Why I’m taking a break from parallel entrepreneurship

When I described what I’m doing now to a good friend, he chuckled and said, “Guess you’re going to have to write a new forward for your book!”

The book he referred to is The Parallel Entrepreneur, of course. It’s hosted free on this blog and generates most of my organic traffic. I still believe in the premise. Side hustling should always be an option for any entrepreneur. However, it’s not the right approach for me right now.

My entrepreneurial philosophy evolved a lot over the past year. It probably started with the realization that climate would be my next big thing. A climate business could not be a side business. The problem is too great, the complexity too rich, and the opportunity too massive. I’ve learned over the years that if you treat a business like a side business, that’s probably all it will be. Most businesses don’t expand and explode by their business physics like a supernova. Most startups require determined, disciplined nurturing over a long while. I decided not to neglect my climate tech baby if I were to conceive one.

Then, slowly, I started to wrap up my side businesses. One by one, I sold or shut down each of them. My Heroku bill got smaller and smaller. Two years ago, I sold EmailFinder, Name2Domain, and Name2Profile to Live Data Technologies. Those web applications generated a few thousand dollars per month in aggregate. I still had eNPS.co and MyKidColors.com. I built eNPS in 2017, inspired by my HR experience at Scripted, when I needed to send quick surveys to our employees every quarter automatically. That business probably made $20,000 over its lifespan. MyKidColors scraped coloring pages from the web and organized them better. It never made money, but the organic traffic came quickly. I never monetized it and never got around to incorporating generative AI to produce coloring book content (I still think this is a great idea!)

I thought I would feel sad when I let these little dreams go. I didn’t. Instead, I felt relief. Even a small weight lifted releases energy that I can put into Shovels, my new company, the one I’m more excited about than all of my past projects combined. It’s that conviction that I’ve found the one, the idea that will become a company that will grow and grow and grow and make a real impact in the world. That conviction overrides everything! No regrets.

Entrepreneurs need to evolve. When starting a company, we grow and learn quickly. The highs are higher, and the lows are lower. We incorporate these lessons into our business psyches. It makes sense that our perspectives should change too. I’m not burdened by my book titles.

I’ve justified my ability to change my approach. Now I’ll explain why I’m changing it.

I want to build

I sent an email a few weeks ago to a friend I made through this blog, a professor in Europe who found me by googling “parallel entrepreneurship” and then discovered we had other things in common. I was thinking hard about fundraising, coming down to the final decision about whether to take outside money for Shovels or bootstrap it.

I told him these two questions are related: whether to fundraise or side hustle. The answer boils down to what I most like to do: build. I made the point that bootstrapping or side hustling is a relatively quick building process. The code is simple (if I follow the formula from my book), so I can usually get to the first release and first revenue within a few months. After that, it’s all launch marketing and long-tail SEO. Then it’s customer support and bug fixes. I don’t add features or think much more about what else the application should do.

These are running activities. I don’t love running companies as much as I love building companies. I can’t build a complex side hustle application because of the maintenance requirements and the fact that, if I’m being honest, I’m not that great of an engineer. As a solo entrepreneur, my engineering skillset tapers off quickly as complexity increases. To get to the next level, I’d need to learn to write tests and incorporate javascript, and neither excites me.

On the other hand, raising money expands my ability to build. I won’t do the hard stuff myself; I have an amazing co-founder for that! Instead, I can continue to build marketing and revenue operations, send emails all day to potential customers (as I did for the first half of this week!), and think strategically about product-market fit. Fundraising means we have a much longer build ramp. We spend more time building, and if we keep fundraising and the business keeps gaining momentum, we never stop building. This is what I want. I want to spend my time building!

I want a team

The other critical difference between bootstrapping and fundraising is pulling a team together.

For years I’ve been bootstrapping alone. It served a purpose then: my kids were young, my businesses were small, and I could do whatever I wanted. I could work full-time on someone else’s company and keep my little apps running in the background. I could teach. I could go on long bike rides, play piano, go to lunch with my wife, and deal with an entire school year of COVID protocols. My solo lifestyle afforded me all of this. Now I neither need nor want it.

I don’t want to be solo on Shovels. It wouldn’t work. It’s too big. I needed a co-founder, and my co-founder and I need a small team to get this off the ground. Fundraising allows us to do this, and I’m confident the economics will work out. We’ll sprint toward profitability, get there, and then take some big calculated risks. Having a team allows me to maximize the opportunity.

I want to win

Finally, I want to win. I wouldn’t say this about my side projects. My little companies were meant to be little, make a little extra revenue, and just… be little. I had no ambition other than to keep them alive.

This time is different. I want to win! I want to compete with the other construction data companies and work harder and faster and smarter than all of them. I want Shovels to do stuff nobody else is doing or even thought about. One benefit of being a novice in the field is that I’m not tied down by industry norms.

To win, I need to build, and to build, I need a team. That’s how this all relates. This is a marathon, and we’ve just started running it.

Posted in Uncategorized

Leave a Reply