Jason Gardner knows a thing or two about starting and scaling a business. He’s already on his third venture, and despite it already being worth billions he could just be getting started.
During our interview on the DealMakers Podcast, Gardner talked about getting 10x results for investors, building a $4.3B company, and what he’s learned about leadership and financing through raising over half a billion dollars in capital.
Born To Hustle
Jason Gardner was born in Washington DC and spent his younger years growing up in NJ. He loved surfing, even in the wintertime.
He also had a passion for technology. He remembers taking his first coding class at nine years old. Before gaming was as common as it is now, Jason says he had a Commodore 64, an Atari and Nintendo.
He grew up very interested in visiting California, and when his dad moved out to San Francisco to open an office, Jason got the chance to visit Silicon Valley. His father drove him by HP and Apple and Intel. After college, he would pack up and move out there himself.
That didn’t hold Gardner back from flexing his entrepreneurial skills in the meantime. At five years old he woke up to the fact that he could hustle for money. He wasn’t afraid of putting in the work either. He would shovel driveways, pull weeds, and whatever else he could do.
He had his first real job by the time he was 14 years old. Working at a video store offering Betamax and VHS tapes. He worked his way through restaurants as a busboy, waiter, and cook. Then at a local surf shop.
In high school, he started a tie-dye t-shirt business. He would sell them on local transit to people traveling to local concerts.
After college, he would go on to start his career as an account executive and business development manager.
The First Rodeo
Jason Gardner’s first company was Vertical Think. Before Upwork, this was a business that connected developers with projects.
He describes it as more of a lifestyle business. It was fun, though he admits he was more enamored with being a ‘CEO’ than building a real business out of it. It ended up being a great learning experience, but not a lasting one.
10x In Three Years
Jason took all those lessons and rolled them into his next venture.
He had planned to move to Australia to start a juice bar chain. Though over breakfast with another entrepreneur, they struck on the idea of enabling renters to pay their rent with credit cards and other online payment methods. Together, five co-founders created PropertyBridge.
They raised $2M, and within just three years they sold the company to MoneyGram International for $28M.
On the journey, he learned even more about scaling a company, hiring people, and the impact decisions. He learned about the balance between wanting to do many things but needing to stay focused.
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