What It Looks Like From the Other Side

There's a kind of advice you can only get from someone who's already finished the thing you're in the middle of. Most people around a founder can tell you what investors want to see, what the textbook version of scaling looks like, or that they're facing the same challenge and you're not alone. Far fewer can tell you what actually mattered, in hindsight, once they'd lived through the whole arc: built it, scaled it (or didn't), raised funding, and came out the other side.

Last month we got that from Phil Wilkinson, a founder who's built and exited several businesses and is now building AI-native ventures while angel investing in the space, in a fireside chat hosted by Ian Merricks.

What makes these conversations land differently is that someone in the room has actually lived through the thing you're in the midst of, and is willing to talk about it plainly, not as a polished case study, but as it actually felt at the time.

The single learning that stuck with us most was Phil's closing one. He said the only reason he can now properly read what's really happening in a fundraising conversation — what an investor is actually testing for, what a founder is actually avoiding saying — is because he's sat on both sides of the table. As a founder, he didn't have that. As an angel investor now, he sees founders without it constantly: ambitious, capable people guessing at a dynamic that someone with his experience can just see.

That's exactly the asymmetry these sessions exist to shortcut. We can't give every founder the experience of having exited a business and then become an investor. But we can put them in a room with someone who has, and let them ask the questions they wouldn't normally get a straight answer to.

Take fundraising signals. Phil's take:

"Raising money at any stage is a bit of a dance, and mostly about velocity. For the business, that means showing investors consistent growth and movement towards your goals. For the raise itself, it means showing you're only in the market for a limited window and that interest and commitments are coming in fast.

An investor who goes quiet, or ends with 'we'll discuss and circle back,' might genuinely be considering it. But if you don't hear back relatively soon, the read is usually that you haven't demonstrated that velocity. Investors don't really know whether your business will be a huge success, so they lean on the signals they can see: how fast you're moving, and how many other people want to give you money.

I pitched one of the top VCs many years ago, they'd already heard about the raise from other angels and VCs before I walked in. One meeting, and they rang back with a term sheet three hours later. When you've got something they genuinely love, you'll know about it very fast. Leverage that."

It's also, frankly, just a relief for a lot of founders to hear that the path isn't a straight line for anyone. Knowing when to carry on and double down versus throwing the towel in.

The questions that came from the floor weren't really about tactics; they were founders checking their own experience against someone else's, looking for the version of "yeah, that's normal" or "no, you should worry about that" that you can only really get from someone who's been there.

That's the value we keep coming back to with these events: not a masterclass, not a takeaway list, just enough honest signal from someone further down the road that founders leave feeling less alone with the decision in front of them. The conversation kept going long after the fireside ended, founders comparing notes with each other, not just with Phil.

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Thanks to Phil for his candour, and to Ian for hosting. If you're building and want to talk to someone who's actually done it, that's a big part of what VenturePath exists for.