Why I’m doing it all wrong

Discuss this post on Hacker News.

Conventional wisdom for doing a startup as a young entrepreneur these days is something like the following:

1.Drop out of school

2.Raise money

A year ago that’s the route that I wanted to pursue. Freshman year of college I interviewed at Y Combinator with two of my close friends: Wesley who went to Penn with me, and Ajay his best friend from childhood. 

We got rejected.

Then we made it to the wildcard round of TechStars NY. Again we ultimately got rejected.

That summer I worked at a startup and built a few cool projects including DomainPolish (which I subsequently sold). When the school year rolled around again Wesley decided to drop out. At the time, I asked him why he didn’t want to go back to school. His reply was characteristically gutsy:

“I just have a feeling that it’s all going to work out.”

That winter Wesley and Ajay applied to YC again. A week before their interview they asked me to fly out and join them for it. I decided not to go.

I remember the phone call that I got from them after they found out they had gotten in to the next YC batch. It was incredible. We had worked for such a long time to get to that point. And it had finally paid off. I couldn’t have been happier.

Again, they invited me to leave school and join them at Y Combinator. But again, I said no.

That moment is something that I’ve thought a lot about. Saying no to an offer like that from my close friends was really difficult. So was saying no to Jason Freedman.

“What if I’m missing out on building the next big thing?”

“What if I never get an opportunity like this again?”

There are a lot of big “what-ifs” in a scenario like this. And you hear from plenty of people who tell you to never turn down opportunities. “Pursue everything that’s given to you because you’ll never know where it leads,” is pretty common advice.

After a long discussion, a good friend of mine who’s running a funded company recently said to me:

“When you decide to make big things happen, let me know.”

My friend is right: I’m not swinging for the fences. I’m not suiting up to go big or go home. All my chips are not on the table.

But why? Why bootstrap in Philly when I could be in San Francisco with an awesome accelerator program under my belt, with cash in the bank?

Let’s examine this further.

“Swing for the fences”

“Scale as quickly as possible”

These are fundamental assumptions of startup building. From these come our conventional startup wisdom:

“Leave school”

“Raise money”

For a long time I accepted the “leave school and raise money” argument because I assumed that “swing for the fences” and “scale as quickly” as possible were inviolable tenets of company building. But it turns out they’re not inviolable. They’re not even tenets. They’re just a common way of thinking about how to do a startup.

And when I really sat down to examine why I wanted to leave school and raise money something became clear: I didn’t want to hit a homerun.

Actually, let me rephrase that. It’s not that I don’t want to hit a homerun, it’s just that hitting a homerun is not what I’m focused on.

While you attempt to wipe the remains of your melted cranium off of your keyboard, let me try to explain.

In order to fully understand why I’m not focused on homeruns, we have to ask a deeper question: why build a company at all?

Why do startups?

I have a few reasons. The first is, quite simply, I can’t help myself. For the last 10 years of my life my default weekend activity has been coding to build products. I can’t remember a single vacation from middle school, high school or college when I wasn’t working on a business.

But more deeply, I came to a fundamental realization about what’s gotten me to where I am:

The only thing that I’ve ever done right in my life is to doggedly pursue the things that I’m interested in. To the detriment of everything else. No matter what anyone else says.

(Aside: that last part is important. No matter what anyone else says. That’s the only way you can be a philosophy major. If you give a fuck what people think you do political science.)

Pursuing my interests regardless of what anyone says has worked well for me. I’m naturally interested in business. I’m naturally interested in coding and design. I’m naturally interested in writing.

And so my goal is this: to be able to do those things sustainably, for the rest of my life.

That, in a nutshell, is why I do this every day.

Now let’s get back to homeruns. Homeruns by definition aren’t sustainable. They’re not predictable. Sometimes you hit one, but most of the time you don’t. That part of things is mostly out of your control.

Because it’s out of my control and not sustainable, I’m not focused on it. For that matter I’m not interested in anything that’s not sustainable.

For example, I don’t think that the current funding environment is sustainable. Right now you can go out and get money for an idea in a way that you won’t be able to in 3 years. Funding can’t be counted on and so I’m not concentrated on it.

So what can be counted on?


Fundamentals don’t go out of style. They are by definition sustainable. Every successful business follows from solid fundamentals. Customers, money, funding. And that’s what I’m concentrated on.

What I’m spending my time doing now is this: learning how to build a real business. And by real, I mean a business that has money coming in the door from day one. Businesses that make money can be started in any investment climate. They don’t go out of style.

That’s why we’re holed up in an office in Philly for $650 a month working 14-hours a day this summer. That’s the goal.

I think there’s a time and place for raising money. I think there’s a time and a place to go for broke. So when I’m asked why I haven’t left school and raised money this is generally my reply:

I’m going to get into the big game eventually. But right now I’m working on perfecting my crossover dribble.

I want to get good at this stuff. And I know that I can do that without leaving school, and without raising money.

Recently Wesley came back and visited me at Penn. We were sitting in a pizza place we used to go to last year before any of this happened.

“You know dude, I think what we’re doing here is running a social experiment,” he said to me. “We both started from the same place, we both have similar goals. I left school and you stayed. It will be interesting to see how this turns out.”

Interesting indeed. And somehow, I have a feeling that it’s all going to work out in the end. For both of us.

You should check out Wesley and Ajay’s startup FamilyLeaf here. Or follow me on Twitter at @danshipper.


20 Jun 2012, 7:27pm | 28 comments


Never miss a new post