Jake & JZ

Our latest thoughts on AI! At Character Capital, most of our investments are in AI companies. How will recent advancements change how products are designed and startups are built? Our cofounder Eli Blee-Goldman returns to the podcast to share predictions and highlight the importance of human agency in an AGI future.

Quick note: This episode was recorded right before DeepSeek R1 came out. We have thoughts, of course 🤓 We’ll record a follow-up soon!

On episode 15 of Jake & JZ, we talked about:

• What stays the same in an AGI future?
• The importance of agency
• The capabilities gap
• Doing meaningful work with people you like
• Surprising lessons from a Design Sprint with an AI bio startup
• What changes in an AGI future?
• How AI can close the gap between builders and customers
• AI ethics and sentience
• And much more

Have a question for us? Send it to [email protected] and we’ll answer it on the show.

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund at Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn, X, and Blue Sky

10 years ago, we learned how caffeine really works, and it changed how we use, consume, and enjoy coffee. Tune in for a Jake & JZ deep dive on caffeine — from working with Blue Bottle, to our current coffee routines, to insights and tactics for making the most of this wonderful substance.

On episode 14 of Jake & JZ, we talked about:

• How caffeine really works
• Learning about caffeine from Ryan Brown at Blue Bottle Coffee
• Going deeper for Make Time
• Two surprising caffeine insights
• Two helpful coffee tactics
• JZ’s favorite coffee maker: The OXO Brew
• Jake’s espresso machine: The Breville BES870XL
• Boon Boona Coffee
• A great book: Deskbound by Kelly Starrett (not about caffeine, still great)
• And much more

Have a question for us? Send it to [email protected] and we’ll answer it on the show.

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund at Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn, X, and Blue Sky

We wrote a new book!!! It’s called Click and it’s all about the Foundation Sprint, our new 2-day method for kicking off big projects!

We are SUPER excited to share it with you all, and this week’s episode is a deep dive into the process of writing the book and how it fits into our investing strategy.

Learn more about the book at theclickbook.com

On episode 13 of Jake & JZ, we talked about:

• How to get early access to Click
• The history of the Foundation Sprint
• Books that inspired us: Psychology of Money, Power of Habit, Building a Storybrand, The Heath Brothers’ books
• What we look for when we invest
• Why we had to share the Foundation Sprint

Have a question for us? Send it to [email protected] and we’ll answer on the show.

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund at Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn, Blue Sky and X

ANNOUNCEMENT: We are hosting a live online event to introduce the Foundation Sprint!! Join us for an early look at our new sprint method and a cool surprise!

On the podcast: Character Labs is BACK, so this week we’re sharing a What-Why-How-style deep dive on the program. If you want to hear our best ideas and tactics for starting new projects, OR if you’re just curious about Character Labs, be sure to check out this episode.

On episode 12 of Jake & JZ, we also talked about:

• The most important moment for every new project
• That feeling when your product “clicks” with customers for the first time
• Lenny’s newsletter on How to know if you've got product-market fit
• The Founding Hypothesis (every project has one; do you know yours?)
• Getting just one customer
• How AI has changed prototyping in Character Labs
• And much more

Here’s that registration link for the event next week.

Have a question for us? Send it to [email protected] and we’ll answer on the show.

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund at Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn and X

We discuss three essential books that help us break through uncertainty and focus on the most important work. If you want to get better at designing products and building companies, we think you should read:

• Getting Real by 37signals, for how to get real about what matters
• Good Strategy Bad Strategy by Richard Rumelt, for how to give your business an unfair advantage
• Deep Work by Cal Newport, for staying focused and actually doing the work

On episode 11 of Jake & JZ, we also talked about:

• Why your business needs an enemy
• Insights from the “survival days” of successful companies (like the Startup Wayback Machine)
• Crafting strategy based on your unique advantages
• Why strategy is a hypothesis
• How to summarize an entire book in 25 words
• More lessons from journalism
• Bad graphic design

Have a question for us? Send it to [email protected] and we’ll answer it on the show.

