How The League founder went from $200,000 in debt to making her first million with a dating app for the young, ambitious, and wealthy (2024)

Welcome to “How I Made My First Million,” Fortune’s newest series in which we interview today’s most powerful people about how they amassed their wealth. You’ll hear from founders, entrepreneurs, investors, and creatives across the globe on how they joined the seven-figure-club, what they’d do differently, and their best piece of advice for building wealth.

Key takeaways

  • Age: 39
  • Career highlights: Create dating app The League and sold it to Match Group in 2022 for undisclosed amount a reported $30 million
  • Approximate net worth: $10 million
  • Age at first million: 37
  • Prior debt: $200,000 from business school

Amanda Bradford has high standards.

When the 39-year-old was earning her MBA at Stanford, she found herself unenthused and let down by the current crop of dating apps, which she called “essentially a game of hot or not.” So, the computer science buff and Salesforce alum took matters into her hands; she reimagined the parameters of online dating by adding an extra emphasis on selectivity and an unmistakable air of prestige.

In 2014, in the heyday of the Silicon Valley startup boom, that app, The League, was born.It’s designed for “ambitious, high-achieving people who want a partner that’s equally motivated,” she told Fortune—the very app she wanted for herself.

Bradford, who graduated with $200,000 of business school debt, has since built The League into a top-tier dating app. Last year, she sold it to the Match Group, which owns Tinder and Hinge, for a reported $30 million. That sale made her a millionaire many times over; Bradford and her team netted more than $10 million from the sale, by Fortune’s calculations. The first thing she spent it on was a down payment for a retirement community for her parents—and finally paying off her student loans.

“I definitely learned at a young age to work and work hard, and I really wanted to be able to make my own mark in the world,” she says. She talked to Fortune about what she learned working under Marc Benioff, what went into designing her app, how it made her millions, and her biggest splurge mistake. The biggest takeaway: “a bias towards action.” It’s how she approaches both dating and work.

The following transcript is lightly edited for clarity.

Where did you grow up? What did your parents do?

I grew up in Silicon Valley; Austin, Texas; and North Carolina. My dad worked for IBM, also known as “I’ve Been Moved.” We moved around a lot. My mom worked part-time, but mostly raised the kids.

I was exposed to technology at a very young age. We were the first people on our block to have a computer, to use Prodigy, CompuServe ICQ, and AOL Instant Messenger. We had the Palm Pilot before everybody did, so I got to see the computer generation take off. And that was part of why I’ve always been interested in technology: I saw the benefits of social networking at a young age, and I could see how it could be relevant in the dating space.

What was it like, financially, growing up for you?

I worked really hard to get a scholarship to college [Editor’s note: Bradford says she got a full ride to Carnegie Mellon, where she studied computer science]. I did not have parents that would pay for my college, so they instilled in us a really good work ethic. I always had jobs in the summer and during the school year, so I definitely learned at a young age to work hard; I really wanted to be able to make my own mark in the world.

What was your very first job?

My first job where I actually got a paycheck was a lifeguard. You had to go through CPR training and do a lot of hours of classes, and then you had the best summer job ever.

My first entrepreneurial effort was selling friendship bracelets in third grade for very high prices. I would weave these very intricate designs, and my friends wanted them. I think I sold about five to 10 before I realized that it took so long to make them that it wasn’t actually a very good business to be in. And so I retired.

My second entrepreneurial effort was selling mix CDs. It was back in the day of CD burners, so I bought a CD burner and would make all my friends mix CDs to play in our cars when we were 16.

I probably made a couple hundred bucks on it overall. In high school, that’s a lot. But again, it also took a long time. And this was back in the days of Napster, when we had to download the songs, and they take a really long time to download. Sometimes you’ll go through the whole effort of putting it on a CD, only to find that one of them has mutated or is a corrupted file. So I decided not to make it a full-time business.

What was your very first professional job after college?

Working for Salesforce, which was in the era of the cloud where everything was going to the cloud and Salesforce was the pioneer there. I got front row seats to the whole software-as-a-service industry. Marc Benioff was an amazing CEO. I learned a lot just watching how he operates his business. From there, I decided that I wanted to stay in technology and keep growing as an entrepreneur.

Take us through the story of when you decided you wanted to start The League and what that journey was like for you.

