My father and his parents snuck out of North Korea during the civil war, landing in Seoul where my grandfather began to grow a successful clothing factory.
Blessed with the income of an upper-middle class life and scarred by the memories of escaping communism, my Dad migrated to Los Angeles and immediately launched his business plan of me becoming a doctor.
M.D degree. D.O.s and Podiatrists not recognized.
So when I decided to become an entrepreneur, my father refused to speak to me for one full year.
In 2001 I started Five9 – the first cloud-based call center platform. I told everyone it stood for 99.999% reliability but secretly it was because I’m 5 foot 9 and wanted to show everyone a short Korean kid could make it.
In 2013 Five9 had an IPO. Two fantastic CEOs – Mike Burkland and later Rowan Trollope – had taken my $10-20M ARR company well beyond $300M+ and established it as the category leader in what analysts labeled “CX.”
But I never wanted to stay in the CX market. I wanted to do something new, and ObamaCare coincided with when I had met my soon to be next CTO Mischa.
Mischa and I were both pretty fed up with the status quo for consumer health, and felt like we could build a communications app that made it much easier for doctors and their patients to communicate.
DoctorBase was also a lesson in competing with better-funded competitors as a near-bootstrapped startup by sticking to your passion for hiring the best software developers so we could iterate and integrate 2x faster than our peers with bigger teams.
Over time this multiplier on our iteration speed overwhelmed our competitors who had raised over $100M+ dollars.
Our closest competitor HealthXXX had raised 30x more money than we did, but at the time of our acquisition we were a totally employee-controlled company and was doing over triple their revenues.

VCs had passed on us because, well HealthXXX had raised much more money and (according to their formulas of prediction) that meant they were going to win.
A very famous VC told us that “HealthXXX is going to run away with the market.”
I printed out his email and taped it to my desk so I could stare at it every Saturday when I showed up to my sublet office on Mission St.
We eventually raised $500k via Angelist only after we were profitable (as a cash cushion) and at a healthy valuation that kept us founders in total control of the company.
When other digital health founders ask me how we did it, the short answer is that we took a contrarian view of how to build a successful health-tech company in an era of “Health 2.0 Hype,” when it seemed that most of the top digital health companies pattern matched to each other.
While our competitors were at health-tech conferences and raising money from VCs (with CEOs trying to make a Forbes list), we instead stayed in San Francisco and worked on EHR integrations, met with two doctors a day for their feedback, used AI/ML long before it was sexy to find statistical insights, experimented with product virality loops that would hook busy doctors and engage reluctant administrative staff, and ran constant experiments on the unit economics of registering patients.

Many folks assume my first startup was more important to me because it became a much larger company, but in truth my time at DoctorBase were the best five years of my life (even better than college!). I think it was because we all felt like we were on a mission, and the team was small enough to feel like family.
At the time we sold the company we had about 18,000 doctors communicating electronically with nearly 9 million American patients. We were small, but we out-hustled and out-coded our competitors to create, at the time, the largest patient engagement + marketing platform for independent doctors offices.
And I wasn’t even a real doctor!
