VC vs. bootstrapping and how to build big things with a small team

Today I'm visiting Stripe's office in San Francisco to chat with Patrick Collison and Courtland Allen, shortly after they announced their latest round of funding, valuing the company at a whopping $20B.

Patrick Collison is the CEO and co-founder of Stripe, an ambitious company aiming to increase the GDP of the internet. The now 1,300 person company was started in 2010 by Patrick and his brother, John Collison, at the age of 23 and 21, respectively. While young, this isn't their first startup. Prior to founding Stripe, Patrick and his brother started and sold Auctomatic for $5M in 2008.

Courtland Allen is a super talented designer and developer. In 2016 he founded Indie Hackers, an awesome community of bootstrappers and makers sharing their stories. Nine months later Stripe acquired the company. Courtland is also a Y Combinator alumnus and an MIT graduate with a degree in Computer Science.

In this episode we talk about:

• Who Patrick and Courtland's role models were when they were building their businesses, and how the right role models today can help build a more inclusive tech ecosystem.
• The influence of Indie Hackers on Stripe and why even with the great tech for online communication today, some of the best interactions between its community members happen at meetups.
• If there's too much or too little funding in tech and how the investor-founder dynamic changes when you move outside of Silicon Valley.
• Why Stripe started a book publishing business (in 2018) and the reading habits of Patrick, Courtland, and others at Stripe.

We of course also talk about some of their favorite products including a product to tell you how you sleep, helpful tools for building your next app, and some “oldies-but-goodies” that you might have forgotten about.

We’ll be back next week so be sure to subscribe on Apple Podcasts, Google Podcasts, Spotify, Breaker, Overcast, or wherever you listen to your favorite podcasts. Also, big thanks to our sponsors, Airtable, GE Ventures, Intercom and Stripe for their support. 😸

Quotes from This Episode

“How do we help increase the number of successful companies that get started in the world? The number of companies that get started is not some sort of cosmological constant, and if it can be increased then I think it's incredibly valuable to go and do that.” — Patrick

“Indie Hackers the movement wouldn’t have been as possible ten years ago, because there's so much more knowledge being exchanged now and so many more tools to help you build things — it's just easier to do with a small team than it ever has been.” — Courtland

“People are subject to extremely strong Girardian herd effects, so I don’t think investors are unique in this regard — they index on this popular conception of things. I think startups outside of the popular hubs are less popular than they ought to be and that people update too slowly based on changing trends.” — Patrick

“There should be more funding in the world, but more spread out and distributed more evenly.” — Courtland

“It all comes back to this idea of, 'how do we grow the GDP of the internet?'” — Patrick

Companies and Products Mentioned in This Episode

Airtable — Realtime spreadsheet-database hybrid.

Firebase — App success made simple by Google.

JUMP — Electrified, dockless bike rentals.

Emfit — Contactless sleep sensing solutions.

Pocket — Save and read news, articles and videos that fuel your mind.

Retool — Build custom internal tools in minutes.

Uber — Get a ride in minutes.

WhatsApp — Fast, cross-platform messenger.

Yelp — Crowd-sourced reviews for local businesses.