Tobi is one of the most thoughtful people in the technology industry. He's also one of the very few people who started as a programmer -- just trying to solve his own problem -- and still runs his company as CEO today even as it approaches a $200B market cap. Tobi has done this in two big ways: first, a willingness throw away his past beliefs in the face of new data, growing into the leader the company needed. And second, by remaining a close observer (and participant!) in how new technology emerges that changes what is possible.

Today we talk with him about both. The first half of the episode is about what has changed for him in the AI era. How he spends his time with AI throughout the day, how he thinks about what AI unlocks philosophically, and what he thinks the impact will be on all of us and what we build. The second half is more about Shopify. How he dealt mentally with the explosion in stock price in 2021 from a 20x revenue multiple to a 70x revenue multiple. And then, what he subsequently did when it all came crashing down. We also talk with him about the leadership and product principles that he's employed to steadily grow the company's revenues to an all-time high today.

Links:

• John Collison's Tweet: "Museum of Passion Projects"

Sponsors:

Koyfin: https://bit.ly/acquiredkoyfin

Is AI just better software? Or something completely different that requires a new paradigm to understand? Today we sit down with Bret Taylor and Clay Bavor, two of the best product builders in the world to tackle that question. Bret and Clay are the co-founders of the AI company Sierra.

Brett's resume reads like a greatest hits of Silicon Valley: co-creator of Google Maps, founder of FriendFeed (acquired by Facebook where he became CTO), founder of Quip (acquired by Salesforce where he became co-CEO), former Chairman of the Board at Twitter, and current Chairman of the Board at OpenAI. Clay spent 18+ years at Google, starting as an APM alongside Brett and eventually running product for Gmail, Drive, Docs (all of Google Workspace), Google Labs, and the company's AR/VR efforts.

In addition to AI, today’s conversation has some great tech industry history discussion and old Google stories, perfect to tide us all over between Google Part I and Part II!

Additional Topics:

• The accelerating adoption curves of technology waves, and if we’ll ever see an app that gets a billion users in one day
• Second- and third-order effects of agents on the internet economy and customer experience
• Making predictions on which AI terminology will stick and what won’t
• New pricing models in the era of AI, like “outcome-based pricing”
• What it’s like to build teams in this new AI era

Links:

• Sierra

Sponsors:

• Plaid: https://plaid.com

The Savannah Bananas have created a whole new sport. It’s baseball, but it’s not. It’s fast-paced, exciting, and incredibly entertaining. For example, if you're batting, and you step out of the batter’s box... it’s a strike. If you bunt, you’re out. If a fan catches a foul ball… you’re also out. Games are capped at two hours with no exceptions. It’s sacrilegious to traditional baseball fans everywhere. But it’s hard to argue with their numbers: they have 3.2 million fans on a waiting list to see them and have been selling out 80,000-seat football stadiums over the past few months!

Today, we sit down with Jesse Cole, founder of the Savannah Bananas and creator of Banana Ball. We unpack the whole story, staring with a failing college summer league team, an air mattress, and a $30 weekly grocery budget. But these days... it's safe to say that Jesse and his wife don’t have to sleep on an air mattress anymore! And they have built the business in their own way, fully under their control, and uniquely “fans first”. They have a unique all-in ticketing model, where your game ticket gets you full access to food along with your seat. There are no ads or sponsorships. There are no ticket fees or middlemen. And in fact, Jesse and crew will even pay the sales tax on your ticket for you! Jesse is just totally obsessed with delighting fans, controlling the end-to-end experience, and thinking long term… even if it means leaving (a lot) of money on the table today.

This may be our most fun ACQ2 (or Acquired!) episode ever. Enjoy!

Sponsors:

• Plaid: https://plaid.com