Square One: Conversations with the Best in Business

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.

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.

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.

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.

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.

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.

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.

“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.

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.

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.