Skip to main content
Square One: Conversations with the Best in Business

Square One: Conversations with the Best in Business

By Romeen Sheth

Square One unpacks the journey of founders, investors, and executives at the cutting edge of business.

The conversations on the show dive deep into a variety of industries, business models, and the stories of how some of the most innovative companies of our time have been built.
Available on
Apple Podcasts Logo
Overcast Logo
PodBean Logo
Spotify Logo
Currently playing episode

18: Hayley Barna, Co-Founder of BirchBox and General Partner at First Round Capital

Square One: Conversations with the Best in BusinessMar 22, 2018

00:00
43:28
121: Luke Burgis, Author of Wanting

121: Luke Burgis, Author of Wanting

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.

May 06, 202201:19:58
120: Ravi Gupta, Partner at Sequoia & Former COO/CFO, Instacart

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

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.

Mar 16, 202201:30:15
119: Songe LaRon, Founder & CEO of Squire

119: Songe LaRon, Founder & CEO of Squire

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.

Mar 05, 202244:24
118: Nick Mehta, CEO of Gainsight

118: Nick Mehta, CEO of Gainsight

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.

Feb 16, 202244:23
117: Sherwin Gandhi, Co-Founder & President of Jeeves

117: Sherwin Gandhi, Co-Founder & President of Jeeves

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, 202156:15
116: Jacob Helberg, Co-Chair of the China Strategy Initiative Working Group at The Brookings Institution

116: Jacob Helberg, Co-Chair of the China Strategy Initiative Working Group at The Brookings Institution

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.


Nov 09, 202144:42
115: Chamath Palihapitiya, Founder & CEO of Social Capital

115: Chamath Palihapitiya, Founder & CEO of Social Capital

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.

Nov 08, 202101:14:04
114: Ryan Breslow, Founder & CEO of Bolt

114: Ryan Breslow, Founder & CEO of Bolt

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.

Nov 01, 202138:48
113: Kunal Bahl, Co-Founder & CEO of Snapdeal

113: Kunal Bahl, Co-Founder & CEO of Snapdeal

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.

Oct 25, 202133:26
112: Helen Vaid, CEO of Foundry; Former Chief Customer Officer of Pizza Hut / BoD of Groupon

112: Helen Vaid, CEO of Foundry; Former Chief Customer Officer of Pizza Hut / BoD of Groupon

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.

Oct 18, 202137:37
111: Brad Feld, Founder and Partner of Foundry Group

111: Brad Feld, Founder and Partner of Foundry Group

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 on Nietzsche and lessons applicable for founders. In today’s episode, we took a different turn and talked about some of the most poignant lessons from the book and how they apply to build companies today.

Oct 12, 202145:59
110: Ran Shaul, Co-Founder and Chief Product Officer at K-Health

110: Ran Shaul, Co-Founder and Chief Product Officer at K-Health

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 Shaul, Co-Founder, and Chief Product Officer at K-Health today because K is one of the most dynamic and interesting companies currently in consumer healthcare.

K has raised close to $300M and is one of the few consumer healthcare companies that has created an enviable data set of anonymized health data. This has allowed their AI and machine learning to surface incredibly applicable insights for customers.

Oct 04, 202127:26
109: Ash Fontana, Managing Director of Zetta Venture Partners

109: Ash Fontana, Managing Director of Zetta Venture Partners

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 startups - he was an early and senior member of AngelList and since joining Zetta has been in generational AI-first companies like Canva, Invenia, and more.

Sep 27, 202134:19
108: Michelle Davey, Co-Founder & CEO of Wheel

108: Michelle Davey, Co-Founder & CEO of Wheel

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 Michelle Davey of Wheel.

Michelle has raised over $70M to empower better patient outcomes and create tools for healthcare workers. In this discussion we talked about the challenges of building in healthcare, where the opportunities sit, and how to build a hyper growth company.

Sep 21, 202132:38
107: Kevin Weil, President at Planet

107: Kevin Weil, President at Planet

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 for it. Kevin Weil served as a Product Leader at Twitter, Instagram and was the co-founder of Libra, Facebook’s cryptocurrency. He recently moved to Planet as President of the organization.

Kevin and I talked about what’s possible when you map and image the entire world in real time.

