Andrew Ross Sorkin does the work of about five people. He founded and writes the DealBook newsletter for the New York Times. He hosts Squawk Box on CNBC every morning at 6am. He runs the DealBook Summit, which has become the premier annual interview event across business, policy, and technology. He co-created the TV show Billions. He wrote the definitive account of the 2008 financial crisis, "Too Big to Fail", and now he's written "1929," a 600-page epic about the greatest crash in Wall Street history. So how does he actually do all of this?

Today we sit down with Andrew to answer exactly that question. We dive into his philosophy on interviewing, his start as a teenage freelancer at the New York Times, how he built DealBook from a daily column into a media empire, and his actual daily routine that somehow fits all of this into 24 hours!

Links:

• Andrew’s new book 1929
• DealBook
• The DealBook Summit
• Squawk Box

Sponsors:

• Shopify

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:

• Plaid: https://plaid.com

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:

• Sierra: https://bit.ly/acquiredsierra

We sit down with Zach Perret, CEO of Plaid, to discuss the remarkable journey of Plaid and the broader fintech landscape over the past several years. Zach takes us blow-by-blow through journey of almost getting acquired by Visa, the challenges faced during the COVID-19 pandemic… which quickly reversed with ZIRP tailwinds, and how Plaid navigated the volatile market conditions to build a diversified business. We explore the company’s strategic pivots, including their expansion into analytics for fraud detection, alternative credit systems, and bank payments. If you’ve ever wondered “how do you turn from one simple product into a more durable business?” this episode is for you.

Links:

• Come see Acquired LIVE at Radio City Music Hall!

Sponsors:

• Sierra: https://bit.ly/acquiredsierra

We sit down with ServiceNow CEO Bill McDermott for a masterclass in the art of enterprise sales — a topic where Bill ranks as one of the all-time greats by any measure. Bill started his career as a bag-carrying salesman at Xerox in New York City (alongside Howard Schultz!) back in 1983, and rose to become the company’s youngest corporate officer at age 36 before going on to become CEO of global software giant SAP. Since joining ServiceNow in 2020 Bill has grown the company from $3.5 billion in revenue over $10 billion today, and a nearly $200B market cap — which makes it one of the largest enterprise software companies in the world. Whether your job directly involves selling or not (and if you’re a founder, make no mistake — selling is the MOST important part of your job) there’s something here to be learned for everyone. Break out your notebooks and enjoy!

Links:

• ServiceNow
• The SPIN selling method
• Bill’s fantastic interview with Ben Thompson on Stratechery

Sponsors:

• Sierra: https://bit.ly/acquiredsierra

Vercel has become the infrastructure platform powering modern web development over the past several years, with companies from Stripe to Adobe to Runway all building their front ends on them. Today we’re joined by founder and CEO Guillermo Rauch, who shares why Vercel has been uniquely successful in the fragmented (to say the least!) world of web development platforms. There are now more than 6 million Vercel users, 80,000 active teams, and users have grown 200% year-over-year. The company also crossed $100m in annualized revenue last May, and Guillermo shared with us that they’ve been growing at 80% since, and were recently valued at $3.25 billion.

This is also a particularly interesting moment for Vercel. Last year they launched a new product, “v0”, which lets anyone create and deploy a working website simply by describing it in English and letting AI take care of the rest. Guillermo shares its origin story within the company (and insanely that it reached $2m ARR in the first 14 days!), and how it’s changed their entire thinking about what’s possible now with AI products.

We also cover:

• How to build a business around an open source project (Next.js)
• How they balance both being a fast and nimble platform for startups with being a reliable platform for enterprises
• Guillermo's unconventional approach to staying deeply technical as CEO at scale

Links:

• Vercel
• V0.dev
• Next.js

Sponsors:

• Sierra: https://bit.ly/acquiredsierra

ARM is an incredibly unlikely story. They were founded in Cambridge, England in 1990 to design a new chip architecture just for low-power devices (like the Apple Newton!), leaving the “serious computing” on desktop and servers to Intel’s x86. Now, nearly three decades later, ARM is the dominant architecture in all of computing today.

ARM is in your phone, your car, data centers, the most advanced AI chips… there are hundreds (or thousands!) of ARM chips you encounter in your everyday life. In this episode, ARM Holdings CEO Rene Haas joins us to tell the story of how ARM become so dominant, weaving through the through the iPod, smartphone, and AI eras. Plus, their wild corporate story of going public, getting bought by SoftBank, going public again, and nearly being acquired by NVIDIA!

Sponsors:

• Sierra: https://bit.ly/acquiredsierra

Duolingo has fundamentally changed the landscape of self-guided education, starting with language learning. It is now a $9B publicly traded company in a space where everyone thought you could never build a large and exciting company. We’re joined by Duolingo founder and CEO, Luis von Ahn. Luis dives into how learning English was transformative in his personal trajectory and opportunities in his life, inspiring him to create the most successful EdTech product of all time. A few topics in this episode:

• How Duolingo became a leader in the gamification and mobile-first movements in the early 2010s
• How the company balances rigorous experimentation with gut instinct to build an app with customer experience at its core
• The backstory of Duolingo’s “unhinged, yet wholesome” green owl mascot trending on your TikTok feed

Sponsors:

• Sierra: https://bit.ly/acquiredsierra

We sit down with Hugging Face CEO Clem Delangue to understand the current state of the open source AI ecosystem. Hugging Face is the leading platform to host and collaborate on AI models, datasets, and applications. They also have a compute offering for AI builders to train their models directly on the platform. Clem has a contrarian take on the future: there will not be just a few major foundation model companies with everyone using their APIs. But rather, that thousands of companies will have their own specialized AI models built in-house for their particular use case. It's obviously a very dynamic landscape and we'll have to see how it shakes out, but Clem has a pretty great viewpoint to see it all, working with their 5 million registered Hugging Face users!

Links:

• Hugging Face
• Hugging Face's Series D valuing the company at $4.5 billion

Sponsors:

• Sierra: https://bit.ly/acquiredsierra