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund at Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn, Bluesky, and X

Jake gets a bit vulnerable and talks about Perfection Anxiety, which he’s struggled with since childhood. If you ever feel stuck, or worry your work won’t be good enough, be sure to check out this episode — we share a BUNCH of concrete tactics for overcoming Perfection Anxiety and getting started.

On episode 10 of Jake & JZ, we also talked about:

• How to run two sprints in one week
• Winter in the Pacific Northwest
• Why discipline doesn’t work
• Working at newspapers
• A great podcast episode: Starbucks on Acquired
• A great newsletter: Spyglass by M.G. Siegler

Have a question for us? Send it to [email protected] and we’ll answer it on the show.

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund at Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn, Bluesky, and X

This episode is about our SINGLE BEST technique for avoiding distraction every day. In part two of our mini series on Make Time, Jake describes the Distraction-Free iPhone — which he started doing 10 years ago!! If you’re looking for a simple, powerful way to block distraction (ESPECIALLY after episode 8’s discussion of the Highlight Method), be sure to tune in.

On episode 9 of Jake & JZ, we also talked about:

• Lord Nelson and the importance of proper provisioning
• Attention Residue
• Why Jake deleted all the distracting apps from his phone (and what’s left)
• JZ’s experience with a Distraction-Free Phone (and what’s NOT on his phone today)
• Why LinkedIn is an adult website
• Treating colleagues as friends
• A great app: How We Feel
• A great Netflix series: Starting 5

Have a question for us? Send it to [email protected] and we’ll answer it on the show.

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund at Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn, Bluesky, and X

How do you make time for what matters? In this episode, we share a simple habit called The Highlight Method, inspired by the Design Sprint, that we both use to focus our efforts on the most important activities every day. Have a question for us? Send it to [email protected].

This week on episode 8 of Jake & JZ, we talked about:

• When it makes sense to use LLMs for writing
• Being secret late adopters
• The big ideas behind our book Make Time
• The danger of defaults in our everyday lives
• How the daily Highlight works
• Strategies for choosing the right Highlight

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund at Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn, Bluesky, and X

This might be our most tactical episode ever. If you’re starting something new, check it out! Not to brag, but it’s FULL of proven tactics for making big decisions about new projects.

This week we also answered our very first audience question. Thanks 1sam1216! Have a question for us? Send it to [email protected].

On episode 7 of Jake & JZ, we talked about:

• Our Name Sprint process for naming your company or product
• A full walkthrough of our Name Sprint for Character Capital
• Why we chose “Character” even though it wasn’t a perfect match for our brand attributes
• How to use Design Sprints to test risky non-consensus ideas
• The importance of moving from abstract to concrete as quickly as possible
• Finding conviction, not consensus
• Anna Karenina by Leo Tolstoy
• Annihilation by Jeff VanderMeer
• NPR Tiny Desk Concerts
• And much more

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn and X

Chapters

0:00 Jake finally reads Anna Karenina

8:10 We visited Google again and gave a talk at YouTube!

11:00 Presenting the Foundation Sprint for the first time

14:00 Helping a founder build something new from day 0 in healthcare

18:05 Should he go direct to patients?

19:30 Design Sprints give you a chance to try something risky and non-consensus

20:35 A lot people told us not to write a book, so we prototyped it

22:10 Prototypes aren’t just for customers; they give founders a chance to see their idea live!

24:30 Our first audience questions!

25:20 Audience question: Do you have a method for naming companies?

26:05 History of the Name Sprint from Google Ventures

28:50 Walkthrough of our Name Sprint for Character Capital

29:45 Step 1: Note-and-Vote on themes of potential names

34:30 Step 2: Note-and-Vote on actual names (as many as possible)

36:40 Jake did not vote for Character

37:45 Step 3: Multiple rounds of voting to narrow down the set of names

38:35 Step 4: Plotting names on 2x2 charts to evaluate brand fit

39:20 We chose Character even though it didn’t fit our abstract brand values

41:05 Step 5: Vetting final names with the pub test (aka the shaky cell signal test)

42:30 Step 6: Final checks (web test, domain, trademark)

44:30 Empty vessel names

47:00 Collecting aspirational domain names (including jakeandjz.com!)

