How I Built and Sold My Company in 18 Months

Save your time and skip this article if you want any tangible takeaways; if you want to know what the company actually DID or how it MADE MONEY, spoiler alert: this article neither mentions or links to anything of the sort.

Without this basic intro description, there’s little to no value in this article to prospective readers- companies aren’t created equal and lessons learned in one industry don’t necessarily translate to others (this is not always true, but without context, I still stand by the lack of utility here).

Why didn't you have any representation, such as legal or a deal negotiator, on your side? Broker isn't your friend. Is there any reason why you saw 2x "earnings" as the golden ticket?

> But no one likes contracts and I don’t like conflict, so I didn’t ever transition to long term contracts. Again my lower brain (fear and the desire to be liked) took control and I decided to stick with month-to-month contracts. Then my upper brain came up with convincing arguments and justified this decision by saying I had created a “customer-friendly” pricing model.

Your upper brain was right. You did the right thing, and this is an example of where building to flip is at odds with doing the right thing for the customer. I hope we'll see more bootstrapped companies that are profitable enough to be sustainable and offer a good living for their owners and employees, but don't maximize profit or valuation at the expense of doing what's right.

This is an interesting, feel-good read and I'm legitimately happy for the OP's success, but I do have a few nits. First this is a pretty simplistic way to value a business, using the tools we were introduced to in 2nd year management accounting. They're all useful but the reality is that different buyers have very different goals and their valuation is reflected in what they plan to do. The approach here is most aligned with purchasing as a going concern. It's the classic built a solid business that does pretty well but still requires a lot of hard work and the owners want to retire. I'm going to be focused on cashflows and growth, historic and projected. This is very different from the types of businesses we talk about on HN everyday, or a value investor looking for things like assets devalued by underperformance, etc. The point is "it's complicated".

My second nit is more philosophical, related to this statement:

>> That’s because the process of creating an attractive business for someone else to buy naturally makes it a better business to own.

I only feel this is true if your definition of a good business to own is one that you can sell at this point in time, which seems a lot like a dog chasing it's tail.

There are lots of counter examples to refute this idea, such as deferring hiring, capital replacement or any real long term investment. Amazon is such a valuable company today because of the things it did through the early 2000's that made it look so unattractive to buy.

> Had I understood these simple concepts I believe I would have made very different decisions in building my business. I would have likely focused less time on maximizing profit (E) and more time investing in future earnings and value (M)

It sounds like he's suggesting that the acquirer didn't care about how profitable the company was. I'd be curious to know if others have found more focus on revenue and less on profitability. I've definitely talked to some VCs that invested based on revenue numbers, and didn't care at all about profitability. Does this happen with acquirers too?

TLDR: this person sold a money-printing machine for just 2x the yearly revenue which means that either he got shafted (a 2x price earning ratio is very low) or the buyer got shafted (company was at risk of tanking very soon, explaining the low PER).

More politely, you could say the risky asset was priced according to risk by both the seller and the seller ("hot potato")