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.

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.

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.

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.

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.

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.

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.

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.

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.

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.