was get somewhere where I just truly enjoy going to work every day,” he says. And on his podcast with Evan Turner, Point Forward, he doesn’t shy away from the fact that being a famous and successful player comes with trade-offs. “When you make it ... you’re lifted up, like ‘you’re here to save us all,’” he explains. “There's so many things that go on with us as athletes that people don't get a opportunity to truly understand because there's two sides.”

In this episode, Andre and Joubin discuss the law of attraction, daily practice, former head coach Mark Jackson, Allen Iverson, the value of sports media, Mahmoud Abdul-Rauf’s Tourette Syndrome, Michael Jordan and Scottie Pippen, the lowest point in Andre’s career, and pivoting to stay alive.

In this episode, we cover:

• What goes through Andre’s head when the game rests on his shoulders (01:17)
• Enjoying work every day and playing under head coach Steve Kerr (05:31)
• Avoiding the newspaper, and why he started a podcast (09:59)
• The trauma of success and basketball as a sanctuary (14:07)
• Playing against LeBron James and with Steph Curry (17:59)
• Being addicted to success and finding joy on the court (21:24)
• Kevin Durant’s work ethic (25:41)
• Are the wins or losses more memorable? (28:30)
• Being a student of the game (32:02)
• Why Andre’s memoir is called The Sixth Man, and what changes in the playoffs (35:34)
• His final season in the NBA, and being a part of the tech ecosystem (42:04)
• The qualities of great players, and the most memorable game of his career (45:50)

Links:

• Connect with Andre
  • Twitter
  • LinkedIn
  • His podcast, Point Forward
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Al Gore, Former Vice President and chairman of The Climate Reality Project

Al Gore has been talking about all kinds of renewable energy for decades. The former U.S. Vice President, Nobel Peace Prize winner, and star of An Inconvenient Truth says it’s “thrilling” to see things like wind power and sustainable forestry becoming the norm. But as humanity continues its struggle against the climate crisis, he says, it’s worth remembering that political will is also a renewable resource. Effective storytellers and political organizers can overcome the entrenched political power of the oil and gas industry, and young people are flocking to work for climate-conscious companies that share their values. 

In this episode, Al and Joubin discuss Abraham Lincoln, Silent Spring, “father of the United Nations” Cordell Hull, downhill skiing, “pursuing a grail,” Watershed, An Inconvenient Truth, the Inflation Reduction Act, trolling Newt Gingrich, former CIA director Bob Gates, “let the glory out,” and Greta Thunberg.

In this episode, we cover:

• Which of Al’s many accomplishments is he proudest of? (01:52)
• What he learned from his parents, a pioneering lawyer and a U.S. Senator — and why he decided to get into politics (05:32)
• Being an underdog and finding the energy to fight injustice (16:15)
• The distinction between work and play, and commitments of the heart (19:28)
• The “hidden truth about human endeavors” (28:05)
• Becoming a great storyteller and getting instant, actionable feedback (31:25)
• Al’s “close as brothers” partnership with President Bill Clinton (36:44)
• Accepting hardship and renewing political will (48:08)
• How does Al renew his own energy? (53:57)

Links:

• Connect with Al
  • Twitter
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Giancarlo “GC” Lionetti, CRO of Zapier

“I live in a constant state of paranoia,” says Zapier CRO Giancarlo “GC” Lionetti, “which I guess is healthy and unhealthy.” A lifelong hard worker who shows up early and stays late, GC could have kept his job at team collaboration company Atlassian, which he joined before the company even offered stock options to employees. But his hunger for new experiences — and desire to learn things about new disciplines, like sales — took him away to unexpected new roles at Dropbox, Confluent and now Zapier. “If you asked me in every single experience what my next experience was gonna be ... I wouldn’t have guessed the one that I ended up doing,” he says.

In this episode, GC and Joubin discuss in-person retreats, the problem with “hybrid” cultures, in-office perks, dyslexia and ChatGPT, Atlassian as a “mini-MBA,” re-directing energy to find happiness, self-service businesses, “fitting the mold,” the space for meetings, and dinner at home with the kids.

