🤝 Why I Sold

Since selling LearnDash, I have received countless messages of support and congratulations, all of which have further validated my decision that Liquid Web is the perfect new home for the LearnDash brand.

And as you would expect, I also have received a number of questions. Many people wanted to know why I sold in the first place.

Recently, I had a Twitter Spaces conversation with David Bisset from Post Status and Marieke van de Rakt (CEO at Yoast). We talked about a lot, but the main point was for us to explore reasons why WordPress companies are selling like crazy, and what this may mean for the greater WordPress market going forward.

While we did venture into a variety of different topics, the overarching theme seemed to be around why a business owner would choose to sell. I gave my thoughts during the call, but they were more general. I have had some time to think more on the topic, especially how it relates to my reasons for making the sale.

The motives for selling all start from the same place.

While the motives may vary from person-to-person on selling their business, the decision to sell the company in the first place is always the result of self reflection. It’s a moment where you assess your desires and measure those against where you spend the majority of your time (working).

This is the same process that people go through when switching jobs. Yes, there are outside motivators (money, more time, better title, etc.) but it starts with understanding personal desires given prevalent circumstances.

When I did this in 2020, I came to realize a few things which ultimately led me to sell:

For me, it’s important to be passionate about what I am doing. When I have passion, I get excited. When I get excited, work doesn’t feel like work. I didn’t have passion, so everything seemed hard.

It was hard to deal with employee requests, it was hard to deal with upset customers, it was hard to deal with software development issues, it was hard to push forward with a timeline. When things feel hard for me, I become less creative. Creativity is why LearnDash has been able to compete so well across both the e-learning and WordPress verticals.

I thought perhaps I just needed to work less. So, I augmented my schedule and empowered other employees to do more, but after some time I still felt the same… worse perhaps.

That’s not to say I was depressed. I was bored, and tired. I was “punching in and punching out” every day. No drive, just getting tasks done. I knew what I should have been doing, but I just couldn’t anymore. I just didn’t care.

This lack of caring made me feel guilty. In my mind, I was letting everyone down, from my employees to my customers. The company deserved better and I knew it. The guilt was probably the hardest part of it all. I hate letting people down, and I was letting everyone down (at least in my mind).

To put it another way: LearnDash wasn’t living up to its full potential. It needed fresh ideas. It needed a new energy and I couldn’t bring it. A sale would infuse the company with exactly what it needed while taking care of both employees and customers.

I sold because it was in the best interest of everyone, including myself. I feel lighter now. I don’t have the guilt, and I am excited to take on new entrepreneurial projects in industries completely unrelated to e-learning and WordPress. I’m just as excited to see how the company takes off now that it has the backing of folks that are willing and eager to take it to the next level.

Exploring Twitter Spaces for personal use.

As an aside, this was my first Twitter Spaces experience. It was pretty cool!

I appreciate how it fosters a dialogue rather than a formal interview or podcast format. Actually, it makes me want to host these with some of my friends. We talk about business pretty regularly. I think having this in a public forum could be insightful for aspiring entrepreneurs.

If you’re on Twitter, then follow-me! This way you’ll be alerted when I'm having discussions on Twitter Spaces. These will be calm, informal conversations. Don’t expect fancy editing or audio. I suspect my friends and I will talk about what we always talk about: the success and (funny) failures of starting, growing, and selling a business.


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