Business Buying Strategies from The Dealmaker's Academy

Jonathan Jay Business Buying Expert
undefined
Apr 2, 2026 • 34min

#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.
undefined
Mar 19, 2026 • 28min

#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.
undefined
Mar 5, 2026 • 33min

#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.
undefined
Feb 19, 2026 • 39min

#345 What kind of business should I buy?

They debate which type of business to buy based on your end goal and why picking the wrong one wrecks future plans. They cover aiming higher on size and profit, three acquisition paths like escape or build-and-sell, and why recurring, boring businesses with strong managers win. Practical warnings on owner-dependent firms, timing, working capital and deal structure round out the conversation.
undefined
13 snips
Feb 5, 2026 • 40min

#344 Inner Circle Mambers Panel - Questions and Answers

Lee, a serial acquirer who learned by buying jobs then building management teams. Johan, an Inner Circle member who times approaches by sector seasonality. Tim, an experienced dealmaker sharing first-deal and negotiation stories. They discuss persistence in sourcing, seller timing analogies, seasonal windows for outreach, scaling by hiring operators, and simple ownership structures.
undefined
Jan 22, 2026 • 53min

#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.
undefined
Jan 8, 2026 • 1h 1min

#342 Podcast Highights 2025 - Part One

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 cash Real examples of smart deal structures (including 100% deferred payments, sale and leasebacks, and profit shares) Why business brokers are often best avoided—and how to source deals direct The mindset shift that separates hesitant entrepreneurs from decisive dealmakers Lessons from multiple industries: manufacturing, beauty, PR, accountancy, care, construction, and more Featured Dealmakers & Their Stories Danny : Bought his first manufacturing business in 2020 using a sale-and-leaseback strategy—without upfront cash. Since then, he's continued acquiring, including a steel stockist business sourced via a broker, proving there are exceptions to every rule. His deals are a masterclass in positioning, rapport-building, and creative funding structures. Cara: Started with a single beauty salon turning over £180k. Now owns nine salons generating over £2 million—in just 18 months. Her story is a testament to bold action, clear negotiation, and using Jonathan's direct letter strategy to source off-market deals. Simon: Built a successful PR firm through five low-risk acquisitions (plus two media businesses). Did every deal with no upfront payment—just structured earn-outs and profit shares. Proves that asset-light businesses can still be bought without debt or risk. Martin: Went from sceptic to super-dealmaker—buying two businesses in the final week of December. Now a key member of the Dealmakers training team, Martin specialises in smart structuring, negotiation, and financing—highlighting the power of taking fast action. Richard: Shares powerful insights from 125+ investments across three decades. From growing up in the Australian care system to early retirement at 34, Richard reflects on the power of resilience, backing the right people, and learning from failure. This extended segment offers wisdom for anyone thinking about buying, building, or backing a business. David: Built a £20m revenue care group from a spare bedroom startup via 17 acquisitions in just a few years. Started by taking over a struggling friend's company, then pounced when two corporates exited the market. Now a blueprint for how to scale fast in a regulated, people-heavy sector. John: Grew a £6m group of six construction-sector businesses by combining organic growth with smart acquisitions—some funded using the target company's own cash. Emphasises the power of accountability, having a group strategy, and executing consistently. Neil: Started 2020 with three clients and two months of savings. Now runs a 600+ client accountancy practicegenerating over £1 million annually. His first acquisition—a micro-fee bank—gave him the confidence to grow faster through acquisition. Key Takeaways You don't need money to buy a business—just the right strategy and structure. It's never the wrong time to act. Deals happened on Christmas Eve and New Year's Eve. Good sellers aren't looking for the highest bidder. They're looking for a safe pair of hands. Confidence grows through action. One deal is often the gateway to dozens more. This is one of the most inspiring and educational episodes we've ever released. Whether you're new to acquisitions or already making deals, you'll walk away with new insights—and renewed motivation. 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.
undefined
Dec 18, 2025 • 31min

#341 Putting the Deal Together

Live seminar highlights on buying businesses without using your own cash. Practical breakdowns of leveraged buyouts, seller finance, asset and invoice finance. How to avoid personal guarantees and combine multiple finance methods into a single deal. Tips on sourcing off-market targets, running tight discovery calls, securing exclusivity and reaching heads of terms quickly.
undefined
Dec 4, 2025 • 33min

#340 One Deal Away: How to Grow, Scale and Exit Through Acquisition

A live seminar walkthrough of buying businesses without using your own cash. Rapid growth via acquisitions, a 36‑month buy‑build‑exit timeline, and one deal that can change everything. Strategies like competitor buys, buy‑and‑build roll‑ups, propco property tactics, and buying distressed or loss‑making assets. Practical talk on avoiding overpaying, due diligence pitfalls, and positioning yourself as a credible buyer.
undefined
Nov 20, 2025 • 33min

#339 From Podcast Listener to Dealmaker: The Fast-Track Path to Your First Acquisition

In this special episode of Business Buying Strategies, Jonathan Jay pulls back the curtain on a pivotal moment in every dealmaker's journey — the point where you stop watching from the sidelines and take real, tangible action. And if you've been listening to the podcast for a while but still haven't bought your first business, this episode might just change everything. Here's what you'll discover: ✅ The biggest mindset shift that separates action-takers from "armchair" dealmakers ✅ Why trying to piece together internet advice is like cooking with three celebrity chefs — and why it doesn't work ✅ The real reason sending letters to business owners is outdated (and what to do instead) ✅ Why getting stuck in the deal sourcing phase is costing you time, energy, and opportunities ✅ How one dealmaker added £9M in turnover and £1.4M in profit — in just 7 months ✅ The hidden power of vendor finance (and how it can benefit both buyer and seller) ✅ Why buying a business transforms you — not just your income You'll also hear inspiring real-life stories from past Mastermind clients — including: A primary school teacher turned £9M dealmaker A beautician who went from £180K to a 7-salon, £2M business group A dealmaker who earned £300K upfront on day one — without spending his own money Plus, Jonathan reveals a limited-time opportunity to attend the 3-day Foundation Programme in December — live and in person — for just £1. This is more than a podcast episode. It's your personal invitation to go from listener to action-taker… to business buyer. 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. Resources Mentioned: Business Buying Toolkit – Free Download Upcoming Deal Club Events 3-Day Foundation Programme

The AI-powered Podcast Player

Save insights by tapping your headphones, chat with episodes, discover the best highlights - and more!
App store bannerPlay store banner
Get the app