The Pragmatist and The Visionary

Their offices were gorgeous. Beautiful wood tables, art on the walls. Employees milling about. It didn’t feel like an office. It felt like a workshop. It didn’t feel like things were being produced, it felt like things were being crafted. It felt special. 

How does this happen?

I went to New York the other day and got dinner with a good friend of mine who also happens to be the CEO of an awesome company. They’re well funded, run by guys who are about my age but dropped out of school. I’ve been to their offices before, but somehow walking in this time it felt different. It felt like things were happening, like they were really working on something important. 

I’ve know their CEO for about a little over a year, before any of this had happened. Back then it was just three guys working in a dorm room. A year ago they were in the same position that I’m in now. Talking to him even then it was clear he had a big vision. He also had a plan for how to get it done.

But it got me thinking: how does that happen? We’ve been working on Airtime for about 7 months now and we’re grinding it on it every day. My goals for it are simple and pragmatic: build it up enough so that we can support ourselves with it full time. That means cold emailing customers, refining the product and trying to get the word out however we can. But the question still remains: how do I get from where I am to where they are?  Continue Reading

29 Mar 2012, 6:50pm | 6 comments

What Does It Mean To Love What You Do?

“Do something you love.”

I hear that all the time. I hear it from articles, from entrepreneurs, from books. But the problem with it is that for a long time I had no idea what it meant. Seriously? Do something I love?

First off what hell is love? Second how do I find what I love? Third how do I know if I love something? In short telling me to do “what I love” is basically telling me nothing. Thanks for nothing self help books.

So how do we start figuring out what we love? Let’s start off small. Just kidding, let’s attack one of the biggest questions of our lives: how do you define love?  Continue Reading

16 Mar 2012, 7:42pm | 10 comments

DomainPolish: From MVP To Exit In 6 Months

Hi my name is Dan Shipper. I’m a sophomore at UPenn and last month I sold my web app DomainPolish.

If you’re new around here DomainPolish is an MVP I built over the course of a few days in August. It’s an MTurk arbitrage that helps companies get on-demand feedback on their websites. Because I think it’s a successful example of the mythical minimum-viable product I’m going to use this post to break down what I did right and what I did horribly wrong during the process of building this product.

We’ll cover everything from pricing to exit negotiations replete with lots of interesting (and sometimes stomach-churning) statistics.

Warning: this post is really long. It’s also really detailed. If you’re not up for it you might want to follow the discussion for this article on Hacker News, check me out on Twitter, or maybe even read some James Altucher.

Still here? Let’s get started. Continue Reading

13 Mar 2012, 2:19pm | 24 comments

Why a Venture Capital Bubble Is Good for Bootstrapped Entrepreneurs

Today I was on the phone with the CEO of a company with almost $10 million in venture funding. This guy was smart, helpful and serious. We were on the phone because we’re running companies in the same space, using similar technologies. But we’re targeting different customers.

“Dan,” he said, “I like what you’re doing. I think it’s interesting. But it’s not a big enough market opportunity for us to pursue.”

It’s very risky to start a business. Some business opportunities are more risky than others. If you’re bootstrapping you can’t target an opportunity that won’t make any money for two years. Similarly you can’t target an opportunity that requires dealmaking with big companies. If it takes too long to turn a profit, as a bootstrapped company you’re dead in the water.

But venture money helps to alleviate some of that risk, and so the total number of addressable opportunities goes up.

That being said, venture money also attracts people with more diverse risk profiles to do startups. So the total number of entrepreneurs trying to start successful businesses goes up. That means that there’s more competition for bootstrappers to deal with. 

That can be discouraging! Look at how many new companies there are every day. How are you supposed to compete with them? They all have investors and funding and connections. 

But think about it this way: you can only get venture funding if you’re pursuing a Big Opportunity. If it’s not a Platform then it doesn’t Move The Needle for most VC’s. And that’s great!

If you raise a big VC round you need to hire. You have responsibility to your employees and to your investors. It’s go big or go home.

But I’m a bootstrapped entrepreneur. I don’t have employees. I don’t have investors. Fuck I don’t even have a goldfish. And that means that I’m free to pursue market opportunities that a funded company can’t. I don’t have to build a billion dollar company, I can build a 50 million dollar company and go home happy.

So how can I talk on the phone with another company in the same space and swap advice? Because they’re funded and I’m not.

And that’s why the rising tide truly does lift all boats.

Like this post? I’d love to hear from you on Twitter

Or check out my startup Airtime for Email.


1 Mar 2012, 9:49pm | 4 comments


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