Everything you need to know about selling a business.

The First Rodeo Guide to Asset Sales and "Distressed" Deals 🤠

When I first set about selling my business, I had no idea what the fuck I was doing.

My friend Tenlie Mourning gave me some extremely sound advice when I told her I needed to walk away and get a job— she suggested that I try to sell it instead of just shutting it down! If she hadn’t told me to strongly consider that, I’m not sure I’d ever have had the confidence to try.

I emailed three competitors, one responded and was interested in a potential asset sale. I had no idea what I was doing, I didn’t try very hard. I was just tired, and I didn’t feel like I actually had anything of value on my hands. It never occurred to me that there was an entire industry built on what I was trying to do— sell a “distressed” asset.

I could never have predicted that I’d find my way into working in M&A and distressed consumer brands— first with the team behind The Hedgehog Company (owners of Baboon to the Moon, The Reset, Felix Grey and others) and now working for the brilliant founders behind Hologram Capital (owners of Tovolo, Spectrum, Rooted and others).

It’s a weird, quiet, “if you know you know” type of industry— and one I had no idea existed when I actually needed to sell my business. I can’t emphasize enough how opaque this industry is. Everything is done through network. If you thought fundraising with only warm intros was hard, selling your (bankrupt or ailing) business to a mystery buyer with no website and a warm intro is much harder.

I’d like to pull back the veil a bit here for those who are curious about how, when and where to sell your start-up.

I specifically have only worked in distressed assets in the consumer/ecommerce space, so everything I share will be through that specific lens. What does a distressed sale typically look like, you ask?

• The founder or owner is parting with the business because something is not working right

• There is often (not always!) a lot of debt on the business that can only “go away” through some form of bankruptcy or an outside buyer who can negotiate with the senior secured lender, etc

• The founder or owner is usually well aware that they are not going to sell for a bunch of millions of dollars or return investors the 10x on their investment that they were seeking

Some examples of “distressed” deals that you may have heard of in recent years? Parade and Outdoor Voices come to mind.

Since I started doing this, I’ve hopped on the phone with a lot of founders to talk them through the process. It’s an incredibly opaque one, and given the intensity around tariffs and the already brutal slog the last 5 years have been for consumer businesses, unfortunately it feels like it’s only getting more relevant.

This letter is basically a half hour to an hour’s worth of my consulting: how to even begin when it comes to selling your business edition. By no means is this an exhaustive guide, and I’ll caveat that I’ve only worked in the sub $50M universe, and by no means have I been doing this for decades! Consider this Step 1 or your first entry to the idea of selling a business— Asset Sale Lite.

(Maybe if I do this well enough, Kim Kardashian will eventually hire me to run SKYY… I have a few ideas for her…)

Me, helping you sell your business.

Curious about how selling works? Scroll on for:

• When to consider selling your business— can you? should you?

• Where to start and what to do to actually get it sold

• How to spot a “good” buyer from a “bad” buyer

• How I’d structure (and price) the sale

• The biggest mistakes founders make in the process

• Positioning a less than ideal outcome in a positive light

• Life afterwards: where to go, what to do!