JEREMY SMITH

Bend the Curve
Chapter Two excerpt: Extreme Bootstrapping

Everyone is familiar with the image of the bootstrapper. Duct tape in one hand. Ramen noodles in the other. Jeremy Smith, co-founder & COO of the popular on-demand parking app, SpotHero, defines bootstrapping as: “Financially hacking your life to allow yourself a desired lifestyle while you grind day in and day out in search of Ramen Profitability.”

Few have mastered the art of the lifehack more than Smith.

In this chapter, we’ll talk about:

• Bootstrapping as a lifestyle
• Checking your ego at the door
• Inspiration happens when you least expect it
• Crowdsourcing (the new way and the old way)
• Never taking your eye off your bank account
• Abundant and cheap forms of startup capital
• The importance of a technical co-founder

“After leaving corporate,” recalls Smith, “I took five months off to enjoy life and find direction. At some point in that time I got into online sales and tried some pretty crazy things. One time I went to the bank and pulled out 75 $2 bills that I ended up selling on an eBay auction for $185! I even received positive feedback from the buyer, WTF? I pushed the envelope even further by going into baby bottles, steel canisters, textbooks, electronics, designer dresses and belts, and dog clothes. I didn’t care because it was a ton of fun and I started to learn the opportunities in running my own small business.”

His personal life started changing as well. “Mark got me into hosting couchsurfing guests. In any given week I would wake up to a crew of travelers sleeping in my main room.

These guests became my built-in group of friends to explore the city with while I lived on funemployment. Most of them were bootstrapping poor so I got used to doing all the fun free things to do around the city. I got into salsa dancing, biking the Lakefront Trail, hitting the beach, going to museums, cheap stand up shows, and a whole bunch more. I got pretty into all the free hacks this city had to offer. I moved into free drinks and food all over the city by checking out websites like brokehipster.com. You would think this would get old, but those were some of the best days of my life. I could get everywhere, explore, and eat at most places for free.

“The free movement occurring in my life was an important factor in shaping my social consciousness and my beginning in giving back to everyone else. I hosted, cooked, and acted as a tour guide for all of my couch surfers. When I moved out of that apartment, I posted all my old stuff, food, and clothes for free pickup on Craigslist. In general I would offer a helping hand in any situation I could. I love working out and so I would help all my buddies move out of their apartments too. They loved the help and always had things leftover that I would then take to my place. That helped me outfit an entire apartment with furniture and electronics for two years. Now that I was a world-class vagabond, I was ready to enter the world as a bootstrapping entrepreneur.”