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 tr...
May 06, 2022•1 hr 20 min
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...
Mar 16, 2022•1 hr 30 min
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 doi...
Mar 05, 2022•44 min
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 categ...
Feb 16, 2022•44 min
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.
Dec 14, 2021•56 min
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 T...
Nov 09, 2021•45 min
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 di...
Nov 08, 2021•1 hr 14 min
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...
Nov 01, 2021•39 min
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 Ca...
Oct 25, 2021•33 min
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. &n...
Oct 18, 2021•38 min
Today was a treat on the show - we had one of the most successful and thoughtful entrepreneurs in the tech ecosystem join us: Brad Feld. Brad has been an early-stage investor and founder for the last 30 years - most notably, he co-founded Techstars, was an early-stage investor in companies like Zynga, Fitbit, Harmonix, and Makerbot, and for the last 15 years has been running Foundry Group, which has raised over $1.5B to invest in the next generation of tech companies. Brad recently wrote a book ...
Oct 12, 2021•46 min
Today we once again dove into the messy world of healthcare and specifically focused on innovation in consumer healthcare. Healthcare, as we’ve discussed before on the show - especially in the US - is complex, convoluted, and perplexing. While we spend anywhere from 50-200% more money than other developed nations, our quality of care here in the US is materially worse. When we introduce technology into healthcare, it opens up a wide variety of opportunities. I was excited to be joined by Ran Sha...
Oct 04, 2021•27 min
You can’t go anywhere today without hearing the term “artificial intelligence” - governments, industry, and startups are thinking through how to build, leverage and harness AI on a daily basis. But what really is AI and how do you build an AI first company? What’s overhyped about AI and what’s underhyped and not nearly talked about enough. We answered these questions and more today with Ash Fontana, Managing Director of Zetta Venture Partners. Ash has built a career building and investing in sta...
Sep 27, 2021•34 min
Today we dove into the messy world of healthcare. Over the last 20 years, hospital services have become more expensive by over 200% in the United States. An oddity of sorts given that most costs have gone down - technology comes in, unleashes innovation and has a deflationary effect on price. Healthcare has been the opposite - it’s complex from a regulatory perspective and an operational perspective. I’m always inspired by founders taking on healthcare and this week was glad to chat with Michell...
Sep 21, 2021•33 min
Over the last 10 years, we’ve seen an incredible amount of progress and innovation in harnessing large data sets. Social graphs, payments platforms, e-commerce - the world is becoming smarter, more efficient and more is becoming possible because of our ability to derive insights from data. But innovation in the earth’s data has been nascent - today I talked to one of the most revered product leaders in Silicon Valley about how might we capture the world’s information and then the possibilities f...
Sep 15, 2021•33 min
Today we’re joined by Gary Hoberman, Founder & CEO of Unqork. One of the hottest topics in software today is low code / no code - and with good reason. Low code / no code empower anybody with an idea to build without the constraints of technical knowledge. Prior to founding Unqork, Gary was the CIO of MetLife where he managed a $1B+ budget and a team of over 8,000 individuals. In this role Gary saw the power of applying low code and no code for the enterprise. Today Unqork has raised over $3...
Sep 06, 2021•34 min
We’ve all heard of “big data”, but the lesser-known is “big code.” This is an emerging challenge and opportunity for companies today - a challenge because the amount and complexity of code is growing; opportunity because its value is also growing. Most tools and practices for code management were not built for an era of Big Code - the implication is codebases that are especially large (which is the case in most at scale organizations) are brittle; any individual change may shatter the whole thin...
Aug 30, 2021•25 min
Today we’re joined by Russ Heddleston, Founder & CEO of Docsend. DocSend is one of the most ubiquitous document-sharing products in the tech industry today. What started out as a simple product to send links has turned into a holistic and robust suite of workflows, privacy settings, and analytics for documents. So much so that large software companies have taken notice - Dropbox recently acquired DocSend for $165 million. Russ and I chatted through the founding story of DocSend, how they gre...
Aug 23, 2021•31 min
Today we’re thrilled to welcome Founder and Investor, Justin Kan. Justin has founded a number of companies over the past 2 decades but the one he’s most well known for is Justin.TV. Justin.TV was one of the early pioneers of live video streaming. After rebranding to Twitch, the company later sold to Amazon in 2014 for $970M. After Twitch Justin spent time as a Partner at YC where he evaluated and funded hundreds of startups. Recently he’s started his own firm GOAT capital. Today we talked with J...
