Business Buying Strategies from The Dealmaker's Academy

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.

  1. #350 Confidence, First Deals and Sector Experience

    30 APR

    #350 Confidence, First Deals and Sector Experience

    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.

    32 min
  2. #349 The Psychology of Business Ownership: Why You're the Bottleneck

    16 APR

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

    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.

    26 min
  3. #348 The Reality of Buying a Business — What No One Tells You

    2 APR

    #348 The Reality of Buying a Business — What No One Tells You

    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 underway Multiple 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 signing Sellers changing their mind at the last minute Lawyers slowing everything down Weeks (or months) of work disappearing overnight One dealmaker shares how they: Rebranded a business Built a website Spent £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 progress Low lows when they fall apart Constant 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 selling Negative reviews being posted by the former owner Directors staying on and disrupting operations Internal 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 necessary Use deferred consideration tied to performance Structure agreements so sellers are incentivised to help, not hinder Use clear consultancy agreements instead of vague ongoing roles Define 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 letters Hundreds of conversations Single-digit response rates Even then: Most responses won't lead to deals Many opportunities won't stack up Persistence is essential But there's nuance: Some deals happen quickly Others take years Luck 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 forward Stubbornness = repeating what doesn't work Successful dealmakers: Learn from failed deals Adjust their approach Delegate and outsource Focus 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 slowly Stay in their comfort zone Chase small improvements While dealmakers: Think bigger Use acquisition to scale faster Double 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 success They return to familiar "safe" levels They self-sabotage without realising To grow, you have to: Redefine what "normal" looks like Push beyond your current identity Think 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.

    34 min
  4. #347 From Employee to £6M Business Owner — How One Deal Changed Everything

    19 MAR

    #347 From Employee to £6M Business Owner — How One Deal Changed Everything

    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 business his partner worked in. But the deal dragged on for two years. Nothing happened.   Everything changed when Pete discovered Jonathan's approach. Within 6–7 months, the deal was done.   The biggest shift? Confidence. Once you realise you can do it, everything changes.   Pete highlights a critical lesson most beginners miss: Never rely on one deal.   Instead: • Send out letters consistently • Build multiple conversations • Create choice and comparison   Because the moment you only have one option, you become a motivated buyer. And that's when bad decisions happen.   The Reality of Distressed Deals   One of the acquisitions was a distressed "£1 deal". On paper, it looked like an opportunity.   In reality? • Key staff left early • Critical knowledge disappeared • Supplier issues surfaced • Unexpected £500k liabilities appeared   It was fixed, and became profitable. But the lesson is clear: Distressed deals are not easy wins.   Peter sees the biggest learning curve as people. Not finance. Not strategy. Not deal structure. People.   Key Takeaways from This Episode Take action - Waiting doesn't get deals done. Don't get emotionally attached to one deal - There are always other opportunities. Don't negotiate yourself out of a deal - Sometimes "good enough" is better than perfect. Build deal flow - Options give you power. Surround yourself with the right people - You can't do this alone.   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.

    28 min
  5. #346 Negotiation, Deal Structuring and Funding: What's Actually Working Right Now

    5 MAR

    #346 Negotiation, Deal Structuring and Funding: What's Actually Working Right Now

