From Founder to VC Fellow: What I Learned Sitting on the Other Side of the Table

I've pitched investors more times than I'd like to count. Some of those pitches went well. Most went... fine. A few were genuinely uncomfortable.

Earlier this year, I joined TRANSFORM VC as a VC Fellow. For the first time, I was on the other side of the table, reviewing decks, running calls, doing diligence, sitting in investment discussions. Six months in, I want to share what that shift taught me.

The view from the other side is not what you imagine

When you're a founder pitching, you tend to assume the investor across the table is evaluating you against some objective scorecard. You worry about your metrics, your market size, your unit economics. You wonder if your revenue numbers are strong enough, if your team slide looks credible.

Here's what I learned: a lot of what investors are actually doing is trying to understand you. Not the deck. You.

They're asking themselves: Does this person have genuine insight into their market, or are they just pattern matching from a blog post? Do they know what they don't know? When I push back on an assumption, do they defend it thoughtfully or just capitulate?

The deck is a prompt. The conversation is the evaluation.

Founders underestimate how much investors talk to each other

I knew, intellectually, that VC is a small world. I didn't appreciate what that meant in practice.

Investors reference check founders constantly, not just at the end of a process but throughout. They compare notes with other VCs they've already spoken to. They ask portfolio founders who they've seen in similar spaces. They remember how you behaved in a process they passed on two years ago.

Your reputation in the ecosystem is a cumulative asset. Or a liability. Founders who are honest about their struggles, transparent about their reasoning, and gracious when they hear "no": those founders show up differently when they come back around.

The questions investors ask that founders rarely prepare for

Most founders prep hard for the obvious questions: market size, competition, go to market, defensibility. Far fewer are ready for the questions that actually reveal the most:

• "What do you think you're most wrong about right now?"
• "If this doesn't work, what's the most likely reason why?"
• "Tell me about a significant product decision you got wrong and what you'd do differently."

These aren't trick questions. They're genuine attempts to understand how a founder thinks. Do they have the intellectual honesty and self-awareness to build through adversity?

The founders who handled these well tended to be the ones I found most compelling. Not because they had perfect answers, but because they'd clearly sat with the hard questions themselves.

Valuation is a conversation, not a negotiation

As a founder, I often approached valuation discussions as a negotiation: a number I'd defend, with a strategy behind it.

On the investor side, I saw something different. The best conversations weren't about a specific number. They were about alignment on the business trajectory and what the next 18 months need to look like for the company to justify the valuation at the next round.

When a founder says "I'm raising at £X pre money," the question an investor is really asking is: "What does this company need to achieve for the next round to be a genuine step change up? And do I believe this team can get there?"

If the answer to the second part is yes, the exact number is often more negotiable than founders assume.

What hasn't changed

For all the perspective I've gained sitting on the investor side, one thing hasn't changed: the founders I found most compelling were the ones building something they genuinely cared about, who understood their users deeply, and who had the energy and resilience to keep going when things got hard.

No deck can manufacture that. It either comes through or it doesn't.

And if you're a founder reading this: the investors who pass on you are often not passing on your company. They're passing because the fit isn't right for their thesis, their portfolio, their timing. That's not the same thing as a verdict on you.

Keep building. The right conversation usually comes around.