Shelton Powell is the founder and CEO of Cart Capital, an eCommerce infrastructure company that handles business setup, supplier relationships, media buying, and backend operations for online brands. He is also developing a product sourcing and fulfillment company and a growth infrastructure agency for agency owners. This Q&A asks him to look backward, at the parts of the last several years he would change if he had the chance to run them again.
If you could go back to the very beginning, what would you change first?
I would have hired for the backend a lot sooner. When I started, I was doing everything myself because I thought that was what building a company meant. Supplier calls, ad accounts, customer service, website builds. I treated it like a badge of honor instead of what it actually was, which was a bottleneck. Cart Capital didn’t start moving until I stopped being the person every task ran through. If I could rewind, I would have made that call at month three instead of month twelve.
Was there a specific moment that made you realize you had to change that?
It was less a moment and more a slow accumulation of dropped balls. Orders sitting longer than they should have. Messages I meant to answer that got buried. Nothing catastrophic, just enough friction to slow everything down. Eventually I sat with the math and realized every hour I spent on something someone else could do was an hour I wasn’t spending on something only I could do. That’s an obvious statement written down. It took me longer to feel it than it should have.
Knowing what you know now, would you have entered the agency space at the same time as ecommerce, or staggered them?
I would have staggered them, but not by much. Running both at once during COVID taught me things about infrastructure that I don’t think I would have learned any other way. Watching how influencer merch operations worked while I was also building my own brands showed me the pattern behind the pattern. But it was chaotic. If I’m honest about what I would change, I’d give myself three or four extra months on ecommerce alone before layering the agency work on top. Not because it was the wrong move. Because I was moving faster than my systems could support.
What about the people you brought on early. Would you build the team differently?
Yes. I’ve talked before about learning to tell the difference between people who are committed to a mission and people who are along for the ride. If I’m doing it again, I’d build that filter into the hiring process itself instead of learning it through experience. I used to hire on enthusiasm. Now I hire on how someone behaves when something breaks. That’s a harder thing to screen for early on, but it’s the only thing that actually predicts whether someone sticks around when the work gets less exciting.
Is there a decision you made too quickly, one you wish you had slowed down on?
Plenty of small operational ones, but the pattern is consistent: whenever I skipped documenting a process because I was in a hurry to launch it, I paid for it later. Something would work fine while I was the one running it, and then it would fall apart the moment someone else touched it because nothing was written down anywhere. Now documentation happens at the same time as the build, not after. That’s a habit I wish I had adopted years earlier than I did.
On the flip side, is there anything you did early that you’re glad you didn’t second-guess?
Leaving Bell Canada when I did. I was nineteen, it was April 2020, and by most conventional logic that was a strange time to walk away from a stable paycheck. I’ve never once wondered if I should have waited. The only regret I have connected to that period isn’t about the decision itself, it’s about how long it took me to fully commit to it mentally even after I’d made it on paper.
If a younger version of you asked for one piece of advice before starting, what would you tell him?
Fund the thing that obsesses you, not the thing that looks credible. Football looked credible. Ecommerce is what actually had me locked in at sixteen, running things in the back of a classroom nobody was paying attention to. I eventually followed the obsession, but I spent real time chasing the credible path first. I’d tell him to trust the thing that keeps his attention without anyone asking him to pay attention. That’s a better signal than anything that looks good from the outside.
Does hindsight ever tempt you to slow down now, given how much you’d change about the pace back then?
No, because the mistakes weren’t about moving fast. They were about moving fast without the right structure underneath me. I still move quickly. I just build the scaffolding before I need it now instead of after I’ve already fallen through the gap. Speed was never the problem. Speed without a plan for what happens when something breaks, that was the problem.
What’s different about how you’d start Cart Capital if you were doing it today instead of in 2020?
I’d design the systems for a team of forty before I had a team of five. Everything I built early on was sized for one person doing the work of many. It functioned, but it wasn’t built to hold weight. Now I try to build infrastructure a size or two ahead of where the company actually is, so growth doesn’t require rebuilding the same thing three times over.
