Business Buying Strategies from The Dealmaker's Academy podcast

#350 Confidence, First Deals and Sector Experience

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From First Deal to Big Exits: What Real Dealmakers Are Doing Differently

Host: Jonathan Jay

Format: Live panel Q&A — Riverside Studios, Hammersmith

Guests: Seven Inner Circle members

Overview

Seven of Jonathan Jay's Inner Circle members — experienced business acquirers — answer unscripted questions from a live audience. This episode focuses on exit strategies, building deal confidence, and how to get a first acquisition over the line.

Exit Strategy

The panel agree: start with the end in mind, but hold the number loosely. One member is building a £25m technology group by 55, with a £100m goal by 60 — but stresses the journey matters more than the figure. Another runs multiple buy-and-build projects in parallel, generating a new exit every 3–6 months and ultimately targeting a move into private equity. The consensus: build like you're selling, even if you never plan to.

Confidence & Competence

Business skills are transferable — sector experience is helpful, not essential. The panel recommend starting with your own supply chain, where trust is already established. Find an accountability partner more productive than you, and lean on your community: you don't need all the answers, you just need people who do.

When Letters Don't Work

One audience member sent 30,000 letters and got just 10 responses — all broker-listed at inflated prices. The panel's diagnosis: check the letter against the proven template, iterate in smaller batches, and never dismiss a broker-listed seller. Reignite their original motivation, get in front of them face to face, and help them see the deal on the table today is more valuable than a higher number that may never arrive.

Key Takeaways

•       Your exit goal will evolve — treat it as a waypoint, not a destination.

•       Sector experience isn't required — core business skills transfer everywhere.

•       Your supply chain is your best first target — the seller already knows and trusts you.

•       Meet sellers face to face — a phone call alone won't close a deal.

•       Follow the system precisely — one small deviation can kill your response rate.

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