The Business I Built to Sell (and How I Almost Blew It)

Your business sale – What made you realize you’d built the wrong type of business? What specifically about that experience shifted how you think about building businesses now? What would you do differently from day one?

If you search online for advice for starting or scaling a business, it’s easy to find a large amount of information on the topic. In fact, there’s almost too much advice in this realm.

However, when it comes to selling a business, the information is both sparse and less relatable. The internet is full of sensational stories of individuals who built a startup that was sold at an impressive figure to a recognizable company, but it can be hard to find stories of everyday people selling their business.

Today, I’ll talk about my experience creating and selling my online business.

I never thought about selling my business in the beginning, it was simply a cashflow business to fuel my lifestyle. However, as my business grew, I realized that I didn’t just have cashflow, I had something that had the potential to be sold.

In order to create a business that can be sold, you have to be able to make yourself totally replaceable by creating systems that will keep the business running without your presence. This means you have to let go of your control and ego so you can delegate as much as you can. Since I was inspired by the “Four-hour workweek” and passive income, I had this in mind from the beginning.

Over the course of 3 years, I found myself going from a solo operator to having a team that did everything I had done before: creating content, dealing with customers, and even running a paid membership. My workweek was reduced to simply checking in to see if everything was working and having an occasional meeting. At this point, my business was ready to sell if I wanted to.

Although at this point I had effectively removed myself and thus built the right type of business to be sold, what I wasn’t ready for were the vulnerabilities and the messy exit that ensued.

Not everything can go perfectly, so even though I did a relatively great job with delegating tasks and profitably removing myself from operations, I still ended up with a forced exit and did not sell at peak valuation despite getting offers.

The moment I should have sold is when the market was hot and I was getting inbound offers from interested parties. Despite excellent valuations, I didn’t sell because I thought I could get even more. I ended up selling for 80% less than my peak valuation due to some key mistakes.

One of the biggest mistakes was not taking security seriously and delegating without thorough due diligence. I had never been too technical, and I had put too much trust in others at times. So at one point, I hired a developer that I didn’t vet thoroughly enough. Long story short, my website was compromised, I had to fire the developer, and I was forced to recover an older backup of my website that was missing hundreds of current articles.

As a result, my traffic tanked and along with it the sales came down, so I went from positive cashflow to negative cashflow for the first time ever.

This led to me needing an investor who eventually bought the business out during a forced exit at a valuation I was not happy with.

Mistakes cost me money, control, and peace of mind—but they also taught me how to build smarter, stronger, and more resilient businesses.

While it was tough to recover from the first sale, I am happy that I was able to learn valuable lessons that are now helping me be more intentional about both what type of business I am building now and how I plan to handle the exit. Of course, I’m also now much more careful with who I hire and delegate critical projects to so I don’t take down my business from the inside as I did last time with a bad developer.

I also think to myself if this thing is worth doing for 3-5 years or more, or if it’s something I want to keep doing for an indefinite amount of time. It’s important to know that a business isn’t just cashflow, it’s entering a long-term relationship. If you can’t imagine doing something for at least 3 years, frankly, you should not start and do something else instead. You have to remember that the business can only have a few outcomes: it might succeed and you keep it for life, it could die eventually, or it will have an exit, whether intentional or forced.

When it comes to the exit, the timing and conditions are impossible to get perfect and much of these are due to factors that are totally out of our control. However, what is in your control is taking the first step to starting your business and taking consistent steps forward to scale it.

So if you haven’t started yet, this is a reminder you can start today, and if you do it right, you can end up with a legacy that you’re happy with whether that means a sale or keeping your business for life.