In this episode, we cover:

• The Grit tip jar and being an “anti-remote” person at a fully remote company (00:47)
• How GC compensates for not being able to walk & talk around the office (06:13)
• The dying art of being early, and GC’s brand of hard work (09:03)
• His father’s exhausting work life, and his first summer job (16:18)
• Is GC a “pusher” or a “puller,” and some crucial advice from Atlassian CEO Scott Farquhar (21:15)
• What he thought in the early days of Atlassian’s ride to the top (27:48)
• What Zapier does and how it has helped GC and his wife as parents (31:29)
• “It was hard to take advice, because nobody understood this world” (34:25)
• Why did GC leave Atlassian for Dropbox? (38:04)
• Passing on paranoia, and is balance required for happiness? (41:16)
• Marketing vs. sales, and the danger of re-running the same playbook in different companies (48:46)
• Fitting into a box, and learning from people with different backgrounds (56:28)
• Why GC doesn’t like traveling very much, and  the place of meetings in Zapier’s GTM organization (01:01:09)
• Separating the “church and state” of work and personal life (01:07:38)

Links:

• Connect with GC
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Claire Hughes Johnson, author of Scaling People and Corporate Officer at Stripe

Former Stripe COO Claire Hughes Johnson’s new book, Scaling People, is not your typical business book: Informed by her experience scaling one of the most valuable private companies in the world, it’s a tactical reference manual, “almost like a textbook,” aimed at helping managers wrestling with a variety of problems. And one of the big uniting themes is that, to solve anything, they’re going to have to look inwards. “Leadership does not start with the other people in the room,” she says. “It starts with you ... if you don’t know yourself, you are not gonna be very successful, because you have to understand your work style preferences, your habits, your blind spots.”

In this episode, Claire and Joubin discuss in-demand books, Google pre-IPO, headcount as a proxy for success, paranoid mentality, self-driving cars, honoring commitments, the illusion of time, customer insights, “act like a founder,” asking for feedback, prioritizing and saying no, “steady Eddies,” imposter syndrome, fruit on the counter, layering titles, and making time for family.

In this episode, we cover:

• Who should read Claire’s new book, Scaling People, and how she expects them to read it (00:57)
• The challenges of building Stripe in its early days: “It was just consumed by it” (04:51)
• Why she left Google to become Stripe’s COO, and what she did for them as the business was starting to take off (12:34)
• How Stripe hired the best people — including Claire — and how they could have done it even better (17:25)
• Leadership starts with self-awareness (26:05)
• Honest criticism that rocks your world, and taking feedback well (29:43)
• The “unauthorized guide” to working with Claire (36:18)
• Getting hired at Google by Sheryl Sandberg, and why Claire didn’t follow her to Facebook (40:26)
• “Pushers and pullers,” a framework for working with top talent (46:43)
• What entrepreneurs can learn from Condoleezza Rice about impact, passion, and ability (58:33)
• Putting your (imperfect) expertise out into the world (01:02:03)
• Implementing Stripe’s first performance feedback process, and why it still doesn’t “do” titles (01:07:06)
• Having a life outside of work, and the “clarifying moment” of a surprise birthday party (01:15:26)

Links:

• Buy Scaling People: Tactics for Management and Company Building
• Connect with Claire
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Rania Succar, CEO of Intuit Mailchimp

Ten years out of college, and with two advanced degrees under her belt, Rania Succar knew she wanted to be an operator. Taking a job at Google taught her a lot, but she chafed under the limitations imposed on her control and personal impact. At Intuit, she finally found what she had been searching for: “We really do have a structure that's set up to give you massive amounts of accountability and responsibility.” For seven years, Rania worked across the Quickbooks team before becoming the CEO of Mailchimp in August 2022. And along the way, she also discovered the “beauty” in jointly owning some functions with her teammates: “It can actually be brilliant.”

In this episode, Rania and Joubin discuss immigrant culture, boundless energy, the search for meaning, the illusion of control, getting back to equilibrium, registering your ambition, “Mailkimp,” prioritizing family, sleep experiments, passing the baton, finding problem-solvers, and meetings that give you energy.

