The 6 things I'd do differently as a founder, if I could do it all again...

2 years after walking away from my start-up, here's how I'd run it back if I could go back in time to my chapter as the founder of a sustainability forward online marketplace.

It can be really hard to see the forest sometimes, you’re so close to a single tree.

That was my experience of being a founder. I don’t think that’s escapable— you have these founder goggles on, no matter how self-aware or rational you are, and you can’t see clearly because you’re so close to your own work.

Operating other people’s businesses for them, whether as an interim CEO or a strategy & growth consultant or a fractional COO, has been an acutely different experience than operating as a founder! That, though, is a letter for another day. (And honey… it’ll be a long one.)

If you’re a new reader, click here for a bit more context about me or the business I started back in 2020.

In my favorite book ever, Ina Garten’s memoir (I’m on my third listen of the audiobook and seeing her tonight on her book tour!), the Barefoot Contessa herself says repeatedly something along the lines of “you never know your good breaks from your bad ones.” Sometimes, missing out on something, failing at something, or not getting something feels like a bad break in the moment— but it’s actually a good one. You’ve been saved or redirected from some worse fate. (In modern day influencer-speak, I believe they say “rejection is God’s protection.”)

There were a bunch of things that I viewed as bad breaks that I now see as good. Not being able to raise a ton of money from venture capital firms, to be example. Now I’m really glad I didn’t lose millions of dollars of their money— it’s already hard to recover from this experience! I couldn’t add another layer of shame to what I’ve been metabolizing these last few years.

I digress. Today’s letter is not about those breaks that felt bad at the time but are actually good, it’s not about things that turned out for the best.

Today’s letter is about navigating the bad breaks that were actually just not advantageous for the business, what I’ve learned, and what I’d do so, so differently. And reader, I know all of this in my bones, it flowed out of me easily and with very little editing (can you tell?). I’m sure I’ll have a different take in a few years when I know more about the twists and turns of the macroeconomic landscape, but 2 years later, here’s where I stand.

If I could do it all again, I wouldn’t start a marketplace at all. I’d have just started a Substack.

But let’s say in this fantasy I don’t get a do-over on that part. I’m stuck with the idea, the same amount of working capital, I’m doing it all in the same timeline.

Ah, the gift of hindsight. No matter what I do in this fantasy, the end outcome would always be the same: there is no venture scale for a sustainable ecomm marketplace.¹

But there are other ways to leverage a business model that no longer works into a future that does work, should you have gas in the tank and/or cash in the bank.

What I’d do so, so incredibly differently? Get shredded, find community, hire differently, innovate faster, pimp myself and pivot.

I’ll explain. 🙃