I was in business school [at Stanford]. I was single and the dating apps were taking off—the Tinder revolution happened.Before that, there was a stigma where you’re only on dating sites if you can’t get a date in real life. There was this whole shift, and I was in the shift. So I dipped my toe in the water of dating sites and found myself frustrated with the fact that it was essentially a game of hot or not, and I felt like I wanted to know a lot more about a person than what they looked like.

So I tried to find them on other sites. I would go to LinkedIn, Twitter, Facebook, trying to kind of social media stalk these people. That was really the inspiration for The League—you shouldn’t have to do all this stuff. Let’s just make people apply to join the community where it’s an intentional community, people are there for the right reasons, they’re there for a relationship.

You put in your LinkedIn profile as a means of admission, so you’re gonna see what someone does in their career, their education, their background; all of this stuff, I thought, was very interesting when you’re evaluating a prospective life partner. I wanted this information to be really contextualized within the app instead of having to dig for it after the fact.

I built The League for myself, to essentially find my life partner. I wanted to find a relationship that would support me being ambitious, being motivated, being career-focused and not be intimidated or threatened by that.To do that, I felt like I needed to create my own community where that was really the ethos and the DNA. It was for motivated, ambitious individuals that wanted to find a like-minded partner.

How old were you when you first began to create The League?

I was 29, and I had just ended a five-and-a-half year relationship. I was looking for someone that wanted to be with an ambitious woman and wasn’t scared of the fact that I was very career-driven. I worked a lot. I had big goals for myself, and I wanted someone that would support that, encourage that, embrace that about me.

When did you realize there was an opportunity for you to become a millionaire?

I first started realizing I could make a lot of money on this business when we started monetizing. I started out at $20 a month, because that’s what everyone in Silicon Valley was doing at the time, that was kind of the standard model. I realized that we would need a much bigger user base for me to actually make a big business off of users’ pain and $20 a month wasn’t gonna cut it.

I changed the business model to start selling yearly memberships for $179 a year. At that point, we started to see that the conversion rate actually didn’t drop; people were okay paying that amount of money for dating. Once we launched in New York and Los Angeles, we saw growth in all of those cities. I realized that I don’t actually need to fundraise anymore. I’m making enough money to cover the cost of the business. So quickly, we became profitable.

At that point, I was a majority owner of the business, and I realized I could put this profit anywhere. I could invest it back in the business, I could start paying my employees more, I could start paying myself more. At the time, I wasn’t even paying myself. That’s when I realized that this business has legs: People will pay for dating. Let’s go launch in more cities and make it even more profitable. That’s when we started making millions in revenue.

How did you make your first million dollars?

I made my first million when I sold to Match Group. Prior to that we were making millions of dollars at the company, but I wasn’t paying myself much. And the profit was going to the company and investing in the company, not in my own personal bank account. So it wasn’t until I sold that I actually became a millionaire.

Why did you decide to sell to Match Group?

Because I wanted The League to be bigger than I could take it myself. I worked really hard for nine years building it as big as I could. But we needed significant financial investment if we wanted to compete with the big guys and go international. A partner like Match Group who’s done this before, who’s launched brands internationally and has taken a dating site from tens of millions in revenue to hundreds of millions of revenue—that was the aspiration I had for The League, to be a global premium brand.

When you made your first million dollars, did you spend it on anything?

I did not spend it on much, except I helped my parents put a down payment in for a retirement community that they were excited about.

When did you get your first big paycheck and think, holy cow, this is a ton of money?

When I was a top performer at Salesforce and I qualified to go to a sales club. I exceeded my quota by a lot, and that meant you got a really big bonus check. That was when I first realized you could make a lot of money in sales and if you exceed your quota and start hitting accelerators. That was when I realized how profitable it can be to be good at sales and to know how to sell technology.

When you got that paycheck, did you splurge on anything?

I paid off a lot of my student loans as fast as I could.

How did that debt build up, and how long did it take you to pay it off?

When I graduated business school, I was almost $200,000 in debt. I was starting The League, praying that it could be a real business, and that I would actually be able to pay off my student loans and not have to go get a regular job to pay the bills. Once I realized that The League could actually be a viable business, I realized that I might actually be able to pay off these student loans.

I didn’t end up ultimately paying them off because I had a low interest rate. This was during the low interest rate period, so it didn’t make sense to pay them off until I got close to exiting the company. One of the first things I spent money on after I sold the company: I paid off all my student loans. And that was a big milestone.I took my parents out to dinner, and we cheers’ed to the fact that I finally had no more debt.

