Square One: Conversations with the Best in Business

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.

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.

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.

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.

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.

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.

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.

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. 

In this podcast, Chris Bakke, Founder and CEO of Laskie, discusses the future of professional services, including the void in the middle market, opportunities for disruption, and common myths. The conversation also explores tech-enabled services at Laskie, challenges in selling time-related services, and the impact of remote work on the industry.

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.