Sep 15, 202132:54
106: Gary Hoberman, Founder & CEO of Unqork

106: Gary Hoberman, Founder & CEO of Unqork

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 $350M from leading investors such as Blackrock, Goldman Sachs and CapitalG and Gary is on a mission to reimagine enterprise application development.

Sep 06, 202133:33
105: Quinn Slack, Co-Founder & CEO of Sourcegraph

105: Quinn Slack, Co-Founder & CEO of Sourcegraph

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 thing.

That’s where Sourcegraph comes in - Sourcegraph has raised over $200M to solve this very challenge. They’ve built software that empowers engineers to navigate the codebase and make changes that don’t have unintended downstream implications

In today’s conversation, I chatted with Sourcegraph CEO Quinn Slack on how he’s thinking through the era of Big Code and how Soucegraph is enabling organizations to operate in a more resilient manner.

Aug 30, 202124:53
104: Russ Heddleston, Founder & CEO of DocSend

104: Russ Heddleston, Founder & CEO of DocSend

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 grew the business through product-led growth, interesting insights learned from being on the other side of 1000s of pitch decks, and what the future for DocSend looks like inside of Dropbox.

Aug 23, 202130:52
103: Justin Kan, Co-Founder of Twitch

103: Justin Kan, Co-Founder of Twitch

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 Justin about lessons learned from founding, building, scaling, and investing in some of Silicon Valley’s best startups.

Aug 17, 202130:09
102: Apolo Ohno, Olympic Champion

102: Apolo Ohno, Olympic Champion

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, 202127:53
101: Ken Nguyen, Co-Founder & CEO of Republic

101: Ken Nguyen, Co-Founder & CEO of Republic

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 investor base was too difficult up until now. 

Enter Republic: an equity crowdfunding platform that's raised over 50 million dollars in venture capital to take on the status quo.

This week, we chatted with Ken Nguyen, Co-Founder & CEO of Republic, to get his perspective on the business and the future of fundraising. 

Aug 03, 202125:48
100: David Sacks, Co-Founder & General Partner at Craft Ventures

100: David Sacks, Co-Founder & General Partner at Craft Ventures

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 successful founder, but he has also been one of the most impressive investors in tech, having personally invested in over 20 unicorns, including Affirm, AirBnb, Facebook, Lyft, Opendoor, Palantir, Postmastes, Reddit, Slack, SpaceX, Twitter and Uber amongst others.

I got David’s thoughts on building and scaling multiple multi-billion dollar companies.

Aug 03, 202125:13
99: Jack Altman, Founder & CEO of Lattice

99: Jack Altman, Founder & CEO of Lattice

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 the last 5 years - we have a "war for talent" amongst employers and leverage has fundamentally shifted to the employee. COVID has provided a decentralization multiplier to this war and increased opportunity sets for talent worldwide. 

In 2018, I had Jack Altman - Founder and CEO of Lattice - on the program to discuss how HR has evolved. Since then, Lattice has raised over $100M and recently hit a $1B valuation. I invited Jack back on the program to discuss the rocketship journey of Lattice and how his thinking on performance management has evolved after serving as an Executive in the space.

This conversation was packed with insights on how to be an effective people leader. Enjoy. 

Jun 09, 202138:16
98: Sean Henry, Founder & CEO of STORD

98: Sean Henry, Founder & CEO of STORD

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 your business?

I invited Sean Henry, Co-Founder and CEO of Stord to come on the podcast and break down these very questions. Stord is solving this exact problem and has raised over $150M to do it. 

There are very few businesses where the proxy for market size is some variant of GDP - Stord falls in that bucket and it’s why I excited to learn from Sean this week.

Jun 09, 202144:53
97: Kara Nortman, Managing Partner at Upfront Ventures

97: Kara Nortman, Managing Partner at Upfront Ventures

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 insights on the state of venture and sports. A topic we nerded out on given Kara is one of the Co-Owners of Angel City, LA’s professional womens soccer team alongside her friends Natalie Portman, Julie Uhrman and Alexis Ohanian.

Tune into this one if you’re into the crossover between sports, leadership lessons and tech. I learned a lot from Kara in this conversation.

May 19, 202149:17
96: Timothy Young, President of Dropbox

96: Timothy Young, President of Dropbox

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 one sense, we dug deeply into the way Dropbox is reimagining the workplace and on the other hand we dove into how these changes in our work environment flow through the underlying products Dropbox is developing.

