#350 Confidence, First Deals and Sector Experience
Business Buying Strategies from The Dealmaker's Academy
Release Date: 04/30/2026
#350 Confidence, First Deals and Sector Experience
Business Buying Strategies from The Dealmaker's Academy
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...
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#349 The Psychology of Business Ownership: Why You’re the Bottleneck
Business Buying Strategies from The Dealmaker's Academy
We continue our live panel discussion, recorded at Riverside Studios in Hammersmith, with Jonathan and his inner circle group of experienced dealmakers. This isn’t about tactics, it’s about mindset. Because the real challenge in business acquisition isn’t finding deals, it’s what’s happening in your head. Most people think success in acquisitions comes down to: • The right sector • The right deal ...
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#348 The Reality of Buying a Business — What No One Tells You
Business Buying Strategies from The Dealmaker's Academy
What’s it really like to buy a business? Not the Instagram version. Not the “Lamborghinis and Dubai” version. The real version. In this episode, Jonathan brings together a panel of experienced dealmakers at Riverside Studios, all of whom have completed multiple acquisitions across sectors including property, construction, accountancy, engineering, and more. What follows is one of the most honest conversations you’ll hear about business buying. Behind the Scenes: Real Deals, Real Numbers This isn’t theory. These are people who have actually done it: 11 deals in 5 years...
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#347 From Employee to £6M Business Owner — How One Deal Changed Everything
Business Buying Strategies from The Dealmaker's Academy
What happens when you stop thinking like an employee… and start thinking like a dealmaker? In this week’s episode, Jonathan talks with Pete, a Masterminder who has gone from earning £50k a year to co-owning a group of businesses generating £6 million in revenue — all within just a few years.  Pete’s journey started as an apprentice engineer. • One day a week at college • Meeting a future business partner • Years of working for other people • A growing frustration that there had to be something more The opportunity came when they explored buying the...
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#346 Negotiation, Deal Structuring and Funding: What’s Actually Working Right Now
Business Buying Strategies from The Dealmaker's Academy
Buying a business isn’t just about finding the right opportunity. It’s about structuring the deal in a way that works for everyone involved. In this week’s episode of Business Buying Strategies, Jonathan hands the microphone to his dealmaking partner Martin, who shares insights from a live webinar with Dealmakers clients. Martin has been directly involved in hundreds of acquisitions and is currently negotiating multiple deals himself. In this session he explains how real deals are structured, how negotiations actually unfold, and what funding strategies are working in today’s...
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#345 What kind of business should I buy?
Business Buying Strategies from The Dealmaker's Academy
What Kind of Business Should I Buy? If you’re thinking about buying a business, this is the question that determines everything. Not how to fund it. Not how to structure it. Not even how to find it. But what kind of business should you buy? In this week’s episode, Jonathan Jay answers the foundational question every serious dealmaker must get right and explains why choosing the wrong business is the fastest way to sabotage your future success . Start With the End in Mind Jonathan opens with a principle borrowed from Stephen Covey: Begin with the end in mind. Before you even look at...
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#344 Inner Circle Mambers Panel - Questions and Answers
Business Buying Strategies from The Dealmaker's Academy
In this special episode, you’re invited to listen in on a live panel from one of Jonathan Jay’s recent Mastermind events — featuring experienced Inner Circle members who have collectively bought dozens of businesses. This is real talk from real dealmakers. They’ve battled through first deals, discovered unexpected sectors, failed forward, negotiated smart structures — and now they’re here to share what actually works. Expect candid insights, live questions from the audience, and stories that will challenge the way you think about dealmaking. In this panel episode, you’ll...
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#343 Podcast Highlights 2025 Part 2
Business Buying Strategies from The Dealmaker's Academy
In the second part of our special two-part highlights series, Jonathan Jay dives into more of the most impactful, practical, and inspiring moments from the 2025 season of Business Buying Strategies. Whether you’re brand new to acquisitions or have a few deals under your belt, this curated episode brings together essential wisdom from trusted voices in the Dealmakers community. Here’s what you’ll hear: 1. The Legal Pitfalls First-Time Buyers Must Avoid Top M&A lawyer John Andrews shares critical advice for getting your structure right from day one. You’ll learn: Why a...
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#342 Podcast Highights 2025 - Part One
Business Buying Strategies from The Dealmaker's Academy
Kicking off the new year in style, this special episode of Business Buying Strategies brings you the best, boldest, and most instructive stories from the podcast in 2025. You’ll hear from real dealmakers—ordinary people doing extraordinary things—who followed Jonathan Jay’s proven acquisition strategies and transformed their lives. Whether you’re starting from scratch or already own a business, this episode will help you understand how growth through acquisition really works. What You’ll Learn in This Episode How complete beginners have bought businesses without risking their own...
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#341 Putting the Deal Together
Business Buying Strategies from The Dealmaker's Academy
This week on Business Buying Strategies, we return to the behind-the-scenes recording of a live seminar where Jonathan Jay walks an audience of ambitious entrepreneurs through his proven approach to buying and growing businesses without using their own cash. Whether you’re just getting started or you’ve tried the “DIY” route with limited results, this is a must-listen for anyone who wants a safer, smarter way to buy businesses. Jonathan breaks down: ✅ Why confidence matters more than cash — and how to build it ✅ What a leveraged buyout (LBO) really means in practical...
info_outlineFrom 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.