49:55 JZ’s Wisconsin accent

50:30 Lantern Ventures: a free brand for any VCs who love camping

51:30 We chose Character Capital because we had conviction, not consensus

52:45 A special thank you to Laura Melahn

53:30 Jake recommends Annihilation by Jeff VanderMeer (the book, not the movie)

56:00 JZ recommends NPR’s Tiny Desk Concerts

57:15 NPR Tiny Desk is the new MTV Unplugged

A special chance to meet Eli, the third founder of Character, and learn about the inner workings of venture capital. This week on episode 6 of Jake & JZ we talked about:

• How Jake got to ride in the very first Waymo (when it was just a prototype on the Google campus)
• Jake’s rollercoaster of emotion meeting Eli
• Eli’s winding path to VC (it led through Botswana!), his famously good intuition, and “Eli-isms”
• Phaidra: Why we invested, how we work with the team, and the real value of a startup board member
• Why we use blinded scorecards to make investment decisions
• Jake’s annotated copy of the viral MrBeast production memo (download it here!)
• The importance of starting at the end
• And much more

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn and X

Chapters

0:00 Jake got to ride in the very first Waymo

3:35 Jake & JZ’s impressions of Waymo in San Francisco

7:55 Welcoming our cofounder Eli Blee-Goldman to the show!

8:15 Jake’s rollercoaster of emotion meeting Eli

10:35 Eli’s winding path to VC (it led through Botswana!)

13:35 How Eli developed his famously good intuition 

15:40 How Eli got his first job in VC

20:20 Showing up and putting in the work

21:50 A fine Eli-ism: The Conviction Punch!

26:05 The mismatch between founders and VCs

30:40 Why Eli got excited about Phaidra

34:00 Wait, what does Phaidra do, anyway?

36:15 Why we use blinded scorecards to make investment decisions

39:30 How Design Sprints make startups more capital efficient

42:15 The role of board members at an early-stage startup

47:40 Why Eli decided to start Character Capital

50:25 The viral MrBeast production memo

52:05 “This is like Sun Tzu, it’s like the Art of War”

52:45 Jake walks through his annotated version of the MrBeast memo

57:05 Start at the end: Choosing the title and thumbnail BEFORE making the video

59:55 Seth Godin: “Marketing is how we create the conditions for people to find what they are looking for”

1:00:50 MrBeast and Lightning Demos

1:03:00 Clickbait headlines and the feeling of success

This week on episode 5, we talked about:

• The music you listened to between ages 12 and 20 (and how it’s the best, no matter how old you are)
• Revisiting the music video for Cannonball by The Breeders
• Speaking at a Stanford BioDesign class led by the founder of Cala Health (we ran a sprint with them in 2016!)
• Lightning Demos, a quick way to gather inspiration for new solutions and a key part of every Design Sprint
• The amazing cover of Made to Stick by Chip & Dan Heath (and why Jake had a copy within reach!)
• A study showing how outside inspiration leads to better ideas
• The three reasons Lightning Demos work so well
• Lightning Demo Demos — we do live Lightning Demos of three websites
• Shiny Object Syndrome
• Playdate’s hardworking headline
• Aligning your “why” with your customer’s “why”
• A great podcast episode: Seth Godin on Animal Spirits
• And much more

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn and X

Chapters
00:00 Musical nostalgia
03:40 Technology and pop culture
06:08 Speaking at Stanford BioDesign
08:15 Lightning Demos
14:00 Outside inspiration leads to better ideas
17:35 How we used Lightning Demos with Cala Health
21:35 Lightning Demo Demos
23:04 Lightning Demo: Oura Ring
27:47 Lightning Demo: Fathom
32:35 Making a palette of Lightning Demos
35:33 Lightning Demo: Playdate
43:55 Review of today's Lightning Demos
45:12 The viral Mr Beast production memo
47:27 Seth Godin on the Animal Spirits podcast

This week on episode 4, we talked about:

