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by Jonathan Jay Business Buying Expert
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- 5 days ago23 min
#351 Transferable skills and remaining detached
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.
- 2 weeks ago32 min
#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.
- Apr 16, 202626 min
#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. <p cla
- Apr 2, 202633 min
#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 Thi
- Mar 19, 202627 min
#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.
- Mar 5, 202632 min
#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. Bridgi
- Feb 19, 202638 min
#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 everythi
- Feb 5, 202640 min
#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.
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About Business Buying Strategies from The Dealmaker's Academy
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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