10 Things You Do After Your StartUp is Acquired.

John Sung Kim Net Worth

2015 was a crazy year for me. Admittedly, I got really lucky. My second startup had just gotten acquired about a year after my first one had an IPO. I hadn’t taken a vacation in, well, never. So I decided to do that for a year.

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.



To be fair, the following are the 10 things that I did (at the time a single, surly Korean-American dude with an endless affection for beer). This article is in no way meant to imply that these are things that normal well-adjusted people do. So you know, don’t be like me. You’ve been warned about reading further.


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 and there are so many competitors. We just don’t see how you can win.”

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 almost 3x their revenues.

It’s why as a hobby angel investor, I never underestimate a roomful of creative people who are die hard about winning.  Smart is good, but scrappy often wins the day in competitive markets.

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* The funny thing about winning heated wars with your direct competitors is when it’s over, you kind of feel sorry for them. After all, startups are hard, we’re all just trying to make it. And yet, we dance.

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 bucket list 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 house with a garage in San Francisco big enough to house them all. Dream = fulfilled.

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

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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, really. I love animals.

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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).

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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!”

See in Silicon Valley, we’re smart, we just lack social graces.  #Aspergers

Or have dinner with celebrities. Not because they like you but because you paid for a fund raiser 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.

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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.


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

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Send family members on vaca. Also, Asian thing.

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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.

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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.

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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?

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

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One of my (ex)employees saw this pic of me “judging” on the event’s Facebook page and she slacked, “JSK, I’ve never seen you look so content.” She was joking I think.



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

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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.

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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.

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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.

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* I am NOT a professional investor. My passion is to design addictive B2B software and build a rabid user base that turns into a meaningful brand. These skills are very different from those of a good professional investor 🙂

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

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


Still, my year off the grid was memorable and I’m glad I had it. Whenever people say bullshit like, “I wish I could have a year like that, JK,” I always tell them that if they quit their day job, then –

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“I’m Searching for a Co-Founder”

Mischa Spiegelmock

I fucking hate hearing this as an angel investor.

It’s often said by the same people who don’t want to tell you too much about their idea because the idea is “Secret.”

There are passionate, competent software and hardware engineers all over the world. The world. If you can’t find one, you’re not looking hard enough or you’re a shitty salesperson.

If you can’t find one engineer to work with you, how the hell are you going to build a company full of them? Finding great talent (technical, operational or creative) gets harder after raising money, not easier.

And duuude. No one cares about your fucking idea. Now go find a good technical partner and treat each other like gold.

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  • These two are the co-founders of a startup that was a copycat of my second company (but in Singapore). They cold called me and asked to meet for some advice, which tickled me pink.  One is the business person, the other person technical. Can you guess which one is which?



JetBridge – My New StartUp

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Software for sales teams “the sales tech stack” is growing in complexity and costs. Multiple enterprise software vendors are fighting for the same $300 per rep IT budget, and most of these solutions are out of reach for the SMB. We see a massive opportunity in this “crowded” space.

The common wisdom is that entrepreneurs find a problem with a big enough TAM, interview potential customers via Lean methodologies, then find your product-market fit. And this is right, but for me I’ve found that it’s better to first start with finding the team you want to work with.

Meaning, regardless of the product, “Would I enjoy riding with this team for the next 4 to 5 years?”

After my second startup DoctorBase was acquired, I wasn’t sure if I would do another software company or if I would just become an investor and advisor. As part of the purchase I had agreed not to solicit any DoctorBase employees as long as they were working for the acquirer, which is quite standard.

But then that company decided to consolidate some of their engineering, there were some inevitable layoffs, and I found that fate had given me an opportunity to work with my core engineering team again. I hired them all immediately without a plan.

So then the questions came up in our group – “What do we code up? What kind of company do we want to build? Can we handle John’s bullshit for another 4 years?”

One of the biggest challenges we had running both Five9 and DoctorBase was growing our sales teams –

We had a variety of wonderful tools for our sales reps, but their cost and complexity meant we had less money to spend on generating leads for them, and reps were increasingly spending more than 30% of their day on IT and admin tasks.

Mischa (who had started DoctorBase with me) and I discussed creating another startup and we came up with these elements that we wanted for our company –

  • We agreed that we had too many expensive software apps for our sales teams that we either didn’t end up getting sales rep engagement or didn’t integrate into other apps, creating administrative overhead for our reps.
  • Running a sales team cost us nearly a third of our operational costs (normal for SaaS) at our previous startups and we did not want to repeat that. We wanted to build a product that was low-priced and so easy to use that we could run a self-service model. This way we could be a price leader and invest heavily into fanatical customer support.
  • We wanted an international team. Over the years we spent building DoctorBase, Mischa and I made friends with brilliant engineers all over the world, and we wanted a chance to be able to work with them.
  • We’re big believers in Machine Learning. While few models in the sales tech stack are true machine learning right now, we think models will emerge where machine learning, and maybe even A.I., can be applicable.
  • We want competitors. DoctorBase operated in the healthcare vertical, where EHR systems fought madly to lock out competing vendors. At JetBridge, Mischa and I both agreed that open platforms where 3rd parties can re-use our base infrastructure to create their own new  features aren’t just better for customers, they make us cooler people too.

We decided JetBridge would build an open software platform for professional communications that’s affordable by all and easy enough to onboard yourself. Built by a team of the best engineers we knew.

I quickly drew up our logo over beers for Mischa and the gang.

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“So you’re basically making our logo look like your new tattoo,” one of the engineers said.

“Uhm. Yeah.” I took a pic of the napkin and crumpled it up. “Look guys, let me worry about the marketing, ok?”

They smiled. It felt like we were back in business again.



By Bye, Panda

DoctorBase Founders

In 2009 my buddy Mischa and I wanted to make a ding in the healthcare universe. We 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 digitally.

Man, we learned some really harsh lessons about the American healthcare system. Namely, the folks who control our national healthcare policies at the highest levels make Russian mobsters look like pussies.

  • If you work for the Russian or Ukrainian mob, please know that I have the highest respect for your craft – no insult intended.

DoctorBase was also a lesson in competing with better funded competitors by sticking to your passion for building the best damn product and ignoring the VC hype machine. 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 almost triple their revenues with nominal churn.

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This took 5 years to build out completely, and by then it was one of the dominant apps in the market with very little funding or marketing. Of course, VCs passed on us because, well HealthXXX had raised much more money and that meant they were going to win. A very famous VC said he felt that “HealthXXX is going to run away with the market.”

At the time I sold the company we had about 18,000 doctors communicating electronically with nearly 7 million American patients. We were small, but we were a bad ass gang. I mean, not as bad as Russian mobsters, but still.