120: Ravi Gupta, Partner at Sequoia & Former COO/CFO, Instacart

Welcome to Square One. This week we took a turn on the normal type of episode we have - I chatted with the author of one of the most influential books I’ve read over the past year - it’s called Wanting and the author is Luke Burgis. We all "want" things in life, but it's hard to pinpoint where those desires necessarily come from. Luke took a deep dive into the origins of desire in his book and shares frameworks that give perspective on how we come to want certain things in life and how we can transform our relationship with desire in ways that allow us to live a more aligned, fulfilling existence with other people. This was an especially interesting episode to me because this mentality and mindset applies as much to our professional lives in thinking about how to operate a business or invest in a business as it does our personal life in leading a fulfill life.

One of the most enjoyable and educational types of conversations we have on this show is with individuals that have operated and invested at the highest levels. It’s a unique blended perspective which provides insight and empathy for founders on their journey to build generational companies. This week I was thrilled to be joined by Ravi Gupta, Partner at Sequoia Capital. Prior to Sequoia, Ravi served as CFO/COO of Instacart. We covered a variety of topics in this wide ranging discussion - how to lead while being demanding & supportive, desperation-induced focus, building enduring culture and the interrelation of agency, trust and authenticity. This was one of the most enjoyable conversations I’ve had on the podcast and I was lucky to have it with my good friend Ravi.

Today we went deep into the world of barbershops - small business tech historically has been an underserved segment of the tech industry but over the last decade a number of interesting businesses have been built serving this cohort which has inspired a variety of applications. I talked to Songe Laron about building Squire - an all in one platform that helps barbers run their barbershops. This was a fun episode - Songe and team have raised over $100M to build this company. And though they’re doing really well, the journey has been anything but smooth (from initially buying a barbershop and running it to learn more about the space to operating through COVID). We broke down building through adversity and more in this conversation.

This week, I was thrilled to chat with Nick Mehta, CEO of Gainsight. Gainsight is a particularly interesting company and story to unpack - they are the "category creators" of customer success. CS is a common place role and function in tech today, but creating software for CS was less than obvious 10 years ago. Since joining in 2013, Nick has led Gainsight through explosive growth, raised $150M+ and grown the team to 700+ people.  In this episode, we unpacked lessons learned building a category creator, how to work through hitting a wall on the journey of explosive growth and how Nick thinks about fundraising in today's market.

Today, I was thrilled to chat with Sherwin Gandhi, Co-Founder and President of Jeeves.   Since launching two years ago, Jeeves raised just about 100 million dollars in equity to develop a new type of financial platform that can lend, ensure, and underwrite capital to global companies.  In this conversation, we dug into how Sherwin thinks about the payment landscape building a global company from day one and how cryptocurrency will change the way we transact.

This week, we go deep into what in the world is going in China. I was joined by Jacob Helberg, Co-Chair of the China Strategy Initiative at The Brookings Institution. Jacob is one of the most respected policy minds on this issue, and I wanted to have him on the program because he has a unique background in policy and technology, previously serving as Google's Global News Policy Lead. We dove into a wide range of topics in this discussion, including;  Whether we're in a cold war with China The idea of dual-purpose technologies and how they can change the rules of the game The right policy framework to be thinking about our engagement with China And a host of solutions on what the US can and should do over the next decade.

Today I was thrilled to be joined by Chamath Palihapitiya, Founder and CEO of Social Capital. Chamath is best known as an early member of Facebook’s Senior Executive Team where he played an instrumental role in the company’s exponential growth. Over the last decade, he has been investing actively in the private and public markets. Some of Chamath’s most notable investments include: Slack, Tesla, Amazon, Bitcoin, Virgin Galactic and Opendoor. We covered a variety of topics in this wide ranging discussion - our impending shift to decentralization, the role of risk capital in society, the myths about the private and public markets, how government and corporations can work together to fix capitalism. We rounded out the discussion on a more personal note and talked about what motivates Chamath and how he defines his north star. This was one of the most enjoyable conversations I’ve had on the pod.

Today we dove into the world of checkout. Everybody is familiar with check-out - it’s the last step in the purchase process when you’re buying something whether in person or online.    A less known fact is that purchase process drop-off is a $10 trillion problem for businesses worldwide. And checkout software is not nearly as easy of a problem as meets the eye.   This week I chatted with my friend Ryan Breslow - Founder & CEO of Bolt. Bolt has created a full Checkout Operating System to help merchants unify / shoppers go through checkout. In this episode, we unpacked a lot of the network effects that they will now be able to take advantage of.   Bolt has grown its valuation 18x in 18 months to $6B and with 10 million shoppers on their platform has hit escape velocity to reach the next level of growth.

The Indian startup ecosystem has been on an absolute tear over the last decade. With the increased success of founders, ever more capital flowing into the ecosystem and structural and cultural changes taking place across the entire country, India has never been more ripe for a promising technology future. Today we chatted with one of India’s most accomplished founders - Kunal Bahl. Kunal co-founded Snapdeal 13 years ago and continues to lead the company as CEO today. He also has started Titan Capital with his co-founder Rohit Bansal - Kunal, Rohit and team have invested in over 200 startups in India over the past few years. We picked his brain on building, scaling and investing in many of India’s most promising startups.

E-commerce and online brands have absolutely exploded post-COVID-19, and with it, a number of interesting platforms have been developed to help e-commerce businesses and brands take advantage of scale.    Today I chatted with Helen Vaid, CEO of Foundry - a brand platform that acquires and grows enduring digital brands. Foundry recently launched with $100M in equity capital from LightBay Capital and Monogram Capital Partners to acquire, integrate and scale enduring online businesses.  Helen has a really interesting background and perspective she brings to the table to lead the company.  She was formerly the Chief Global Customer Officer of Pizza Hut and has built a career scaling omnichannel for CPG companies. She’s also the only woman CEO amongst 60 aggregators that have raised almost $6 billion in capital since April 2020.