Jonathan David Nelson has lived a stranger founder journey than most: missionary kid in Latin America, trauma nurse, software engineer, founder community builder, and now capital markets contrarian. After building Hackers and Founders from a bar meetup into a global startup community, Jonathan now runs HF Capital—an AI-native investment bank focused on IPOs, secondaries, and M&A.

In this episode, Jonathan breaks down why he believes the U.S. public markets are failing most companies below decacorn scale, why the London Stock Exchange may be a better path for growth-stage startups than another brutal private round, and how AI could rebuild the infrastructure behind investment banking.

In Today's Episode We Discuss:

00:01 - Introduction to Jonathan David Nelson and HF Capital

01:23 - From Missionary Kid in Latin America to Trauma Nurse

03:10 - How Hackers and Founders Started as a Bar Meetup

04:26 - Why Fundraising Is a Brute Force Algorithm

05:37 - Understanding Capital Flow Like Blood Flow

08:15 - Advising the SEC and the Limits of Crowdfunding

09:40 - Why Startup Exits Remain the Broken Piece

10:47 - Why U.S. Public Markets Fail Smaller Companies

13:02 - The Origin of HF Capital and Tokenized Stock

15:26 - Discovering the London Stock Exchange Alternative

17:05 - Lower IPO Costs, Sponsor Banks, and Less Litigation

19:23 - Why Founders Still Default to U.S. Markets

21:19 - The “50 and 50” Growth-Stage Startup Profile

24:28 - When an IPO May Not Be the Right Move

26:34 - SPACs Explained and Why They Often Collapse

30:32 - Private Rounds vs. IPOs for Growth-Stage Companies

31:37 - Liquidation Preferences and Founder Dilution

35:24 - Why Boards Resist Alternative IPO Paths

36:23 - Capital Markets as a “Capital API”

38:02 - Building an AI-Native Investment Bank

40:14 - Why HF Capital Is Becoming the Bank, Not Just Selling Software

41:11 - The Coming Explosion of Smaller AI-Native Startups

42:26 - Secondaries, Latin America, and Undervalued Growth Companies

44:39 - What Startup Secondaries Actually Are

45:30 - Anthropic Hype, SPVs, and Risky Secondary Deals

47:13 - Custody, Forward Contracts, and Secondary Market Due Diligence

Jonathan is blunt, funny, and allergic to sacred cows. His view is simple: venture, IPOs, secondaries, and capital formation are not laws of nature. They are systems. And broken systems can be hacked.

Pull quote: “The system is broken, must fix. The ecosystem is sick, must heal.”

Pull quote: “I think of capital markets, stock markets as a capital API.”

From wiping asses and saving lives in the ER to reengineering how founders access liquidity, Jonathan’s story is a reminder that sometimes the best person to fix finance is the outsider who never agreed to pretend it made sense.

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