3 min read

Inexperience Debt: The Hidden Cost of Entrepreneurial Growth

The hidden benefits of selling your company to private equity, and why I'm glad I did it. Including streamlining processes and confronting my inexperience debt.
Inexperience Debt: The Hidden Cost of Entrepreneurial Growth

60 days ago, I bought back my old company from private equity. And let me tell you, it was a wake-up call.

As I peeled back the layers, I realized how much work I had ahead of me. The PE firm had made some rookie mistakes between over-focusing on Amazon, neglecting DTC, and letting agencies run wild. But they also did some things right which I'll get into below.

You see when I started BestSelf back in 2015 I had no idea how to run a business or a team. Before this, I'd had companies of one (me), with a few contractors when I needed them. I'd also never taken a business class nevermind gotten an MBA. With this inexperience came mistakes, inefficiency, and steep learning curves.

When we launched BestSelf we went from zero to 2.2M in 9 months, winning the Shopify Build-a-Business competition. Then we scaled 3X in the 12 months after, winning the Shopify Build a BIGGER Business 😱

It felt like I was trying to build the plane while it was in takeoff mode — and I had no experience with how to do either thing.

Inexperience debt

Running a company over an extended period can lead to the accumulation of "baggage" – inefficient processes, outdated strategies, or misaligned priorities. This is magnified further when you are inexperienced.

I didn't know what I didn't know. You can read all the books in the world, but experience is a whole other beast. I figured it out (mostly). But I made some costly mistakes along the way, some of which I've shared on this blog (embezzlement, business partnership etc).

In tech there's something referred to as technical debt. Technical debt could be using a janky workaround to solve a code problem because the ideal solution will take too long. It works in the short term but will catch up with you at some point.

Like monetary debt where you accrue interest, tech debt is the same. The interest accrued is when you build on top of the janky code and later you have to fix even more things.

Apply the same concept to inexperience debt.

All companies take on water and bloat if you run them for long enough. Especially if you're a new entrepreneur with little experience. You're building a team, company and business on janky workarounds because you don't know what you're doing.

The great thing about having MBA's and consultants working on your company is that they have no allegiance. They follow numbers and data. They look at everything objectively through the lens of someone who has studied a lot of businesses.

They also likely learned how to properly format folders, documents and naming structures from their time in consulting. I've never seen a more organized google drive folder. God bless them.

Gone are the messy supply chain spreadsheets, replaced with MBA style excel documents with linked pages, macros and a bunch of things I barely understand.

It's like I got paid for a bunch of consultants to come in and streamline everything that wasn't driving revenue. Necessary? No, but nice to have.

The buyback presented a clean slate. There's few opportunities to buy back a brand, inventory, sales — at a great price but without the overhead. Everything was back to the drawing board, but with a lot of assets and resources.


60 days down, and we've already come a long way. I'll share more about the biggest problems I found in future post. Everything from plugging leaks in our operations to taking the fight to counterfeiters, I've made some serious progress in getting BestSelf back on track.

If you've run a company for a while, ask yourself this question:
"If you sold your company tomorrow, what are the first 3-5 things a new owner would want to fix?"

Start here and start today! Even doing one small thing a day to pay off your inexperience debt will compound over time.

Being an entrepreneur is never easy, but it's always worth it. Every curveball, every setback, is a chance to learn, adapt, and come back stronger.

And as I dive into this new chapter with BestSelf, I'm reminded why I fell in love with this crazy game in the first place. The thrill of building something out of nothing, and the satisfaction of making a real difference to people with our products.

So to all my fellow founders out there facing your own battles, here's my advice: keep pushing. Embrace the chaos, learn from your missteps, and never forget why you started. Because with grit, hustle, and the right crew by your side, there's no challenge you can't overcome.

And to everyone who's been riding with me on this wild journey, thank you. Your support means everything, and I can't wait to share the next chapter of the BestSelf story with you. 🙏🏻

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