In this episode, we cover:

• The importance of family to Syrians, Persians, and immigrants (00:43)
• Navigating two cultures at the dinner table, and Rania’s entrepreneurial father (04:48)
• The arc of her career, and figuring out where she wanted to put her energy (08:59)
• What motivates & energizes her, and what takes energy away (14:28)
• The need to own things end to end, and the beauty of sharing the controls (18:32)
• What Rania has learned over seven years at Intuit, and how she pushes to do more (24:32)
• Mailchimp’s “genius” sponsorship of Serial, and preserving its scrappy culture (30:46)
• How Rania allocates her time every week, and finding “30% more efficiency” (34:13)
• Learning about the importance of sleep “the hard way” (38:45)
• Getting through the early months of COVID and being authentic with her team (43:30)
• Learning from leaders like Intuit’s Bill Campbell and Scott Cook, and defining the “next chapter of exceptional” (46:51)
• How a visual impairment became a source of strength (52:54)
• Setting priorities and being a prisoner of one’s calendar (57:16)

Links:

• Connect with Rania
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Lesley Young, CRO of Gem

Lesley Young’s favorite book is “The Obstacle Is The Way,” in which Ryan Holiday argues that the process of working hard to achieve something is more important than the achievement itself. When you find yourself in a position of leadership, the Gem CRO says, “you realize there’s a lot of wisdom that you’ve gained in those experiences that you’ve had.” One of her passions is helping other people develop in the careers, which includes convincing them that “that hard yards are going to be the ones that are gonna grow them the most.”

In this episode, Lesley and Joubin discuss speaking vs. observing, meeting your heroes, the Great Depression mindset, developing people, Workplace by Facebook, the power of discontent, choosing to show up, controlling the controllable, repeatable success, being “open for business,” getting fired up, remote work, “only the paranoid survive,” and hard feedback.

In this episode, we cover:

• Prepping for public presentations (00:59)
• Meeting Salesforce CEO Marc Benioff and working with Snowflake CRO Chris Degnan (04:44)
• Fear of everything evaporating, and becoming resourceful (09:28)
• The “purpose statement” Lesley wrote for her career, and why she loves to learn (14:16)
• Choosing to not be *the* leader all the time, and taking a risk on Facebook (20:35)
• Her relationship with her parents and being motivated by unfinished work (25:45)
• Ryan Holiday’s “The Obstacle Is The Way” and the journey to the achievement (29:32)
• How to work with founders such as Box CEO Aaron Levie (35:58)
• Former Segment CEO Peter Reinhardt and asking the right question (41:03)
• Why Lesley joined Gem on the eve of a hiring downturn: The long-term play (47:26)
• Why Gem CEO Steve Bartel is an “amazing recruiter,” and the return of in-person collaboration (52:14)
• The toughest feedback Lesley has ever gotten about herself (59:42)
• Why delivering tough feedback is harder than receiving it (01:03:49)

Links:

• Connect with Lesley
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Guest: Javier Molina, CRO of Starburst

Starburst CRO Javier Molina’s peers, former colleagues, and even his wife often tell him the same thing: He’s difficult to read.  That doesn’t mean he’s not listening, though. In fact, he’s focusing on many different things such as speech patterns, the words being used, and the priority of those words while simultaneously keeping a pulse on social cues as well. This uncontrolled habit he describes as both a superpower and his achilles heel. “It allows me to interview really well and assess talent,” says Javier, who describes himself as a social introvert. “It allows me to read situations … understand room dynamics… It helps me understand my customers [but] I think a lot of people like extroverts because of how they’re so expressive and flashy ... and that’s not me.”

In this episode, Javier and Joubin discuss Austin culture, making eye contact, social introverts, living in the future, self-awareness, betting on yourself, workhorse culture, reverse job interviews, short-term wins, in-car WiFi, great partners, and world-class interviewing.

