Ten lessons in bootstrapping from the founders of Urbanspoon

By Adam Doppelt 

 Ah, the romance of bootstrapping your own startup. Start with an innovative product idea. Incubate in your basement with a few friends on borrowed equipment. Land some deals to bring in a trickle of money, then use the cash to grow.

Eventually you need an office, but only to make your startup feel more serious. A year later, you finally have enough money coming in to pay fast food level salaries. Another year, and big companies start calling and try to buy you out for untold millions. It's a beautiful dream.

Bootstrapping appeals on many levels. There won't be any pesky investors offering up advice or veiled threats. Because the founders retain all the equity, it's possible for a smaller company to have a relatively lucrative exit. Entrepreneurs don't have to suffer through expense reports or PTO requests.

Sadly, bootstrapping isn't for the faint of heart.

A bootstrapped startup is a pressure cooker. Say goodbye to vacations, dentists, and most of your savings. Instead of investors, spouses will offer up advice and veiled threats.

The founders collectively scrutinize and second guess every major decision, and agonize over each week of effort. Everybody on the team wonders - am I working hard enough, or perhaps too hard? Sometimes the stress bubbles up as back pain, insomnia or a heart murmur (yes, really).

Ready to jump in? After the wild ride we've had here at Urbanspoon, I'd like to offer up ten principles that other bootstrappers may find useful:

1. Start with savings. The math here is pretty simple. Assume you and your cofounders will have to go a minimum of two years without meaningful salary. Can you do it? Just as importantly, can they? Prepare to tighten your belt.

2. Found with good friends. The founding team will be slogging it out together in the trenches for years, and then heading out after work for beers. Remember that you can still be friends long after your company is only accessible in the Internet Archive.

3. Spend nothing. Nobody gets a salary. Don't attend conferences, don't travel, and don't throw office parties. That stuff is for companies with investors or cash flow. Use Google Apps and Ubuntu. Buy everything at Costco and Newegg. Our only marketing expense was t-shirts, and we hoarded them like gold.

4. Ship quickly, and often. If your team is strong and your idea is manageable, ship a crappy version of your product in two months. Then keep shipping every few weeks. If something catches on, double down. Companies that don't ship for years tend to fail.

5. Buy a big whiteboard. Don't use calendaring, bug tracking or project management software. Put it all on the whiteboard. At the start of each week, erase and start over. Worried about losing something? If you erase it and forget, it wasn't that important in the first place.

6. No time for pri-twos. In project parlance, a "pri-one" is a work item that is essential to the success of the project. Bootstrapped companies don't have any pri-twos. Once you determine that a task is a pri-two, forget about it forever. Sadly, this is why Urbanspoon still doesn't have "hours of operation" for our restaurants.

7. Outsource. Hire contractors carefully and treat them well. Find a great lawyer who doesn't work at a firm. Deploy your product on ServerBeach or EC2. Use AdSense, but don't plan on getting rich with it. For real leverage, discover new ways to use Mechanical Turk.

8. Follow the money. At a certain point in your company's timeline, even the pri-ones may need to get tossed in favor of following the money. No amount of features can compensate for a lack of cash.

9. Hitch a ride. Bootstrapped companies can hitch a ride on larger companies with deep pockets. For example, we hitched rides with Apple (iPhone), Facebook (Connect) and Google (SEO).

10. Live your dream. Focus obsessively on what you're good at, and ignore or outsource the rest. Don't be afraid to enter a crowded market if you think you can compete. Dream of being Markus Frind of PlentyOfFish, with 1 billion page views and no employees. If he can do it, why can't you?