Author: johnsungkim

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 john.k@jetbridge.com – we’re hiring in all operational departments and I’d love to chat and get to know you!

In 2009, I started a digital health company. One of the first people I hired was a sales rep who I’ll nickname “Bruiser.” 

Our company’s big idea was to get doctors to message with patients by rewarding them not with money (those attempts by earlier startups had mostly failed) but with verified reviews instead.

Whenever we encountered problems Bruiser would declare, “I’m an immigrant from the toughest part of the world — this is nothing.” His confidence gave the rest of us confidence. 

But the more successful our SaaS company became, the more difficult he became. At each growth milestone, he wanted to renegotiate his position with clauses like “anti-dilution guarantees.”

Meanwhile, the business was gaining traction and soon hit $1 million in annual recurring revenues. Before we could celebrate, Bruiser called. He wanted to renegotiate.

I let him go on the spot. “Let’s chat on Monday and figure out your exit package,” I said.

He agreed saying, “I love you but you’re too difficult to work with.”

I remember thinking, “Well that was cordial! I thought he was going to break something.”

On Monday I got a letter from his attorney demanding $750,000.

We didn’t have the money, or an attorney. The closest thing I had was a friend who had just started his own law practice. It was so new I had designed their logo a few months back.

On Monday I gathered my team with my friend the attorney and explained the situation. “I’m worried,” I admitted. “But he’s muscling us and I don’t want to settle. What do you guys think?”

“No. I can’t settle,” said my Operations Manager without hesitation. The others nodded.  We were officially embroiled in my first lawsuit.

We responded letting Bruiser’s lawyer know we were fighting.

And then something unexpected happened. Bruiser’s attorney dropped out of the case. But why?

Using the power of positive thinking, I told my team that Bruiser was likely getting a cheaper lawyer.

A week later we got a letter from Cotchett Pitr McCarthy. They were Bruiser’s new attorneys. Known as “Cotchett,” they had successfully sued companies like Eastman Kodak and Citigroup. Their founder Joe Cotchett was described by a popular legal website as “The Bully of Bullies” with the subtitle “Why does Joe win so often?” 

So much for positive thinking.

Cotchett introduced us to their firm by sending in a wheelbarrow of documents four feet tall containing every email, contract or anything thing else that could produced from a commercial laser printer. 

“Total intimidation tactic, so Cotchett,” marveled my attorney. 

We had an open floor plan and we stared speechless with looks on our faces like the primates in the movie 2001, where the obelisk suddenly appears and confuses the monkeys.

I broke the silence by getting up slowly from my fake Herman Miller chair and announcing, “We’re going to win. I promise you.”

I’m not sure anyone believed me, but I packed my laptop and went home early. I didn’t want anyone to see me looking stressed. Later that night I brought half of that pile home (my attorney graciously took the other half).

It was time to ping my network. My friend Jay was the former in-house counsel for Twitter. A Harvard educated attorney Jay knew technology and the law, he was brilliant.

“John,” he said, “if you were in a knife fight, with Cotchett Bruiser just brought a gun. You sure you don’t want to settle?”

But I had told my team too much about standing our ground to settle now. If I settled I would lose all credibility.

We continued on as if I was running two operations – my company and this lawsuit. Evenings after work I sifted through documents until I passed out drinking a glass or two of scotch. Maybe three. 

Also, I picked up smoking.

My life kept going on like this until my phone rang at 3:00am one morning.

“Get up!” My attorney was shouting like he just discovered who killed JFK. “What year did you incorporate?”

“2009, I think,” I was still groggy. “What time is it again?”

“And when did you buy the .com domain name for your company?” he asked. “Look at the sales contract that Bruiser signed with a customer. What year did you buy the .com name?!”

To me, it looked like a regular sales contract.

“You incorporated in 2009 but bought the domain name in 2010,” said my attorney. “So why does this sales contract from 2009 say the agreement is with the .com name you bought in 2010?”

“Because he forged these sales contracts,” I said, flabbergasted.

There were other sales contracts with the same error. But why would he do this?

“Because Bruiser plans to show that he was instrumental in the success of the company, so he faked these documents,” my attorney said.

I immediately called my Operations Manager. “Get up!” I shouted when he picked up the phone.

About a week later we demanded an early deposition of Bruiser from Cotchett. One of the lead attorneys at Cotchett asked if we really wanted to do this, saying it was unusual to call such an early deposition. But we called their hand and at the deposition, we presented Bruiser and his attorney with the evidence.

Another week passed and we got a call from Cotchett. They wanted to settle.

“It’s a fraction of the original demand amount,” my attorney reported.

I balked. “I’ll pay to cover their clerical costs for printing that pile of crap they sent to our office, but that’s it.”

I don’t know a large law firm’s internal cost structure, but I’m guessing Bruiser and Cotchett walked away with about that and not much else. 

It was also a lesson for me about surrounding yourself with the right people from day one. When I told my managers we were being sued that Monday morning, even though I could see the fear on their faces, not a single one of them sold out their sense of morality for practicality.

And when that inevitable time comes, maybe you shouldn’t either.