Square One: Conversations with the Best in Business

We are notorious as a society for falling in love with the next “fitness fad.” Whether its diet types, workout regimens or new fitness equipment, we’re suckers for “quick fix” schemes. It’s pretty rare that we come across a product that revolutionizes the way we workout — and in the age of connected hardware and software — we’re living through a paradigm shift that allows us to reimagine the fitness experience from first principles. This week, I got the chance to chat with Brynn Putnam, Founder and CEO of Mirror, a connected fitness system that streams live and on-demand classes to users in-home via a sleek responsive display. Mirror enables users to train with experts, work out with friends and get real-time personalization. The confidence from the venture community for Mirror runs deep — the company has raised $40M+ from leading investors, including Spark, First Round, and Box Group — and it’s easy to see why. The market is huge, the product is fantastic and Brynn is an incredibly thoughtful leader. I found many of her reflections insightful; specifically it was most interesting to hear her talk about: (1) running a combined hardware, software and content business, (2) thinking about the business as a “media company” vs. a “technology company” and (3) the pathway to evolve Mirror from a fitness business into “the defacto screen in your life.”  It was a pleasure to have Brynn on the show to get her thoughts on the future of connected home. This is going to be a fun company to follow.

The future of education and skilling is becoming very interesting. When you apply first principles thinking, the classroom experience, curriculum and economic model are all up for grabs. This week I chatted with Shaan Hathiramani, Founder and CEO of Flockjay, a 12 week immersive online sales academy that only charges students IF they secure a $50k+ job upon completion of the program.  We hear a lot about bootcamps in tech and the idea of the income share agreement is becoming a more popular way to align incentives, but we have yet to see these concepts married together for sales. So what inspired Shaan to start the company? He spoke with 250 universities and asked them a simple question “Did they have any courses that teaches anything related to Salesforce?” A resounding “no” empowered his belief that college curricula and the necessary skillset to be productive in the marketplace was out of balance. I got a chance to learn more about Flockjay’s current cohort and the backgrounds of the students are incredibly inspirational. Some are first generation Americans, some have done tours in Afghanistan and some grew up in foster care. The coolest part about Flockjay is it works for all demographics, all ages and all backgrounds. All you need is grit. It was a pleasure to have Shaan on the show to get his thoughts on the future of skilling. Watch out for this company — Flockjay is going to be really interesting to watch over the next decade.

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. With this increase in asset volume, there’s a slew of complexity and change on the horizon — social migration will change the distribution of construction, the changing nature of cities presents a wider range of risk and return opportunities and technology is playing a deeper role in we re-think the physical world. Though there’s significant macro change on the horizon, participating in the market today feels less than inspirational — transacting is expensive, messy and lacks transparency.  Enter Opendoor. Opendoor brings machine learning and a thoughtful user experience to bear to dramatically simplify the end-to-end residential real estate transacting process. The company has raised $500M+ over the past few years and has scaled to 1,000 employees in less than half a decade. JD and I chatted at length about: (1) the technological shifts that make Opendoor possible, (2) key lessons he’s learned in scaling a business so quickly, (3) the flywheel effect for Opendoor and why its different from other marketplace businesses, and (4) the challenges incumbents face in entering this space. It was a pleasure to have JD on the show.

In an age of speed, overstimulation and FOMO, it’s easy to get caught up in the latest tech trend. This mindset doesn’t discriminate and is often most pervasive amongst the most sophisticated people in the world. Over the past year, I’ve had a number of conversations with Fund LPs and often I hear comments like “What crypto investments should we make?”, “When will VR take off?” and my favorite “Did this fund invest in a scooter company yet?” It would be naive to write off any of those sectors and think that massive value won’t be created by the winners in those spaces. What I find most interesting though is how little airtime we give to the massive sector of value creation that lives and breathes on the complete opposite side of the spectrum. These are not the businesses that will 10,000x their value in 5 years, but they are ones that print material and consistent cash flow over outsized periods of time. Or as our guest in this episode likes to call them: “boring businesses.”  Brent Beshore is the Founder and CEO of adventur.es, a extremely unique PE firm in Columbia, Missouri. Brent has raised $50M of capital for his fund and partners with entrepreneurs with the intention to never sell his ownership stake. We chatted at length about boring businesses, evaluating fads vs. trends and some of his biggest philosophical learnings from looking under the hood at over 12,000 companies.  It was a pleasure to have Brent on the show. He’s undoubtedly a sharp investor, but he has a refreshing amount of empathy which I appreciate the most.

“First principles” thinking gets a lot of lip service today in technology and venture capital. While its in vogue to acknowledge this way of thinking, very few actually adhere to it in practice. In this episode, I chatted with Ali Hamed, Managing Partner at CoVenture — one of the most “first principles” thinkers I’ve had the privilege of speaking with and hosting on the show.  In this episode, Ali opened up what is possible when you think creatively — whether its how to structure a firm across multiple asset classes (lending, venture capital and crypto), invest in new digital asset classes (e.g. rolling up Instagram accounts) or evaluate a company’s progress (debunking the fallacy of MRR and growth thresholds necessarily indicating progress). Ali covered it all in this conversation.  It was a pleasure to have Ali on the show. He pushed my thinking through the conversation and I learned a lot from him. 