In this episode, we cover:

• San Francisco vs. Austin and the flood of techies moving to Texas (01:08)
• The “movie that you can’t turn off” and assessing people quickly (05:49)
• Patience, focus, and being present (14:10)
• “What is a common misconception of you?” (19:53)
• Self-awareness as a proxy for potential, and feeling different from the crowd (25:04)
• Buying houses, and betting on yourself (32:00)
• Being hired as an executive, and the culture of teams at bootstrapped companies (39:00)
• What Starburst does and turning the tables on CEO Justin Borgman (45:44)
• Being intentional, celebrating wins, and “enjoying the climb” (50:31)
• Getting away from work, and the strength of entrepreneurs’ relationships (57:22)
• The little things in interviews, and why “a problem well stated is half solved” (01:02:50)
• How to screen for grit (01:07:41)

Links:

• Connect with Javier
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

All of Dennis Lyandres’ mentors — and even his parents — thought he was making a mistake when he joined Procore in 2014. At the time, he was working at the “it” company in Silicon Valley, Cloudera, and the startup was more than 10 years old without any major wins under its belt. But he knew someone “was gonna build a massive company” in construction software, and he found out that Procore’s team was uniquely obsessive about making its customers successful: “It felt like a culture that wouldn’t lose,” he says. 

In this episode, Dennis and Joubin discuss the power of food, being a “prep maniac,” finding satisfaction, the potential for greatness, the tickle of urgency, imposter syndrome, construction software, magical CEOs, internal pep talks, learning from failure, the wisdom of others, strong relationships, the Procore IPO, and life partners.

In this episode, we cover:

• The Procore campus and employee experience (01:03) 
• How Dennis prepped for this podcast and lifelong learning (05:00)
• “Have I plateaued? Is this it?” (11:31)
• Channeling energy into your work, and knowing what you can change (17:42)
• Dennis’ parents and how he thought about work for most of his career (22:30)
• His first jobs and why he left Cloudera for Procore (27:11)
• The first “oh shit” moment and the 10-year success story (34:25)
• The winning culture and what Dennis would do with a second chance (39:47)
• Scaling to nine-figure revenue and personal growth through failure (43:20)
• Great vs. terrible leadership and finding the right mentors (48:21)
• Procore CEO Tooey Courtemanche and relationships built on trust (55:08)
• Fixing the technology in construction (58:19)
• Powerful advice about ethics and interpersonal relationships (01:02:49)
• Thoughtful gifts and making space for another person in your life (01:08:58)

Links:

• Connect with Dennis
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

In the middle of the Great Recession, Thomas Dohmke quit a stable job at a good company because “I wanted to build stuff again.” Specifically, he was inspired by the release of the first software development kit for iOS, and wanted to be part of the mobile revolution. Two companies later and halfway around the world, he is the CEO of software development powerhouse Github and on the precipice of another revolution — that of AI tools such as Github Copilot. Up to 40 percent of Copilot users’ code is already being autocompleted by AI, and Thomas predicts that number could get to 80 percent in the next five years. “We are heading into a world where developers are much more architecture and system designers,” he says.

In this episode, Thomas and Joubin discuss staying excited, A/B tests for life, triggering emails, “the toys you can’t have,” self-driving car sensors, the first iPhone SDK, app testing, US work visas, life-changing money, Xamarin, is Github a social network?, being ultra-transparent, ghost text, ChatGPT and Midjourney, generating passion, rehearsing forever, Mittelstand companies, and the zen of LEGO.

In this episode, we cover:

• Titles at Microsoft and working with CEO Satya Nadella (00:58)
• Being “85% happy” and the temptation to leave big companies for a startup (05:33)
• How Thomas went from early user to CEO of GitHub (09:22)
• Growing up in East Germany and the fall of the Berlin Wall (13:19)
• Why Thomas quit his job at the height of the financial crisis: “I wanna build stuff again” (22:28)
• Being acquired by Microsoft and coming to America (27:26)
• The startup mindset and “open-source” values (34:09)
• How Github’s “AI programmer,” Copilot, will change everything for developers (40:32)
• When will generative AI have its “iPhone moment?” (45:44)
• Exponential change and preparing your kids for the unknown future (50:57)
• Communicating in English, and whether Thomas’ family would ever go back to Germany (57:21)
• Tech culture in Europe vs. Silicon Valley and the pressure of “more” (01:01:19) 
• The “LEGO room” in Thomas’ house (01:07:18)

Links:

• Connect with Thomas
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Freshworks president Dennis Woodside copes with stress by running as often as he can, a habit that began when he was CEO of Motorola Mobility. So far, he has run “16 to 17” Ironman triathlons. He’s also continually challenging himself in his professional life, leaving Motorola in 2014 to advise the founder-CEOs: Dropbox’s Drew Houston, Impossible Foods’ Pat Brown, and now Freshworks’ Girish Mathrubootham. Dennis’ advice for anyone working with founders is to “have empathy” for what they’re going through, and to understand what motivates them. Without that understanding, he says, you won’t be able to arrive at a shared vision for the company.

