Let’s be honest. A lot of what we do in Tech DD could be labelled “Project Fear in a Box”.
Our job is, fundamentally, to align with an investor’s mindset and ask: What might go wrong?
We pressure-test teams, systems, processes. We scan for fragility.
We’re hired to worry.
And that works — because humans are hardwired to prioritise threat detection.
(“Bad is stronger than good” is a real psychological principle. Our brains have evolved to remember threats more vividly than positives. Look up Baumeister et al., 2001 — it’s fascinating.)
But here’s the thing: “Project Fear” is easy mode.
It’s much harder — and much more useful — to shine a light on what great looks like. Not perfection. Not some big-tech fantasy. But a founder and team who are doing the right things, consistently, in the real world.
The One That Stood Out
This particular case was a tech-enabled professional services firm going through a buyout. On paper, I wasn’t excited. Looked like a routine IT diligence — not the juicy product stuff that usually gets my brain going.
But I was wrong.
From the very first call, I knew this was going to be different.
1. The MSP Was In The Room
Most founders keep their IT providers at arm’s length during diligence. Some don’t even tell them it’s happening. We end up playing Chinese whispers: from us to advisors to management to the MSP, with context getting lost and answers delayed.
- This founder didn’t play that game.
- He brought the MSP into the first call.
- No theatre. No secrets. Just clarity and alignment. You could tell they had a strong working relationship built on mutual respect.
2. The MD Was All-In
Every single question — technical or otherwise — was answered in full, quickly, and without defensiveness.
The data room was fully populated. Not drip-fed. Not “coming soon”. Just there.
That’s table stakes, yes. But rarely done this well.
3. But the Real Gold Was in the Story
What I enjoyed most was the set of interviews with the founder and the MSP. Their shared decision-making history was clear. You could trace their logic. They didn’t just explain the what — they gave us the why.
They knew their gaps. They weren’t defensive.
They had a vision for how to fix those gaps.
And they already had momentum.
We walked through the full customer journey — and here’s where my founder/marketer brain kicked in. I don’t just look at the point of service delivery. I start with awareness:
- How are people finding you?
- What’s the conversion process?
- Where does onboarding fall down?
- What happens post-payment?
- How do you re-engage?
In every area, the founder had a clear line of sight. His concern for the customer wasn’t performative — it had depth and history. It was lived. The kind of “data and dignity” approach you can’t fake for an investment round.
4. They Had the Map
We asked for a system architecture diagram. They already had one.
We asked what could be improved. They told us.
We asked what they were working on. They showed us — and it was already in progress.
The MD and the MSP were, quite clearly, on the same side of the table.
That’s rare. And powerful.
The Earn-Out Question
One final reflection: the MD was on it. Every hour of the day. Fast responses. Deep knowledge. Genuine care. It made our Tech DD process smooth, accurate, and ahead of schedule.
But there’s a looming question for the acquiring team:
What happens after the earn-out?
Because this founder is the business. His identity, his time, his energy — it’s all in.
That level of dedication is priceless… but it’s also fragile.
As a buyer, you want to understand how you transition that value into something sustainable — not just personally dependent.
Not Every Story Is a Warning
So here’s why I’m writing this:
We spend so much time surfacing risks and red flags that we often forget to celebrate when someone aces it.
This was a founder who had nothing to hide, who brought his partners into the room, and who understood his customers and systems inside-out.
It was a refreshing reminder that Tech DD doesn’t have to be “Project Fear”.
Sometimes, it’s just a chance to recognise someone who’s quietly nailed it — and built something strong, clear, and deeply thought-through.
