Why I Moved My Latest StartUp From SF to Tampa

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!

Why 99% Of New Apps Developed By Outsourcers Fail

Why would top developers be looking for gigs on online marketplaces when elite coders can make 3.5x more (with benefits) working for a VC funded startup or an Amazon (which lets many devs work from home)?

Or, why would average developers work for an outsourcer when they can get 2x more in an online marketplace?

Five9 Founder John Sung Kim

Nothing about the claims of online marketplaces (“Hire ex-Googlers to work!”) or outsourcers (“We work for Microsoft!”) make any sense. But people always want to believe they found a $100 bill for $20…

Like “Dave” (not his real name) who sat across from me at a cafe in Kiev, nearly falling out of his chair with excitement. He was a very fit, middle-aged London banker who had an idea for an iOS app and had hired an outsourcing firm in Kiev.

$150,000 into his yet-to-be-launched app, he kept saying “I’m certain.”

It doesn’t occur to many first-time product founders that success in this game is all about the team you have.  Your ideas are for shit. 

But here’s the dirty truth outsourcers don’t want the public to know:

Outsourcing is a grueling business that relies on tier C talent, with 10% to 25% margins at best, and that doesn’t account for the constant churn as developers leave you for better-paying positions, nevermind the sales and marketing costs.

Almost every outsourcer I know is working on their own product, hoping one day to leave outsourcing. That’s why 99%+ of apps developed by outsourcers fail.

If outsourcers could build successful products, they wouldn’t be outsourcers.

Dave became upset when, instead of joining in his excitement, I told him “Dave, you’re a great guy but if I could short startups, you’d be first.”

I really got to work on my tact.

However, a few months later Dave sent me a Facebook message with the all too common, “John, I should’ve listened to you… hey can you meet up for coffee?”

Well, who the fuck are you to say, John?

Call it luck or psychotic determination, but both of my startups have had profitable exits and nearly all of my clients who I’ve been a growth advisor to have had: an IPO, a Series A investment, or been acquired.

Who is founder Five9 john kim
Who knew this website I designed for my first startup in 2004 would become a $3.5 Billion company? I certainly didn’t!

When I think of why “luck” has been on my side, my belief is that it has to do with one core habit I’ve developed with my colleagues over two decades of building, advising and investing in new software projects that I call the CMP model:

Every successful project is a product of Consistent Mini-Pivots based on a relentless collection of data. 

Too often I hear younger founders say something like, “We failed because of _______ but we learned a lot!”

I don’t believe failure is anything to celebrate. And most of the time I’ve seen that it could’ve been avoided with CMP.

At my first startup Five9 we were the David versus multiple Goliaths, so we had to come up with a 10x better product with a 3x better marketing strategy using the CMP model with our engineers and marketer.

Based on CMP grew from $0 to $10 Million in annual recurring revenues within 24 months. $20 Million in just 35 months. Quite frankly it felt easy, it was fun (while our competitors used words like “grinding,” to describe their lives).

It just happens that CMP is the exact opposite of how outsourcers operate profitably – they have to give you the cheapest developers for the highest price taking the most amount of shortcuts. 

There are no guarantees with any project, but I believe the CMP model gives a project multiples more chances of success, and in this gambler’s game – it’s all about playing the odds by reaching for the best hand. And team.

So what now?

At my new company JetBridge we’re disrupting the terrible performance of software outsourcing with our CMP and “Boots On The Ground” model. Reading our client reviews it’s clear we’re onto something – our devs often outperform our client’s in-house teams! Send us a message if you have a need for excellence & speed with the least amount of risk.

Five9 DoctorBase founder John Sung Kim
We don’t just teach geeks how to code like us, we teach them how to be entrepreneurs like us. Learn more at the JetBridge blog

10 Things You Do After Your StartUp is Acquired.

John Sung Kim Net Worth

Selling your baby company is somewhat bittersweet. The money and sense of accomplishment with your team is undeniable, but at the same time it’s odd to go from CEO to employee. Half of my former employees kept asking me, “You ok, JK?” and the other half would give me an occasional look like, “Don’t you dare tell me what to do – you ain’t the boss!”

I came into the office on a Thursday evening – first clue we were acquired – no one was in the office at 6:30pm. I gathered all of my belongings in a CostCo box, turned the lights out and left DoctorBase for the last time.

1. Said goodbye to competitor. Most of my career I’ve heard VCs say, “We like you, but ABC Co. has raised so much money…”

So one of the first things I did was gathered my core team and danced in front of the grave office of my closest competitor who had raised 30x more money (yeah, 30x)! At the time of our exit we had about 2.8x their ARR (Annual Recurring Revenues) with far less churn (percentage of cancelling customers).

