Startups Anonymous: The startup life of an OG

By Startups Anonymous , written on March 19, 2014

From The News Desk

[Editor's Note: This is a weekly series that brings you raw, first-hand experiences from founders and investors in the trenches. Their story submissions are anonymous, allowing them to share openly without fear of retribution. Every Wednesday, we'll run one new story chosen by Dana Severson, who operates StartupsAnonymous, a place for startups to share, ask questions, and  answer them in story-length posts, all anonymously.]

Lately I've been struggling with my age. I'm 37, soon to be 38.

I expected to be much further along professionally at this point in my life. Looking back, I remember thinking that I'd have already made my millions by the time I was forty. My goal was to be an active investor by now. Taking what I had earned and learned and passing it along to other entrepreneurs that were in the position I was 10 years ago. That was the dream.

Now, 10 years later, I find myself in roughly the same position I was in when I had that original thought, at least financially. I've grown as an entrepreneur. I've grown a ton. My maturity, business acumen, knowledge, network, etc. has all grown.

Yet, I still struggle with the fact that I'm no better off financially than I was when I started on this journey. In fact, it's worse. I now have a wife, three kids, two dogs and a mortgage. All of that meaning that I can no longer take big risks. I need health insurance. I need a salary — and that salary needs to cover my family expenses. And, because I've ran so lean for the past 10 years, there is really nothing to fall back on.

You may wonder why I don't just bite the bullet and find a well-paying job? That's what I'm doing now and it's what led to my anxiety.

First, as any entrepreneur can attest, getting a "job" is pretty much the worse thing you can imagine. It's submitting to failure, even if just temporarily. It's denying yourself the pleasure of following your passion. Deep down you know that wherever you go, it won't be for long and you'll constantly be thinking of what's next. Lately though, I've been wondering if I'll even get another shot.

I feel like an aging musician that finally realizes that he needs to stop playing in dive bars, cut his hair and get a real job.

The idea of taking a job is dreadful, but it's really the only safety net that I have.

My age is starting to catch up with me though and that has me scared. I'm no longer as marketable as I once was. That safety net is starting to fray. All of those years of farting around with projects that went nowhere has left me without a consistent skill set. What I mean is, as an entrepreneur, you end up being a little bit of everything, which means you're also a whole lot of nothing. Same as a company that tries to please everyone and ends up pleasing no one.

You believe that what you've done is impressive, but it really doesn't translate. The only real thing that's clear is that you're a flight risk. To be fair, I would probably think the same thing if I was hiring me.

I'm feeling the pressure and can practically hear the clock ticking. Maybe that's normal for my age. Maybe I'd feel this way regardless of my financial position. Or maybe this is the start of a midlife crisis.

Whatever it is, I'm moving on...

I now have a job, and it pays well. One month in and I'm already looking to scratch an itch. Maybe I need startup rehab so I can hold a job. Then again...

Fuck it, I've got two years before I'm 40. I'm going all in.

Hmm, wonder if this is a sign of early onset dementia?


A Startup OG

[Illustration by Hallie Bateman for Pando]