Aug 17, 2021•30 min
Today I’m thrilled to have 8x Olympic Champion Apolo Ohno on the show. Apolo is one of the most decorated Winter Olympians in United States history. In this episode, we unpacked what it takes to be a champion – dedication, sacrifice, and, most importantly, mental fitness. Apolo walked us through how his mindset matured over the years, how he applied it to his sport, and how he continues to apply it today in business.
Aug 09, 2021•28 min
The world of private fundraising is going through a generational moment - meme stocks, NFTs and Robinhood. Everybody is looking to become an investor and with the right reason - the vast majority of wealth creation in the world has come from private assets, not public assets. The challenge historically, though, has been a lack of connectivity and access for the private investor. Private investors couldn't get involved, and the operational complexity for companies to take advantage of this invest...
Aug 03, 2021•26 min
This week we had David Sacks back on the podcast for round 2. There are few individuals in the world that have seen, built, and led multiple of the world’s iconic companies. David is one of them. He was a core member of PayPal and served as the company’s first product leader and COO. David went on to found enterprise collaboration company Yammer, one of the fastest-growing SaaS startups in history - Microsoft acquired Yammer for $1.2B just 4 years after its founding. Not only has David been a su...
Aug 03, 2021•25 min
This week we dove into the world of performance management - the last decade has seen significant change across virtually every function in business; the evolution of marketing, sales, customer success, product and operations departments has been tremendous. HR on the other hand, has been a laggard; historically a back office cost-center, typical HR organizations have followed the mandate of being compliant, administrative and "doing less." This curve has started to shift materially over t...
Jun 09, 2021•38 min
We’ve done a lot of deep diving into the infrastructure of e-commerce and marketplace on this show. We’ve explored shipping as an API and shipping infrastructure in developing countries. This week we took another spin on the topic - we talked about the cloud supply chain. Ok what does that mean? Simply put - if you had one software platform that could manage all of your fulfillment, shipping, warehousing and logistics needs - what would that look like? More importantly, what would it unlock for ...
Jun 09, 2021•45 min
Whenever you think of major cities in North America, they all have a vibe - NYC is legendary for Wall Street, San Francisco for Tech and LA for Hollywood. But over the last 25 years, one firm has blended the best of all 3 worlds: UpFront Ventures. Upfront is LA’s largest venture firm and has invested over $2B in startups across notable winners like Bird, Ring, thredUP, TrueCar and GOAT. This week I chatted with Kara Nortman, Co-Managing Partner of Upfront. Kara’s cool - she had a lot of unique i...
May 19, 2021•49 min
The theme of the past year - in an obvious sense - has been how we continue to lead progressive, efficient, and normalized work lives in a highly unnormal world. The pandemic has forced us to rethink how we collaborate, engage and connect from first principles. One of the most ubiquitous products we all use in that effort is Dropbox - and it’s why this week I was thrilled to be joined by Timothy Young, President of Dropbox. Talking with Timothy was unique and interesting on multiple levels - on ...
May 18, 2021•56 min
This week we dove into healthcare. Everybody listening has had a subpar experience with our healthcare system - whether it’s a friend, a colleague, a family member or a personal experience, our healthcare system is fraught with challenges. Part of the reason the system is so difficult is because of how the incentives are set up - patients, primary care physicians, specialists, health care systems, insurance companies have a web of complex intertwined interests. That’s also what makes it so inter...
May 12, 2021•39 min
One of the most transformational companies of the last 20 years has undoubtedly been Uber - in a sense it’s incredible to think in 15 short years we’ve come from the launch of the iPhone to now powering a global transport system with the click of a button on that same phone. This week I caught up with someone that was largely responsible for making that transformation a reality - Manik Gupta, Former Chief Product Officer of Uber. Manik and I spent time chatting about Uber, but also extended the ...
May 11, 2021•47 min
We’re going through a renaissance period in consumer health right now - new tech enabled products are coming out for sleep, telehealth, diet, nutrition and more. This week’s guest took us deep into what optimizing the metabolic function looks like. As I learned in prep for this conversation, seven of the 10 leading causes of death in the U.S. are strongly related to metabolic dysfunction - metabolic function improves energy, endurance, memory, mood and cognitive performance. Josh Clemente has bo...
May 04, 2021•58 min
We’ve talked a lot on this podcast about emerging and resulting trends that will stick with us a function of COVID-19: higher education being disrupted, consumer health being further tech enabled, the rise of crypto, and AI and machine learning impacting functionally every industry. But underneath the core of every industry we’ve talked about is people and global workforces. It’s why this week I was excited to chat with Alex Bouaziz, Founder and CEO of Deel. Deel is solving the incredibly comple...
May 04, 2021•38 min
