Lesson: I don’t regret the dollars I spent. I regret what I expected them to do.

I’ve made a lot of spending decisions as a solo founder, some smart, some not so much. And in the moment, they always felt justified. I wasn’t chasing hype or trying to look bigger than I was. I just wanted to move with intention, to put capital toward things I thought would get us further.

One of those costly decisions was a short, animated video I thought could go viral, a funny skit I wrote, using cartoons to feature the product in a way that felt clever and catchy. I thought it had the potential to punch through, or at least give us something different for brand awareness and drive sales. So I hired someone who had experience creating animated short reels. But the process dragged. He blew past the contract deadline, and the final video missed the mark completely. It didn’t reflect my vision at all, and I was hoping the final edits would fix my doubts. I was actually embarrassed to watch it, let alone share it. That video’s still sitting in the blooper vault. Maybe I’ll use it someday, just not how I planned.

That wasn’t the only one. I also spent money on custom retail signage and in-store fixture concepts to help drive sales in store placements as I was closing deals with retail businesses. I thought I was being proactive. I figured if I made it easy for retail partners to display the product, they’d run with it. But most never could due to limited space, and paid shelf space took priority. For bigger retailers, it turns out that in-store assets need corporate-level approvals. I didn’t ask. They didn’t use it. Another sunk cost.

And then came the influencers, hired to boost social proof through creators who looked good on paper: big followings, clean metrics.. The idea was simple: get the product in their hands, have them enjoy it on camera, and post something that felt effortless and aligned. I gave it multiple shots. Used platforms. Worked with agencies. Shared brand guidelines. But most influencers cared more about having me as a client than actually understanding what I was building. I was just a paycheck to them, nothing else. Even with the right targeting, clear direction, and solid engagement numbers, the output still felt off. It wasn’t for lack of effort; we just kept forcing a fit that wasn’t real. It wasn’t cheap either, and the ROI never showed up. I wrote more about the influencer piece in one of my previous drops here: The Influencer Illusion: Beyond the Hype.

Looking back, I don’t regret the money I spent. I regret expecting those spends to shortcut the work, to create traction just because they looked like the “right” moves. But each one taught me something I wouldn’t have learned by playing it safe. And the fact that they happened early, before the stakes got bigger, paid off more than I knew at the time. Now? I move differently.

Every decision gets pressure-tested. Not just by me, but by people who know how to challenge my thinking, who don’t owe me agreement. I ask if it fits where the brand actually is, not where I want it to be. If it doesn’t, I hold the line. Doesn’t matter how well it worked for someone else; that doesn’t mean it was meant for us.

Referenced Insight: From the Investopedia article How Many Startups Fail and Why, many startups collapse not just because they run out of cash, but because they spend on the wrong things too early, like flashy marketing before product–market fit or copy-paste tactics that don’t match the brand. These aren’t just theoretical traps; I’ve stepped in most of them, too.

Closing Thought.

Every founder spends on something they hope will work. Sometimes the only payoff is perspective, the kind you only get when the bet doesn’t hit. The money’s gone, yeah, but it reveals what money can’t do. It shows you that even ideas that make sense still need brand alignment, no matter how much money is spent. So spend like it matters. Because ROI doesn’t just live on a spreadsheet.

Stick around. I’m just warming up.

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