Lesson 4: Get paid up front

VisionIT: Founded by David Segura with $100

David Segura was working at an IT consultancy in Detroit in 1996 when he got his big break. As a moonlighting gig, he agreed to set up a network, hardware, and software for a tortilla chip maker.

When it was time for him to collect his $7,000 fee, however, the owner refused to write a check to Segura's personal checking account. "You've been talking about starting a business," she said. "Go do it."

Segura didn't quit right away, but he did set up a business bank account. A few months later, he met with the CIO of the hot dog company Ball Park Franks, who offered him a job. He declined it, then asked what it would take for Ball Park to hire him as a consultant.

The company had a complicated software system, the CIO replied. Segura would need to learn about it before proposing any changes. After signing a confidentiality agreement, Segura spent nights and weekends at Ball Park studying up.

After three months, he drafted a 10-point plan. The CIO liked one of Segura's ideas (revamping the sales system) and hired him for $20,000 -- with $10,000 paid up front. "I drove around for a couple of hours with that check thinking, I got my shot!" says Segura. Last year, VisionIT, which now focuses on IT staffing, grossed $10 million.

Bootstrapping Tips

Dress the Part

Even

when he was skimping in the early days, David Segura drove a burgundy Ford Expedition, wore a nice suit to meetings, and ordered business cards with an expensive foil logo. "You don't have to be cheap to the point where people see that in you," he says.

Smart Prospecting

Segura found that it was effective to establish Web domains for potential clients for free (it cost him $100), before proposing that they hire him for more complex IT work. He also won clients by volunteering to create websites for nonprofits and then asking for referrals.

Will Work for Cubes

During one meeting, Segura noticed that the prospective client's offices were half empty. So he offered to build the organization's website in exchange for two cubicles and phone lines for two years, plus daily access to a conference room. That's how he got his first office.

Read on: Lesson No. 5