We spent a lot of time talking about Dropbox’s new “Virtual First” strategy, how companies overcome friction when introducing new ideas, building the right model and environment for employees and the challenges of remote work - at the employee, team and management levels.

I learned a lot from Timothy and this was one of the most engaging discussions we’ve had on the pod.

May 18, 202155:42
95: Sid Viswanathan, Co-Founder & President of Truepill

95: Sid Viswanathan, Co-Founder & President of Truepill

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 interesting to tackle. This week’s guest was Sid Viswanathan, Co-Founder and President of Truepill. Truepill has created an API to help enable pharmacy fulfillment and delivery, white label packaging and product design. Their goal - simply put - is to create a pharmacy infrastructure grounded in technology and automation to build a next generation healthcare platform.

Sid and team have raised over $100M to bring this vision to reality. In this conversation we discussed the challenges of innovating in healthcare, how Truepill provides customers with a better experience and the ups and downs of leading a hyperscale business.

May 12, 202139:08
94: Manik Gupta, Former Chief Product Officer of Uber

94: Manik Gupta, Former Chief Product Officer of Uber

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 conversation to leadership lessons and how he thinks about evaluating startups - we talked about how to think about resource allocation in hyperscale, the tradeoffs when developing product and the learning curve of leadership (he had over 1,000 people report to him in the span of 2 years).

We rounded out the latter part of the discussion diving into an ecosystem both he and I have been actively investing in lately and are excited about - India.

May 11, 202146:59
93: Josh Clemente, Founder of Levels Health

93: Josh Clemente, Founder of Levels Health

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 bought a biowearable metabolic sensor to market to help solve this problem - Levels is an innovative platform that pairs continuous glucose monitoring with an impressive software suite to provide the wearer with deep insights about their health.

In advance of this conversation, Josh’s team sent my wife and I both a Levels to see how the product works and it was incredible - it provided us actionable health information and helped us understand how specific foods, exercise and timing of day affected our metabolic health.

This episode was fun - Josh has experience at some of the most innovative companies in the world, like SpaceX and brought that experience to Levels to build a next generation category winner in healthcare.

May 04, 202157:40
92: Alex Bouaziz, Founder & CEO of Deel

92: Alex Bouaziz, Founder & CEO of Deel

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 complex and simultaneously important issue of global payroll.

As workforces have gone remote and international over the course of the past year, Deel has developed software to help companies stay compliant with local laws and tax systems while keeping international onboarding smooth and seamless. Deel has raised over $200M over the past year and just publicly announced a $1B valuation.

May 04, 202138:16
91: Erik Torenberg, Co-Founder of Village Global & On Deck

91: Erik Torenberg, Co-Founder of Village Global & On Deck

Higher education is currently undergoing one of the most significant transformational shifts the world has ever seen. On this podcast, we’ve talked to a number of companies disrupting higher ed - online bootcamps, vertical labor marketplaces and coaching platforms.

This week’s guest is taking aim at the entire "university bundle" - network, community, credentials and education. Erik Torenberg is the Founder and Chairman of OnDeck and Co-Founder of Village Global, a $150M venture fund.

On Deck aims to take the “university bundle” and apply it to the entire lifecycle of a person’s career. On Deck recently raised a $20M Series A led by Keith Rabois of Founder’s Fund to build “the Stanford of the Internet.”

In this episode, Erik and I chatted about his early experiences at Rap.fm and being employee #1 at Product Hunt. We then dove deep into all things OnDeck - specifically, how he is thinking of building a new type of university that will be around for the next 100+ years.

Apr 28, 202141:16
90: Anthony Pompliano, CEO of POMP Investments

90: Anthony Pompliano, CEO of POMP Investments

Crypto has taken the world by storm - a niche computer science topic less than a decade ago has finally entered the purview of mainstream today - Coinbase has filed to go public, institutions are accepting that Bitcoin and more broadly crypto should be a part of their asset allocation strategy and we’re starting to see a variety of interesting projects and applications take shape - one of the most popular as of late has been Bitclout.

But it hasn’t always been so obvious or so popular. One of the earliest and most consistent proponents of bitcoin has been Anthony Pompliano, Co-Founder of Morgan Creek Digital and current CEO of Pomp Investments.

