I lost my money. That’s what I told myself the day the founders messaged me to say they were shutting down.
This is the story of my first startup investment, a small SAFE cheque I wrote into a B2B marketplace serving the flexo printing industry. I’m not going to name the company, mostly out of respect that they’ve shut down, and there’s no reason to drag their name through a blog post. But everything else here is exactly as it happened, because the lesson only works if I’m honest about the numbers and the timeline.
How I Got In
I didn’t start as an investor. I started as a growth advisor.
The founders had been in the flexo printing industry for 15+ years, not first-time founders chasing a trend, but operators who knew the supply chain, the buyers, the pain points, all of it. They were building a marketplace to bring flexo printing supplies; plates, inks, anilox rollers, the whole category online, in an industry that had run almost entirely on phone calls, emails and personal relationships for decades.
I believed in the vision. More than that, I believed in them. When you’ve spent 15 years in an industry, you’re not guessing about the problem, you’ve lived it. So when they asked if I wanted to put in a small SAFE investment alongside my advisory work, I said yes. It was a low ticket size, the kind of cheque where the downside is bounded and you write it because you believe in the people, not because you’ve modeled out a 10x return.
Where It Got Hard
For a little over a year, I worked with them on finding product-market fit. And here’s the part that’s easy to gloss over in hindsight: the GMV wasn’t the problem. Monthly transaction volume through the marketplace was in six figures, that’s real money moving through the platform.
The problem was how it was moving. Most of those orders weren’t coming through the “Buy Now” button. They were coming through email. Printers and suppliers in this industry were comfortable sending an email to place an order but actually clicking “buy” on a marketplace? That leap wasn’t happening, no matter how good the product experience was.
We were early. Maybe too early. The category had real demand, but the behavior the business model needed, self-serve online buying wasn’t there yet. And without that behavior shift, MRR didn’t grow the way a marketplace needs it to. You can’t scale a business on a metric you don’t actually own; the orders existed, but the channel we needed credit for didn’t.
After a year of trying everything we could to bend the market toward the product, the founders made the call to shut down.
The Part I Didn’t See Coming
When they told me they were shutting down, my mental accounting was simple: my investment is gone. That’s how SAFE notes in a failed startup usually go, and I had made peace with it. It was a small cheque, I’d learned a lot, and that was the return.
Except the founders didn’t see it that way.
Even after the marketplace itself shut down, the orders kept trickling in the same email orders that had quietly been the real engine of the business all along. The founders kept fulfilling them, kept making a small, steady income from a business that technically no longer existed as a “startup.”
And a year after shutting down, they paid me back. My full capital, plus a small interest on top.
I want to sit on that for a second, because I don’t think I’ve fully gotten over it. There was no legal obligation pushing them to do this. A SAFE doesn’t behave like debt. When a startup shuts down, investors are usually last in line for whatever scraps remain, and often there’s nothing at all. These founders weren’t required to make me whole. They chose to.
What This Taught Me
I still believe, maybe more than before that there are founders out there building because they actually want to build something real, not just to raise the next round.
It’s easy to get cynical in this ecosystem. You read about down rounds, founders who raise millions and deliver nothing, investors who get diluted into irrelevance, and you start to wonder if anyone left in startup-land actually cares about the people who bet on them early. Then you meet founders like these two, who had every excuse to walk away clean, and they didn’t.
This was my first startup investment. It failed. The business model didn’t work, the market wasn’t ready, the marketplace shut its doors. By every normal definition, I should write this off as a loss. But I got my capital back, with interest, from a company that no longer exists. And somehow that makes me more excited to keep backing early founders, not less.
The product failed. The founders didn’t.