In this episode, Dennis and Joubin discuss mega-acquisitions, the smartphone paradigm shift, triathlons and competitiveness, winning every category, “softening up,” global cities, Google interview questions, spreading Silicon Valley culture, the “chrome panda moment,” hiring the right people, “Where do you want to be in five years?”, evaluating new opportunities, and building trust with founders.

In this episode, we cover:

• Google’s acquisition of Motorola and how Dennis went from ad exec to first-time CEO (02:00)
• Did Dennis like being the CEO of Motorola? (08:04)
• The stress of the new job and dealing with it through exercise (13:02)
• Dennis’ impressive résumé and what dinner conversation was like growing up (18:37)
• Going to Korea and choosing the harder path (23:00)
• Joining Google in 2003 as a general problem-solver (26:23)
• Hiring “scouts” all around the world to better understand the internet (30:41)
• Leaving Motorola to mentor Dropbox CEO Drew Houston (39:12)
• Checking your ego and the listening tour that wasn’t (42:20)
• Dropbox’s IPO and why the stock has been relatively flat (48:38)
• Changing jobs without breaks, and spotting new opportunities like Freshworks (52:19)
• Tips for working with founders and interrogating the status quo (58:02)
• Dennis’ most unique OKR at Dropbox (01:02:39)

Links:

• Connect with Dennis
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

The best advice Brex founder and co-CEO Henrique Dubugras ever received came from Snap CEO Evan Spiegel: The best CEOs, Spiegel told him, are “extremely authentic to themselves ... If you try to emulate being Elon Musk and you’re not like that, you’re just gonna fail.” This wisdom has empowered Dubugras and his co-founder, Pedro Franceschi, to focus on the places where they can be most effective at Brex, and to be more authentic with their coworkers. 

In this episode, Henrique and Joubin discuss coaches vs. therapy, mutual crushes, “hacker famous,” big egos, why missions are overrated, dropping out of college, CEO’s identities, the “Silicon Valley mold,” trojan-horsing Max Levchin, pivoting after two years, going to the ground, compensation and hiring myths, core customers, fixing expense report policies, and joining the Expedia board.

In this episode, we cover:

• Growing up in Brazil and Henrique’s relationship with his mom (01:07)
• The first company he sold, Pagar.me, and his co-founder Pedro Franceschi (07:11)
• Becoming “successful” and why it’s fine to have a “f**ked up motivation” (10:35)
• ADHD, dueling superpowers, and focusing on the right things (15:56)
• Being an authentic CEO and not reading books (19:51)
• The radical changes Brex has experienced in the past three years (24:40)
• Brex’s new spend management product and landing initial customers (30:30)
• The messages sent by how Brex structures its employee compensation (34:07)
• How Henrique and Pedro recruited top talent when they were just getting started (38:57)
• Pivoting a $12 billion company: “We can’t do all these things” (43:33)
• The challenges of becoming more of an enterprise company than a Fintech one (50:34)

Links:

• Connect with Henrique
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

“When you create something,” says ServiceNow CEO Bill McDermott, “that gives you the ability to help and do good and achieve for the most people possible.” Bill left his first corporate job at Xerox for a short stint at Gartner, then served as CEO of SAP for nearly a decade. He made one more transition three years ago because he saw a great opportunity to help make ServiceNow a defining enterprise software company. “I knew it could happen,” he says. “What I didn’t know is just how unbelievably right I was.”

