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BOOTSTRAPPING

10 Crazy Bootstrapping Stories

What these entrepreneurs lacked in funds, they made up for in gumption. Read on for inspiring tales of daring, dedication, and desperation.
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There's no question that turning a great idea into a profitable business is exciting. But it's tough, as well, especially if you're bootstrapping. So I wondered--what are some of the craziest things people will do to self-fund their businesses?

Ah, the stories entrepreneurs tell about keeping their companies alive--it's nail-biting stuff! Here are 10 tales of daring, dedication, and in some cases, desperation, to inspire you.

Live in an RV for Years

After selling about $100,000 worth of plastic comb-bound books to interior designers via direct mail, Kimberly Causey wanted to get a real book onto the shelves of bookstores but couldn't afford to professionally print them. Her solution? She bought $200 worth of professionally printed covers for her home furnishings buying guide, printed the interior pages on her home printer, folded and scored the covers and glued them all together in her kitchen using a hot glue gun and a butter knife. Within two years proceeds from her book were supporting her full time, she got an 800 number, and a credit card processing account, and she was regularly driving through the night to appear on morning TV shows all over the southeast.

With a small book run professionally printed she started approaching bookstores including Barnes & Noble, which let her give talks and sell her books in its stores. Encouraged by her success pitching bookstores, Causey gave up her apartment, bought an RV to live in, and traveled around the country promoting her book for three and half years, eventually convincing Barnes & Noble to pick up her book in its stores nationwide. Years of self-promotion paid off big when she landed an appearance on The Today Show, which catapulted her sales to seventh place on Amazon the day of its airing. Since then, Causey's advice has appeared in a slew of national media outlets and she just published "The Furniture Factory Outlet Guide, 2014 Edition."

Dogsit and Rent out Your Car

Marissa Hu and Andy Fortson thought their idea for Co-Ed Supply was a good one: get parents to lay down $20 a month to send a college student a care package once a month. But testing it out last year demanded their attention and they didn't have time for an extra job to pay the bills. Their solution? Months of dog sitting through DogVacay and renting out Fortson's car via Relay Rides.

"Based on the progress we made during that period, we were able to get into startup accelerator The Brandery, move to Cincinnati, and raise some investment money," Fortson says. "The sharing economy really gave us the lifeline we needed--some income to pay the bills while validating and building the foundation of our business."

Bike Thousands of Miles

The route to founding Hoboken Coffee Roasters in Guthrie, Oklahoma, was a literally a long one for founder Trey Woods and his wife, Mallory. Shortly after marrying in early 2008 the couple sold a car and used the money to move to Oregon to immerse themselves in the coffee culture of the Pacific Northwest. Once fully educated they used the proceeds from selling their other car to buy and ship an espresso machine to Oklahoma. Then they biked 2,200 miles home.

"It was an adventure to say the least," Trey recalls, as he tells the story on his company's website.

Mooch, Skimp, and Avoid Paying for Things

Galen Ward, CEO of the house-finding platform Estately, says the story he and his co-founder Douglas Cole share is all about being incredibly cheap. Ward quit his job with enough money to live on for a year, talked his co-founder into dropping out of grad school and each of them took $2,000 out of savings to buy "the cheapest, crappiest server available at $500, paid to incorporate and put a little in the bank for random expenses," Ward says.

Beyond those investments, however, the duo grew Estately by grabbing as much free stuff as possible, including mooching server hosting from another startup, using online tools such as Google Apps and Google Voice, taking free lunches and dinners whenever possible and working out of Cole's basement apartment where Ward took over Cole's wife's desk while she was off getting her PhD. They found their first broker on Craigslist and told him they couldn't pay him until they were making money. And their first developer worked for free to earn internship credit at a local art school.

After launching in 2007 Estately has raised more than $1 million and is running profitably with a team of 17. "But the early days left us with a very frugal culture," Galen says.

Beg

The note-taking service Fetchnotes may have the most colorful story in this lineup. Back in 2012 the startup attracted a decent amount of publicity and an odd uptick in usage after accidentally sending out a test email message calling users "bitches."

"Needless to say, we were using far worse language as we began running around our office screaming and panicking like chickens with our heads cut off (this sums up our initial reaction)," co-founder and CEO Alex Schiff wrote in a blog post.

A few months later the startup was in the news again, this time for asking for donations to the service through the Gumroad digital product marketplace. In return for cash, Fetchnotes co-founders Schiff and Chase Lee promised to send donators a video of them singing karaoke.

