Episode Details

Jake spent 12 years selling data analytics software at SAP, MicroStrategy, and Informatica. Then SAP reassigned him from federal government sales to retail. He decided to take his career into his own hands.

He acquired a money-losing, 7-person government data analytics firm with 100% seller financing. Zero cash out of pocket.

❌ No playbook for buying a business
❌ No community or infrastructure around acquisitions
❌ Business was unprofitable on day one

10 years later, he sold it for $35 million at 11x EBITDA.

In this episode, Jake breaks down how he negotiated 100% seller financing on a deal nobody wanted, how he went from 54% customer retention to 95%, and why the hustle that saved the business early on was the same thing holding it back from growing.

◼️ The two-valuation trick that got both sides to agree on the price
◼️ Why the sellers financed the whole deal (and how to find sellers like this)
◼️ How he went from stuck at 5% growth to hitting 35-40% growth rates
◼️ The $35M exit and why his financial advisor told him to take it
◼️ The PE earn out nightmare — and how he eventually collected

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