In this episode, Bill and Joubin discuss fist-pumps, shoplifting teens, Bill’s superpowers, needing to be needed, marriage as a partnership, why every relationship matters, difficult relocations, breast cancer, the FDNY’s chaplain, and the Medal of Honor. 

In this episode, we cover:

• Why Bill bought a deli when he was in high school — and how he competed against 7-Eleven (04:00)
• Interviewing at Xerox and wanting it more than anyone else (08:17)
• Unwavering optimism and being a source of strength for others (12:34)
• How a love of work has shaped Bill as a person (16:44)
• Facing challenges and keeping a promise to his father (22:00)
• Enjoying the present and keeping an eye on the future (30:01)
• Leaving Xerox for Gartner and learning from a tough experience (33:29)
• Sloan Kettering and Father Michael Judge (39:22)
• Following the “original dream” vs. building something new at ServiceNow (44:59)
• Losing an eye and getting a pep talk from two Medal of Honor winners (51:15)
• Why Bill started and ended his book with quotes from two Kennedys (01:01:21)

Links:

• Connect with Bill
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

With more than 1,200 employees, it isn’t easy for Gong co-founder and CEO Amit Bendov to stay in touch with everyone. So, his team has established a series of regular programs to communicate the company’s priorities and give workers a chance to ask questions. And despite the revenue intelligence company’s scale, they’ve established a core value called No Royalty: “You’re supposed to be able to communicate with anybody in the company,” Amit says. “You’re no better than anybody.”

In this episode, Amit and Joubin discuss name pronunciation, education and culture, communicating in English, family as pseudo-co-founders, remote work, AI customer management, missing the quarter, “Google for enterprise,” drinking your Kool-Aid, “win as a team,” GPTChat and other AI breakthroughs, and solving problems vs. pursuing opportunities.

In this episode, we cover:

• The “captain’s table” and spreading company priorities (02:12)
• Amit’s first jobs and splitting his time between the US and Israel (06:47)
• The differences in work culture between the two countries, and returning to the office (14:19)
• Amit’s pre-gong jobs at Click Software, Panaya, and Sisense, and how he got the idea for Gong (18:40)
• Starting a new company in your 50s and why “nobody wanted to invest in us” (24:58)
• Gong’s brand, its culture, and the lines before personal and professional (32:15)
• The art of company-building and enjoying the ride (34:59)
• Professional struggles and two embarrassing stories about cars (39:57)
• Being on autopilot, and the pros & cons of letting your mind wander (45:05)
• Automation vs. personal human relationships, and what AI can do that humans can’t (48:04)
• If Amit were starting Gong over from scratch, what would he do differently? (55:08)

Links:

• Connect with Amit
  • Twitter
  • Linkedin
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Jon Levin has been teaching at Stanford for more than 20 years, and has been the dean of the famous Graduate School of Business since 2016. Although teaching at Stanford puts him in contact with some of the most promising future entrepreneurs in tech, he says he hasn’t yet been tempted to leave academia for a startup because “I actually love being part of an institution that’s gonna be around for hundreds of years.” As public trust in institutions has eroded in recent years, Jon and his colleagues have had to make changes. For example: Proactively challenging GSB students to think about “What does it mean to be a leader of an organization in today’s world?”

In this episode, Jon and Joubin discuss honorific names, applying research in the real world, matching med school students, the “endless frontier,” the globalization of innovation, the entrepreneurial “itch,” the erosion of trust in institutions, US-China relations, students from Ukraine and Russia, what the GSB admissions staff looks for, self-awareness, the “Touchy Feely” class, and the serendipity of in-person classes. 

In this episode, we cover:

• The John Bates Clark Medal, and researching economic topics like auction design (01:56)
• Nobel Prize winners at the Stanford GSB and the uniqueness of the US university system (10:15)
• Teaching entrepreneurial students and the value of institutions (16:30)
• Being affirmative vs. reactive and how Jon measures success (23:07)
• International MBA students and the importance of geographic diversity (27:27)
• Growing up in an academic family and how Jon’s theory of teaching (34:47)
• The qualities that “great” GSB alumni have in common, and the gradual changes to business school cohorts (39:12) 
• The qualities of “great” faculty and what was lost when classes moved to Zoom during COVID (47:06)

Links:

• Connect with Jon
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

“Think about the pandemic without the internet,” says Cloudflare co-founder and COO Michelle Zatlyn. The world’s sudden shift to doing almost everything online only worked because network engineers, IT administrators, and internet infrastructure companies like Cloudflare had done the work. Michelle says that, both personally and professionally, she’s fine being under the radar because she doesn’t need to be publicly reminded of the importance of her job: “It's like all the roads, the tunnels, the bridges ... when it works, it's magic. Really, you don't even know we exist.”

