“My earliest memories are of my garage being filled with weird guys with ponytails and servers.”
Jake Heller grew up in Silicon Valley, and was raised in Cupertino and Sunnyvale. His dad started a company in the early 90s — Internet Business Systems, actually the first company to have a name with “internet” in it.
Very early in his life, his dad taught him to code very early on, and he fell in love with it. Heller tinkered with the Atari computer, and programmed in BASIC, making Mad Lib games to impress his friends and crushes.
By high school, he found other passions, namely speech and debate, but Heller kept up with programming as he studied politics and economics. He was active on the debate team. After high school, he attended Pitzer College, graduated early, and programmed for his dad’s company for about a year because they had hit a rough patch.
Throughout undergrad, Heller became more interested in the intersection of law and technology. All the problems with the economy, the distribution of wealth, things that were being invented, who gets elected — he considered them important challenges, much bigger than typing words into a computer screen.
“That excited me, problems that were not mathematical and precise, but huge problems,” he said.
He was passionate about copyright and the rise of the internet, of patent systems and solutions for problems through the system of law. He thought, “Why was there being more money spent on male patterned baldness than there was on drugs that can cure diseases?” and wanted to fix the system that established those incentives.
So he decided to go to law school at Stanford.
In law school, he interned for organizations that protect consumers, worked on free speech and internet, and spent a summer at the White House Council office. After law school, he got a clerkship with a judge in Boston, since his wife went to Harvard Business school at the same time. They stayed in Boston for a few years, and he worked as a lawyer at Ropes & Gray LLP.
Heller loved his job, but there was an idea that he’d had since the beginning of law school that kept nagging him. Something Heller had always been passionate about was the open source community for developers. It was built into his ethos, and he latched on to any community that used the model, from Wikipedia to Yelp to Github. It was the way the world should work, he thought.
He said he was fascinated by the idea that “there are thousands of people out there collectively building things that is not only as good as, but better than, more responsive, quicker to update, than places like Microsoft and Apple.”
Then he went to law school. And when you show up to a law program, Heller said, you’re handed an access card to online legal databases and you get access to repositories of knowledge and information. The difference? Instead of an open source model, they charge millions of dollars to access the law and basic understanding of it, because they have to hire experts rather than tapping into a huge community of knowledge.
Heller always thought somebody should take the open source model and apply it to the world of law.
“For literally seven years, I said ‘somebody, someday, is going to do this,'” he said. “And eventually my wife, who is a major catalyst in all things and especially this, said, ‘you know what dude, you’ve been talking about this idea for six years now. We don’t have kids, we don’t have a mortgage. Either do it now or regret it for the rest of your life.'”
So, he put in his two weeks at his firm. Without raising a penny in venture capital, or writing any code, he set out to start Casetext — a platform that integrates legal commentary with legal documents, and makes it open and accessible to the public. He applied to Y Combinator and was accepted, and that experience was incredibly beneficial to the company.
“It takes people like me who have an idea and in three months turns it into a fully functioning wonderful product that people are using,” he said. “And by wonderful I mean deeply broken in millions of ways.”
But that’s one of the best parts about software development, he said. You can get something together quickly, get it out to the public, and people give you feedback on what to fix. When he feels bad about what Casetext looks like today, since it’s still in its nascent stages, he just looks at early images of Twitter or other sites to make himself feel better.
“At its core, a lot of these services start out really ugly and broken, but they tap into a real need that people want,” Heller said.
When the company started out, it was a few people in a living room, coding a website. A lot of what Heller brought to the table as a founder was based on what he learned in law school — how to be an effective doer, and making sure things are always done on time. But now, with 16 team members and a tight-knit, more collaborative culture of a startup, his role has changed. His job is trying to help make other people effective, which has been a humbling experience.
“I had some real lessons where I was like, ‘I’m just not that good at this yet,” he said.
But he’s a different person now, and he thrives in the atmosphere. Most importantly, he focuses everyday on his passion for open source technology. Originally, he thought young attorneys would be the ones Casetext would catch on with, but what he found was that most people wondered why it had never been done before. So for example, a 70-year-old partner at a Boston law firm turned out to be a Wikipedia editor, and latched on to the idea quickly. It showed Heller that a lot of the people you least expect are the ones who are the most active in online communities.
“I knew conceptually there was this really interesting and deep power to tap the knowledge and wisdom of the crowd,” he said. “But it’s really exciting every single day.”
Casetext has a specific company culture, based on a few things. First, law is free. They have been pressured to go behind a paywall to compete with databases like LexisNexis, but they’ve refused. One part will be free forever. Another value is honesty, within the offices and outside of them. After all, the company is founded by lawyers.
But one of the best perks? Legal lunches. Instead of going out for lunch, the team nerds out with classic legal movies — Heller’s personal favorite.
In his own words…
What are some of your hobbies?
“I’ve already said I’m a super nerd and I’m going to dig myself deeper into that hole. I love to play really complicated board games. Technically, called German style board games. One most popular in America is Settlers of Catan, it’s a gateway drug to the kinds of games you should be playing. It is five levels too simple. One of my favorites of all time is Agricola, which I play with my coworkers now. It’s so intensely complex, but the complexity pays off. You have to think 12 steps ahead like chess, but it also involves farm animals and growing vegetables. There’s something very satisfying about that.
“My wife and I are huge tv and movie fanatics. We watched all of IMDB’s top 200 movies like a few years ago. I took all of one film class in undergrad, so I don’t know anything about it, but I love all different kinds of film. We don’t go to the movies that much…I am stupidly cheap, but netflix is our best friend. We used to rent tons of movies, I remember one summer in high school — we’ve been together since well over a decade now — she worked at a Blockbuster just so she could rent the movies on an unlimited basis.”
What advice do you have for entrepreneurs?
“This will sound like a downer, but one of the things you hear and don’t let sink in is no matter how good things are going, it’s always tough. It never gets easier. The funny thing is, that sounds disempowering, but there’s something liberating about that. Every single day is going to be a new and different challenge…There’s different, bigger, weirder challenges as you grow. If you embrace that and learn to love it, being an entrepreneur is fun.”