Interview with Jake Levine ’08: Creator of BreakupText


I interviewed Jake Levine ’08, a successful Wes alum in the tech industry this past July, when he had just launched the iTunes app, BreakupText. Since then, he’s launched the app’s sequel, MakeupText and continues to be a maverick in the digital media world. I was originally intrigued because Levine created an app that allowed people to break up with their significant others in under five seconds, but I quickly figured out that he was an inspiring entrepreneur with an already successful career. He’s the general manager of, owner of well-groomed social media accounts, and great promoter of Wesleyan in the tech industry.

While our conversation at the time focused on his (now month-old) app, Levine had some great advice for people interested in creating their own start ups and in becoming involved in the tech industry (hint: if you’re a Wes student, you are guaranteed to find a Wes alum currently working in the industry). If you’re one of these people, get on this e-mail list for Digital Wesleyan (it’s already 600+ people strong) so you can stay informed about meet-ups with Wesleyan alums in tech (Levine organizes these).

Click past the jump for an insightful interview with someone Forbes has deemed one of the top 30 under 30 people in digital media today:

Can you explain the gist of the app and your inspiration for it?

BreakupText is an app that makes it easier to break up with people via text message, and I guess the first thing I should say is it’s a total joke. There are a couple of bloggers and folks in the press who are writing about it as if it were actually a way to break up with people and saying like, ‘we recommend not using this app, but instead we recommend a face to face conversation,’ which is pretty funny. I built it because a friend of mine at work and his buddies just spent a year abroad in Hong Kong and they would meet women at bars and get their numbers and then text them the next day to hang out and 1 out of every 2 times they wouldn’t get a response. And so they thought it would be funny to send really long emotional break-up text messages saying, ‘hey…things just aren’t working out, I don’t really feel like we have a connection anymore…’ and I just thought that was hilarious. And so my friend, Lauren, and I…do you know texts from last night?

Yep!Jake Levine

Ok, so my friend Lauren started that company, like 3 or 4 years ago. We were working together at Betaworks and thought it’d be fun to do this. The first thing we did was make the web application, which was You fill out a little bit of information and it sends a text message to a number of choice. That was something I did 6 months ago and Lauren wrote all these text messages. And that went well. A bunch of press wrote about it; something like 5,000 or 10,000 people broke up with somebody [the day that it launched].

I needed a project because I wanted to learn how to make an iPhone app. And I thought that BreakupText for iPhone would be a funny project. So I used the same text messages and developed an iPhone application.

Did you have any app or web development experience at Wesleyan?

I took Intro to Programming at Wesleyan, which I would say was responsible for, like, 5% of my learning. Most of my learning happened after Wesleyan… teaching myself the basics using online tutorials and asking friends for help. A lot has changed [curriculum wise] in the last 5 years and curriculum tends to move slower than the rest of the industry. I think it certainly could use an update.

What were you involved with at Wes?

I was a CSS major and an Econ major. I did Econ because I thought I wanted to go into investment banking. I did investment banking for a year and then bailed to controlling a startup. I’ve been in technology and startups ever since.

Where do you work now?

I started a company called about two years ago and we acquired Digg last year. I’m the general manager of, which is now Digg.

What does that job entail?

I run the business side of digg; that means finding new users, figuring out how we’re going to make money. It means partnerships with publishers and with advertisers and all sorts of other things. I also do some work for Betaworks, which was actually founded by some Wesleyan guys (John Borthwick ’87 and Andrew Weissman ’88). It’s an organization that creates companies and invests in other startup technology companies.

What advice would you give to someone who was trying to create their own startup after graduation, or trying to make a successful app like you did?

I would say, “call me.” Call somebody who’s doing it. I’m thinking in terms of when I was at Wesleyan, the best thing I did was talk to people who were doing what I wanted to be doing. In reality I had no idea what that actually was. The two things that I would say are: talk to people, like find alumni that are in the field. You can email any alumni and there is a very high chance that they will e-mail you back. I probably meet with Wesleyan students or recent graduates like once a week. I think it’s true of Wesleyan alumni that they will take time to help younger current students or recent graduates. Number two, learning how to design an application is not rocket science; in fact, there are tools you can use today that make it so much easier than it has been in the past. If there are students on campus that are entrepreneurial or eager to be entrepreneurial or eager to understand what entrepreneurship means, building your own software is a lot easier than they think.

breakup text

Do you have any advice for attaining the resources to create your own startup?

