Not many teenagers have the confidence to drop out of school without telling their parents. Even fewer have the confidence to drop out to start their own business.
But Bill Smith wasn’t your average kid.
Over the last 15 years, Smith started, built, and sold three companies. He sold his previous business, grocery delivery service Shipt, to Target in 2018 for half a billion dollars. But Smith didn’t rest on his success. The same year he exited Shipt, he started Landing, a flexible and furnished rental apartment service.
So what’s next for this wunderkind turned startup mogul?
The answer goes back to a fateful meeting in his high school counselor’s office.
Extracurricular Concerns
Smith asked for a briefcase on his fifth birthday, and it’s been all business since.
“I never really loved school,” Smith says. “I always wanted to be in business.”
When he was in high school, Smith started selling Nextel cellphones, generating up to $6,000 per month in revenue.
“Without telling my parents, I leased an office space at 16 years old for this little business I had,” Smith says.
“Without telling my parents, I leased an office space at 16 years old for this little business I had.”
Eventually, he stopped showing up to school, instead focusing on growing his business. The school took notice and arranged a meeting with Smith, his parents, and the guidance counselor.
When Smith’s extracurriculars came to the surface, the guidance counselor offered some bizarre wisdom to his concerned parents.
“They said, ‘We’re not worried about Bill. He’s gonna be just fine.’ Which was probably not what you’d normally hear from a school counselor,’” Smith says.
It took time for his father to come around, but eventually, he became Smith’s first investor.
“He kind of flipped,” Smith says. “I ended up partnering with my dad on my first company, and he’s invested in everything I’ve done since.”
After expanding the cellphone company to multiple locations, he sold for a small exit and started building his next business.
Asking for Insights
In 2009, Smith went to a prepaid technology conference and met a software developer. He peppered him with questions about all things prepay. The experience inspired him to start Insight Card Services, a reloadable prepaid credit card company.
“I’m very curious about business, and the way I learn is I find people and ask a million questions,” Smith says. “I’ve been that way as a kid and still am today.”
Smith started building his team through his learnings, and Insight took off.
“There’s a lot of trial and error in building a business,” Smith says. At 20 years old, Smith wasn’t slinging cellphones after school. Instead, he was leading a full-fledged business with teams of employees.
He admits he was just a kid then and didn’t have an MBA like other executives and founders. Instead, he had to learn management, executive decision-making, and financial planning while on the job. Smith says that although he made plenty of mistakes, he quickly realized that the most critical part of business is people.
“I figured out that the key to success was getting the right people on board, treating them really well, and getting them bought into the vision.”
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Source: ( foundr.com / Financementality.com )
