What I Learned at a Startup

Glenn Goodrich

  • Reading Time  Min Read
  • Publish Date January 27, 2015

If you’ve been within earshot of me at any point in the last three years, you know that I was working at a startup. It was something I wasn’t shy about sharing. Often, I would introduce myself as Glenn “Did you know I work at a startup?” Goodrich, LLC. It was a major decision for me to jump from the warm, cushy embrace of an established company to the prickly thorns of a startup. I agonized over the decision, due to some of the preconceptions I held about “startup life.” After three years, were my preconceptions confirmed? Was the agony of the decision merited? Now that it’s over, how am I going to introduce myself to people?

I will focus on three major preconceptions I had before joining a startup, ending with a moral that I took away from it following my own experiences. For those of you that have never taken the plunge, my discoveries may affirm or refute your thoughts about startups. For me, it was more about taking a hard look at that time in my life, both personally and professionally. This should be interesting…

Preconception #1: Eat, Sleep, Work (where Eat = Work and Sleep = Work and Work = Work)

This notion of work is as true as you want it to be. For much of my time at the startup, I worked constantly. Evenings, weekends, vacations, open-heart surgeries, weddings, kids’ sporting events — name an event and I bet I worked during it. This practice was a choice. A really, really stupid choice. I missed out on much of the “life” part of my life, nearly had a nervous breakdown (really), and temporarily forgot about so many of the good things. One day, I overheard my son say to my wife, “I feel sorry for Daddy. He works all the time and he doesn’t make a million dollars. He should.”

Furthermore, it wasn’t like I was cranking out top-notch, quality code either. When I got tired, I was mistake prone and quality averse. For example:

  • I deleted our top user’s account from the production server, including a ton of data that user owned. I moved too fast.
  • I stopped writing tests, often, because I could deliriously rationalize how I’d come back and fix it “when we’re done.” In other words, I threw out my craft.
  • After a particularly gnarly, cache-related bug, I left a 4-letter word (in full <h1> tag glory, mind you) at the top of a page in production. I lost sight of what was important.

I am lucky. I have a wife who knows how to slap the idiot out of me. She’s had years of practice, after all. I can laugh at some of it now, but there is a big part of me that knows how not funny it was.

Moral: If you work somewhere that expects you to work at an excessive pace or if you feel compelled to do so, don’t. While you will feel pressure to work all the time, you can’t. Repeat after me: Work is not life. When it was all said and done, I made this preconception come true.

Preconception #2: Startups are for the Young and the Kidless

Youth is a matter of perspective, right? Well, you may be shaking your head now but, as you age, you’ll start nodding. Startups are for younger people. I was the oldest person at my startup. I have a (shockingly large) family, brimming with four kids. I am not in my 20s. If startups advertised, I would not be anywhere near their target demographic.

I went to startup life because I wanted a change. I’d spent years in the corporate(ish) ranks, writing the same code, going through the same motions. I wanted to be on the edge, change my technical chops, take my shot. I have always believed that seeing these desires fulfilled is not a right exclusive to the Young and Kidless. So, with a firm grip on the anvil of old(ish) age and family responsibility, I shed my parachute of benefits and a fat salary, and I jumped.

Startup life is like any other massive life change (kids, marriage, bad haircuts); it exacerbates everything. When you have a family, health benefits are huge. Having to get them on your own hurts. Startups typically come with lesser pay. Again, this hurts more when you’re feeding more than just your own mouth. These are problems of a family, though, not of age. If you plan for this pain, it can be managed.

Still, I believe my age brought some wisdom to the job, even if I was being patently unwise about work/life balance. I’ve been around the block a bit, so I knew, in many cases, what the company needed to succeed. Often, I knew which fork in the road to take and wasn’t afraid of decisions. Age, or more accurately, experience helped me here.

Joining a startup forces you to prepare just a bit more for the worst. Your paycheck may disappear at a moment’s notice. Benefits are your responsibility, and they may be different than what you once had in corporate life. Your corporate friends will likely go on awesome vacations and do things you can’t afford. Your weekend may be eaten by production issues. These things bubble up (or roll down) to you because there is no one else. You have to prepare for all possible problems because you’ll have to handle them when/if they spring up.

Moral: Prepare for Startup Life, and it’s manageable. Don’t prepare, and you’ll find yourself without a paycheck. If anything, this kind of preparation favors age and responsibility.

Preconception #3: Startups are a Home Run Shot

I think almost everyone I told that I was going to a startup replied with some sort of, “Well, if it takes off, you’ll be set for life!” – all while looking at me like I had a third eye. I didn’t go the startup route for the potential avalanche of money when we sold. I didn’t do it for the yacht. I did it to learn a ton, expose myself to different technology, get away from bureaucracy, and gain freedom. If you’re doing it primarily as a swing for the fence, don’t. The vast majority of startups don’t reach billion-dollar-Instagram status.

For most people, the potential carrot of riches won’t be enough to get you through the hard times. When your boss tells that the company may not make payroll after you just worked three all-nighters, you won’t care about the potential riches possibly (but probably not) coming in three years.

Moral: Join a startup for the right reasons. Do it for the challenge, do it because you believe in the company’s goals, do it to change your career. Just don’t do it for the money.


Three years ago, I felt like I was walking through a dimensional portal. Will they speak my language in this new land called Startupistan? What will they eat? If they have two heads, which one do I look at when I’m talking to “them?”

The truth of the matter is a job is a job and a company is a company. Every company has a culture, and the culture of my startup was driven by the need to get stuff done as soon as possible. We were working on investors’ dimes, not pulling in any revenue, etc. This environment exacerbates everything. Every mistake hurts more, every success feels like winning a marathon.

The rules, however, are the same as a “normal” company. Communicate well and fail fast. Involve your users from day one. Test and test and test, then test some more. Any software development company should do these things, they’re just a bit closer to the surface in a startup.

I have no regrets about my foray into Startup Life. I wanted to learn a lot, and I did. I wanted a change, and I got one. I wanted a major challenge, and it was the greatest challenge of my career, so far.

If you think you have the Startup Itch, here’s a few questions to ask yourself:

  • Do you know when to walk away from work? Do you have someone that will help you do that?
  • Are you prepared for the worst? Where are your health benefits coming from? How long could you last with no pay? How fast could you get a new job?
  • What are the real reasons you are joining a startup?

If you like your answers to those questions, then you’re one step closer to the cliff’s edge. But don’t worry, the cliff is probably more of a step, and it could be the best career decision you’ve ever made.

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