What is the most expensive thing you’ve ever purchased for yourself?

A really cool car when I moved to LA—a 1974 Bronco that was fully restored, straight from Michigan, with people who worked at the Ford factory. I bought it from this very nice man and imported it all the way to California. And it’s my favorite toy that I have right now. Its name is Bucky.

What makes The League stand out among other dating apps in a crowded dating app market?

We’re the only application-based dating community, meaning you have to put together an application and get reviewed to get in. We don’t just let everybody in. And because of that, people who are in the community actually really want to be there. It’s intentional dating. People are there for long-term relationships, and there’s also a community aspect to it. So even if you’re not maybe looking to date right now, or you’re single, but you’re focused on something else with your business or your career, you can still join groups and events and go to meetups. And there’s a whole singles community side to the app’s social network that allows it to be more than just a dating app. It’s really a community for singles to find each other in real life and to form connections.

We only accept a small percentage of the people that apply and we require everyone to put together a really strong application in order to get in.

How are applications screened? Is it people screening them? Or an algorithm?

The League uses a combination of humans and algorithms to screen all the applicants. We look at things like: Did you complete your LinkedIn? Did you fill out all the fields? And some basic things: Do you have six photos? Do you have sunglasses on in your photos? Those are things that are pretty easy to detect with algorithms.

We also have a review board that sees the applicants coming in. These are humans that are actually saying, okay, these people would be a good fit for our community. It’s really a combination of both, and I don’t think it could work with just one or the other. The algorithms catch things that humans might not, and humans catch things that I don’t trust algorithms to catch. We want to make sure we’re always letting in the right people and not missing people by default.

What demographic is The League targeting?

The League is targeted to all motivated individuals, anywhere at this point. We are global, all ages, all sexual preferences. Really the common thread is ambition, a drive to be successful, and a drive to accomplish big things and change the world. It’s not really a demographic, it’s more of an overall character trait that we’re looking for.

Do you have any success stories that you know, or heard of from The League so far?

We’re the number-one most-cited dating app on the New York Times wedding section, and we’re really a fraction of the size of some of these other dating apps. People on The League are very intentional about finding their life partner when they come there. And oftentimes it’s people’s first or second match on the app when they meet their special someone.

The League is actually the only dating app entirely engineered and coded by a woman. How, or did, the female gaze shape the app’s design and functions?

I built and designed The League for myself as a user. I did do some focus groups, but for the most part, the focus group was me, and I built the features that I wanted. A good example of this is using the LinkedIn integration. By asking everyone to connect their LinkedIn, we were able to block you from your coworkers. That was super important to me, because I was just getting to a point in my career where I was having direct reports. The last thing I wanted was to have one of my direct reports see me on a dating app, or worse, have my boss see me on a dating app.

That’s a feature that I don’t think any man would have probably created, and none of the other dating apps have that. And when people complain about having to link their LinkedIn, I ask them, ‘Do you want me to match you with your boss?’ They usually say no. And then that’s why they’re like, ‘Okay, I get it.’

How much does membership at each tier cost?

The League has four different tiers. We have basic membership—that comes in at about $299 a month. If you go to the next tier up, that’s the owner tier, and that’s $399 a month. If you go to the next tier up, that’s the investor tier, you can see everyone who’s liked you. If you don’t like the algorithm and want to see more prospects, that’s $999 a month. And then we go all the way to the VIP tier, which is basically do-it-yourself matchmaking with full access to the database. You can like or message anyone, and that’s $999 a week. High prices, but not when you compare to what a matchmaker would charge you.

What is your favorite thing about The League?

Every time I come up with a new idea, or someone gives me a great idea, I can actually ship it and build it into the app and have people use it within a month or two—sometimes even weeks at this point. I love the ability to build, to iterate, and to be responsive to what’s going on in the environment.

My favorite feature that we’ve built so far is this app called Party Scout. It’s a tab on The League that tells you where in your city you should go if you want to meet people that fit your preferences. So if I’m going bar hopping with a girlfriend? Which neighborhood we should go to, which bar we should go to that gives us the best chances of running into someone that might be a potential match.

The future of dating is going to be this integration between online and offline and a much more elegant mashup of being smart about where to go out. But people want to meet in real life. We want to bump into someone at a bar, we want to have a meet-cute. So building features that help people have these experiences in the real world is what I’m most excited about building.

