Jay Hoag - Calibrating Market Adoption - [Invest Like the Best, EP. 244]

My guest today is Jay Hoag, co-founder of TCV. If you look at Jay’s investment track record, it’s a “who’s who” of tech giants with Airbnb, Netflix, Peloton, Zillow, and a list that does not stop there. Needless to say, Jay has a Hall of Fame career. During our conversation, we talk about his own journey founding TCV, what advice he has for visionaries, and why he sees advantages for private to public crossover investors. Jay has such a wealth of experience that is on display throughout this episode. Please enjoy my conversation with Jay Hoag. For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------ This episode is brought to you by Canalyst. Canalyst is the leading destination for public company data and analysis. If you've been scrambling to keep up with the deluge of IPOs and SPACs these days, Canalyst has models on Robinhood, Marqeta, Grab, and everything in between. Learn more and try Canalyst for yourself at canalyst.com/patrick. ------ This episode is brought to you by Hall Capital Partners. Hall Capital is always looking for exceptional investment talent at any stage and size, so if you are raising capital or looking for a career change in the San Francisco or New York areas, you should check them out at hallcapital.com or e-mail at invest@hallcapital.com. ------ Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes. Past guests include Tobi Lutke, Kevin Systrom, Mike Krieger, John Collison, Kat Cole, Marc Andreessen, Matthew Ball, Bill Gurley, Anu Hariharan, Ben Thompson, and many more. Stay up to date on all our podcasts by signing up to Colossus Weekly, our quick dive every Sunday highlighting the top business and investing concepts from our podcasts and the best of what we read that week. Sign up here. Follow us on Twitter: @patrick_oshag | @JoinColossus Show Notes [00:03:13] - [First question] - Some of his early key formative experiences that shaped his worldview as an investor [00:06:29] - How much software businesses have changed since he started investing in them [00:08:28] - The key insight that led him to create TCV [00:11:36] - Generating returns by swinging less and raising your average [00:15:06] - Understanding and evaluating a value proposition in its early stages [00:22:08] - What slightly crazy founders look like and why it’s important for a company [00:25:47] - Whether or not we’re in the golden age of content already [00:28:27] - Why Peloton was rejected so many times before TCV invested in them [00:32:32] - Things founders often need from him and how he helps them succeed [00:36:15] - Lessons learned from investing in public markets versus private ones [00:41:35] - Advice for founders when it comes to conveying their ideas to investors [00:44:55] - The social dimension of interactive and network building content [00:46:18] - How important maintaining a focus in the early days is for a new company [00:48:07] - The most challenging aspect of executing his strategy today [00:50:48] - One of the most emotionally stressful episodes while launching TCV [00:53:44] - Supporting your founders during the good and tough times [00:55:16] - New potential headwinds and tailwinds in the tech space writ large [00:59:14] - Things people might be overlooking today that could be great opportunities later [01:02:58] - Whether or not internet companies are threatened by the crypto boom [01:04:32] - What most has him most excited about the world today [01:06:20] - Advice for company building in the investing world in general [01:09:48] - The kindest thing anyone has ever done for him