In today’s conversation, Pomp and I discussed how his interest in bitcoin evolved - he was in the Army, led Growth teams at Facebook and eventually went full steam into crypto. We started at a foundational level breaking down questions like: “what is money” and evolved more deeply into BTC specifically and its implications. We spent the latter half of the discussion on Pomp’s budding media empire - with almost 700,000 followers on Twitter and a variety of other initiatives going, Pomp is building something special.

Apr 06, 202101:09:05
89: Li Jin, Founder of Atelier Ventures

89: Li Jin, Founder of Atelier Ventures

Over the last few years, a new section of our economy has surged - what’s now known as the creator economy. Creators are individuals that are directly reaching consumers and participating and generating economic values through mechanisms previously unused. Now the idea of creating content online isn’t new, but what we’ve seen through trends over the last 5 years and a shock to the system in COVID has caused unparalleled momentum for the category.

We’re now moving to a phase in this economy where it’s not just individuals sharing existing skills. Platforms are resegmenting and categorizing those skills in new ways - whether it’s NFTs or influencers - and in new business models.

Li Jin is one of the most thoughtful individuals on what’s really going on in this space. Formerly a Consumer Investor at Andreessen Horowitz, Li has recently founded her own firm Atelier Ventures to specifically focus on the all the emerging activity in this space.

Apr 02, 202140:12
88: Tobenna Arodiogbu, Founder & CEO of Cloudtrucks

88: Tobenna Arodiogbu, Founder & CEO of Cloudtrucks

When you think of the most common job in the US - it’s pretty typical to think about service workers: retailers, cashiers, fast food. But the most common job in 29 states is truck driving. Over 3 million Americans work as truck drivers and hundreds of communities and over 7 million workers provide services to truck drives - including working at truck stops, loading and unloading freight and servicing vehicle.

There’s been a lot of talk about the impact of self-driving technology and the implications for labor markets. One perspective is it’s going to take a lot of money off the table for truckers and we need to be resilient in the way we think through creating a transition pathway for many of those workers. The exciting thing is there’s a number of promising companies in the space that are working on providing more autonomy and tools to truckers to graduate up the stack -

This week I chatted with Tobenna Arodiogbu - Founder and CEO of Cloudtrucks on exactly that topic. He’s raised over $25M and is focused on empowering truck drivers to leverage software to compete and participate in the new world order.

Apr 02, 202141:25
87: David Sacks, Founder of Craft Ventures

87: David Sacks, Founder of Craft Ventures

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 statups in history - Microsoft acquired Yammer for $1.2B just 4 years after its founding.

Not only has David been a successful founder, but he has also been one of the most impressive investors in tech, having personally invested in over 20 unicorns, including Affirm, AirBnb, Facebook, Lyft, Opendoor, Palantir, Postmastes, Reddit, Slack, SpaceX, Twitter and Uber amongst others.

I got David’s thoughts on a variety of lessons leading, operating and investing in multiple multi-billion dollar companies.

Mar 18, 202141:13
86: Michia Rohrssen, Founder & CEO of Prodigy

86: Michia Rohrssen, Founder & CEO of Prodigy

The classic American dream consisted of three things: (1) a suburban house, (2) a pension and (3) a car. The Internet era transformed each of those elements - people became more attracted to cities as our economy became services oriented, companies shifted to the 401k and other retirement products and our usage of cars has transformed with Uber and Lyft.

But while the experience of cars has changed, purchasing cars has largely stayed the same.You go to a dealership, look at all the cars, find one you like, test drive it, haggle over the price and then drive home.

It’s a transaction almost everyone goes through. It’s why I was excited to chat with Michia Rohrrsen, Founder & CEO of Prodigy this week. Prodigy has reimagined the car buying experience and expanded the possibilities of automotive retail when software is introduced every step of the way.

We talked about the digitization of car buying and what the ideal dealership would look like.

Mar 10, 202149:05
85: Jeremy Cai, Founder & CEO of Italic

85: Jeremy Cai, Founder & CEO of Italic

This week we went deep into e-commerce. E-comm has been all the rage throughout COVID and it makes sense why: we’re all at home now and brands are able to get to us in more and more ways.

A company I’ve been keeping an eye on in the e-comm space is Italic, a marketplace for luxury goods; in this episode I chatted with Italic’s Founder/CEO Jeremy Cai.

Lux goods are interesting - they’re desired but super expensive. What I didn’t know originally was how much of that money is kept by the brand vs. the actual manufacturer. Italic has flipped the model and unlocked manufacturers ability to sell directly to consumers. So now you can buy products from the factories that make Prada, Gucci, Tumi, etc. at factory price. A win for the manufacturer and a win for the consumer.

