Big Company vs. Startup

As many of you may know, I made the jump from Cisco to run Sales Engineering for a small startup in the valley. Even though my gig at Cisco was awesome, I am confident this was the right move for me. I know there are a lot of folks out there wondering whether or not they should take the plunge (because it is a huge risk), so I thought I would talk a little bit about my thought process in making this move. 

I have always been a risk-taker. I love fast cars, snowboarding, skating, cliff diving… you name it. My wife always tells me I’m missing that little voice in the back of my head that says ‘are you sure you can do this?” So I guess you could say my personality is slightly unhinged to being with… but that’s only part of the reason why I love startup life.

 I began my career as a sales engineer at a startup in 2007. I was employee number 25 in a company based in Boston with a satellite office in LA (I was in LA at the time). I was the 4th SE hire, which was impressive for a company of that size, but the way the model was built we had two SEs in Boston and two SEs in LA. 

I had no idea what I was doing, but I loved it. 

I was getting in early to prep and spending time with the engineers to learn the technology and the industry late night. The days were long, the office was a dump, my sales team was a shit-show, and my commute was horrific… but I didn’t care. I was learning new things at lightning speed, living in the awkward every day, learning the iron-clad fundamentals of what it takes to be successful, and attempting (and succeeding) at doing things I had no business doing. It was fun. 

I have often reflected on what I thought made this absurd lifestyle enjoyable for me. Why on earth would someone do that for a few days and then not run for the hills? For me, the reason is the challenge, the opportunity for rapid career growth, and the love of the unknown. My then CEO had this great saying that we were all just “bozos on a bus”, and I like that. 

I can actually sum up why I love startups in one quick back-and-forth in 2008 with one of my early mentors. We were out for a “career lunch” which you need in your 20s at a startup because you’ve been working insane hours and there’s no money yet for a raise and your manager needs to give you a pep talk and discuss the “long run”. Anyways, I was baffled about how she knew so much and always seemed to have a plan. So after a few beers I asked her, “You seem to know exactly what you’re doing… how do you know it’s the right decision? Have you done this before? When do you know what the next move is going to be?” 

Her answer would forever change my outlook on business and life. 

“Matt”, she said. “I just make it up as I go along. I never know what the next move is going to be, I make the most educated decision I can and if that doesn’t work, we say fuck it and try something else”. 

That’s why I love startups. Big companies can take chances as well, but if a decision is made to change something there are many layers of bureaucracy that your idea has to pass through before it can be implemented. What I love about startups is, if your idea is better than the idea currently in place, your idea becomes the company idea. The opportunity is always there to swing for the fences and make a huge impact in a very short amount of time (not to mention the upside potential, but more on later). 

That said, startups are not for everybody… and even with the ability of extreme influence and upside, not all startups are something you actually want to do. My first gig was pure luck. I interviewed on a whim, got the job, and it turned out to be one of the most rewarding decisions I’ve ever made. It started me on the path to where I am today. The thing is, if I hadn’t been willing to put in 12 hours a day for 3 or so years non-stop, it would have been a blown opportunity. 

That’s the other thing, in big companies everything is already established… tried and true. You can just leverage what others have done before you to make yourself successful. I think of it as hiking in the jungle. Big companies have already cut a trail for you that you can get to the top of the mountain. The path is well-formed with benches and supply stops, but it’s a roundabout way that’s going to take you a while to traverse. A startup has a general direction to the top of the mountain… maybe a few people have cut back some branches here and there… but it’s essentially bushwhacking. You have a map and a compass so you know where you need to go, and the way is potentially much shorter, but you have to figure it out (and you could be heading in the complete wrong direction). No supply stops, no rest areas, just a general idea and a goal. 

So why did I drop one of the cushiest jobs I’ve ever had to go bushwhacking again? Because I love the hunt. I love just "figuring it out." I love working with a bunch of intrepid explorers in uncharted territory, blazing a trail where there’s never been one. New technology, new market, new challenges... I love trying something new and failing because failure helps you grow. I love trying something and succeeding, I love helping other people succeed where they thought they couldn’t. I love the camaraderie, the “everybody does everything” mentality. I love the possibility of a MASSIVE payout if we pull it off. I love accountability and transparency. I love the trust that everyone in it is working just as hard as the next guy. 

So should you drop everything you’re doing and go join a startup? I don’t know… like I said earlier it’s not for everybody. There is also the very real possibility that the startup you join will crash and burn… most do. I must have turned away at least 60 or so companies before I finally made my choice… Cisco is a great company and I wasn’t going to leave for just any ol’ group of kids with a good idea. Going with a startup is losing your safety net… but with great risk comes great reward. At this point in my life my wife and I are in build mode so we’re swinging for the fences. It takes hard work, sacrifice, and “balls like church bells”. I’ve only been in it two weeks and I'm working as hard as I’ve ever worked my life… and I love it. So I guess you have to ask yourself “am I willing to work my ass off and take that risk?” For me, that wasn't even a question because that's what I do.