Why am I launching another startup?
With so many easier paths to take, why am I once again choosing the path of most resistance?
When I think back on the most exhilarating periods of my life, I find that they invariably coincide with times that I was at a significant crossroads. Of course, when you’re at a crossroads, you’re also at a moment of pause. And while that moment is awfully transient, it is also wonderfully powerful, for in that moment everything is possible.
I found myself in one of these amazing moments again this year. I left a company which I co-founded and built up for 8 years, and suddenly had free time on my hands. With no firm plans in place for what to do next, I breathed. I stepped back. And then I hopped on a plane and flew across the country to San Diego. I rented a blue Mustang convertible and began slowly driving up the Pacific Coast Highway, all the way to San Francisco. Two weeks. Staying in little beach towns along the way. Alone. Something I’d always wanted to do. When else can a family guy spend two weeks alone? Never is the answer.
While driving up the coast, with nothing but solitude and blue seas beside me, I took measure of my life, as one is wont to do on a ride like that. And a familiar feeling emerged. I recognized it instantly. It was the same feeling I had at other significant crossroads in my life; when deciding which college to attend (Tufts), which career to choose after college (professional musician), whether to take the plunge into matrimony and domestication (I did!), which career to pivot to when I needed to make “a real living” post-music (started my first tech company). And now I had that exhilarating feeling once again. Ah, what to do next.
When you drive up the Pacific Coast Highway, you’re reminded of how simple, easy and beautiful life can be. And I thought for a moment… ok, maybe for my next “thing,” I’ll choose something easy. Something easier than launching a professional music career. Something easier than launching a new tech startup. Something slightly more predictable. After all, I had a wife, two kids, 3 pets, and everything that goes along with trying to be the best dad ever. And yet, despite all the good reasons not to, despite my best attempts to convince myself otherwise, I resolved rather quickly to start another completely new venture… from scratch. The pull to do so was — and is — too strong. That’s all I’d really ever done my whole life. Start things from scratch. Take them as far as they can go. And that’s all I really ever enjoyed doing. Despite everyone advising me to choose something easier, I couldn't. I needed a blank canvas.
So this year, 2013, was indeed a crossroads for me. I could’ve gone several different ways. But subconsciously, or consciously, I’d planted a seed months ago. There was one great original idea that’d been swimming in my head for quite some time, and I needed to pursue it. It was the centerpiece around which I felt compelled to build my next company. Yes, I would launch another tech startup. Just what the world needed! Ok, maybe not. But I had the idea, knew I could execute on it, and started the company — UpdateZen — before the end of 2013, with a product launch targeted for Spring 2014.
In starting UpdateZen, I have relegated the foreseeable future to doing something very, very hard. Starting, building and running your own company means that every day - for as far as the eye can see - you are going to wake up, get punched in the face, struggle to your feet, get your bearings, wipe yourself off, move on, and then get punched in the face again. Then go home, see your kids, do your best to not let them know you got punched in the face twice that day, put them to bed, and accept that one of the two punches — the one you didn’t recover from - is going to keep you up all night. So you take an ambien about 2am, and eventually fall asleep. And then you wake up, hop out of bed, check your email and get punched in the face again. This is life running a startup.
Now I try to keep perspective. It’s not that hard. I’m not curing cancer. I’m not fighting in a desert in Afghanistan. I’m not trying to feed 6 kids on a mailman’s salary. That’s REALLY f@#$!#%!n hard. I’m just trying to change the world… a little bit at a time. I’m trying to solve a big problem with an innovative solution. But having done this before, I know firsthand how painfully hard the life of a startup founder is. It is not glamorous. It is difficult and humbling on a daily basis. And there are no guarantees you’ll ever make a dime.
So the question is… Why? Why put myself through this? Why not find something easier? Something more stable. Something more secure. Something more predictable. Something that won’t keep me up all night, every night. Something that will allow me to have more of a social life, pursue more of my hobbies, live a more “normal” life. Something that will involve fewer punches to the face!
And the answer is… because starting, building and running your own company (or any other venture), while painful on a daily basis, is also the most exhilarating, invigorating, rewarding and everything-is-possible experience I've ever had. And I wanna have it again.
Does it suck when you can’t find that brilliant developer you need to hire yesterday? Yes. (Although I finally found two!)
Does it suck when you can’t raise money before you have a product in the market with initial traction? Yes.
Does it suck when you do hire a great designer but he turns out to be a total non-fit for your team? Yes.
Does it suck when everyone tells you that your idea - while “wonderful” and “amazing and “genius” — is gonna be impossible to do because (a) you’re not in Silicon Valley, and (b) almost all startups fail? Yes.
Does it suck when you’re in New Jersey and there is no tech ecosystem producing “A” players that you can recruit from? Yes.
And does it suck when you can’t lure that high-paying genius from his comfy BigCo job in NYC? You bet.
Does it suck when you can’t get home before 11pm for four straight nights because you’re solving yet another one of those punch-in-the-face problems that require your completely obsessive 24/7 focus to resolve? Yes.
And does it just generally suck alot of the time? Yes.
So why not choose an easier path? The simple answer is I really dig doing hard things. I really dig working on something that, if successful, will change the world… or at least a substantial slice of it. I really dig those rare moments when absolutely everything seems possible, even if your logical mind says it’s all terribly improbable. I really dig not being bored. I mean I REALLY dig not being bored. And in some counter-intuitive way, I think I actually dig not being able to sleep because a hard problem is keeping me up. And if I’m being real honest with myself, I’ll admit that I actually love working towards something when everyone tells me it can’t be done. And yes, in some sort of sadistic way, I think I actually enjoy getting punched in the face daily. It reminds me that I’m alive. It reminds me that I have a purpose. It reminds me that I matter. It reminds me that I’m working on something consequential. It reminds me that I’m doing something really, really hard. And when I recover from that punch — and I almost always do, eventually — ahhhh, it feels good. And when the next punch comes, I remind myself that this too shall pass and this too has good in it.
Lastly, when it comes right down to it, we only get one go’round on this earth, so why not try to make a dent in the universe while we’re here?
My twin boys want to be the starting backcourt for Duke in about 10 years. Some dads — and I completely understand why — would try to manage their kids’ expectations so that they don’t have a huge letdown one day. I just don’t feel that way. I want my boys to dream big dreams. And I want them to work as hard as they possibly can to achieve those dreams. And if they fail, so what? So fucking what?? Getting punched in the face, falling down, losing your bearings, getting up, finding your bearings, wiping yourself off, and figuring out another way to “take the wall” is what life is about. Or at least that’s what startup life is about.
Here I go. Again.
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