You decided to bootstrap and not pursue funding with Vagrant, have you encountered any roadblocks or benefits with that approach?

There are benefits. I don't have the pressure of [venture capitalist]'s. I've met with fifteen. I call tell there are some that are really awesome and get your vision, and there are a lot that are saying if you don't make ten million dollars the first year you're useless. I don't want to go through life as a founder with that much pressure on my back. There are cons too in that I don't have advice from these huge people that see companies day and day out. Luckily, I have friends that introduced me to really cool people and the friendlier VC's are super happy to give advice.

How do you get that friend circle or those connections to give you advice?

Just work at a startup company, work in the ecosystem where there are VC's surrounding you. I'd say, avoid places like Twitter; I know they're a startup, you don't have VC's flocking around you very often.

When did you first realize this could go from being a fun little project into a business?

I think I was at a conference and within a thirty minute period after my talk five people asked me about support plans. You know, that's not a very glamorous thing but it made me realize people wanted to pay me money for this. I was in denial a long time about not wanting it to become a business. I didn't know I could actually do it, it was an open source project and it might not work out. I'm confident now.

How was it like leaving a plush 9-to-5 desk job to pursue this full time?

The worst thing is watching your bank account only go down. [Laughs] This is going to be silly silicon valley — I had a week where I didn't know how to eat lunch because I'd [normally] have lunch catered. It'd be like 3pm, I'd be starving and I wouldn't know why. It's because no-one would be feeding me. Luckily I learned how to feed myself.

Now that you don't have an office, where do you normally work?

I started out working out of cafes, but that was pretty quickly depressing. I was used to working out of cafes for fun side projects that I just did on the weekend. I didn't like going into a cafe and being like I have to get real work done that needs to support my life. I luckily have friends at old companies and they're lending me office space.

If you don't have the luxury of friends with office space, where do you recommend people work?

Cafes. [Laughs] Fighting through the pain. Get a desk at a co-working space, it's really inexpensive. There's less trendy ones that's just a desk and it's about $100 a month.

You're taking an open source project to enterprise. How was that transition? Have you had any feedback from the community?

The core product is open source. Future products will be both open and closed source. The early people I've talked to about it have be okay with it. The biggest fear with turning open source into a business is that the open source project becomes cripple-ware, the idea being you purposefully cripple it so people pay you for the fully functional version. That's not my intentional at all.

What advice would you have for people that have these little side projects that might want to turn into businesses or pursue full time?

If you could make a side project, do it. One advice I have is, charge early. I had an old side project that I can't name, I didn't start charging until three years in. The day I flipped that switch going from free to paid, that business quarter I made like $30,000. So the thought was, what if I just charged for the first three years?

What was that transition like, from free to paid?

There was one angry email I got from out of thousands of people. I made sure that when I changed it from free to paid there was a big notice that stated, 'why we are doing this.' It was a big cost to run the project. I was paying out of my own pocket, and it was too much. I could add more features if I had money to invest into it. And, no-one was upset. Totally unexpected, I started [that project] six years ago and four years later I could have never imagined that I sold it and was able to fund HashiCorp [the parent company of Vagrant] with it. Things like that can happen which is really crazy.

So you actually used those funds to bootstrap Vagrant?