(Big Disclaimer: This page is long and probably boring. Read at your own risk).

Like many investors, I started out as an entrepreneur. “Serial entrepreneur” to use the trendy term. I founded roughly a dozen small businesses, all bootstrapped. I was in the trenches day-in and day-out, frequently working on multiple projects at once, probably just like many of you reading this.

Everything from SaaS, ecommerce shops, my community, health products, and my long-standing search marketing agency. I’m not going to lie, entrepreneurship can be really damn hard, and can go from extreme bliss to complete exhaustion and back all in a matter of hours.

And I loved almost every minute of it.

Over the many years of grinding hard, learning from my mistakes, and from the guidance of others, my entrepreneurial skills slowly improved. I got fairly good at getting traction on projects and executing quickly. As some of the projects continued growing far bigger than I ever expected, I wound up being lucky enough to have some take-off, leading to a couple of sizable exits.

Post-exits, I did what most do, I became “an investor” (insert eye-roll here). I allocated capital to just about every type of investment out there. Dozens of angel investments in traditional high-risk high-reward startups, an LP in half a dozen funds, dabbled in public equities, private debt deals, real estate, and last but not least… started buying online businesses in their entirety to add to my growing portfolio. I was in search of “my thing”. A type of investing that I could latch on and pour my professional soul into, something that provided great returns, but also something that felt right.

So, guess which one I decided to double down on?

None of them. 

There is nothing wrong with any of the above types of investing, but they just aren’t right for me.