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Business Buying Strategies from The Dealmaker's Academy

Business Buying Strategies from The Dealmaker's Academy

By: Jonathan Jay Business Buying Expert
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The Business Buying Strategies Podcast comes from The Dealmaker's Academy, the world's leading training on buying and selling businesses - without risking your own money! Each week we talk to leading experts, discuss business buying strategies, offer hints and tips and cover the essential skills you will need to buy and sell businesses effectively.The Dealmaker's Academy 2023 Economics Leadership Management & Leadership Personal Development Personal Success
Episodes
  • #351 Transferable skills and remaining detached
    May 14 2026

    Host: Jonathan Jay

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

    Guests: Seven Inner Circle members

    Overview

    The Inner Circle panel at Riverside Studios tackle one of the most important questions in business acquisition: how do you remain a strategic investor after buying a business, rather than sliding back into day-to-day operations? The episode also covers sector selection for first-time buyers, and how transferable skills apply across industries.

    Stay at the Top of the Quadrant

    The panel are unanimous: go in as an investor from day one, not an owner or operator. Getting sucked into running the business is a slippery slope — one panellist warns that 18 months later you can find yourself the accidental Operations Director. Your highest-value task is strategy and growth, not delivery. Buy a platform business with an existing management team, so you can step back immediately.

    Choosing Your First Sector

    For a former military officer in the audience wondering where to start, the panel's advice is practical: begin by eliminating sectors you won't touch, then follow the private equity money. Subscribe to deal flow newsletters, look for fragmented industries with proven trade and PE buyers, and pick something close to home geographically for your first acquisition. One panellist chose barbershops purely for the cash flow model — no debtors, daily revenue — and used the income to fund school fees and a car. Another built a hands-off holiday let portfolio using other people's money, taking just 15 minutes a week to manage.

    Mindset Shifts After Five Years

    Asked what they've learned about themselves, the panel give rapid-fire answers: resilience is everything; stop exchanging time for money; you are more capable than you believe. The biggest identity shift for several panellists has been moving from 'business owner' to 'acquisitions entrepreneur' — a reframe that changes how others see you and how you see yourself.

    Key Takeaways

    Buy a platform business — one that runs without you from day one.

    Follow the PE money — if private equity is active in a sector, there's a proven exit waiting.

    Geography matters for your first deal — keep it local and manageable.

    Cash flow businesses beat debtors — recurring, upfront revenue reduces risk.

    Community accelerates everything — you can't do this as well alone.

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    24 mins
  • #352 Using AI and the role that business partners can play
    May 28 2026

    Host: Jonathan Jay

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

    Guests: Seven Inner Circle members

    Overview

    Two big topics dominate this episode. First, the Inner Circle share exactly how they're deploying AI — not in theory, but in practice, right now. Then the conversation shifts to business partnerships: what makes them work, what makes them fail, and two cautionary tales from panellists who learned the hard way.

    AI in Practice

    The panel go well beyond buzzwords. One member is building private internal large language models to train salespeople rather than replace them — capturing every call to create an expert system. Another has automated six hours of compliance work per client into seconds: call recorded, transcript uploaded, CRM populated, recommendation letters generated, all without human input. A third used Claude to sift 200 job applications down to a ranked shortlist and hired the top candidate. Practical tools mentioned include Otter, Fireflies, and Crisp (for analysing discovery calls). The panel's warning: AI will tell you what you want to hear — always interrogate the output.

    Business Partnerships — the Honest Version

    The panel are candid. Partnerships almost always end, and rarely cleanly. One consistent failure mode: one partner outworks the other and resentment builds. The advice — never go 50/50, always have a majority partner, write a thorough shareholders' agreement (not a £750 cut-price version), include a 'bad leaver' clause, and build in a fair buyout mechanism where the person making the offer doesn't get to choose whether they're buying or selling.

    Jonathan's Partnership Story

    Jonathan shares a personal case study: a business growing to £200,000 a week in sales, two indicative offers (one at £21.5m), that collapsed when his partner refused the non-compete clause, withdrew his contacts, and then demanded £10.5m for a stake in a business now in freefall. The legal bill alone was £50,000. The lesson: never skimp on the shareholders' agreement.

    Key Takeaways

    Use AI as a thinking partner — feed it your challenges and let it build your plan.

    Automate the admin, free the humans — AI should handle low-value tasks, not replace relationships.

    Never go 50/50 — someone must have the casting vote.

    Spend properly on your shareholders' agreement — it is the cheapest insurance you'll ever buy.

    Build in a buyout mechanism from day one — and agree the exit strategy before you start.

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    38 mins
  • #350 Confidence, First Deals and Sector Experience
    Apr 30 2026

    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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    32 mins
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