In this episode, Michelle and Joubin discuss the pressure of success, advice for founders, low-drama startups, the power of the Cloudflare blog, internet security, the cross-country U-Haul trip, sweating the details, San Francisco as a “power center,” helping the next generation of founders, “the airplane effect,” injecting tension, why learning is a superpower, and choosing to feel the bumps in the road.

In this episode, we cover:

• Carrying the torch for women in infrastructure and “just getting started” (01:15)
• Being under the radar and the over-glamorization of founders (07:19)
• Why it’s so hard to hire & empower a great team (15:35)
• How Cloudflare is building a better internet (22:08)
• How Michelle, Matthew Prince, and Lee Holloway met and why they started Cloudflare (28:23)
• “Losing” at TechCrunch Disrupt’s Startup Battlefield — and turning it into a win (34:10)
• Building remote vs. choosing to be in the SF Bay Area (40:54)
• “I don’t understand why anyone starts companies” (46:28)
• How to run the best board meeting ever (55:31)
• Why Michelle brought her kids to the New York Stock Exchange for “Mom’s Special Day” (01:00:51)
• The skill that sets good founders apart from great ones (01:02:34)
• How a back injury took away a year of Michelle’s life (01:10:16)

Links:

• Connect with Michelle
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

Grit has never been just about business, and success is not a vaccine against stress, anxiety, or depression. On today’s special episode, Joubin looks back at nine past interviews and the advice shared by guests who have been through difficult personal challenges. You can find links to the full interviews these clips came from below.

In this episode: 

• CCO Forter, Ozge Ozcan on burning out like a phoenix and the “dark side” of grit (01:05)
• CMO Samsara, Sarah Patterson on the value of being vulnerable — and specific — with your employees (06:14)
• Co-Founder & CEO Clari, Andy Byrne on his “dark year” and reframing big problems as moments in time (11:00)
• Former CRO at Notion, Olivia Nottebohm on accountability, empathy, and what people will remember when you’re dead (21:28)
• Former CRO at HubSpot, Mark Roberge on crippling anxiety attacks and the importance of finding time for your own health (28:25)
• Founder & CEO Thrive, Arianna Huffington on the growing cultural acceptance of talking about burnout, stress, and sleep (37:13)
• Co-founder of Intuit, Scott Cook on spending time with family and recording your memories (44:11)
• Former President at NetApp, Tom Mendoza on how to find out who your real friends are (49:15)
• CRO Snowflake, Chris Degnan on the motivating power of fear (55:53)

Links:

• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

SAP Executive Board Member Scott Russell used to avoid talking about his personal life with coworkers. But “we want to understand and relate to each other,” he says, and being more open has made people more willing to trust and follow him. “Authenticity, you cannot manufacture that,” Scott says. “When you’re only showing a part of who you are to your team, you’re not showing your true, authentic self.” 

In this episode, Scott and Joubin discuss European business structures, three-year contracts, creating a positive impact, informed feedback loops, maintaining a good emotional quotient, too much optimism, tough phone calls, playing the movie forward, helping your community, life balance, implicit trust and authenticity, finding new opportunities, considering other points of view, and speedboats vs. load-bearers.

