The Measure of Real Wealth

Respecting the Grind

When Brown was 12, every now and then his mother would buy them an avocado—an unspeakable luxury. He would eat it with a sprinkle of salt. 

“One day,” his younger self thought, “I’m going to be rich enough to eat as many avocados as I want.”

Brown was already working as a teen—pouring concrete and selling menswear at factory outlets—to help his mother support their family. At Boston University, he worked multiple jobs to pay tuition. “I didn’t get to just be in school,” says Brown. “I was working 100 hours a week while attending college full time.” But when his finances weren’t adding up, he decided to spend his summer break going door-to-door persuading people in his hometown to hire him to paint their houses.  

He made so much money that first summer that he paid for two and a half years of school—and was able to scale his single-person endeavor into a full-fledged company. By the time he graduated, the business had 400 employees. He was able to graduate without debt—and with enough money to buy a condo. He wasn’t rich, but to him, it was unbelievable wealth.

“From that point on,” he says, “I knew business was the future for me.”

Brown cofounded subscription-based tech support company Bask.com in 2004—just two years after undergrad—and sold it in 2007, before entering business school. 

“I had all the scrappiness and intuition for how to build a business, as well as the actual mechanics, but I knew I was missing some understanding of the form,” he says. “I wanted to refine my knowledge and sophistication around how you build and finance a business.”

High Leverage

Standing in front of one of Tally’s first big potential investors, Brown flashed back to a course he had with James E. Schrager, clinical professor of entrepreneurship and strategic management.

Schrager told the class about a manufacturing company, the Marmon Group, he studied as a PhD student, and how he took on the work of turning around a small factory. Schrager noticed there that brief, unplanned encounters—whether with factory employees or the CEO of the conglomerate—could be pivotal to how people saw him moving forward. The moments usually weren’t the planned presentations he had worked so hard on. The tough questions asked afterward, or even the casual encounters and spontaneous conversations on the factory floor—those had outsized impact on whether people were ready to sign on to his plan or not.

“Careers and deals are often made in brief moments of intense leverage,” Schrager summarized to his students, including Brown. “Will you be ready when your moment comes? Or will you watch it pass by?”

This, Brown realized, was one of those moments. He had one hour to get his investor to understand a concept that had never existed before—and to get her to write a $2 million check for a 10-slide deck. 

“My entire life—who I was, how I grew up, going to Booth, all of it funneled into this one hour of being able to communicate both the emotion behind Tally and the raw math and finance concepts behind it,” Brown says. “I think about that Schrager quote often. When people think about their career, those moments are the ones that matter, and you have to be ready for them.”

Tally, in some ways, was a tough sell. But venture capital firms including Kleiner Perkins and Andreessen Horowitz could see the potential. “They saw that we weren’t trying to build a tool,” says Brown, that “we were trying to build an A.I. that would be able to, by itself, save people money. They were forward leaning enough to see that this new experience that hadn’t existed before—a new interaction model between humans and finance—was something worth putting money behind.”

Living the Life

Today, Jason Brown is thriving both professionally and personally. Like his 67-year-old mother, who has run her business for 35 years and is a raw vegan who enjoys exercise, Brown carries focus and discipline into everything he does.

Brown makes sure to block half a day once a week—preferably in the morning, when he does his best thinking—for unstructured time to walk and then sit around and get bored. “Giving the brain some space allows it to think about things that aren’t tasks or rudimentary factors,” he says, which often leads to new ideas and breakthroughs.