#336 The 14 Rookie Mistakes Business Buyers Must Avoid
Business Buying Strategies from The Dealmaker's Academy
Release Date: 10/23/2025
#339 From Podcast Listener to Dealmaker: The Fast-Track Path to Your First Acquisition
Business Buying Strategies from The Dealmaker's Academy
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 —...
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#338 More Dealmaker Questions Answered by Jonathan
Business Buying Strategies from The Dealmaker's Academy
In this week’s episode of Business Buying Strategies, you’re invited to sit in on one of Jonathan Jay’s live “Coffee with Jonathan” sessions — where he fields rapid-fire questions from aspiring dealmakers and delivers straight-talking, practical answers. From metaphors that make sense to advice that saves you from million-pound mistakes, this episode is packed with real insights, real examples, and real momentum. Here’s what you’ll learn this week: The Spaghetti Analogy That Could Change Your Approach Forever Discover why Jonathan says business buying is like choosing...
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#337 Bonus Episode: Inside the Business-Buying Foundation Course
Business Buying Strategies from The Dealmaker's Academy
In this special short episode of Business Buying Strategies, Jonathan reveals what really happens at his live Business-Buying Foundation Course — and why it’s become one of the most transformative events for first-time business buyers. Jonathan explains why he created the Foundation Programme for those who are tired of endless webinars and ready to learn in person — surrounded by like-minded people who are serious about taking action. Over three immersive days, attendees get clarity, confidence, and a proven process for buying their first (or next) business. In this episode, you’ll...
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#336 The 14 Rookie Mistakes Business Buyers Must Avoid
Business Buying Strategies from The Dealmaker's Academy
In this straight-talking solo episode, Jonathan Jay reveals the 14 most common mistakes first-time business buyers make – and how you can avoid them. After a decade of mentoring hundreds of entrepreneurs through their first (and second, third, even 20th) acquisition, Jonathan has seen the same mistakes crop up again and again. Some cost people time. Others cost them tens – even hundreds – of thousands of pounds. And a few can cost them everything. Whether you’re just starting out, stuck in analysis paralysis, or partway through a deal, this episode will give you clarity,...
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#335 Live Q&A with Jonathan: No Slides, Just Straight Talk
Business Buying Strategies from The Dealmaker's Academy
This week, we take you behind the scenes of one of Jonathan Jay’s exclusive Zoom coffee mornings — a live, unscripted Q&A session where aspiring business buyers put their real-world questions directly to one of the UK’s most experienced dealmakers. No slides. No fluff. Just straight-talking, practical answers from Jonathan on everything from company structure and personal guarantees to due diligence, PGs, investor myths, tax efficiency, and how to avoid wasting months of your life chasing the wrong advice. Highlights include: ✅ Do you need a Board of Directors? (Spoiler: probably...
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#334 Negotiation Masterclass with Martin
Business Buying Strategies from The Dealmaker's Academy
In this week’s episode, Jonathan Jay introduces Inner Circle member Martin, one of the sharpest negotiators in the business buying world. What follows is a complete masterclass on negotiation — packed with practical insights, real-world stories, and strategies you can put into action right away. Martin pulls back the curtain on how to approach deals with confidence, credibility, and control. From mindset techniques to financial structuring, from role-playing negotiations to managing seller expectations, this session is full of wisdom you won’t find on YouTube. What you’ll learn in this...
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#333 Legal Pitfalls of Business Acquisitions
Business Buying Strategies from The Dealmaker's Academy
In this week’s episode, Jonathan sits down with his long-term legal partner, John Andrews, for a masterclass on the legal do’s and don’ts of buying a business. With over 250 deals completed for Dealmakers clients and three decades of M&A experience, John shares the essential legal knowledge every buyer needs — especially if you’re serious about avoiding costly mistakes. Whether you’re preparing for your first deal or scaling up your acquisition strategy, this episode gives you the legal edge to navigate deals with confidence. What You’ll Learn in This Episode: Why a...
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#332 Ask a Business Acquisition Expert ANYTHING
Business Buying Strategies from The Dealmaker's Academy
In this episode, Jonathan does something a little different: a live Q&A session with listeners and aspiring dealmakers. You’ll hear real, unscripted questions from entrepreneurs across the UK (and beyond) – and Jonathan’s direct, practical answers drawn from decades of dealmaking experience. In This Episode Why traditional “day-one finance + deferred consideration” deals are becoming outdated. The big difference between the “vanilla” advice on YouTube and the full-flavour strategies inside Mastermind. Should you start with a small (£500k turnover, 5 staff)...
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#331 From Redundancy to £1 Million: Neil’s Journey from Scratch to 650 Clients
Business Buying Strategies from The Dealmaker's Academy
In this week’s episode of Business Buying Strategies, Jonathan speaks with Neil — a former accountant who lost his job in early 2020 and built a million-pound business in just five years. Neil shares how he went from doing the odd tax return to running a team of 12, managing 650 clients, and completing three acquisitions in just two years. You’ll hear how he turned redundancy into opportunity, overcame the chaos of COVID, and used acquisitions — not marketing — to scale rapidly and strategically. What You’ll Learn in This Episode: How Neil built his business from scratch...
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#330 Fast-Tracking Business Acquisitions: Lessons from Success Stories
Business Buying Strategies from The Dealmaker's Academy
In this week’s episode of Business Buying Strategies, Jonathan shares valuable insights from Inner Circle members who have successfully purchased businesses. The episode considers the transformative power of a single acquisition, featuring examples such as Nick's printing business expansion and Jas's recent ventures. Jonathan stresses the importance of validating the business model to ensure sustainable growth. Lessons include the importance of empowering employees, maintaining quality management, and the strategic considerations of business consolidation and rebranding. It’s an episode...
info_outlineIn this straight-talking solo episode, Jonathan Jay reveals the 14 most common mistakes first-time business buyers make – and how you can avoid them.
After a decade of mentoring hundreds of entrepreneurs through their first (and second, third, even 20th) acquisition, Jonathan has seen the same mistakes crop up again and again. Some cost people time. Others cost them tens – even hundreds – of thousands of pounds. And a few can cost them everything.
Whether you’re just starting out, stuck in analysis paralysis, or partway through a deal, this episode will give you clarity, confidence and practical tips to avoid painful pitfalls and accelerate your journey to a successful business acquisition.
In This Episode, You’ll Discover:
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Why getting your information from random internet sources is a fast-track to failure
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The dangers of mixing advice from YouTube, blogs and podcasts – and why you need a single, structured approach
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Why deal sourcing is easy – but getting deals over the line is what actually matters
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The myth of sending out letters – and the smarter, modern ways to generate deal flow
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The critical mistakes buyers make when valuing a business – and how overpaying can sink your deal
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Why “buying a business for £1” is not the shortcut you think it is – and what to do instead
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How to build credibility with sellers – even if you’ve never bought a business before
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The terrifying reality of personal guarantees – and how to avoid them
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Why relying on YouTube or Google to find your deal team is a massive mistake
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The hidden danger of “saving money” by skipping proper due diligence
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Why small deals can be more trouble than they’re worth – and what profit level to aim for
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The truth about broker sites, proof of funds, and why off-market deals win
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The #1 reason most people never buy a business – and how to make sure you’re not one of them
If you’re serious about buying a business – and avoiding the mistakes Jonathan outlines – book a free Clarity Call with one of his team:
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.
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