Bootstrapped to Exit: How Justin Gray Built, Sold & Now Backs Founders
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Bootstrapped to Exit: How Justin Gray Built, Sold & Now Backs Founders
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Serial entrepreneur turned VC, Justin Gray, joins Alejandra to unpack how he built LeadMD from a bedroom idea to $17M in revenue, exited at the top of the market, and why his operator-immersive VC model bets on singles, doubles, and triples, not unicorn lottery tickets. We get tactical on making revenue predictable, using equity to retain A-players, diagnosing a real pipeline (not hope), and knowing when it’s time to sell emotionally and operationally. If you’re scaling a services or vertical SaaS company, this is your masterclass.
You’ll learn: bootstrapping vs. VC, GTM hiring that actually works, partner ecosystems that spark M&A, and how to prep your business so buyers believe your forecast.
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Show notes/highlights.-
Bootstrapping mindset vs. venture fuel
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Building predictable revenue (and what “real pipeline” means)
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Equity as a retention engine in services
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Timing the exit: performance + founder energy
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Operator-immersive VC: hands-on GTM help
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Partners as your M&A on-ramp
You can connect with Justin Gray on
https://www.linkedin.com/in/inrevenue/
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