Square One: Conversations with the Best in Business

This week we dug into the future of education, but a bit differently than in ways we’ve previously explored - we talked homeschooling. COVID-19 has placed 74 million children in the US in some version of homeschooling overnight. Innovation in education is a massive opportunity. Thriving in a complex world requires creativity and original thinking, but our education system is designed for mass production — not unlocking imagination and individuality. We won’t be able to solve 2050s challenges with an educational supply chain built for the 1950s. Now is the time to dig into homeschool from first principles. It’s why I was so excited to chat with Ryan Delk, Founder and CEO of Primer. Simply put, Primer is homeschool with superpowers. As Ryan described to me in our conversation, the education system is systematically underestimating our next generation; Primer is building a learning experience well suited for 2020. We dug into a number of topics in this conversation: (1) the growth of homeschooling, (2) distance learning vs. homeschooling pedagogy, (3) the benefits of unencumbered creative time, (4) why homeschooling gets a bad reputation and (5) how teachers are the current heroes of our time.

This week we dug into the future of banking. When you think of the macroeconomy top down - banking and financial services are bar none the largest market in the world, constituting just around ~20% of GDP. Even though the market is so large, we’ve continued to see consolidation and asset aggregation in the largest institutions in the world - and for historically good reason: banking requires strong compliance, risk and trust protocol. After we hit the onset of the financial crisis, trust began to erode in many large financial institutions and we started to see the onset of the challenger bank. Banks focused on a targeted experience and technology set attractive for millennial and Gen Z consumers. This week I chatted with Immad Akhund, Founder and CEO of Mercury Bank. Simply put, Mercury is a bank for startups. In this conversation we talked about the evolution of the banking experience, the landscape of consumer banking, how he thinks about every company seemingly becoming a fintech bank these days and leading a company in the time of COVID.

This week we dug into real estate - when I had JD Ross, Co-Founder of Opendoor on the podcast, we chatted about how massive of an opportunity real estate is - the global stock of institutional grade real estate is set to triple over the next 15 years with some estimates pegging values at $70 trillion. It’s why I was so excited this week to chat with Keith and Gelena Wasserman (CEOs of Gelt and Skya Ventures respectively). Keith and Gelena started in this industry from scratch at the peak of the recession in 2008. Fast forward a little over 10 years and they’ve amassed a portfolio with an asset value of over $1.3B. In this episode we explored a couple different themes. We talked about the nuances of real estate - the fundamentals, how to value a property, characteristics of a good investment; we talked mentality (an immigrant’s mindset, an entrepreneur’s mindset and the philosophy of “making money on the buy). And we snuck in a little bit of tech - impact of tech on real estate, cloud kitchens and autonomous vehicles and the early stage venture fund Keith and Gelena started to get exposure to other industries.

It’s been well documented that Hollywood and Silicon Valley have always had a close relationship - even though these industry centers exist within the same state, the underlying state of mind has always been somewhat different. There is a clear perspective to be had with melding the best of both worlds. This week’s guest has been at the forefront of that intersection. Matt Mazzeo spent his formative years at CAA, joined Chris Sacca as Managing Partner of Lowercase Capital and is now a General Partner at Coatue Management. Matt is one of the sharpest consumer investors in the world and we touched on a number of topics including: (1) the blending of the Hollywood/Silicon Valley mindset, (2) his partnership and time at Lowercase, (3) how he’s thinking about a post COVID world and (4) the future of education and rehiring.

In the last several months, I’ve had a number of Founders on the podcast building companies to drive innovation in how we work. A timely issue given pre-COVID 19, one in four Americans lived in locations with little or no economic growth; meanwhile tens of millions of city dwellers are increasingly squeezed by rising costs of living. This has only been exacerbated by COVID-19. I was excited to chat with Sean Linehan, Co-Founder and CEO of Placement this week to further that dialogue. Placement’s mission is to unlock the earning potential of millions of Americans. Placement is the modern day talent agent - enabling individuals to land opportunities in fast-growing, affordable cities or in remote roles. By reducing friction and eliminating the barriers to geographic mobility, Placement is shifting who captures the value in the country’s economic growth. We touched on a number of topics in this episode: (1) location arbitrage, (2) flipping the funnel, (3) what at scale data tells us about economic mobility, (4) democratizing access and process to landing higher paying jobs, (5) engineering momentum and (6) the decision to focus solely on placement (vs. admissions and training).

