Revenue Room – The session summary, notes and insights.
Thursday’s Revenue Room was one of the best conversations we’ve had.
The topic: Is your business sellable? The commercial audit.
I brought in Paul Cooper — 30 years in M&A, helped build JEGI Clarity in London, advised on some of the biggest deals in media and tech. We were also joined by Ralph Kaiser co-founder of Ingenia AI and someone who has been on both sides of the acquisition table, plus founders, operators and advisors at different stages of the exit journey.
Here’s what came out of the room.
THE THING THAT KILLS MORE DEALS THAN ANYTHING ELSE
Maria Jafri has worked with over 350 M&A clients — private equity, investment banking, brokerage. She didn’t take long to get to the point. ❝
“This person’s built their entire business — their brother does the books and their wife does this. And if they step away for five minutes, everything comes crumbling down. And even if it’s making $35 million a year, it’s worthless.”
That’s the number one reason deals don’t go through. Not the numbers. Not the market. Not the legal complexity.
Founder dependency.
The business is making real revenue. The growth story is credible. But take the founder out of the room for a month and the wheels come off. The sales calls don’t happen. The relationships don’t hold. The decisions don’t get made.
Buyers see this quickly. And when they see it, they either walk away or restructure the deal so the founder stays financially tied to delivering the plan — sometimes for three, four, five years post-close.
Dominic Baldwin, who has run his own business for 25 years and now works with founders on exactly this transition, shared what his coach told him a few years ago: make yourself redundant. Prove the business doesn’t need you. He took six weeks completely off the grid. The business thrived. ❝
“As a CEO and a founder, if you’re looking to have a capital event, the first thing you have to be able to do is prove that you’re not needed within the business model going forwards.”
That’s the test. Not whether you could leave. Whether the business would be fine if you did.
WHAT DUE DILIGENCE ACTUALLY LOOKS AT
Most founders assume commercial due diligence is about contracts and trailing revenue. It is. But that’s not where the value is won or lost.
Paul Cooper framed it like this: buyers aren’t really looking at the past. They’re trying to use the past to predict the future. And if you can make the future look inevitable — with data, account plans, conversion rates, expansion patterns — they might apply the multiple to your forward numbers, not your backward ones. ❝
“If you can make your forward numbers just an inevitability… instead of them applying 10 times to the backward number, they might apply 12 times to the forward number.”
The difference between a 10x historical multiple and a 12 or 15x one isn’t magic. It’s evidence.
And here the thing are areas that matter most:
— Existing customer growth. Can you show a track record of growing accounts year on year? Do you have account plans? Have you delivered against them?
— New logo pipeline. Not just “we have a pipeline” — but a funnel with consistent conversion rates, predictable deal sizes, and data that defends the forecast.
— Repeatability. Is the revenue re-occurring or truly recurring? Both are valuable. But you need to know the difference, and so does the buyer.
The founders who walk into DD underprepared think they need to tell a good story. The ones who walk out with the best deals tell a story backed by two or three years of data that makes the future feel unavoidable.
THE DATA ROOM IS YOUR FIRST IMPRESSION
Ralph brought a perspective I hadn’t heard framed quite this way before.
Before the numbers, before the contracts, before anything else — there’s the data room. And most founders treat it as a filing exercise. A place to dump documents so the buyer can dig through them.
The better framing: the data room is an experience. It’s the first time a potential acquirer gets to feel what it’s like to deal with your business.
Ralph’s advice on who you’re designing that experience for was sharp: ❝
“An ideal investor is not anyone that can fog a mirror.”
Know exactly who your ideal acquirer is before you build the room. What do they expect to see? How do they expect it to be structured? Design backwards from that.
Paul built on it: start with your equity story. Write the narrative first. Then structure the data room to follow it. When the buyer moves from the management presentation into the data room, the structure should feel familiar. The same story, evidenced.
Ralph’s practical suggestion: a short video at the entrance. 90 seconds, the founder walking the buyer through what they’re about to see and why. Nothing produced. Just the same energy you bring to your best sales conversation — setting the frame before the digging starts. ❝
“M&A is all about storytelling.”
ONE MORE THING
Dominic’s closing thought was worth sitting with.
Most of the work his business does happens after the sale. Not during it. Because the thing founders consistently underestimate isn’t the legal complexity or the due diligence process or even the earn-out. It’s what comes after.
Two months after selling the thing they built, a lot of founders are lost. The business was the engine. Take it away and there’s a gap that a yacht or a long holiday doesn’t fill.
Worth thinking about before the exit process even starts. What is enough? What’s next? Those aren’t soft questions. They’re commercial ones.
ON EARN-OUTS AND WHAT PEOPLE GET WRONG
There’s a lot of anxiety around earn-outs. Most founders hear the word and think of risk — of not getting what the business is worth, of being locked in, of years of uncertainty.
Yes, earn-outs can pay out spectacularly well. They can also give you the highest day-one payment in the room. The question isn’t whether there’s an earn-out. It’s whether the milestones are fair and whether the business — without you being the hero of every deal — can actually hit them.
And then there’s the thing nobody likes to talk about openly. ❝
“Most people lie about how much money they take off the table when they sell their business and everybody else is under NDA and nobody can talk about it.”
I’ve been through the earn-out process myself. It’s not always comfortable. But the founders I’ve seen struggle most with it aren’t the ones who got bad terms. They’re the ones who hadn’t decoupled from the business before the deal closed — so every milestone felt like it still depended on them personally. Which, of course, it did.
That’s why the commercial infrastructure matters so much before you go to market. Not so you can claim the business runs without you. So that when someone tests it, it actually does.
Watch the full session here: https://fathom.video/share/sEyPHyusTAG3zVLQXgbnhptzvt3FnWs
If anything from Thursday’s conversation sparked a question about your own business — where you sit on the sellability spectrum, what your commercial infrastructure actually looks like, whether the business would hold up without you in the room — I’m always happy to have a private conversation on these topics.
I make my living helping founder CEOs figure this stuff out. Have a read through my website if you feel there could be alignment, book a time and lets talk about your goals, ambitions and how we can achieve these things together
Book a time here: https://calendly.com/simon-revenueandbeyond/consultation
See you in the next one.
Simon
Revenue & Beyond simon@revenueandbeyond.com www.revenueandbeyond.com