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!
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.
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 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!
On our AWS episode, we talked briefly about the next chapter of cloud: data warehouses. But what makes them so powerful? Why do enterprises rely on them? And how will cloud customers collaborate on data stored in multiple clouds?
We sit down with Kamakshi Sivaramakrishnan, the co-founder and CEO of Samooha, a new company backed by Altimeter and Snowflake Ventures to tackle the problem of secure data sharing and collaboration in the cloud. Kamakshi has an impressive background to speak to this problem, having been a part of AdMob (sold to Google), and the founder/CEO of Drawbridge, which sold to LinkedIn. She then went on to work in Microsoft's Office of the CTO, where she obviously had a lot of experience understanding the needs of cloud customers.
If you want a better understanding of how enterprises use the cloud, multi-cloud architecture, and how security and privacy works with customer data at scale, this episode is for you!
Statsig CEO and former Facebook VP Vijaye Raji joins us to discuss democratizing the tools of big tech. Before starting Statsig, Vijaye spent 10 years at Facebook where he led the development of their mobile ad product (yes — THAT mobile ad product that’s the core of FB today).
We talk all about about Facebook’s early days in mobile, and the internal building and shipping process that let them continuously experiment and roll out features out to billions of users, which Statsig is now bringing to engineering and product teams everywhere. This episode is a must-listen for product builders at all stages!
Listen in any podcast player.
We sit down with Altimeter Capital’s head of Capital Formation Meghan Reynolds (who previously was TPG’s global co-head of Capital Formation for 10 years) to talk about everything that goes into the LP - GP relationship at venture funds. We cover how (and why) to think strategically about Capital Formation, why it should be about so much more the just investor relations / fundraising, and also why and how it’s going to change dramatically over the next decade. This was a GREAT conversation, and very relevant for GPs, LPs, and also company founders and employees heading into 2023 and post zero-interest-rate capital markets.
Listen in any podcast player.
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On this episode of ACQ2, we are joined by Chetan Puttagunta, General Partner on Benchmark, talking his investment philosophies, enterprise technology trends, and the uniqueness of Benchmark. How is this firm with only five partners and no associates so repeatably successful? Chetan shares the story of his very first investment, MongoDB, and lessons learned from his other investments and board positions in Elastic, Sketch, Duffel, Mulesoft, and many others.
Chetan also helps us understand how he balances staying open-minded enough to let founders shape his vision of the future (and not the other way around), while staying educated on areas where he thinks the future is bright.
Tracy Lawrence, founder and CEO of Chewse (@chewse) takes us on the journey of how and why she founded Chewse. Tracy, Ben, and David discuss most of the traditional topics (early days, product-market fit, mission alignment), but spend most of the time talking about non-traditional topics like mental health, vulnerability, and love for company and self. If you’re a founder, this episode will perk both your IQ and your EQ. For everyone else, your faith in the future of tech might get restored. Enjoy!
We're joined by Stanford professor and senior advisor to Airbnb, Uber, Stitch Fix and Wave Capital, Ramesh Johari, who is one of the world's leading experts in marketplaces. Ramesh has been advising David and his partners at Wave since day one, and we're super excited to bring his incredible experience and insights to all of our ACQ2 listeners. In this conversation we dive deep into nearly every aspect of starting, building and then operating a marketplace at scale. Whether you are a marketplace entrepreneur, employee, investor, or just curious about how some the most powerful businesses of our time work, this is not one to miss!
Ben and David discuss the newest development in the venture ecosystem, startup studios, through the lens of Pioneer Square Labs (which Ben cofounded in 2015). David manages to trick Ben into sitting on the other side of the table and being interviewed about how PSL works, how he and his partners started it, and what lies ahead!
For more information, check out PSL
Ben and David couldn’t agree on topic for this LP episode with the clock winding down to our recording going live... so we decided to “do it live” and commentate on our Twitter feeds haha (and discuss your survey feedback). We hope you enjoy this fun slice of randomness, and we’ll be back with more actionable interviews and company building topics very soon!
We dive into one of the most critical components of company building, recruiting product leaders (and executives in general), with Andrew Abramson of Riviera Partners -- one of the most elite search firms in silicon valley. We cover first how companies and founders should think about recruiting senior leaders, from knowing when you're ready to working with search firms. Then we dive into the other side, how product managers should think about managing and progressing in their own careers toward senior leadership roles. Thanks to Andrew for joining us and we hope everyone can take away something applicable for their own companies and careers!
In this episode, Ben and David dive into the evolution of Seed Funds and how early stage investing has changed in the last two decades both for investors and founders alike. Understanding the past changes in the ecosystem helps founders and investors establish themselves for the future. If you are an early-stage founder, this episode will contextualize the information you need to prepare your company for investment.
The right amount of diligence is a great topic to think about, whether a company is ready for investment or not. This episode was made for founders getting ready for investment, or founders who want to start asking the right questions about their work. Ben and David discuss in depth what you can reasonably expect from VCs conducting diligence, and how to set yourself up for long-term value creation. Most importantly, Ben and David discuss the questions you should be prepared to answer and the questions you should be prepared to have asked about you.
We are very excited to be joined by Phil Kimmey, one of the co-founders of Rover (and a frequent member of various 30 under 30 lists), who designed Rover in its infant stages at a Startup Weekend! In this episode, we dive into Rover’s initial design, how the business model was proved, and wrap up with a lengthy discussion on Value-Add Features vs Data-Driven Features. Phil also provides his opinion on what makes new tech and development teams successful and explains why PayPal still sends Rover’s monthly summary statements to his parent’s house.