They Got Acquired - Lean business = $4.5M sale

January 20, 2023
​Read on web​

Before we get into today's story...

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We often spotlight lean businesses.

Usually, that means a founder or team of co-founders grows the business on their own, or with just a few employees or contractors.

But today's story features a woman who took a different approach to the lean-team mentality: she hired a CEO.

Her business was running with just her, the CEO and a few contractors when it sold last year for $4.5 million.

Caitlin Pyle started Proofread Anywhere, a training center and community that helped people earn money through proofreading, in 2014, teaching others what she'd learned.

By 2022, the business generated up to $300,000 per month and had an impressive email list of about 300,000 subscribers.

But behind the scenes, that growth wasn't smooth. Pyle suffered from some serious personal challenges that led to burnout.

One of those challenges was a divorce, which drained her savings. And the only financial asset she had was her business, so she knew she couldn't blow it.

That led her to hire a CEO while she focused on her health. Two years later, the business sold for a multiple of 3.3x EBITDA.

More on how she did it 👇

​She hired a CEO to strengthen her online training business, then sold for $4.5M​

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LOI explainer

First time signing an LOI? Here's the low-down:

✅ LOI stands for Letter of Intent. It's an expression of intent to buy your business. So the potential buyer is saying, we'd like to look more closely at your company because we're keen to buy it for a certain amount of money, and you're agreeing to that.

✅ Never sign an LOI without having a lawyer review it. (Here are a few lawyers we recommend if you need one.) While the document is technically not binding, it sets expectations for the sale that will be difficult to change later. Too many first-time sellers shrug this off as a simple expression of interest, but it's more than that.

✅ You also should probably have engaged an M&A advisor before you sign an LOI, or at least considered it. (Again, if you need one, ask us for help.) An advisor helps you negotiate terms that are favorable to you. If you bring in an advisor after you've signed an LOI, your options for improving the deal will be limited.

✅ Make sure you've negotiated with or at least tried to find other buyers before you sign an LOI. Having multiple offers is the best way to drive up the price of your business.

✅ Ensure you're emotionally ready to sell. When unsolicited offers quickly turn into LOIs, some founders haven't given themselves the time to make sure they truly want to part with a company they've poured their sweat into.

Want more ideas? Here's what to think about before you sign an LOI.

See you next time,

Lexi Grant
Founder & CEO
​They Got Acquired​
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Our mission is to redefine startup success by showcasing companies that sell for $100K-$50M. Learn more about us or follow us on Twitter.

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