2015 was a craazzy 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.
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 15 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.
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.
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 garage in San Francisco big enough to house them all. Dream = fulfilled.
And if you really like a particular model, why not buy two?
3. 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.
4. Throw fun parties. And this being San Francisco, most of my guests will be both beautiful and smarter than me. But only with things like math, you know.
And make friends with other founders and VCs so you can all laugh at how ridiculous Silicon Valley life can be sometimes.
Because let’s face it we’re incredibly lucky to live in this part of the world. But please don’t move here, the rent is expensive enough. Telecommute, if you must.
Unless you’re really good at math. Then you should totally come and look me up.
5. Retire your parents. It’s an Asian thing, I guess.
6. Send family members on vaca. Also, Asian thing.
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.
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.
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?
9. 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.
8. Visit Eastern Europe because the Internet says there’s a lot of beautiful women there. Which, turns out, is largely true.
I found Eastern Europeans to generally be super smart, very resourceful and real bon vivants. It’s an amazing part of the world and I really enjoyed my time there. Now before the Internet crucifies me it should be told – sometimes single guys who were the nerds in school dream of going to another country and meeting beautiful and interesting people. So guilty.
Yes, I am the worst human being on the Internet for today. But I wanted this post, like all my writing, to come from a core place of honesty. Otherwise who gives a fuck?
9. Become a judge for a foreign country’s Miss Universe beauty pageant.
One of my (ex)employees saw this pic on Facebook and she jokingly slacked me, “John, I’ve never seen you look so content.” She was joking.
A common question I get is – ‘How the hell did you end up a judge in a Miss (Ukraine) Universe pageant?”
The thing is, I was graciously invited by someone in a manner in which I thought it culturally impolite to refuse.
10. 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.
11. Get invited to the White House and chill with politicians.
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.
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.
12. Have a 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.
13. And if you’re really lucky – meet the girl of your dreams and convince her to marry you. Again, I got lucky.
OK, gross I know. I’ll stop.
14. Start to miss your desk at work. When you had a job. And purpose.
15. Get back home, realize that you miss building something. 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 –