The worst thing I hear when I meet somebody and they tell me they want to start their own company, is when they proceed to tell me all the things that are in their way. It’s definitely hard and you don’t have to tell people that. I think what you should do is just start. There’s nothing actually holding you back from starting something. In fact, I always say I wish I used my time at Wesleyan better because that’s the time you’re surrounded by your peers. You have time to work on side projects in a way you don’t after you graduate and there’s nothing holding you back from building a prototype. You don’t need to raise money to build software, you don’t need to outsource it to somebody on the other side of the world because you don’t know how to program. It’s easy to program, it’s easy to learn how to build things, and I wish that I had known that five years ago.

Are there any other Wes alums that worked on the BreakupText app?

No. I had a few people help me, but they’re not Wesleyan people.

But to sort of answer a different question, there are so many Wesleyan people in technology startups and digital media. And that’s not totally clear to current students. What I would like to do is help make that clearer to people. I’ve got 600 people on a mailing list in New York City that have signed up on their own that come to these Digital Wesleyan events every few months and I wish that was better known to the existing students.

If you could hook me up with more of those events…

Go to and you can sign up for the mailing list. I want to start doing more stuff on campus and I want to make sure I have a running list of the students that would attend events or are interested in meeting alumni that are in the field.

For example, we did a Digital Wesleyan internship program this summer. I raised money from alumni to pay for the internship of three students in startups in New York City.  And I’d love to get the word out more about the program.

Do you think you’ll continue working in the tech industry?

I’ve been interested in tech since Wesleyan and so I think I’m here to stay.

How would you market this app to the typical college student?

I think it’s sort of a funny and a fun little app. I would say that if you are in a relationship and you want to end it, one of the simplest ways is to use an app like BreakupText and you can end it in under five seconds. It’s the most efficient way to end a relationship.

Where was it publicized?

Laughing Squid, Huffington Post, a Glamour mag blog, Mashable…it was kind of silly, the press reaction. I didn’t expect anyone to write about it. I just expected my 10 friends to download it, so it was sort of surprising when people started writing about it.

What do you think the existence of this app says about the current state of dating? 

What felt news worthy about it is that people interpreted it as needing technology to manage our relationships, and that’s about as deep as I’m willing to make it go. But it’s also a total joke and people shouldn’t spend too much time thinking about it.

[Samiraan example of a BreakupText my friend sent. Ze just checked off three options and the app generated an elaborately written text.]


Are you working on any other apps currently?

I’m thinking about making an app called MakeupText [ed. this was released on Aug 4]. It’s basically going to be a very similar application, except obviously the text messages will be different and I’ll probably charge more money for it. If you made the mistake of breaking up, it’ll cost you to make it better.

How are you able to tell when an app will be successful?

Ask people. And when you make the design, show people the design; when you make the prototype, show people the prototype. And when every time you do that they laugh or say that it’s a good idea or say that they’ll use it, more importantly, then you know it’s a good idea. You look for more and more validation. The goal is just to do as little work as possible to get as much validation and feedback on your ideas as possible. The other thing you need to be aware of is that most of your friends and family will tell you that it’s a good idea even if it isn’t. So you really have to force them to think about whether or not they would actually use it.

How did your Wesleyan experience inspire you to work at a tech startup?

There are so many Wesleyan people in technology and when we get together to do Digital Wesleyan events, this is often a topic of conversation: how did we all end up here? What about Wesleyan made it likely for us to end up in technology and startups and digital media? The best explanation that I can come up with is that Wesleyan students are creative; they like to build things and make things that don’t look like what already exists; they like challenging existing institutions and companies and ways of doing things, and they like doing so with personality and with a strong sense of where they see themselves in the world. They thrive when they have an opportunity most of all to be creative, and that for many people is why startups are so attractive.

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