I graduated Cal Poly San Luis Obispo in December '94 with a four month old daughter (ok she didn't actually graduate with me, but you know what I mean), was married to her mother a month later and left my college job at KFC for good (they gave me a check for $500 as a 'thank-you' for my service) to join a startup doing inside sales. They gave me a Mac with a 9" black and white monitor, a gyne colored cubicle, a yellow pad of paper with a Papermate pen and a Nortel desk phone. Nine months later the CFO of the company pulled me aside told me the lead investor (who was a 'strategic' and major brand for decades) wasn't going to see the company through much longer. He gave me a sticky note with the name of a woman called Rita and a phone number. He said, "Call her, she's be expecting your call. She's looking for a guy like you."
Was Rita an A&R exec ready to sign my band? A scout looking for a half Mexican with a perfectly receding hairline? A call girl? A meter maid? Ok I'll stop now. She was an HR director at another startup with reputable investors with revenues ramping but at a strategic crossroads. I joined Rita's company and ultimately participated in the company's IPO a year later. Then a year after that joined another startup which a year later was acquired by a 20,000 person company. I did about a year at the 20,000 person company and learned I was becoming just a cog, just a social security number in the rank and file. So naturally I joined another pre IPO startup, who like clock work did an IPO about a year later. What sounded so risky [startups] on the outset had paid off. And so went the 90s and the build out of the Internet...
Not too far into this century came what would become a long, cold, nuclear winter. I joined my boss at a new startup he would take over, and finally - after three great runs in a row, I landed a dud. Granted, had the markets continued to flourish, it had all the makings of a blockbuster hit. When that didn't work out I thought it was about time I take what I'd learned and found my own startup. If nothing else I'd get some great experience and find myself a better place on the cap table for when the markets got back to normal. What I didn't admit to myself at the time, was the great run I had experienced was probably a once-in-a-lifetime thing. After all the odds are typically stacked way against startup success.
I learned that the hard way when I tried my hand at founding three startups inside of six years. Although a lot was accomplished in those startups as far as innovation and execution, none of them yielded the level of returns I'd experienced in the 90s era startups. Some of it was me, some of it was hiring mistakes, some was the feasibility of the companies, some was market dynamics. On more than one occasion I thought about what would have been, had I gone the route of many of my early colleagues, and work my way up the ranks in a big company. I most certainly would have earned better compensation during the 2000s. But I wouldn't have had nearly the level of breadth, creativity and scrap that I have now.
I got a call from a recruiter the other day who was sniffing around. (It's always good to keep recruiters up to date on yourself because no one else will). I talked her through the triumphs, trials and tribulations of the last 15 years. And her question to me was "You're a startup guy, what are you doing at a big company?"
That's when I explained to her, like I've explained to my own team, that there are merits to both paths, and your best bet is to diversify your career path based on the opportunities both that present themselves and that you can create within them. For example, my last startup was in a seed stage and in its short term we built a useful product and had 100,000 users. That's notable in its own right because that's really hard to do without spending money to do it. But I sold that company to a bigger company, and now rather than fret about how to grow from 100,000 to 500,000 people using it, I got to refactor and rethink it as it relates to big co, and ultimately launch something into over 100 million users. It's not everyday you get to do that, so you have to do it when you can.
Whether it's a big co or startup, It all comes down to the opportunity you have and can exploit, i.e. the market timing, the funding and/or exit climate, the earning potential, and the risk/reward.
If you're young and getting started and have roommates and so forth, you can play a high risk profile and bounce around from startup to startup and learn a bunch in a short amount of time. On the other hand if you can ride the ranks in a big co you can establish the credibility and scale that could perhaps make you a better in the long run.
If you're an old timer with a family you might prefer the stability and comp of a big co, but perhaps you can find your sweet spot in a later stage startup that is less risky. There are a handful of those companies that have already created significant value but are still pre IPO.
A lot of people in the industry like to characterize people as startup people or big company people. While you can find success in either, there's no reason you can't be great for either stage or in between. In any case, it's all a matter of your individual situation, dynamic, ambition and risk profile.