The Deal Flow Show

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


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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

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The Deal Flow ShowBy Ivan Acuna