Jeremy walked me through the way he thinks about e-comm, what the US can learn from China, where the value is trapped in this space and how to build a world class consumer experience.

Mar 08, 202148:43
84: Andrew Yang, Candidate for Mayor of New York City

84: Andrew Yang, Candidate for Mayor of New York City

Over the past 3 years, it's been a great honor of mine to develop a friendship with Andrew Yang. I remember walking down a street in New York City a few years ago with Andrew talking about all the challenges we faced as a society - he looked at me with determination and said: if we want to solve the problem, we need to be a part of the solution.

Since deciding to run for President, Andrew raised the level of discourse in our country and forced us as a citizenry to challenge many of our most basic assumptions. He has elevated a vision for a more humane capitalism and stressed the importance of country allegiance over party allegiance.

Andrew had a sentiment he often used to express on the campaign trail - his vision and policies were not about moving the country left or right; rather, they were about moving the country forward.

Andrew joined me and 30 of Atlanta's most senior leaders for an intimate fireside chat to provide a perspective on how we move forward as a society. Since then he has announced his candidacy for Mayor of NYC and I'm thrilled to be an early and avid supporter.

Enjoy the fireside chat. 

Feb 23, 202143:53
83: Chris Bakke, Founder and CEO of Laskie

83: Chris Bakke, Founder and CEO of Laskie

Professional services is simultaneously one of most difficult and attractive opportunities to disrupt today. On one end of the spectrum you have large consulting firms like McKinsey and on the opposite side you have freelance platforms like Upwork. But the middle hasn’t really been fulfilled. And with more companies in the middle being startups/technology businesses, the void has never been larger.

So this week I chatted with Chris Bakke, Founder and CEO of Laskie on how he’s thinking through the future of professional services. Chris sold his previous company to Indeed and was Head of Product where he led a suite of products that helped 250M+ find their next job.

In this conversation Chris and I unpacked the professional services landscape, specific opportunities that can create the highest impact and some of the misnomers/myths of this market.

Feb 23, 202152:26
82: Tim Ellis, Founder and CEO of Relativity Space

82: Tim Ellis, Founder and CEO of Relativity Space

On this podcast we frequently chat with Founders changing the world - everything from autonomous checkout to vertical labor marketplaces to the creator economy and the no code movement. But one of the areas I’ve been most recently intrigued by is space. And so this week we talked to one of the sharpest and most interesting entrepreneurs in today’s space movement - Tim Ellis, Founder & CEO of Relativity Space. Relativity’s mission is to make mankind a multi-planetary species. To make this mission a reality, the company is radically changing the infrastructure and manufacturing process to build a rocket shrinking the launch process from 180 months to 60 days.

How they’re doing this is what’s especially mind blowing to me - 3D printing. In this episode we talked about the space economy, 3D printing, aerospace supply chains and how Tim is using a fresh fundraising round of $500M to change the way we think about space.

Feb 18, 202147:47
81: Julien Smith, Founder and CEO of Practice

81: Julien Smith, Founder and CEO of Practice

Coaching and mentorship is one of the simultaneously overrated and underrated topics. It’s overrated because we talk about it a lot and recognize the importance of coaching, but it’s underrated because we have a perception that there’s a fixed barrier to be a coach and there’s a finite number of coaches in the world. But what if you could leverage technology to abstract away all the difficult parts of running a coaching practice and give coaches a platform where they could focus on their true strengths. The result would be significant market expansion and additional coaches being unleashed into the world.

This has interesting at scale ramifications - we could move to a world in which everyone in some sense has a personal coach, unleashing our own personal creativity by an additional factor.

These possibilities are what we talked about this week with Julien Smith, Founder and CEO of Practice. Julien was formerly the Founder/CEO of Breather, where he raised over $120M to revolutionize co-working spaces. Julien is one of the most interesting entrepreneurs of our generation and I had to bring him back after we had a great discussion in Episode 41. In this conversation we touched on scaling, self awareness, behavior change, pricing power, and support networks.

