When I first started delivering tech due diligence for investors, it felt like standing on the edge of a cliff. Sleepless nights. Reports that were far too long. Endless second-guessing.
It took years of sharpening my approach—and a lot of humility—to gain the confidence I have today.
The key shift? Resetting my mindset.
Approaching this world with a beginner’s mind—willing to listen, learn, and adapt—was the real game-changer.
Here are 10 lessons I’ve learned from working with investors daily after a decade, the kind of lessons no handbook will give you:
1. The Stereotypes Are Wrong
There’s this popular belief that investors are cold, ruthless, and only care about spreadsheets.
It’s just not true. They’re human—driven by curiosity, ambition, and yes, even emotion.
2. If You Don’t Know, Just Say It
Just a life thing.
Early on, I thought I needed to have every answer.
Honesty wins more trust than guessing. A clear “I don’t know, but I’ll find out” is better than any bluff.
But in this job, it’s not answers that matter, it’s questions.
3. Deals Are Emotional
Buying a business isn’t just transactional—it’s emotional for everyone involved.
It’s about vision, legacy, and the people who’ve built something from scratch.
4. The Dance Happens Before We Arrive
By the time we show up for due diligence, founders and investors have already spent weeks—sometimes months—courting each other.
We’re stepping into a relationship that’s already in motion.
5. Most Problems Are Opportunities
What looks like a red flag is often a chance to add value.
Investors are rarely scared off by challenges—they want to see how they’ll be solved.
6. The Report Is 35 Pages, but 3 Matter Most
There are three key pages in any report—the ones investors will pore over.
But here’s the thing: you can’t know which pages they’ll be unless you write all 35 with the same care.
7. They’ll Test You Casually
Investors will fact-check you—sometimes over coffee, sometimes during dinner.
It’s not about catching you out. It’s about seeing if your story holds up when you’re relaxed.
8. People Are the Deal
Every investor says, “We invest in people.”
It’s not just a slogan. It’s real. Strong management teams make or break a deal.
9. Their Job Isn’t Easy
I’m not sure I could do what they do—balancing risk, vision, and capital.
It’s a constant mental workout.
10. They’re Not Scary
Once you break through the formalities, you realise they’re just as curious, driven, and flawed as the rest of us.
The Personal Payoff
The personal development from this work has been enormous.
It’s made me sharper. Clearer. A better writer and thinker.
As someone who loves storytelling, writing reports that shape deals is thrilling. Each report isn’t just a document—it’s a narrative, a bridge between tech and the deal itself.
And I always remind myself:
Every time I assess a business, it’s like someone is assessing mine.
That mindset keeps me honest, engaged, and relentlessly focused on impact.