    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 market.  This episode is packed with practical advice drawn from real negotiations happening right now. What You'll Learn in This Episode Why negotiation skills matter more than clever deal structures Many new dealmakers become fascinated by complex deal structures. But Martin explains that the structure itself is rarely the difficult part. The real skill lies in negotiating terms that work for both sides. Successful negotiators focus on three outcomes: • Getting the business cheaper • Getting better payment terms • Getting more value for the same price When you negotiate with these principles in mind, both sides feel they've achieved a good outcome. Why deal structure can change a business's value dramatically One of the most striking insights from the episode is how the same business can be valued very differently depending on the deal structure. Martin shares a real example where four potential deal structures valued the same business between £1.2 million and £3 million. Nothing about the business itself changed. Only the structure of the deal. Ironically, the structure with the highest valuation turned out to be the best deal for the buyer because it produced significantly stronger annual cashflow. It's a powerful reminder that: Price alone never tells the full story. Why preparation matters – but expecting the unexpected matters more Many first-time buyers believe they need to be perfectly prepared before approaching a seller. Martin explains why this mindset can hold you back. In real negotiations, unexpected moments happen constantly. He shares a story about visiting a potential acquisition target and discovering—mid-conversation—that the seller spoke Danish, which unexpectedly became a useful rapport-building moment. The lesson? You cannot prepare for every possible outcome. But you can stay flexible and genuine. The difference between objections and buying questions A key negotiation skill is recognising the difference between: An objection and A buying question Often when sellers raise concerns, they are not rejecting the deal. They are simply participating in the buying process. For example, when a seller asks: "How do I know you'll actually pay me the deferred payments in the future?" This is usually a buying question rather than resistance. Martin explains how to respond by: • Sharing your long-term vision for the business • Explaining why reputation matters for future acquisitions • Highlighting legal protections within the deal Handled correctly, these moments can build trust rather than derail negotiations. The most common funding options used in acquisitions Funding a deal doesn't always require traditional bank loans. Martin outlines several financing options frequently used in acquisitions:   Invoice Finance One of the easiest and most flexible funding sources, especially for B2B businesses. Asset Finance Funding secured against equipment, machinery or vehicles within the business. Bridging Finance Often used when property assets are involved. Cashflow Lending Possible but generally riskier because it relies solely on the borrower's ability to repay. Interestingly, Martin's preference is often no external finance at all, using seller-funded structures instead. These can dramatically reduce risk for the buyer. The danger of majority share purchases Another important insight relates to buying majority stakes instead of full ownership. Martin warns that shared ownership can lead to serious problems if the relationship between directors breaks down. Whenever possible, buying 100% of the business is usually the cleaner and safer option. If a minority stake remains, it's essential to agree upfront how future exits will be handled. How to handle seller concerns about deferred payments One of the most common objections sellers raise is concern about receiving payments years into the future. Martin explains how to reassure sellers by emphasising: • Your long-term strategy for the business • The reputational damage of failing to honour agreements • Legal protections within the share purchase agreement • The mutual incentives to make the business succeed When positioned correctly, deferred payments become a shared success model, not a risk. Key Takeaway The biggest misconception about buying businesses is that deals depend on complicated financial engineering. In reality, successful acquisitions come down to three things: • Strong negotiation skills • Smart deal structures • Clear alignment between buyer and seller Master these, and opportunities open up quickly. If you want to understand how real deals are negotiated and funded in today's market, this episode is essential listening. Expect practical advice, honest insights, and real-world examples from the front lines of dealmaking.   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.

    33 min
  6. #345 What kind of business should I buy?

    19 FEB

    #345 What kind of business should I buy?

    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 sectors or valuations, you need clarity on your outcome. Are you: Escaping corporate life? Growing your existing business? Building a group to sell for seven or eight figures? Each goal demands a completely different acquisition strategy. If you want to replace your salary, Jonathan challenges you to aim higher than feels comfortable. If you want to scale your current company, acquisition is the fastest way to move the needle. If you want generational wealth, buy-and-build might be your path. But the type of business you buy must match the outcome you want. Why Most First-Time Buyers Aim Too Low One of the most controversial sections of this episode? Size. Jonathan argues that most first-time buyers go too small — and pay the price. Businesses making under £100,000 net profit often: Depend too heavily on the owner Lack proper management accounts Have fragile teams Leave no room for post-acquisition wobble Instead, he shares what he looks for: At least £1m revenue At least £200k net profit Stable margins (15–25%+) Strong management in place Recurring or repeat revenue The effort required to buy a £200k profit business is not ten times harder than buying a £20k one. But the impact on your life absolutely is. The Three Core Acquisition Paths Jonathan breaks down three common strategies: Escape the Day Job: Buy a business that produces serious income — ideally 10x your salary. Grow an Existing Business: Acquire competitors, suppliers, complementary businesses, or geographic expansions. Buy-and-Build: Acquire smaller businesses at lower multiples, combine them, and sell the larger group at a higher multiple. He explains: What fragmented markets are Why M&A activity above you matters How multiple arbitrage works Why strong management becomes critical at scale And importantly — why one deal can change your life. The Worst Types of Businesses to Buy Jonathan doesn't hold back here. Avoid: Owner-dependent businesses Fad businesses Highly volatile or "spiky" profit businesses Overleveraged acquisitions Companies reliant on family members Businesses where relationships walk out the door with the seller He also explains why buying too small can mean buying yourself a job. And that's not what this is about. Funding, Risk and Structure This episode also covers: Why over-leveraging kills deals Why working capital matters more than most buyers realise Why your first deal is the most important Why corporate structure must be set up properly Why personal guarantees should be limited and contained Jonathan's position is clear: Deal number one sets the foundation for everything that follows. Get it right, and you build momentum. Get it wrong, and you may never do deal two. The Big Takeaway Buying a business isn't just about buying something. It's about buying the right thing. With: The right margins The right management The right structure The right funding And the right strategic fit for your long-term goal Clarity at the beginning prevents regret later. Listen Now If you're serious about buying a business in 2026 — or even just thinking about it — this episode gives you the strategic filter you need before you start looking at opportunities. Listen now and make sure your first deal is the right one.   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.

