Hey Reader

I bought a business!

It closed officially last Friday and I got "handed the keys" an hour later.

(By keys I mean 1Password vault access of course.)

Btw I've found the process of buying and selling companies to be underwhelming. You build and grow something for years, then with a few clicks on Docusign and poof, it's gone.

Compare this to when we did a house refinance a few years ago. We had to go to an office across town and spend an hour under fluorescent lighting signing paperwork with a title agent. Yes it's annoying, but there's an "event" around it which feels appropriate given the size of an asset.

They even give you a big cheesy key and take your picture:

I got this underwhelming feeling again this time as I closed on this business last week. This time it was clicking docusign on my phone while dropping my toddler off at daycare...

Background

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I sold BestSelf in late October 2022 after starting and running it for 7 years.

I spoke in my annual review a few weeks ago on the aftermath of the sale and trying to figure out what I've wanted to do next. It had been 14 months since the sale and I still wasn't sure what I wanted to be "when I grew up".

Then in mid-December the CEO of the company who bought BestSelf approached me and asked if I wanted to buy it back...

I can't go into too much detail (nor do I know very much) but the TLDR is that the main tranche of investment money promised never came. They were going to be shutting down. Part of this meant selling off the brands they'd acquired — which included us.

If you've been in the space or watching over the last few years then you know this has been a common story (hi Thrasio bankruptcy👋🏻).

Now when they asked if I wanted to buy it back, I didn't think I was interested. There were good reasons I sold it. And now there was no longer my team in place running the day-to-day. Almost all of them had left after their 6-month retention bonus.

But I kept the conversation lines open because I wanted the brand to continue so I explored options. I spoke with a few people I thought might be interested in running it if I took a minority position and continued to negotiate the deal.

Negotiation points:

• They were a very incentivized seller.
• They were being pressured by board to get assets off their books.
• No-one on their team had skin in the game as far as putting their own money into the buying us the first time. (no loss aversion to maintain higher price.)​
• The company were already down to a skeleton crew running the business. It was going to be very difficult to sell to a random buyer as migration would be tough.

It was a great deal to negotiate because I had a unique situation that made me the obvious person to sell to. They could give me the logins and leave 👋🏻

With anyone else they'd need to do a transition period which would cost time and money. Someone once told me that the side that wins the negotiation is the one that can walk away.

Given I was lukewarm in the first place I was willing to walk away if the terms weren't right. I wasn't going to buy it back out of emotional attachment alone.

So I started to mull over how I could do it better this time.

My thought process:

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Since the sale I've been messing around with learning to code, AI tools and automation. And different ways of using Chat GPT to manage cognitive load (which has been nothing short of magical.)

But it was difficult as I didn't yet have a business use-case to apply what I was learnin which limits how far I could go. I think this was a big reason why I felt lost. I love taking action of things but everything I was working on felt theoretical.

The best way to cement learning new skills is by applying them IRL.

What if I got BestSelf back and started applying what I'd learned into a real business use-case? Like a scientist in a lab experimenting. That sounded like something I would enjoy 🤔
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Not to mention, every business I've started began as a side-quest from something else. Likely part of the reason I was struggling with finding a new thing was a lack of constraints or new problems.

When you boil it down, businesses are problem-solving machines. I was about to buy back a bunch of problems and one of those could become my next obsession. This may carve the path to whatever I decide to do next.

And if not, how do I negotiate a deal that makes it a no brainer even if that doesn't happen? A deal so good by itself that anything further down the line was a cherry on top. Protecting my downside.]

The deal we ended up doing felt risk-free even to someone new coming in, nevermind me who had years of experience.

So why did I buy it Reader?

I love a good deal and never back down from a challenge.

(and it'll make a good story however it ends up!)
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12 days until V-Day! Valentines day is coming up, pick up a gift from BestSelf.co for your partner -— or galentine. (use code BACKINTHESADDLE for 25% off 😁)

Want to look over my shoulder?

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One of the ways I am considering doing business differently this time is starting an inner circle where I share the ins and outs of what I'm doing with the business as it happens.

This would be me sharing experiments, tools, real numbers and the kind of insights that are usually kept under lock and key.

You've likely done courses, read blogs, and attended webinars in the past. But when was the last time you were able to look over the shoulder of someone actually doing it in real-time?

For obvious reasons it's not stuff I want to share publicly — but I do want to document the journey. Having a close-knit community of people that I'm accountable to sharing for would be a great forcing function for me to do this.

Initial ideas on what I'd be sharing:

• Deal structuring & negotiation: I’ll bring you in live and share how I negotiated this deal (yes, including actual emails) — including how I almost walked away 24 hours pre-close.
• AI and Automation: Step-by-step guides on leveraging technology to do the heavy lifting, cutting costs, and skyrocketing efficiency.
• Delegation & Hiring: How I'm going to build a new team from scratch, processes, delegation maps etc
• Operational excellence: Access to spreadsheets, tools, and systems that keep the engine running smoothly, from managing supply chains to daily tasks.

I'm not gonna lie, there's a lot of work to be done with the business to get it back to where it was.

This won't be a shiny polished course. This will be emails, random loom videos, screenshots, decision documenting, experiments and whatever else I think is useful.

If you're interested in being part of this you let me know by responding to this email. If enough people want it I'll put something together.

Picture of the week (and book rec 📖):

Back in 2013 when I was running my first Shopify store I bought Noah Kagan's first dollar course — it was $300 (a TON of money for me). This meant I took it seriously and did everything he told me to do.

Turned out to be an incredible investment as it taught me many of the crucial skills that got me to where I'm at in business. From launching products, validating ideas to getting my first customers.

Now he put everything from that course into a book and more. Not only is it better than the course, it's only $27. It's called Million Dollar Weekend: The Surprisingly Simple Way to Launch a 7-Figure Business in 48 Hours. He also did a great podcast on Tim Ferris about the book here.

Best,
Cathryn

P.S I'm serious about the inner circle idea, lmk if you'd be interested and why?
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P.P.S. My first ever sponsor 😆:

12 days until V-Day! Valentines day is coming up, pick up a gift from BestSelf.co for your partner -— or galentine. (use code BACKINTHESADDLE for 25% off 😁)

2028 E Ben White Blvd #240-5675, Austin, Texas 78741
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