Feb 16, 202136:39
80: Hiten Shah, CEO of FYI and Former CEO Kissmetrics

80: Hiten Shah, CEO of FYI and Former CEO Kissmetrics

How would you feel if you had a billion dollar opportunity right in front of you and you squandered it? That’s what we talked about this week with Hiten Shah, CEO of FYI and former CEO of Kissmetrics. Hiten coined the term “my billion dollar mistake” in an iconic blog post several years ago. In it, he detailed how his team at Kissmetrics was 3 years ahead of the market, well funded, had great customers and ultimately lost the lead. It was a lesson in management, leadership and self awareness.

This week I chatted with Hiten about all things leadership and management - we dug deep specifically into lessons learned from that experience, but also broadened it out to his observations of what’s going on in the market today - how are Founders in 2021 approaching fundraising, what are the common mistakes they’re making and what, if any, downstream impacts will the abundance of capital have on the early stage ecosystem.

Feb 02, 202157:37
79: Jonathan Hsu, Co-Founder of Tribe Capital

79: Jonathan Hsu, Co-Founder of Tribe Capital

This week we went deep on the impact of data science in venture capital. Most investors form their experience based on a combination of anecdote, pattern recognition and experience. And candidly over the majority of time venture capital has been a meaningful asset class, there hasn’t been another way to do it. The last decade has fundamentally changed that - as compute power has significantly increased, the ability to store, harness and analyze data has transformed. Not only has this led to many of the most prominent businesses of our time - e.g. companies likes Facebook and Slack - but it’s also fundamentally opened up a new approach to investing.

I chatted with Jonathan to dissect this phenomena. Tribe has pioneered one of the most novel frameworks in the industry - akin to traditional accounting and financial statements - to unpack early stage technology businesses.

We touched on a number of topics: (1) the myth that product market fit can’t be quantified, (2) the 3 fundamental units of analysis that every early stage company can be dissected against and (3) finding atomic units of value in businesses.

Jan 29, 202135:49
78: Avlok Kohli, CEO of AngelList Venture

78: Avlok Kohli, CEO of AngelList Venture

This week we dove into the future of venture capital. For an industry that is singularly focused on disruptive innovation, venture capital has largely stayed out of the spotlight from new challengers and disruptors. Until now. It’s why I was so excited to chat this week with Avlok Kohli, CEO at AngelList Venture on the future of venture capital, opportunities for innovation in the system and the implications for expanding entrepreneurship.

AngelList Venture is focused on answering the question - what is possible if software played a bigger role in how we financed companies. Avlok brought a deep first principles perspective to the show and we touched on a number of topics: (1) the importance of expanding the pie vs. zero sum thinking, (2) how a venture fund would be built today if it was on the rails of software vs. traditional service guilds, (3) how the internet gives creators infinite leverage and (4) why we are in the bottom of the first inning for technology.

Jan 21, 202148:40
77: Nick Donahue, Founder and CEO of Atmos

77: Nick Donahue, Founder and CEO of Atmos

This week we’re diving into the future of homes. The 3 henchmen of the American economy are education, healthcare and construction. Construction and real estate have always been a pretty underrated topic in tech - but it’s one of the markets that has an almost limitless TAM. The global stock of institutional grade real estate is set to triple over the next 15 years with some estimates pegging aggregate values at ~$70 trillion.

It was a pleasure to have Nick Donahue, Founder and CEO of Atmos on the show today. Atmos is creating a full end to end solution for consumers to build custom homes. I love what Nick and team are building and I invested in him after he came out of YCombinator. In this conversation we touched on a number of topics: (1) COVID’s affect on national real estate prices, (2) how software allows you to vertically integrate in construction, (3) building a business that deals with atoms, not just bits and (4) dismantling the myth that you need to be a homebuilder to provide consumers a 10x experience when purchasing homes.

Jan 12, 202124:31
76: Jason Traff, Founder and President of Shipwell

76: Jason Traff, Founder and President of Shipwell

This week we went deep on supply chain and logistics. I know what you’re thinking - supply chain isn’t exactly the sexiest topic, but it’s deceptively important. Every commerce transaction in the world requires interdependent supply chains. There are very few businesses where it feels like the proxy for the market size is some variant of GDP. Amazon is a really obvious example of a business that would fit this description. Shipwell is another.

It’s why I was so excited to speak with Jason Traff, Founder and President of Shipwell this week. Shipwell has raised over $50M to develop a supply chain operating system for the enterprise, transforming supply chains by replacing manual process with a fully connected logistics ecosystem. Jason and I talked about a lot of topics in this conversation - (1) the fundamental leaps in quantum computing that power a company like Shipwell to exist, (2) how big of an opportunity this really is, and (3) how he’s grown 400% through COVID.

