Why He Said NO to Uber CTO to Revolutionize Math Education

What we talked about.

In this episode of The Sunny Ray Show, Jason Roberts, founder of Math Academy, joins host Sunny Ray to discuss his winding path from math major to entrepreneur. Roberts describes growing up in Atlanta, discovering programming as a teenager, and being mentored by a physicist teacher who pushed him toward calculus and advanced coursework alongside classmates like future Google engineer Jeff Dean. He recounts founding his first company in high frequency trading during the mid nineties and co-founding roughly six ventures since. Roberts shares the story behind his popular concept of luck surface area, developed during a conversation with DuckDuckGo founder Gabriel Weinberg. He also details turning down Travis Kalanick's offer to become Uber's CTO in 2010, choosing instead to consult and help build Uber's original real time dispatch system from his home office using Node.js. The conversation closes with the origin of Math Academy, sparked when Roberts and a friend volunteered to coach a fourth grade math club with only worksheets and candy, discovering the kids' surprising gaps and enthusiasm for learning.

Math major turned trader who declined Uber's CTO role, then built Math Academy, an adaptive platform revolutionizing math learning.

The questions, and the answers.

Can you give us a sentence or two on the math academy you've built?

Math Academy is a fully adaptive online math learning platform that creates a customized course for each student, whether that's a homeschool parent, a parent of gifted kids needing more than school offers, or a struggling student trying to catch up. Over half our customers are actually adults skilling up in advanced math for machine learning or university level courses.

Where did your story begin, before you got into entrepreneurship and tech?

I was a math major at the University of Chicago, but I started out in high frequency trading and derivatives, building software for the trading industry in the mid nineties. Within a few months I knew I had to start my own company. Even as a kid I had these big get rich quick schemes, always looking at what was happening and thinking we could do it better.

What was it about math that captivated you as a young person?

Honestly, math was just homework to me until high school. I was into programming and electronics, and a physicist teacher named Steve took an interest in me. He told me to teach myself calculus so I could understand circuit design, even though I was only in ninth grade geometry. He pushed several of us, including Jeff Dean, and that direction shaped everything I did afterward.

You've co-founded around six companies since college, spanning trading, web, and mobile. What was the through line connecting all these ventures?

The through line was always working on whatever I thought was really cool. Making money mattered because it gave me freedom to keep doing that, not for a big house. Whether it was high frequency trading algorithms or building software, the real drive was tackling hard, interesting problems alongside smart people, not chasing a particular industry.

You coined the term luck surface area. Can you talk about that?

I coined it while talking with Gabriel Weinberg about how he generated opportunities. The idea is you increase your luck surface area by doing something you genuinely care about and then talking about it publicly. If you only work quietly, you're an unknown mad scientist. If you only talk without doing real work, people see through it. Doing both makes serendipity almost inevitable.

You turned down the CTO title at Uber but ended up building much of its original real time dispatch technology. What was that like?

Travis called me in December 2010 wanting me to move to San Francisco as CTO, working eighty hour weeks. With three kids and a shaky mortgage, I said no but offered to consult. Curtis Chambers and I combined high frequency trading style, in memory, real time architecture with Bit Torrent concepts and built the new dispatch system in Node.js from my home office, replacing a slow PHP system.

The origin story of Math Academy started with you and Sandy volunteering to coach a fourth grade math field with worksheets and Jolly Ranchers. When did you realize something extraordinary was happening?

We got roped in after a parent teacher conference and ended up coaching eighteen fourth graders during their lunch period. Sandy suggested testing them first to find gaps, and I was stunned some didn't know what a negative number was. I started teaching what I thought was cool, running it like soccer practice, keeping every kid engaged, and they lit up asking questions like what pi actually is.