I Made $25,000,000 Investing in AI Start Ups to Fix the US Government

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The Deal Flow Show

Ivan Acuna

14 episodes

1 day ago

The Deal Flow Show is where private equity gets real. No scripted answers, no corporate fluff—just raw, unfiltered conversations with the top dealmakers in the game. We pull back the curtain on the industry, sharing the stories, strategies, and hard-earned lessons that you’d normally only hear behind closed doors. Whether you’re deep in the world of M&A or just starting to navigate private markets, this is where you get the insights, mentorship, and war stories that actually matter.

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I Made $25,000,000 Investing in AI Start Ups to Fix the US Government

The Deal Flow Show

1 hour 5 minutes 50 seconds

4 months ago

I Made $25,000,000 Investing in AI Start Ups to Fix the US Government

In this video, Herbert Drayton shows how he used AI to build a $25M business helping small companies get government contracts. He talks about growing one business from $900K to $6M and turning it into six startups. You’ll hear how he finds real problems, uses AI to fix them, and helps thousands of minority-owned businesses win deals. This is a story about government contracts, AI tools, startup growth, and making money by solving boring problems.Sign up to our newsletter where the heavyweights of high finance share their off-market playbook: https://offmarketmemo.beehiiv.com/ 00:00 Meet Herbert02:20 Military to business journey04:40 Lessons from the Marines08:30 $900K to $6M growth11:00 Why he dropped Medicaid13:00 Started 6 software companies17:00 What is Nexus RFP?20:30 AI writes the proposals23:30 The $25M contract story27:10 When to sell a company31:30 His biggest mistakes35:00 Raising money the smart way41:00 Why minority founders struggle46:00 Picking real AI winners50:00 Fixing trauma before it starts54:00 His faith and morning prayer1:01:00 Why he keeps building1:06:00 How to connect with Herbert