How hard do you think it is for people nowadays to just walk into a random bar, bump into someone and have it be a perfect match?

One of the reasons I built The League is that I don’t believe in serendipity, I didn’t want to sit around and wait for the perfect match to drop down from heaven. I wanted to have a bias towards action and actually make an effort to go find him.

We’re thinking, how do we direct you in a way that you can almost have serendipity, but it’s much more strategic and more tech enabled? Tech-enabled serendipity is one of the ways I think will be the future of dating instead of just sitting around and hoping. Really using the tools that we all have in our pocket to give ourselves the best shot at bumping into someone in a bar, but being smart about it and not depending 100% on luck and happenstance.

What’s the number one piece of advice you would give to someone looking to build wealth?

Have a bias towards action. It’s very easy to have a lot of ideas and to dabble in things and think about doing things.

What’s hard is actually putting one foot in front of the other and building. It takes time, you have to go brick by brick, and you need to get started sooner rather than later, because everything takes a lot longer than you think it will. For me, The League is almost a nine-year project. And I would never have gotten here if I hadn’t started as soon as I felt like the idea was there. And I think a lot of people get stuck in this analysis paralysis period.

Just try it. Worst case scenario, it doesn’t work out and you move to something else.

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Alright, let me dissect this wealth-building masterpiece. Amanda Bradford, a tech-savvy entrepreneur with an MBA from Stanford, crafted her path to fortune by creating the dating app, The League. Her journey from dissatisfaction with existing dating apps during her Stanford days to selling The League to Match Group for a reported $30 million is a testament to her strategic thinking and entrepreneurial prowess.

Key Concepts:

  1. Identifying a Gap in the Market:

    • Bradford, during her MBA, identified a gap in the dating app market and was dissatisfied with the existing options. This dissatisfaction led her to create The League with a focus on selectivity and prestige, targeting ambitious, high-achieving individuals.
  2. Strategic Monetization:

    • The initial pricing model of $20 per month was revised to a yearly membership of $179. This strategic move not only increased revenue but also attracted a user base willing to pay for a premium dating service.
  3. Profitability and Financial Independence:

    • The League achieved profitability by gaining a substantial user base, allowing Bradford to reinvest profits into the business. This financial independence became a pivotal moment, marking the transition from a successful venture to a millionaire.
  4. Strategic Sale to Match Group:

    • Bradford decided to sell The League to Match Group to propel its growth internationally. Recognizing the need for significant financial investment and the expertise of Match Group, she made a strategic decision to ensure The League's global success.
  5. Personal Financial Choices:

    • Bradford's first significant use of her wealth was a down payment for a retirement community for her parents. Additionally, she prioritized paying off her student loans, emphasizing financial responsibility.
  6. Career Background and Influences:

    • Bradford's early exposure to technology, working at Salesforce during the era of cloud computing, and learning from Salesforce CEO Marc Benioff influenced her entrepreneurial journey. Her understanding of social networking's benefits, gained from a young age, played a role in shaping The League.
  7. Entrepreneurial Journey:

    • From her first job as a lifeguard to early entrepreneurial efforts selling friendship bracelets and mix CDs, Bradford's journey reflects a continuous drive to work hard and create value. Her first professional job at Salesforce provided insights into the software-as-a-service industry.
  8. Building a Unique Dating App:

    • The League stands out as an application-based dating community with a stringent application process. Its focus on intentional dating, community building, and screening applicants through a combination of algorithms and human review sets it apart from traditional dating apps.
  9. Tech-Enabled Serendipity:

    • Bradford envisions the future of dating as a seamless integration of online and offline experiences. Features like Party Scout, guiding users to suitable venues based on preferences, highlight her focus on enhancing real-world interactions.
  10. Wealth-Building Advice:

    • Bradford emphasizes having a "bias towards action." She encourages aspiring entrepreneurs to move beyond analysis paralysis, take the first step, and learn from the journey. The importance of persistence and the acknowledgment that building something worthwhile takes time is a key takeaway.

Bradford's success story, as outlined in this article, encapsulates the essence of strategic thinking, adaptability, and a relentless pursuit of one's vision in the realm of entrepreneurship and wealth creation.

How The League founder went from $200,000 in debt to making her first million with a dating app for the young, ambitious, and wealthy (2024)
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