• Jake's train station
• A disappointing dialog at the end of Diablo 3
• What’s so incredibly great about hoodies
• Teddy Ruxpin, the original edtech product for kids
• Curiosity Labs, a Character portfolio company building educational AI companions for kids
• The founding story of YouTube Kids
• Getting new product ideas from real-world customer behavior
• Two different ways to pitch the same company
• Should founders follow “best practices” when pitching investors or try to stand out?
• Fathom’s Series A
• How we found Fathom (and then decided to invest)
• Authenticity in sales
• Why we go out of our way to pitch ourselves to founders
• Our Design Sprint with Fathom
• Almond butter in oatmeal
• A great book: Against the Gods
• And much more

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn and X

Chapters

00:00 A diabolical dialog box
03:54 The importance of throughline
05:45 Where is Jake's sweatshirt?!
07:39 How sweatshirts work
09:13 Teddy Ruxpin
11:24 Building the pitch for Curiosity Labs
17:04 How a side project became YouTube Kids
22:49 A better way to pitch VCs
33:56 How Fathom got to Series A
40:30 How VCs do outbound sales
45:48 How authenticity shows up in products
53:21 Good beans
57:14 An extended self-congratulatory ad for Character and Design Sprints

This week on episode 3 of Jake & JZ, we talked about:

• The Seinfeld Moviefone episode (”Why don’t you just tell me what the product does?”)
• The Startup Wayback Machine (continued!), our technique for learning from successful companies in their early days
• Websites through the years, including Uber in 2011, iPhone in 2007, Slack in 2014–2017
• Solving one problem well before you try to solve a bunch of problems
• A great LinkedIn post from Kushal Byatnal (founder of Character portfolio company Extend) about selling your product before you build it
• A fun tabletop analog game called KLASK (check out this epic game on YouTube)
• A great movie: The Eagle Huntress
• And much more

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn and X

Chapters

00:00 Seinfeld and "Moviefone"
05:13 The Wayback Machine
09:09 Wayback: Uber
18:01 Wayback: iPhone
25:42 Wayback: Slack

This week on Jake & JZ, we talked about:

• What Why How, our simple framework for great marketing
• How successful companies apply this framework… or don’t! We compared Oura, Fathom, Playdate, Fletch, Meta Quest, and Apple Vision Pro
• How Nintendo redefined not just themselves, but the entire video game market
• Why founders should start with the story and differentiation, not the product
• The Startup Wayback Machine
• A great book: Pattern Breakers by Mike Maples Jr
• A great article: The Idea Maze is a Useless Idea by Cedric Chin
• Taking action to generate information

However, we did NOT talk about the election 😉

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn and X

Chapters
00:00 Nintendo zags when the world zigs
04:49 Character Labs
05:34 What-Why-How Framework
09:18 The Importance of a Clear Story
12:28 Examples of the 'What, Why, How' Framework in Action
21:39 Crafting Clear and Compelling Messaging
23:47 More What-Why-How Examples
33:32 Apple Vision Pro vs Meta VR: Marketing
43:47 Lessons from 'Pattern Breakers'
50:47 Challenging the Idea Maze

This week on Jake & JZ, we talked about:

• Advantages of remote vs IRL work for startup teams
• Character Labs, our sprint program for pre-seed founders
• Why some founders feel anxious when they aren’t writing code
• Our first exit of a Character portfolio company (Reclaim was acquired by Dropbox)
• The ongoing quest for a distraction-free phone (Jake ordered the Lightphone III)
• The story of Nintendo on the Acquired podcast
• Bit Timer, a nice timer for iPhone
• And much more

📩 Get an email about every episode at JakeAndJZ.com

💸 Learn more about our seed fund Character Capital

🥸 Find Jake on LinkedIn and X

🤠 Find JZ on LinkedIn and X

Chapters
00:00 Jake’s Sketchy Business Expense
06:39 Introducing This Podcast
08:10 Character Labs
10:24 Even More About Character Labs
22:11 The First GPU? Maybe?
23:17 In-Person is Special
25:38 Geographic Memory
36:25 Dropbox Buys Reclaim
40:18 How We Invested In Reclaim
42:11 That One Really Long Taylor Swift Song
42:35 Reclaim’s Multiplayer Sprint
43:35 Sort of a Magic Recipe
44:06 JZ Needs a Decent Timer App
49:46 $17 Per Week?!
51:56 Jake Talks About Nintendo For A Long Time