"When all was said and done we raised a few hundred dollars. It's not much in the grand scheme of things, but that summer we were raising money and had to pay for travel so it made an impact," Schiff says. "A few months later, we ended up getting into Techstars Boston and $425,000 right after that. Not only did the karaoke thing generate some PR for us, but it showed the Techstars folks--and other investors--we were scrappy and would do anything to make our venture succeed.

Fetchnotes is now a team of six based in Cambridge, Massachusetts, and boasts more than 100,000 users.

Become a Key Influencer

Twitter and Klout are good platforms for scoring free stuff says Nickolaus Trevino, social marketing strategist for the iOS opinion app Votopin. "We have gotten everything from free tickets to this year's Social Media Week NYC, a free Driscoll berry drop-off package, to even some free cocktails delivered to us," he says about Twitter. "Klout.com has been a great tool and has perks for its key influencers. In our case, our team has a high Klout score so every so often we get free promotions to go to tech happy hours and conferences. It's awesome."

Barter Brownies

Before founding My Luck Club, a platform that connects people who need things done with others who want to help, Phyllis Pierce owned a Los Angeles pie company. "I was able to bake amazing cookies, bars, cupcakes, etc. So when I started My Luck Club on a ramen-noodle budget, I would barter my baked goods and my baking services to get help and services that normally would cost me hundreds of dollars," she says.

Bet on Your Domain Expertise

Normally, gambling wouldn't exactly be the most sure way to fund a startup, but if you can win the World Series of Poker, it's probably a different story. That's David Daneshgar's story. After capturing the title in 2008 he entered the Booth School of Business at the University of Chicago and met Gregg Weisstein and Farbod Shoraka who were working in Los Angeles. After graduating, David joined Weisstein and Shoraka in L.A. where they dreamed up the online floral marketplace BloomNation, although they needed $25,000 to launch the site.

Their solution? A local poker tournament in which 70 players laid down $1,000 to enter to win a first prize of $27,000.

"Less than 24 hours later it was down to my opponent and me. We went all in, with my co-founders nervously waiting with the company on the line," Daneshgar recalls. "I walked over and said the words that would forever change the course of our company, 'Don't worry, it's flower time.' We won the prize money, developed the site and were able to recently secure $1.7 million in funding from some of the biggest investors in the world. The reality is that without winning that poker tournament and taking on the risk of putting it all on the line, we probably wouldn't be here now."

Hire Someone to Drive You Around

Anybody who has ever bootstrapped a company knows how much grueling work can go into staying alive long enough to become profitable. When getting ready to found his first company Stan Woodland, now CEO of strategic media buying and planning company CMI/Compas, worked a full-time job during the day and cleaned offices at night. Once he quit both jobs to become an entrepreneur he did all the usual things such as borrow money from family and friends and max out his credit card. But looking back, he says the smartest thing he actually did was hire a driver to take him to meetings so he could work in the car.

"I was living in Southern New Jersey and pitching clients throughout New York, New Jersey, and Philadelphia, which meant some days I'd commute six hours round-trip just for one client. At the time I was billing $120 per hour, so hiring a driver for $40 per hour made perfect economic sense," Woodland recalls. "But it was more than the money. Ensuring that I was able to use that time to deliver on promises helped me build trust with clients, and my entire business is built on trust and relationships."

Sell All Your Stuff

Desperate people often turn to Craigslist, and it's no different for entrepreneurs.

"We have pretty much sold everything we own through [Craigslist] to fund the company. From household items, office equipment to surfboards and kids clothes, everything is fair game when it comes to paying the bills and keeping the lights on," says Rob Farrow, co-founder and CEO of the wedding planning website Aisle Planner. "Our household is a little sparse, our offices look about the same, but the lights are always on, [the] site is always up and customers are happy."

Matthew Griffin, president and CEO of Baker's Edge, used a similar strategy when starting out in his basement in 2006, although eBay was his medium of choice.

"Old ceramic bank? 15 bucks. Motley Crue T-shirt? 50 bucks! Old Nintendo games? 100 bucks. Goodbye leather coat and vintage Ball State Track and Field suit, hello a few more months of inventory," he says. "I was converting everything in arms reach into cash fuel. Then to top it off I would ask my buyers to check out my website and share with their friends. [It was] totally shameless and necessary."

Want to read more about bootstrapping? Check out "10 Extreme Bootstrapping Ideas."

Last updated: Feb 26, 2014

CHRISTINA DESMARAIS

Christina DesMarais is an Inc.com contributor who writes about the tech start-up community, covering innovative ideas, news, and trends. On Google+, add her to one of your circles. Have a tip? Email her at christinadesmarais (at) live (dot) com.




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