Business Buying Strategies from The Dealmaker's Academy

Host: Jonathan Jay
Format: Live panel Q&A — Riverside Studios, Hammersmith
Guests: Seven Inner Circle members
 

Overview
Two big topics dominate this episode. First, the Inner Circle share exactly how they're deploying AI — not in theory, but in practice, right now. Then the conversation shifts to business partnerships: what makes them work, what makes them fail, and two cautionary tales from panellists who learned the hard way.
AI in Practice
The panel go well beyond buzzwords. One member is building private internal large language models to train salespeople rather than replace them — capturing every call to create an expert system. Another has automated six hours of compliance work per client into seconds: call recorded, transcript uploaded, CRM populated, recommendation letters generated, all without human input. A third used Claude to sift 200 job applications down to a ranked shortlist and hired the top candidate. Practical tools mentioned include Otter, Fireflies, and Crisp (for analysing discovery calls). The panel's warning: AI will tell you what you want to hear — always interrogate the output.
Business Partnerships — the Honest Version
The panel are candid. Partnerships almost always end, and rarely cleanly. One consistent failure mode: one partner outworks the other and resentment builds. The advice — never go 50/50, always have a majority partner, write a thorough shareholders' agreement (not a £750 cut-price version), include a 'bad leaver' clause, and build in a fair buyout mechanism where the person making the offer doesn't get to choose whether they're buying or selling.
Jonathan's Partnership Story
Jonathan shares a personal case study: a business growing to £200,000 a week in sales, two indicative offers (one at £21.5m), that collapsed when his partner refused the non-compete clause, withdrew his contacts, and then demanded £10.5m for a stake in a business now in freefall. The legal bill alone was £50,000. The lesson: never skimp on the shareholders' agreement.
Key Takeaways
•       Use AI as a thinking partner — feed it your challenges and let it build your plan.
•       Automate the admin, free the humans — AI should handle low-value tasks, not replace relationships.
•       Never go 50/50 — someone must have the casting vote.
•       Spend properly on your shareholders' agreement — it is the cheapest insurance you'll ever buy.
•       Build in a buyout mechanism from day one — and agree the exit strategy before you start.

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.

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.

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.

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.
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