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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
  • #350 Confidence, First Deals and Sector Experience

    #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
  • #349 The Psychology of Business Ownership: Why You're the Bottleneck

    #349 The Psychology of Business Ownership: Why You're the Bottleneck
    Apr 16 2026
    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 • The right timing But the truth? You are the biggest variable in the entire process. Your thinking. Your habits. Your willingness to let go. This episode explores what changes when you stop working in the business… and start thinking like an acquirer. Why business buying is a mental game first • Your mindset shapes how you negotiate, source deals, and make decisions • Confidence and self-perception matter more than technical knowledge • The biggest breakthroughs come from changing how you think, not what you do The founder trap (and how to escape it) · Why building from scratch can cost you years of time, stress, and missed opportunities · How acquisitions can accelerate growth instantly · The hard truth: many founders realise too late they took the long route How to stop being the bottleneck in your own business · Why your name is probably in every box on the org chart · The cost of holding onto control · Practical ways to step back and build a leadership team One powerful idea: If you're not doing the one thing you're world-class at, you're losing money. The mindset shift around delegation · Why letting go feels uncomfortable (and often irrational) · The real reason you resist paying others to do tasks · How to value your time properly A simple but confronting example: If your time is worth £500+ per hour, why are you doing £120/hour tasks? Building a business that runs without you · How experienced dealmakers structure their time · Why some owners are almost invisible inside their own companies · The difference between owning a business and running one Fear vs ego: what's really holding you back? · Why most people don't delegate (and it's not what they think) · The hidden fear of losing control and not knowing how to recover · How self-awareness becomes a competitive advantage What happens when you lose everything One of the most powerful moments in this episode: A dealmaker shares how they lost everything… And rebuilt it all in just 64 days. The lesson? Skills and mindset are more valuable than money. Once you know how to create value, you can do it again. Why your peer group matters more than you think · The difference between personal friends and professional peers · How being around the right people stretches your thinking · Why growth often requires changing your environment The long-term game: hunter vs hunted · Why acquisitions allow you to leverage years of someone else's work · How to build a group of businesses strategically · When to switch from buying… to becoming the asset others want Key takeaway You don't build wealth by working harder inside a business. You build it by: • Letting go • Thinking bigger • Leveraging people, systems, and acquisitions And most importantly… Becoming a different person in the process.
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    26 mins
  • #348 The Reality of Buying a Business — What No One Tells You

    #348 The Reality of Buying a Business — What No One Tells You
    Apr 2 2026
    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£17M group revenue£26M in acquisitions underwayMultiple buy-and-build strategies across sectors And yet, despite the success… every single one of them has faced setbacks, stress, and deals falling apart. The Truth: Deals Fall Apart (Often at the Last Minute) One of the clearest messages from this episode: Expect things to go wrong. You'll hear examples like: Deals collapsing on the day of signingSellers changing their mind at the last minuteLawyers slowing everything downWeeks (or months) of work disappearing overnight One dealmaker shares how they: Rebranded a businessBuilt a websiteSpent £15,000 preparing …only for the seller to walk away at the final moment This is normal. The Emotional Reality Buying a business isn't just strategic, it's emotional. High highs when deals progressLow lows when they fall apartConstant uncertainty As one dealmaker puts it: It's a rollercoaster. Expect to strike out more than you succeed. If you're not prepared for that, it will catch you out. Seller Problems You Don't Expect Even after completion, challenges don't stop. Real examples from the episode include: Sellers sabotaging the business after sellingNegative reviews being posted by the former ownerDirectors staying on and disrupting operationsInternal conflict damaging performance These are rarely talked about, but they happen. How to Protect Yourself The panel shares practical ways to reduce risk: Avoid keeping sellers as directors unless absolutely necessaryUse deferred consideration tied to performanceStructure agreements so sellers are incentivised to help, not hinderUse clear consultancy agreements instead of vague ongoing rolesDefine responsibilities and expectations upfront The key idea: Alignment matters more than goodwill. Deal Flow: The Numbers Game No One Warns You About Another reality check: Finding the right deal takes volume. Thousands of lettersHundreds of conversationsSingle-digit response rates Even then: Most responses won't lead to dealsMany opportunities won't stack upPersistence is essential But there's nuance: Some deals happen quicklyOthers take yearsLuck plays a role The only constant is this: You need to keep going. Persistence vs Stubbornness This episode draws an important distinction: Persistence = keep moving forwardStubbornness = repeating what doesn't work Successful dealmakers: Learn from failed dealsAdjust their approachDelegate and outsourceFocus on higher-value activity They don't just "try harder" They get smarter Why Most Business Owners Stay Stuck A powerful theme emerges: Most business owners: Grow slowlyStay in their comfort zoneChase small improvements While dealmakers: Think biggerUse acquisition to scale fasterDouble or triple revenue through deals The difference isn't intelligence. It's mindset. The Hidden Barrier: Your Own Thinking One of the most striking insights: Your growth is limited by what you believe is possible. Many people unconsciously cap their successThey return to familiar "safe" levelsThey self-sabotage without realising To grow, you have to: Redefine what "normal" looks likePush beyond your current identityThink at a different level Key Takeaways If you're considering buying a business, take this seriously: 1. It's not glamorous Ignore what you see online. This is hard work. 2. Deals will fall apart Build resilience. Expect setbacks. 3. Sellers can become problems Structure deals to protect yourself. 4. Volume matters More conversations = more opportunities. 5. Learn and adapt Don't repeat the same mistakes. 6. Think bigger Acquisition is a faster path than organic growth. 7. Your mindset sets the ceiling If you don't change how you think, nothing else changes. If you're serious about buying a business – and avoiding the mistakes Jonathan outlines – book a free Clarity Call with one of his team: 👉 dealmakers.co.uk/clarity You'll get 15 minutes of expert insight to help you decide which next step is right for you – whether that's attending a Deal Club evening, joining the 3-day Foundation Programme, or stepping straight into the Mastermind. Subscribe & Review If you enjoyed this episode, please subscribe and leave a review. It helps more future dealmakers discover the show – and succeed in their first business acquisition.
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    34 mins
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