As software eats the world, the idea of moats and the power of compounding have taken a new turn of influence. I chatted with Leo Polovets, General Partner at Susa Ventures on the importance of these two fundamental concepts and why they are so powerful, but yet still so counterintuitive in 2019. In this episode, Leo expanded on his experience from being one of the first dozen employees at LinkedIn to experiencing hypergrowth at Google and how this has enabled him to find and support the next set of generational companies, e.g. Robinhood, Flexport, Andela and LendUp. He expanded on Susa's investment thesis in funding entrepreneurs that are building highly defensible companies that leverage data, economies of scale, and network effects to build value and achieve longevity. We also touched on nuanced philosophical concepts in company creation such as "position vs. momentum" and "ego vs. perception." It was a pleasure to have Leo on the show. He's one of the most thoughtful venture investors I've had the privilege of getting to know.

Today, the mental health crisis has reached a tipping point - one in five adults has a mental health condition and over the last 20 years there has been a 30% increase in suicide rates and 130% increase in depression amongst young adults. From a economic perspective, we're facing a staggering ~$200 billion in lost earnings (per annum) attributed to mental illness.  In many ways, there are troubling signs that these numbers will actually get worse - these conditions are further exacerbated by two phenomena: (1) uneven access to mental health services (the Mental Health America study found that 50+% of Americans don't have access to basic services) and (2) the stigma against mental health (many don't get the care they need even if they have access, because of the associated label).   Despite the sheer size and growing demand for services, (e.g. over 2.5 mental health providers for everyone one primary care physician and a labor market growing 25% per annum), the space is incredibly fragmented and underserved. NYC alone has a staggering 90% of its providers working as solo practitioners. The lack of sophistication, quality of user experience and shortages that follow sub-scale practice add up. In this episode, we unpacked all these dynamics and how software and design play a pivotal role in improving the patient and provider experience with Harry Ritter, Founder and CEO of Alma. Alma is a new practice model for therapists designed to elevate the therapy experience and simplify access to great care. It was a pleasure to have Harry on the show to discuss this distinctly important topic.

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." However in 2018, this is all changing. In a world where the leverage in the "war for talent" has shifted to employees, HR is becoming a strategic asset; companies are understanding more and more they are above all in the people business. This mindset shift has pushed HR to focus on employee experience, improving engagement and overall organizational health.  In this episode, we unpacked all these dynamics and how software plays a pivotal role in the new HR world-order with Jack Altman, Founder and CEO of Lattice. Lattice offers an elegant user experience on the front end with a rigorous data engine on the back-end to help organizations drive best in class performance management. It was a pleasure to have Jack on the show.

In 2018, Uber is a household verb. The company is on an absolute tear; Dara Khosrowshahi has assembled a world class management team and Uber is evolving from a ridesharing company into a full scale transportation business. The company now has multiple business units at multi-billion dollar run rates; earlier this year Uber announced Eats is at a $6B+ bookings run rate. Excitement around the company is steep and in 2019 we are likely to see an IPO. The early view on pricing is Uber will enter the public markets at $100B+ market cap. Back in 2011 however, Uber was anything but a foregone conclusion. The company had raised a small Series A and the incumbent taxi industry threw everything they had at the business. Fights were prevalent in every market, but the battle in New York City was especially high stakes. The world was watching New York and if Mayor DeBlasio succeeded in shutting Uber down, it was only a matter of time before the rest of the world followed. Founder and then-CEO Travis Kalanick engaged Bradley Tusk to help with the fight. One of the most public and epic battles between private enterprise and city hall, Bradley ran a genius political campaign that ultimately kept Uber up and running as a business. We unpacked how it all went down in this episode.  It was a pleasure to have Bradley on the show; we spent most of the time chatting about Uber, but we also touched on how he's using blockchain to empower mass mobile voting - a key initiative to fix low voter turnout - and whether his former boss Mike Bloomberg will run for President in 2020.

Education is broken. Since 1996, only three sectors have materially risen when adjusted for inflation. Construction is a bit more expensive than the inflation benchmark, healthcare and childcare prices have risen ~2x the benchmark, and college education has risen 4x inflation!  This rising cost is having a significant impact on the economy - millennials are less likely to start businesses, own homes and are taking longer to "settle down" due to the crippling impact of student loans.  A lot of companies have been trying to disrupt the higher ed space; one of the companies I've been most impressed by in the space is Lambda School - a 30 week immersive coding school that only charges students IF they secure a $50k+ job upon completion of the program. Lambda is one of the fastest growing startups in the Valley and just announced a fresh round of capital this week, led by Google Ventures and Stripe.  It was a pleasure to have Austen on the show to get his thoughts on the future of education. Watch out for this company - Lambda has the potential to be one of the most important and impactful companies in the next 20 years.