The startup life of an OG

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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


  1. I think if you don’t keep pursuing your startup dreams, you’ll regret it for the rest of your life. Something tells me that you’re not the type to be satisfied with just giving up and settling for a decent job. I think you should keep going. The founder of KFC didn’t succeed until he was an old man even though he had been creating businesses his whole life.

  2. Get a job at a well-funded early startup. Best of both worlds, kinda (equity).

    • I second this. I am 40 and spent 10 years building failed startup after another. I wished I’d joined some well funded startup instead.

  3. Been in the exact spot twice – the fact of the matter is down to this: what’s the alternative? As CEO of a start up (or even just as a regular guy/gal) you always have to ask yourself that question – I don’t know all the details, but it seems that if you keep the staff, you are going to remain with a key to an office + 100% of employees that were fired….. So, as I said (and I am a softee), alternatives – had to fire a large percentage twice – once it saved the company and the second time it gave us a second chance…. Think about it – would be happy to hear you came through.
    If not there is always a new start :-)

  4. 40 here. One sort of successful startup under my belt, lots of failures. Not a whole lot of financial security. No mortgage, 2 kids, 1 wife, etc.

    So, you are going to do another startup. Let’s just take that for granted. You may not quit your job to do it, but it’d be nearly impossible to stop.

    So, the question is, what are you going to do differently next time?

    My mistake was that I was focused on the wrong thing in my startups. I wanted to build a product / scratch an itch / change the world. Well, the world didn’t care.

    Now, I’m doing another venture (more like a small business than a startup) I started 6 months ago, and I’m already generating 5 figures in revenue.

    What’s changed?

    I just listened to what people wanted, and it was something that I could do, and then charged them for it. The customers came flooding in.

    Best of luck, see you when you get back in the game!

  5. You give up when you give up. Ignore the doomsayers and haters. Be yourself and keep your eye on the prize if that’s what you really want.

  6. As an employee who worked for startups in the past, I really liked (after the fact) that when times got tight, that the management implemented an optional/mandatory salary reduction strategy, a stop to matching contributions, and compensated with an increase in perks. The idea was to keep the talent until we could get more funding / customers, but it didn’t happen. Despite it not working out, we all appreciated the effort to keep us on-board!

    On the other hand, at a larger & more established firm I worked out, they used to have layoffs every October. There was always a shift in morale that time of year, and over subsequent years, it got worst until there was a change at the top.

  7. 28 and feeling the same way. I always think of myself in terms of this quote: “Jack of all trades; master of none.”



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