Daniel Gross is one of the most interesting members of the startup community today; he is the youngest YC founder in history and sold a company to Apple at 23 where he ultimately rose to lead Apple's efforts in machine learning. After his time at Apple he joined YC as a Partner in 2017 and ultimately moved on to found Pioneer. Pioneer is a fully remote accelerator dedicated to funding projects and startups built by the ambitious outsiders of the world. Daniel founded Pioneer to provide some of the non-intuitive benefits of Silicon Valley to many more people. Pioneer provides capital to jumpstart ideas, but most importantly Pioneer broadens people’s horizons of how they view themselves. We spent this conversation talking about a number of topics: (1) how the world will bounce back from COVID, (2) the philosophical underpinnings of Pioneer (e.g. believe in oneself, curiosity, etc.); (3) the nature of games and (4) why an organization like Pioneer is so valuable to flattening the innovation curve.

Tribe Capital is one of the most interesting firms in all of venture capital today - a highly quantitatively driven firm, the Tribe team comes from deep data science backgrounds at leading companies like Uber and Facebook and applies an operator's lens to investing. I was excited to chat with Arjun Sethi, Co-Founder and Managing Partner at Tribe this week. We touched on a number of topics: (1) the transition from operator to investor, (2) the lingua franca of 2020 businesses, (3) quantifiable frameworks (e.g. how to quantify product market fit), (4) underwriting risk and capital allocation across stages, (5) loss ratios, (6) force multipliers, (7) atomic units of value, (8) 1 of n vs. n of 1 companies and (9) retesting underlying assumptions in the era of COVID-19. This was one of the longest discussions I've had on the podcast and one of the most interesting. Arjun is a wealth of knowledge. 

Union Square Ventures is one of the most revered venture firms in New York City. This week I was thrilled to chat with Rebecca Kaden, General Partner at USV. We started off the conversation talking about some of Rebecca’s fundamental beliefs on how to succeed in venture - primarily the importance of matching horizontal and vertical perspective and providing value in each interaction. We then spent the majority of the dialogue on USV’s Thesis 3.0 and dove deeply into the future of education before rounding out with how Rebecca expects venture capital to change over the coming years.

Checkout is one of the oldest and most painful elements of a purchase process. If you're buying something other than on Amazon, chances are you have to re-login. There is a significant conversion dropoff for businesses when this happens and a subpar experience for consumers. Fast is here to fix that. Fast wants to be the intermediary for consumer interaction - in simple terms, Fast wants to provide consumers with a one-click login, one-click payment and one-click data collection.   This week I chatted with Allison Barr Allen, Co-Founder and COO of Fast. Fast raised $3M last November and followed up with an aggressive $20M raise just 4 months later. And for good reason. Today Fast's product is login, but at scale Fast could solve the problem of silo'd identity on the internet and be the central repository for all identity management. This conversation was a ton of fun and I learned a lot from Allison. 

More than 25 million Americans were laid off in April and that’s just the official count. Economists are estimating that unemployment could soon exceed 30% and have massive sectoral impact - service and retail to engineering and product management. Traditional tools - job boards, LinkedIn, etc. are going to be challenged at handling the volume we will be seeing over the next few years - this is where vertical labor marketplaces come in. This week I was thrilled to chat with Mike Slagh, Founder and CEO of Shift. Shift is a digital talent marketplace and community that connects veterans with world class companies. Shift aims to map military backgrounds to specific hiring needs while helping veterans acquire new skills, secure referrals and master corporate hiring processes. Shift extends full stack from education and re-skilling to mentorship and coaching.