Justin Fishner-Wolfson - Secondary Investing in Private Markets - [Invest Like the Best, EP. 227]

My guest today is Justin Fishner-Wolfson, founder of 137 Ventures, a venture capital fund focused on providing liquidity solutions to founders, investors, and employees of private businesses. In our conversation, we discuss what early career experiences led Justin to start 137 Ventures, the counter-intuitive information asymmetry between public and private markets, and the interesting trend of digitization in the physical world. I hope you enjoy my conversation with Justin.   For the full show notes, transcript, and links to the best content to learn more, check out the episode page here. ------   Invest Like the Best is a property of Colossus, Inc. For more episodes of Invest Like the Best, visit joincolossus.com/episodes.    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 [00:03:47] - [First question] - Why he started 137 Ventures and what’s unique about it [00:05:31] - Overview of secondary equity markets in the tech sector [00:07:06] - Step by step process of how a secondary market investment works [00:09:37] - Scale of secondary transactions in markets today [00:10:19] - Valuations of secondary transaction rounds versus primary ones [00:11:37] - Defining great in private market investments and the competitive landscape [00:13:13] - Why there seems to be more information available in private markets [00:16:23] - How better capital allocation may result from less asymmetry [00:19:14] - What excites him about companies when meeting them for the first time [00:20:34] - Example of applying his philosophy of investing in a defensible business [00:22:20] - Counter positioning and inversion models to gain an advantage [00:24:17] - Lessons learned from Palantir about unlikely competitive advantage  [00:25:57] - Building good businesses when selling them to the government [00:26:59] - What technology means in the current era [00:28:34] - Methods for evaluating potential sources of defensibility and a lack thereof [00:30:30] - Considering focus and expansion when scaling [00:32:52] - Shared qualities of entrepreneurs who build these types of businesses [00:33:50] - The business that individually taught him the most writ large [00:35:01] - Defensabilities that might appear beyond the seven powers framework [00:36:21] - Thoughts on what seems to be craziest in the world today [00:37:15] - What’s surprising on the low end of the valuation side [00:38:11] - Interesting business models and ones he’s averse to  [00:40:31] - Constructing a portfolio with companies that have a customer focus [00:41:21] - Additional companies in their portfolio that aren’t of a similar model  [00:42:08] - Lessons learned from SpaceX’s growth [00:44:46] - Watching a SpaceX launch in person [00:46:03] - Advice for entrepreneurs when seeking capital and capital partners [00:48:04] - Investors he finds most impressive that he knows well [00:49:26] - Defining the cost of capital and what it means to him as a venture investor [00:50:56] - Is giving entrepreneurs too much money dangerous? [00:54:14] - What great capital allocation looks like to him [00:55:29] - Accelerating learning curves with tighter feedback loops [00:55:57] - Useful metrics for customer acquisition and retention [00:57:06] - Whether or not investing firms can and should behave defensibly [00:59:13] - What is going in the world that has his attention lately [01:02:06] - Key factors that have allowed him and his firm to succeed [01:03:47] - What he thinks about when his mind isn’t focused on investing [01:04:08] - The kindest thing anyone has ever done for him