Freckle: A Study in Bootstrapping
June 11th, 2009The Entrepreneurial Bible always is impressed by groups of people that bootstrap their dream on the side while they pay the bills with other employment. This kind of activity shows real grit and determination. This is what we saw recently during an interview with Amy Hoy and her small company of entrepreneurs who are building online tools for small teams & solo businesses. Their first product is Freckle .
To quote Amy:
We’re bootstrapping because we’re all consultants or former consultants (including the author of Scriptaculous), and we’d really like our new business to be all our own. We have friends who have accepted VC and then had difficulties pursuing their vision, due to pressure from the investors — who of course, want to protect their investment. Because our #1 goal is a sustainable business, we feel we can make choices that others can’t, when they are answerable to an investor. (Even if it’s their Uncle John.)
Here is our interview:
Q: When did you decide that you were not going to take VC funding?
A: From the outset, when we were brainstorming what we’d do as a company. (Freckle is just the first app in a series of apps we want to develop. Clearly taking VC just for a time tracking app would be overkill.)
Q: How did you have to adjust your business plan by going the bootstrapping approach?
A: We’re two small companies (2 and 3 people) working together, and we both pay our bills with consulting. That means that we have to work extra hard to make time to focus on our product, and handle support questions, write documentation, blog, promote, etc. Our lead time on designing and developing features, tuning the marketing materials, etc., is all much longer because we can’t devote all our time to it.
But on the other hand, it gives us perspective because we use Freckle to track our own time for our clients — our other business relies on it. And it means that we don’t have to scramble for every potential customer to pay our bills, which means it’s easier for us to stick to our vision and just say “No” to some people who say “I really like your product but can we change everything about it?”
Q: How often have you had to turn down VC overtures?
A: I don’t think we’ve had to turn down any *serious* offers yet. A couple people have mentioned it in passing. But again, from the outside, we look like “just another time tracker” — once our more ambitious plans come to light, I think we’ll have to work on a polite deflection!
Q: What is the biggest sacrifice you have had to make having gone the bootstrapping route?
A: Time and focus. We’re pulled in two directions, with our “real” businesses and our budding Software-as-a-Service products. It’s a challenge.
Q: Do you ever see yourself taking a round of funding? If so, what would be the driver to do that?
A: Yes, with some caveats. We have a very clear vision of where we want the business to go, and how our products should look and act. We know what we don’t want to ever build and the customers we do not want to have.
If we were to find an investor who agreed with our direction and would trust us to do our best work, we’d absolutely be interested in taking a small amount of funding. We’d especially be interested if that funding brought us an amazing advisor, like 37Signals with Jeff Bezos.
Q: What is the biggest thing you are missing as you bootstrap without the assistance of a VC?
A: Freedom to focus on our products 8 hours a day, 5 days a week.
Q: So do you see your goal to be another 37signals?
A: No, we want to be more of ourselves
We think there’s a lot of good things we can learn from studying the strategies of companies like 37Signals, the stuff that startup bloggers often don’t write about, but we didn’t set out to emulate anyone.
Our similarities are: SaaS, bootstrapped by consultants, focus on design. The differences are in everything else


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