In this episode, we cover:

• Living around the world and away from HQ (01:05)
• Signing a three-year contract with yourself (08:09)
• The responsibility of delivering $1 billion in revenue every week (11:55)
• Getting to the truth when you’re near the top of a huge organization (14:07)
• The unintended consequences of optimism (17:11)
• Missing earnings and “what’s the worst thing that could happen?” (20:11)
• Scott’s childhood in Australia and his lifelong passion for basketball (26:21)
• Why the “work version” of Scott isn’t the best version (30:15)
• Being authentic with coworkers and how to drive outcomes in your personal life (33:53)
• The one place Scott’s family hasn’t been able to relocate happily (38:47)
• Loyalty to your work and your family (42:42)
• How competition drives better performance and keeps you honest (47:45)
• Finding discipline in your schedule and forcing yourself to relax (54:46)
• Where SAP is hiring, and Scott’s view of  potential M&A or strategic partnerships (57:08)

Links:

• Connect with Scott
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

In Silicon Valley when business is good, it's normal for top talent to hop from company to company to company. But GE's Linda Boff, described by at least one of her peers as the "Beyoncé of CMOs," has stayed at the 130-year-old conglomerate for nearly 20 years, through radical changes to the business structure, and with plans to split into three public companies on the horizon. She attributes her longevity to the fact that four out of five days of any week, she's excited to come in: "I believe in this company," Linda says. "I would have the hardest time if that went away, and it never has."

In this episode, Linda and Joubin discuss helping young people succeed, finding your passion, the 1980 Winter Olympics, Thomas Edison, Twitter advertising, sticktoitiveness, being excited for work, being impatient, trying to please everybody, and calendar time management.

In this episode, we cover:

• How a chance encounter with Video Monitoring Systems founder Robert Cohen changed Linda's life (03:17) 
• Where Linda's work ethic came from, and her serial internships (06:21)
• Elon Musk and brand safety on Twitter (12:47) 
• Why Linda has worked at GE for almost 20 years, and how it became an "industrial powerhouse" (15:22) 
• Choosing to stay and giving a shit (21:40) 
• How much should you love your job? (25:57) 
• If she were starting over, what would Linda do differently? (32:09) 
• Getting the truth & what other people think (34:38) 
• Linda's calendar and writing thank-you notes to coworkers (38:55)

Links:

• Connect with Linda
  • Twitter
  • LinkedIn
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm

PagerDuty CEO Jennifer Tejada has mixed feelings about how she is often portrayed in the press, as a “badass woman CEO.” The scarcity of female executives in enterprise means that it’s often the first thing anyone wants to talk about — not her performance leading a $2 billion company, or her team. She has specifically designed that team to include more under-represented people like her, so that she is not “the only one in the room” — but one executive team isn’t enough. “In my peer group, there’s still not enough Hayden Browns, there’s not enough Yamini Rangans, there’s not enough Safra Katzes,” Jennifer says. “And that is a failing of the industry.”

In this episode, Jennifer and Joubin discuss IPO chasers, the P&G Mafia, reward-centered leadership, participation trophies, serving others in a crisis, working women, plate spinning, perfect girl syndrome, unconscious bias, competitive offshore yacht racing, disconnecting from work, “re-finders,” interrupt work, consistent high standards, beginner’s mind, talent identification, weird but beloved brand names, and dealing with grief.

In this episode, we cover:

• The good side of market corrections, and investing in people (00:58)
• Learning how to fail and where Jennifer’s work ethic came from (05:28)
• Her father’s death and how she adjusts “when shit hits the fan” (13:03)
• Recognizing your own limits and working for your family (17:43)
• The double-edged sword of being a visible female CEO (23:13)
• Taking a break from your career to work on yourself (28:42)
• Identity in Silicon Valley and getting put in a box (35:09)
• How Jennifer got to PagerDuty and delivering value to customers (40:17)
• PagerDuty’s IPO in the middle of a major pivot (45:23)
• Responsibility overload and self-criticism (49:36)
• Founder-led companies and the advantages of being a “re-finder” (52:55)
• PagerDuty’s transition from one product to many (57:56)
• The “unfathomable loss” of Phylicia “PJ” Jones and being vulnerable with coworkers (1:00:36)
• Why grit is a requirement for success (01:06:52)

Links:

• Connect with Jennifer
  • Twitter
  • LinkedIn
  • Email: [email protected]
• Connect with Joubin
  • Twitter
  • LinkedIn
  • Email: [email protected] 
• Learn more about Kleiner Perkins
• This episode was edited by Eric Johnson from LightningPod.fm