It’s why as a hobby micro-angel investor, I never underestimate a roomful of creative people who are die hard about winning.  Having connections is great, but scrappy often wins the day in the long run.

best email tracking for outlook


2. Visit Africa. The first trip I made was to go to Morocco to ride camels and haggle for things I didn’t want.

The pictures look great but believe me, the desert is cold, boring and filled with cats. Yes, cats.

John Sung Kim DoctorBase

Which in a way made sense to me because the Sahara looked like a large litter box. However, the people of Morocco were quite lovely and I highly recommend going shopping through the maze like streets of Marrakech – a bucketlist worthy experience.

I returned home to San Francisco after ten days in Africa and ate a super burrito every day for a week.  God is great, truly.

3. Buy a bunch of stuff you’ve always wanted (obviously).  In my case, motorcycles. I always wanted a different bike for each day of the week and a victorian garage in San Francisco big enough to house them all. Dream = fulfilled.

Best StartUp Blog

And if you really like a particular model, why not buy two?

Best StartUp Blog

4. Buy your (ex)employees things that make them happy. Because let’s face it, without them I’d be a monkey with a powerpoint presentation. No offense to monkeys as I love animals. 

best email tracker for outlook

5. Throw fun parties. And this being San Francisco, most of my guests will be smarter than me and way more accomplished. Note the tall handsome dude in my kitchen is Coach Mike Brown (former head coach of the Cleveland Cavaliers, my Los Angeles Lakers and now with the Warriors).

john sung kim coach mike brown lakers cavaliers warriors

Some of my guests (after I explicitly asked them not to) asked him questions like, “Who was worse to coach – Lebron or Kobe? Tell the truth Coach!”

In Silicon Valley for some reason we lack social graces.  #Aspergers

Or have dinner with celebrities. Not because they like you but because you paid for a fundraiser dinner benefitting a charity you actually know very little about. 

“Yo Yao!” I said, but I don’t think he got my sense of humor. Man I love basketball.

Leading email marketing vendors

And have a real convo with your childhood idol. When I was a kid I loved Janes Addiction. Being able to talk about the music industry with lead singer Perry Farrell was a dream come true.

best email tracking for outlook

6. Retire your parents. It’s an Asian thing I guess.

Free Email Open Tracking

Send family members on vaca. Also, Asian thing.

Best Email Sequencing Software

My baby cousin and her husband are both so smart and good looking and young they make me want to puke.

7. Speak at your university and drink beer with students like you’re still an undergrad. And actually puke.

Email Sequence Software Vendors

Or people from far off countries will ask you to come speak about startup life, which was also great for me considering I would never had gone to Norway otherwise.

Insidesales.com competitor

And for some reason after you have an IPO or exit, people who own boats invite you onto them. I never knew some many people owned boats. And you know what? Everyone is in a great mood on a boat. You never hear of a fistfight breaking out on a boat. Am I right?

Best Sales Software App

8. Do “VIP” stuff like become a judge for a foreign country’s Miss Universe pageant.

Best competitor to outreach.io and salesloft

I’m married to a wonderful lady now so I have to disclaim: I had a terrible time at this event. Awful. 


Or get invited to the White House and chill with politicians.

best software tools for sales

Charlie Rangel may have left his office with some controversy (after decades of public service) but he’s still one of the best sales professionals to ever pitch. I wish I could’ve gone drinking beers with him afterwards.

Best email sequencing software

Traveling the world for a year makes you very bereft of potential girlfriends dates (ok, so I didn’t have a lot of dates before then either) so my friend Kyra packed her dress, hopped on a flight to D.C. and came to my rescue as my +1 for the White House gala. Thanks pal – I’m lucky to have friends like you.

What is better than insidesales.com

9. Become an angel investor and support other amazing founders by hustling hard for them. Cliche but true, in this town you must add value to get into good deals when you’re writing checks as small as mine.

John Sung Kim investor

10. Start to miss your desk at work. When you had a job. And purpose.

Best Email Tracking for Outlook

Also, even your friends at Facebook seem to be working on interesting projects, and so inevitably you get back to f**king work like a real grown up.

Still, my year off the grid was memorable and I’m glad I had it. Whenever people say crap like, “I wish I could have a year like that, JK,” I always tell them, “if you really want it, then –

Best Email Tool for Outlook for Sales

So now I’m back with another startup mission – to reinvent software outsourcing at JetBridge. If you need the absolute best software developers for your company, come check us out. As you can see from our reviews, our devs often outperform our client’s in-house teams!   

I Fought One Of America’s Most Powerful Law Firms, And Won.

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.