Raising money for the first time

I built Exposely for three years without raising. I built LiveRecover for three years without raising and sold it. This year, for Vigilance, I raised outside money for the first time — around $250,000, almost all of it from operators inside the Shopify and DTC world.

Given how much I've written about not raising, that deserves an explanation.

What changed#

Not my view of dilution. I still think the standard argument for raising — you need capital to move fast — is often a story people tell to avoid a harder conversation about whether the business works.

What changed is what I was buying.

Vigilance blocks coupon-code injection at checkout. Browser extensions cycle through discount codes on behalf of the shopper, and most of those codes were never authorized for that customer. For a brand doing volume it's a real leak, and stopping it is worth real money.

The problem isn't the product. The problem is that it's an unfamiliar claim. A merchant has to believe this is happening to them, that we can see it, and that we can stop it. That's three leaps, and each one is easier if someone they respect has already made it.

So I raised from people whose names do that work. Operators in this ecosystem, not funds. I wanted the cap table to be a list of people a skeptical merchant would recognize.

Whether that's a good reason#

I've turned this over a lot and I'm not fully sure.

The case for: distribution is the actual constraint on this business, the people I raised from are distribution, and $250K of their money is cheaper than the alternative ways of buying credibility. That seems right.

The case against: I've now attached obligations to a company for a benefit that's diffuse and hard to measure. If the round produces introductions and credibility, great. If it produces a group chat and quarterly updates, I've sold equity for a feeling. The literature on "smart money" is mostly written by people selling smart money.

The honest answer is that it's cheap enough that I can afford to find out. $250K is small. It doesn't come with a board, it doesn't come with a required outcome, and it doesn't put a floor under what I'm allowed to sell for. That last one is what I've always actually been protecting, and this round doesn't threaten it.

The part that feels different#

Having other people's money in the company is a different feeling and I want to record it before I normalize.

When it was my money, a bad quarter was a bad quarter. Now there are people who backed me, whose names are on this, and who I'll have to talk to if it doesn't work. That's motivating in a way I'd describe as mostly healthy and partly not.

I've also noticed I'm more inclined to say things are going well than I was as a bootstrapper. Not dishonestly — just a subtle pull toward the optimistic framing when writing an update. I don't think I'm unusual in this and I think it explains a lot of how startup information gets distorted before it reaches anyone.

What I told them#

That this is a product built on a specific behavior of a specific platform, and that the platform has opinions about checkout.

I said it out loud because it's true and because I'd rather be the person who flagged it than the person who didn't. Everyone nodded. Everyone in this ecosystem has heard "platform risk" enough times that it lands as a formality rather than as a fact about the future, which is a thing I've now noticed about myself too.

If that risk ever comes due, I'd like this paragraph to be on the record as having existed beforehand.