    39 min
  7. #344 Inner Circle Mambers Panel - Questions and Answers

    5 FEB

    #344 Inner Circle Mambers Panel - Questions and Answers

    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 hear: ✅ Why some people close deals after 9 letters — and others need 9,000 ✅ The Domino's Pizza flyer analogy that explains seller timing ✅ How one letter arriving on a seller's birthday triggered a deal ✅ What not to do if you want to avoid buying yourself a job ✅ Why having a "sector" might not matter as much as you think ✅ The power of being the deal maker not the operator ✅ How one member grew to £20M in revenue through targeted acquisitions ✅ The truth about tax structures, holding companies and when to keep it simple ✅ The hidden benefits of buying a business — including instant access to teams, clients, and new energy You'll also learn what separates the dabblers from the doers — and why mindset, patience, and smart support systems make all the difference. Whether you're planning your first deal or your next ten, this behind-the-scenes panel offers valuable takeaways, practical strategies, and straight-talking wisdom. Listen now and learn what experienced dealmakers wish they'd known at the start.   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.

    40 min
  8. #343 Podcast Highlights 2025 Part 2

    22 JAN

    #343 Podcast Highlights 2025 Part 2

    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 shareholders' agreement is vital — and when to draft one How share classes, company articles, and director agreements protect you long term What to expect (and budget) for legal fees How to choose the right lawyer — and why experience matters more than cost 2. The Real Skills Behind Closing a Deal Master negotiator Martin, a Dealmakers Circle member, delivers a no-nonsense mindset and negotiation masterclass. He breaks down: Why confidence (not cash) is your most powerful asset How to handle questions you don't know the answer to — without losing credibility What to say when a seller gives you an unrealistic price How deal fees, PGs, and over-leverage can ruin a good deal — and how to protect yourself 3. Coffee with Jonathan – Real Q&A with Aspiring Buyers Join Jonathan as he answers live questions from attendees during one of his informal "Coffee Morning" Zooms. Topics include: How to set up the right holding company and deal structure Why boards of directors are unnecessary distractions for most first-time buyers The truth about debt, due diligence, and using ChatGPT for business advice How to protect your existing businesses when you start acquiring others 4. Jonathan's Live Seminar – No Money Down… Explained Get an insider listen to a live seminar where Jonathan walks business owners through: How to buy a profitable business without risking personal funds The difference between deal flow and deal completion How to use real estate to complement your acquisition strategy The 36-month "Buy, Build, Exit" roadmap — and why it starts now You'll also hear Jonathan's own backstory — including the deal that changed his life, the competitor he bought (and shut down), and what buying 48 businesses during a pandemic really taught him. 🎧 Whether you're looking for clarity, inspiration, or a practical edge — this episode is packed with the real-world knowledge you need to succeed. 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.

    53 min
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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.

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