The Neurologist Who Wrote Code Between Rounds
At Stanford University Medical Center, neurology residents don't have a lot of free time. There are patients, charts, procedures, and the chronic fog of post-call exhaustion. Scott Zimmerman used the gaps to code. Not as a hobby. Not as a distraction. As a calculated bet that he was building two parallel careers simultaneously - and that one would eventually eclipse the other.
He chose Stanford for residency specifically because it sits in the middle of Silicon Valley. That's not how most neurologists pick their training program. Zimmerman had an MD from Brown Medical School and a BA in Economics from Columbia, but his real education was happening between 11pm and 2am, writing Python for a genomics lab, analyzing structural MRI data for a research group, and building a Facebook application that mined congressional voting records from thomas.gov to show constituents exactly how their representatives voted. He reportedly never watched television during this period. Every minute not spent on medicine went into code.
"Medical training shaped my software approach: rigorous investigation and accurate problem diagnosis prevent building solutions to non-existent problems."
That diagnostic instinct is the thread running through everything Zimmerman built. A neurologist isn't guessing at symptoms - they're building a systematic picture of what's actually broken. When Zimmerman looked at the travel industry in 2011, he saw the same kind of diagnostic problem. Airlines had real-time seat inventory. Hotels had sophisticated property management systems. Car rentals had their own tech infrastructure. But the businesses running whale-watching tours, escape rooms, white-water rafting trips, and cooking classes? They were managing bookings by phone, running schedules on whiteboards, and collecting payments with physical card imprinters.
This wasn't a small corner of the economy. The global tours and activities market was then estimated at $135 billion - larger than car rentals. It was simply invisible to the venture-backed technology companies that had already modernized every other segment of travel. Zimmerman co-founded Xola with Anush Ramani in fall 2011 to fix that specific gap.
He describes Xola's ambition plainly: "We're like the Apple of booking and e-commerce solutions for these businesses - easy, intuitive, and delightful to use." The comparison isn't about aesthetics. It's about the approach - making powerful enterprise-level software accessible to operators who don't have IT departments, who are running half-day hiking tours and trying to figure out abandoned cart recovery at the same time.
What Xola built is a full operating platform: online booking, payment processing, staff and guide management, customer relationship tools, marketing automation, digital waivers, dynamic pricing, abandoned cart recovery, review generation, channel distribution to OTAs like Viator, API integrations, and a point-of-sale system. The company has offices in San Francisco, Houston, Bangalore, and Belgrade - a global build-out for a product serving operators from North America to Western Europe.
The investor lineup that backed Xola's early stages is one of those details that suggests Zimmerman had a nose for unusual connections. Michael Burry - the hedge fund manager who famously shorted the 2008 housing market and was depicted in "The Big Short" - invested in Xola's angel round. So did Scott and Brett Crosby, who co-created the analytics platform that became Google Analytics after Google acquired their company Urchin Software in 2005. That combination - a contrarian short-seller and the architects of the world's most widely used web analytics tool - is not accidental. Zimmerman was building a data-driven booking company, and the people who understood data-driven markets backed it early.
The $1.8 million angel round in 2014 gave way to a $5 million Series A in April 2016, led by Rakuten Travel - the travel arm of Japanese e-commerce giant Rakuten. That partnership wasn't just about capital. Rakuten Travel gave Xola a strategic gateway into the Japanese market and a global distribution relationship with one of Asia's most recognizable consumer brands. By the time of the Series A, Xola had averaged 500% growth over the prior two years. The pitch wrote itself.