I arrived to San Francisco in 1999 with six credit cards, a U-Haul truck tied to my used Jeep Cherokee and a singular dream – create a successful startup of my own with my Compaq laptop. I had no fucking clue this would end up being a $12 Billion software company 20 years later.
The first dot-com bubble was in full swing when I got to SF but as a recent college grad with no connections, nor any knowledge about tech, I instead settled for a job at Charles Schwab as a receptionist-clerk.
But I noticed something fascinating as I worked 8 hours a day collecting checks from walk-in customers – the clients with $100k in their accounts were miserable (and liked making Schwab employees miserable) but the clients with $1M plus accounts were really nice and laid back. And the folks with $10M plus accounts all had one thing in common – they were startup people.
I lasted at Schwab for 6 months before I finally quit. My baby cousin Steve was dying of Non-Hodgkins Lymphoma and I suddenly realized life was very short.
My cubicle neighbor Arnie said, “John, Schwab is always rated in the top 10 best places to work – don’t quit just because you read about startup success stories in the Wall Street Journal. They never publish failures, and most people fail.” Afterward, he adjusted his tie neatly into his collared shirt and took off in his minivan.
I remember watching him drive off the parking lot and thinking “Fuck. That.”
And that’s pretty much how I started Five9, maxing out my credit cards and pivoting my idea for virtual call centers until it became a real business. Eventually, it had an IPO and the stock kept climbing to where it is today (an unimaginable valuation). On a drunken dare from one of their editors, I wrote about this first startup journey for TechCrunch.
While my first startup was in the call center space (because I thought it was a good idea) I yearned to build a product that was meaningful and loved (everyone hates call centers, let’s be honest).
So my buddy Mischa and I created DoctorBase – a software platform that made it easy (and profitable) for doctors to email & text with their patients. Our idea now (thankfully) has numerous copycats and today many Americans enjoy being able to communicate with doctors via an app, an almost unheard-of idea back in 2009.
But in 2016 we got an offer for the company that I thought was too good to pass up, and the acquiring company (who was 25x our size and growing fast) was in a much better position to fulfill our vision of allowing every American and private practice doctor to communicate digitally.
So being jobless and with a lot of time on my hands, I decided to live out all my life fantasies (or most of them anyway) before deciding to start my 3rd company – JetBridge (disrupting software outsourcing).
But when I returned to San Francisco I noticed something funny –
Communism was becoming cool in SF (and California).
Having spent a lot of time in Ukraine and learning about the effects of their Soviet past, it was alarming to see this trend happening in my home city: Neighbors “canceling” each other for alleged racist thoughts, Asians now being “white,” math being racist, and self-described “radical socialist” politicians coming into power (and majority control) over the city of San Francisco.
Crime skyrocketed along with street-dwelling drug addicts, gangs openly sold fentanyl without fear of punishment, city council members shouted “Fuck the Police Officers Association!” to drum up their radical base, and schools were closed and renamed (apparently Abraham Lincoln was racist and a High School named after him was unacceptable). Anyone that dared complain was cancellable or deemed a “white supremacist.”
Slowly and steadily, the politicians began to try and control all aspects of our lives from the number of security cameras we could install, where we could go outside, and what words we could say out loud. Local politicians would even go after you for not agreeing with their legislation.
When Covid hit, many people in the startup industry decided enough was enough and voted with their feet by fleeing SF. Many went to Austin, others to Miami, but I chose Tampa.
“Why Tampa and not Miami?” is the most common question I get.
For some reason, I feel at peace here in Tampa. I have the same sense of ease here as when I’m in San Diego or Hawaii, but with a sensible government, lovely neighbors who I don’t fear, and all of the major entertainment and sports options (except for basketball).
Maybe the biggest reason I chose Tampa is that I’m a startup person at heart. Miami doesn’t need me (they’ve got enough momentum now to eventually take over San Francisco as the tech hub of the nation, along with Austin). But Tampa feels like a place where I can mentor the next generation of young techies, help build and invest in its first wave of unicorns and – to be 100% honest – where I can ride my motorcycles without dying in the first 90 days (yes I’m talking to you, Miami drivers).
If you’re looking to break into tech or want mentors that can take your career to the next level, email me at email@example.com – we’re hiring in all operational departments and I’d love to chat and get to know you!