Why I Love Working at Startups

In case you didn’t see it, Evan published a great essay yesterday over in Napkin Math arguing that it’s a bad idea in the vast majority of cases to work at a startup. It was a fun piece to edit, because I completely disagree! 😅

Ok ok, I don’t completely disagree—I think Evan is probably right that startups are currently somewhat overrated, and they’re not right for most people—but as someone who’s worked in startups for most of my career, I feel like I’ve gotta stick up for them a bit. For a particular type of person, in a particular type of circumstance, startups can be an amazing choice. So here is my friendly rebuttal. 

*cracks knuckles*

The Case Against Joining Startups

Evan’s piece focuses on busting what he sees as the two major myths that lure people into taking startup jobs:

1. It’ll make you rich
2. It’ll be fun and fulfilling

Because the stories of unimaginable wealth getting dumped into startup employees’ bank accounts are so pervasive, most people overestimate their chances of getting rich off a startup. But Evan looked at the actual numbers and reckons that only 2% of seed-funded startups will do much financially for anyone beyond the founding team. And similarly, our culture tells us that working at a startup is more fun and fulfilling than corporate cubicle life, but Evan asks us to honestly consider whether it’s actually so bad to work at a big company and find meaning in our communities, families, faith, charity, and hobbies.

And I think he has a point! The process of editing this piece helped me come to a more nuanced understanding of the pros and cons of working in startups. Before this, I was pretty much all startup all the time. Now, I’m more measured. In particular, it made me question my cherished belief that working at a big company is always soul-crushing, and I now admit for most people it probably is not. It also made me reconsider how likely financial success in startups is, and I agree the probability is lower than I thought it was for most people.

But—I still don’t regret my choice to work in startups over the past decade. And furthermore, I plan to continue doing so for the foreseeable future.

To understand my perspective, you need to know a little about how my brain works and where I came from.

Startups: Islands of Misfit Toys

Ask anyone who’s worked with me in the past what it’s like to be my colleague, and they’ll probably tell you that I’m smart and nice but prone to occasional bouts of intense emotional attachments to ideas. Otherwise known as “giving a shit.” I try to manage and contain it to make life easier for my coworkers—I really don’t want to be a jerk!—but I can’t ever escape the fact that I have trouble going along to get along. This may or may not be part of the reason my cofounder Dan and I go to couples therapy. I’ve been like this ever since I was a kid.

I’m not sure what it would feel like to be the kind of person who can plug into a team with ease, but for some reason it’s always been incredibly difficult for me. I remember my first job in college was at Michigan State’s International Business Center. They ran a website called globalEDGE that compiled statistics and research about what it’s like to do business in various countries around the world. My job was supposed to be fairly simple data entry stuff, but of course I made it more complicated than that. I asked a bunch of annoying, existential questions in our routine weekly meetings; I proposed wildly infeasible new project ideas during unrelated conversations; I had emotional discussions with colleagues about the editorial principles underlying the website blog—in other words, I was a pain in the ass.

Now, over a decade later, all grown up, I still give way too much of a shit about whatever is right in front of me. I pour my whole self in. I know theoretically you should be able to care deeply about your work and not be a pain to work with, but this has always been hard for me. It still is. I’m like a firehose with no “off” switch—if I’m pointed in the wrong direction it can be dangerous, so the coping mechanism I’ve developed is to choose my projects with care. I can only work on things where it makes sense to pour my whole self into it. Like startups.

The main thing that’s changed over all these years is I used to struggle with my relationship to work, and now I couldn’t be more proud of it. I love my brain. It took a lot of work to get here.

I don’t know why I’m like this. My parents loved and supported me as a child, and made me feel like I could do anything. Even when I got terrible grades and my 7th grade science teacher called me the “personification of ignorance,” they still believed in me. I received an ADHD diagnosis around that time, so I think this is just the way my brain is wired.

Regardless of how I came to be this way, it’s the way I am. And for me, startups are the only container I’ve found that can withstand my kind of hyperfocused passion.

I don’t think there’s anything superior or special about working at startups. If you work at a big company, or at a non-profit, or at a university, or in government, that’s awesome too. Society would not function without you. But for me, I’m pretty certain I need to be at a startup.

The awesome thing about startups is they give you a vehicle to try out your ideas, learn your own lessons, and experience responsibility in a way that is hard to find anywhere else. This is great for the obvious reasons that startups reward passion and intensity in a way that big company jobs mostly do not, but also for another,perhaps more important reason: I’ve developed a much healthier personality because I’ve been able to experience this. I’m pretty certain I would have been a completely insufferable know-it-all if I hadn’t had the grueling and humbling experience of failing with dozens of ideas that I once thought were genius. I couldn’t have learned any other way about just how rare a good idea is, and just how hard execution is, and just how crucial healthy relationships are. Startups have made me more empathetic and open than I would have been otherwise. 

Now, not everyone may need the same kind of moral education that I did. But I think if you’re like me, you’ll benefit a lot from it.

But… at what cost? And can you really not get it anywhere but startups?