For a brief period of time after college, I ran a small consulting firm with a partner. During that time we had a short but insightful conversation with the CEO of a client company, asking for his advice and talking about general motivations. Several things he said really stuck with me - this post is about one of those things.


My partner and I incorporated an LLC for our firm. We had not attempted to hide the fact that consulting was not our end goal as a company; we hoped to consult to get a cash ‘safety net’ in the bank and make some contacts in industry with the ultimate goal of spinning off into a startup / product company, à la 37Signals (now Basecamp). We told the CEO this, and one of the first questions he asked us both was simple and direct:

"Why do you want to start a startup?"

Despite this seeming like a trivial question, I was stunned I didn’t had a ready-made answer to give. I had always assumed starting some sort of venture was just ‘in my blood’, without really pinpointing any one particular reason close to my heart. I could think of a couple possible answers, although none of them truly described me.

Some ostensible reasons to start a startup:

1) I don’t want to work for anyone else

This one resonated with my partner more than me. At the end of the day he couldn’t stand the idea of building someone else’s dream rather than his own, and wanted total control over his own business, product, and team without having to answer to a higher authority (it was quickly pointed out that if you take investment this does not necessarily continue to be true). I’ve never liked the idea of working for “the man” as a nameless engineer at a multi-thousand person corporation, so I’ve always been drawn to smaller environments and companies, but this was not my sole motivating factor above all others.

2) Money / glory

It’s hard to watch the Social Network without wanting a piece of the action. Startups today are glamorized to no end. Who wouldn’t want to scale a darling startup to 100MM+ users before selling out for umpteen billion dollars and retiring carefree at 28? Although tempting, this was not a driving factor for me. Most startups fail. Out of those that succeed, some miniscule fraction spiral into insanely profitable behemoths. If it’s solely money you’re after, your odds are better taking a job at one of the big players and negotiating for a very cushy (and stable) salary. By doing this you lose your shot at walking away from an exit with millions in your pocket, but for some this may be a perfectly acceptable tradeoff to make. Consulting pays well enough as is, but I didn’t want to stay in it forever, and I’m not terribly compelled to try and push a product in front of as many eyeballs as humanly possible.

3) Why not?

Fresh out of college, this was not a terrible answer. When you’re young and carefree the amount of risk you can realistically take on is close to an all-time high. Consulting was paying our rent for the time being, and were we to ever spin off into a full-blown startup, the worst possible outcomes did not seem disastrous. Neither of us had families to tend to, nor significant debts looming over our heads at the outset (which is an incredibly fortunate position to be in). If our attempt at a company were to never even get off the ground, we would pick up our shattered egos and take a steady job in industry. This helped my confidence, although I don’t think it’s the most solid answer to the question.

(in addition, Paul Graham has posted on reasons to not not start a startup.)

I told the CEO that I wanted to make a real impact on a company. Not just from a technical perspective, but on a holistic level. I want to shape the direction of a business and craft a product and a team from the ground up. I want to build something truly great, make customer’s lives better, and solve difficult problems along the way. This is true, but at the time it felt like I was making it up on the spot!

The CEO asked me if I would ever be the second employee/engineer at somebody else’s startup. I thought about it and admitted that I probably would, assuming I felt it was the right team and a good product. At that point, I felt like I could still make a significant impact, and I don’t have a hard idealistic opposition to being anything but #1. He then asked if I would be the 20th, to which I hesitated and said probably not. He asked where the line was for me, and I couldn’t answer. I think he was mostly proving a point. Could I still have that degree of control and impact as employee number 12? Number 7? At what point do you go from being an integral early employee to just another hire? There is certainly not a number that answers that for all people. For many people it does not matter.

After the conversation I was not fully satisfied with the answer I had given. It really sent me into a spin - maybe I’ve just been telling myself I’m an entrepreneur at heart this whole time, but not really meaning it. I spent a bunch of time on forums and sites for entrepreneurs, searching for inspiration or answers perhaps, but came away with little. I found many people who made their entrepreneurial living selling books/courses on entrepreneurship, doing silly things like starting X “companies” in as many months, or selling to-do list software aimed at insanely specific verticals. My lack of interest in these things made me question even more whether or not I was an ‘entrepreneur’, which I suppose is silly in hindsight. Not to say that there’s anything wrong with these - these people seemed to be die-hard self-starters, and free as a bird. For some, their ventures enabled them to live and travel all over the globe, without being constrained by a 9-to-5 schedule. That I can admire, but truthfully I am not that person, and that is not my ultimate goal. I know at least that I am certainly not an aspiring “serial entrepreneur”. I’d rather nurture a single venture to something great in my lifetime rather than looking for an exit right out the gate and circling back for round two. Of course, this conversation had me wondering if that notion was just a work of fiction in my head.

I still question my motives sometimes. Time passed, and I took a job as an early engineer at a startup, and I’m very happy with the decision. True to his word my partner from the firm is currently pursuing his own software venture. There’s no telling what life holds down the line, and maybe my answer to the question will change as time goes on. Maybe our firm will rejoin to form a world-changing startup, and maybe it won’t. If you’re an entrepreneurial spirit at heart, I suggest you really ask yourself: “why do you want to start a startup?”