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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