My cousin Jake is a better entrepreneur than I am.
He helped found College Humor when he was a teenager, and then used his knowledge from that experience to create Vimeo. When he made money from these companies, he used the proceeds to make three angel investments: Tumblr, MakerBot, and, my company, Bleacher Report.
So, he is clearly a better investor than me, too.
Last year he raised a $1.5 million round of capital for a new stealth project from a host of famous angel investors. And tried his best to stop the press from even finding out about it. That’s probably not the Jake Lodwick you thought you knew.
Jake is not interested in self-promotion these days. There was a period of time when he was very much interested in self-promotion, and that was probably the least productive period of his life. So he quit that and now enjoys an audience of a mere few hundred Twitter followers.
Jake doesn’t let people interview him these days, but lucky for you he’s my cousin. So I’m going to go ahead and recount some of the best lessons that I have learned from one of the best product creators in the Web’s nascent history. Am I totally biased? Absolutely. He’s my cousin. But he may still be pissed at me, because I didn’t tell him I was doing this.
Consider this an interview without my subject even knowing that it’s happening…
Lesson 1: You are the only user who matters.
Jake really doesn’t care about other people. It’s not because he is selfish, but because he cares so much about enhancing his relationship with himself. He is addicted to self-improvement, and constantly asks himself why he does the things he does, right down to the smallest action.
And he creates products that will be successful even if he is the only person who finds them useful.
Millions of people use Vimeo. How many people use NowDoThis, his personal task app that never gained popularity?
It doesn’t matter, because the product’s success is contingent only upon Jake finding it valuable.
If that is the philosophy by which you approach entrepreneurship, you will succeed.
Currently, too many people start a business by saying, “Imagine if you could get millions of people to…”
But a product won’t change millions of lives until it has made your own life so much better.
One of Social Media’s negative contributions to innovation is that it has conditioned entrepreneurs to think of problem solving in terms of the masses.
A small few of those — like Groupon and Zynga — achieved great success. But those companies ultimately stumbled, because they approached problems for a large group, not for an individual. Groupon’s deals were not useful to the individual restaurant. Zynga games were cheap, crappy ripoffs that ceased to be of value once their spammy viral methods were put to rest. Ditto companies we’ve already forgotten about like Blippy.
But think about how many children can sit quietly in a library corner playing Angry Birds by themselves… it’s a game that would delight us if we were each the last person on earth.
Jake is that guy. He builds things for himself, because he will like using them — sometimes millions of others will also find them useful, sometimes it’s just him.
And if he were the last human on earth, he would still use his own products… until the lights went out.
Lesson 2: Coming to terms with failure is not enough — you must learn to ignore shame.
People tell themselves that failure is ok — part of the process, even.
In fact, Silicon Valley has almost created a cult of ‘failure’, celebrating it as though it were a badge of honor.
But people don’t fear failure. They fear shame.
They don’t fear the consequences of failure — not getting rich, having to do their old job again, etc. They fear the shame of looking their old co-workers in the eye.
And they fear the shame of little things too…
They fear being ashamed when they sit at a table with their co-founders and try to come up with a name for their new company. Do you know why so many companies have shitty names? Because all the co-founders were afraid to throw out crazy ideas that might get laughed at. So they end up with horrible names like Trippy or Contently.
Jake has conquered shame.
When I was ten years old, Jake and I were at a beach resort and they had a talent show for kids. Most of the kids went up and played an instrument, sang a song, or juggled or what not. Jake went on stage and tried to do a comedic song and dance routine that was not funny and flopped terribly.
My parents were ashamed for him. But Jake was not ashamed.
Beware the entrepreneur who says that he is alright with ‘failure’, because his company’s failure may not be his own failure. He might burn through a million dollars of other peoples’ money, and then trumpet his failure into another great career opportunity. But if he was too ashamed to come up with a wild name for his company, or if he was too ashamed to move back home with his parents when the company was being started, or too ashamed of his real life, such that he creates a bullshit one on Twitter… then he has already blinked.
Lesson 3: Sometimes it is ok to be nobody, useless, anti-social, and alone.
One time I visited Jake when I was in New York. He had just made millions of dollars, had the most read blog on Tumblr, and was freshly broken up with socialite girlfriend Julia Allison.
My buddies and I met up with him for dinner on a Saturday night, and we assumed that we were going to hit the town afterwards, get drunk, meet up with internet celebrities, and feel cool.
After desert, Jake split the bill with us and went home, because he wanted to be asleep before midnight. We couldn’t believe it.
Shortly thereafter, he gave up blogging, flew to Melbourne for several weeks, where he did not know a single person. He did not go to a single bar or nightclub the entire time.
We live in a Fear Of Missing Out (FOMO) Era — everybody is afraid that they are missing out on something. We worry that if we blink, the next great opportunity will pass us by. We worry that the greatest party in history is the one that we missed last night. We stare in awe at our Facebook friend’s picture, because he is standing shirtless on a beach with seven hot girls… none of whom, it turns out, want to sleep with him.
How many entrepreneurs quit their jobs in 2010 to build a Daily Deal company? FOMO. How many founders pivoted their potentially-great companies to instead develop cheesy games or social/local/mobile/location-based iPhone applications? FOMO.
All of the wonderful inventions of the last ten years have created a FOMO pandemic, and it is hitting the entrepreneur, and the people who fancy themselves entrepreneurs, so hard.
Life lasts a long time. You can disappear or be useless for weeks. If you are coming off several years of hard work, you can disappear and be useless for months… and the only impact that it will have on your success is that it will make you more successful.
You are missing out on nothing.