Dec 10, 202042:20
75: Nikhil Basu Trivedi, Former General Partner at Shasta Ventures

75: Nikhil Basu Trivedi, Former General Partner at Shasta Ventures

This week we dove deep on what in the world is going on in venture capital - we started off in March with a Black Swan Memo from Sequoia on how COVID was going to fundamentally disrupt the economy. There’s no question that happened, but what’s happened for startups and technology hasn’t been as intuitive - the capital markets are more active then ever, technology businesses are booming and deals are getting done at breakneck speed. This week I chatted with Nikhil Basu Trivedi, Former GP at Shasta Ventures to unpack what’s going on.

Nikhil coined the term “solo capitalist” this year and it speaks to a really interesting dynamic in the venture landscape. In this conversation we talked about: (1) agglomerators vs. specialists and how to chart positioning of different firms in the ecosystem, (2) price elasticity on venture deals and why different firms’ have different sensitivity thresholds when pricing deals, (3) what matters the most in a fundraise, (4) and the rise of solo capitalists.

Dec 03, 202038:46
74: Josh Childress, CEO of Landspire Group and Former NBA Player

74: Josh Childress, CEO of Landspire Group and Former NBA Player

“More than an athlete” is a phrase that’s significantly taken off over the past year. But it’s not just a phrase - it’s lifestyle, sentiment and mindset. That’s why I was so excited to have Josh Childress, CEO of the Landspire Group and former NBA Lottery Pick on the podcast this week. Josh is the perfect embodiment of the American dream. He grew up in inner city Compton, went to Stanford, had a successful NBA career and has transitioned to a successful real estate investor having an impact on local communities across the country. We talked a lot about mindset and being bigger than yourself in this episode. We talked about the psychology of putting your best foot forward and honing in on a larger purpose.

Josh has worked tirelessly to create opportunity for minorities in the country and in many ways is just getting started on the impact he will continue to have for years to come. Some of my favorite topics we discussed in the conversation were: (1) his background growing up in Compton, (2) his experience in the NBA and playing overseas, (3) the misconceptions of mental health for athletes, (4) his entry into business via owning a laundromat and (5) why he always pushes himself to be the least smart person in the room.

Nov 17, 202001:05:28
73: Sahil Lavingia, Founder and CEO of Gumroad

73: Sahil Lavingia, Founder and CEO of Gumroad

This week it was awesome to dive deep into startups with Sahil Lavingia, Founder and CEO of Gumroad. Sahil’s seen it all in Silicon Valley - he was employee #2 at Pinterest, started Gumroad with a traditional venture backed structure, pivoted the business to be venture free and now has a rolling fund he operates in his spare time investing $7M a year in startups. We talked a lot about the differences in running a venture backed company vs. a company that lives and breathes off the balance sheet. We chatted about the difference in psychology of running these types of businesses and how clarity of thought comes through when you get out of the echo chamber.

Sahil has worked to remove friction and increase democratization in nearly everything he’s done - a lot of this principle is what underscores Gumroad. He’s taken this same perspective to investing. Some of my favorite insights from this conversation include: (1) how to leverage community and audience, (2) why everyone should invest in early stage companies, (3) the trope of the world’s venture capital being perfectly allocated and (4) how democratization and access will continue to lift humanity out of its early J curve.

Nov 11, 202050:58
72: Tom Uebel, Co-Founder and CEO, CommandE

72: Tom Uebel, Co-Founder and CEO, CommandE

Whenever I watch engineers work, it feels like an alternative universe. Not least of which is because devs have unique superpower tools at their disposal - tons of different productivity hacks and niche plugins; one of the things I've been interested in most lately is finding overlapping use cases between technical and non-technical folks and then diving into the use cases where there are tools for technical folks, but nothing for non-technical folks. That's how I found the guys at CommandE.

CommandE has developed the ultimate cross-app search tool. I chatted with Tom Uebel, Co-Founder and CEO on how he came up with the idea, what the product looks like today, how he sticks out in a crowded space and developing implicit virality. Tom has raised from great folks like First Round, Bain Capital and Craft Ventures - this episode was fun diving into how he believes the future of search will unfold.

Oct 21, 202033:32