Burning the Ships

Written by on December 3, 2013

When you start a business, you wake up every morning with confidence or doubts as to whether it’s going to work. Which of those you feel just depends on the day. 

If you decide to seek venture capital funding to start your company, you’ll have a team of people behind you, including a board of directors and a relatively deep founding team. You’ll have a built-in support network when times get tough, and will be paid a regular salary along the way. Even if you have your doubts now and then, your team and investors will help keep you going.

When you bootstrap, however, you might be entirely on your own–and you might end up not making any money at all for some time. If you want to quit the venture and go back to a regular job, that’s your choice, and you probably won’t be letting anyone else down—just yourself.

So if you give up on being a bootstrapped entrepreneur, what are your options? They will depend on whether or not you have “burned the ships.” Hailing back to Cortes’ conquest of the Aztec empire, this phrase refers to when soldiers of a vanquishing army would sail to a foreign land, and burn the ships behind them so they couldn’t retreat from battle. Giving up was not an option: they would be victorious in their endeavors, or die trying. 

When I bootstrapped my business, I felt like I had burned the ships. I quit my job at a Bay Area software company not only because I didn’t love the job anymore, but because I no longer wanted to work for someone else. And while I didn’t want to be a middle manager at a tech company, I also wasn’t in a position to get a job as a senior executive, or join a venture capital or private equity firm. And to top it off, I had moved to Montana—where I had no support network—to begin my entrepreneurial journey. 

Maybe I had more opportunities at the time than I perceived, but I felt like this was it: I was either going to be victorious, or I’d have to retreat to California, get another job like my old one and be out a lot of my own money, to boot.

I left my previous job in July 2004, and began a long, winding path to what would become Software Advice. In June 2006, I went live with our first website—but it wasn’t until the fourth quarter of 2007 that my business partner and I saw the light at the end of the tunnel. For about three years, there was a lot of uncertainty, and on more than one instance, I felt like giving up. But retreat was not an option; I had to make it work. Ultimately, I’ve been successful, but who knows… if I’d had a way out, I just might have taken it.

In fact, I first tried to quit my job in 2002, intending to do some traveling before striking out on my own. Instead, my boss offered me three months of travel time and a warm desk when I got back. I accepted, and in the relatively unproductive two years that followed at that job, I wished I hadn’t. 

There are a lot of scenarios in which bootstrapped business owners have “ships” they can retreat to, making their entrepreneurial endeavors less of a risk. Maybe they’re building the company on nights and weekends, and still have their day job to pay the bills—or they have the financial support of a working spouse. Maybe they have other, comparable business opportunities: for example, they’re qualified for a job as a CEO. Maybe they are skilled in an industry with a great deal of job availability, or maybe the job they left has a door that’s always open for them. Whatever the case, when one of these ships is available, it’s less likely the entrepreneur will fight to the death for the business. 

Of course, not everyone is cut out to be an entrepreneur–and even those who are qualified need a little luck and a lot of things to go their way in order to be successful. I’m not necessarily advising that you burn your ships; in fact, it could prove detrimental to you, your family and your mental health. Just be aware, as a bootstrapper: if your ships aren’t burned, it’ll be a lot easier to retreat. 


Photo by brookpeterson.

Posted Under: Execution
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Don started Software Advice in 2005 after a ten-year career in the software industry. Previously he held positions as an ERP analyst at an investment firm and as a corporate development executive at a pioneering CRM software company. Don lives in Austin, Texas with his wife Lauren, daughter Hudson, son Stone and Bernese mountain dog Stinson.

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