Rebecca Liebman - CEO & Co-founder @ LearnLux

“You have to figure out what your flaws are, how to build around that, and how to bring people on to fill those gaps.”

Meet Rebecca Liebman, CEO & Co-Founder at LearnLux. Rebecca started LearnLux when she was an undergrad, and built an idea into a platform that empowers people to understand and take control of their finances. We chatted with Rebecca about reinventing a legacy industry, why being a student founder has many advantages, and how her view of leadership has changed over the years.


Tell us about yourself.

Here’s a story that sums it up: when I was eight years old, I was in a Girl Scout meeting and we were all making an arts and crafts project with tissue paper. I made something different and got yelled at because we were supposed to end up with this flower and I didn't do that. I took what I was given, and made something else, which I think is comical now because that's pretty much what I've done in life.


That’s a great story. Can you tell us about how you founded LearnLux?

I was working at a lab at MIT, and my whole lab was Ph.D.s and Postdocs, looking at machine intelligence and network effects. Every day at lunch, people in my office would have lunch in Kendall Square and they kept asking me all these finance questions: “How do I open a retirement account? What do I do with my student loans?” I thought it was comical that the smartest people I knew didn't know how to open a retirement account, which seemed like it should be a simple thing for a Ph.D.

I called my brother Michael who was working at a bank. I told him what was happening in my lab and he said the same thing was happening at his bank where people knew corporate finance, but not personal finance.

We realized that your ability to make money doesn't mean you have the ability to manage money. Many times the most intelligent people are the most scared to ask questions.

I went back to school (Clark University) for my last year, and wrote my thesis on the idea that most people think they're bad at personal finance. In reality, financial services aren’t meant to serve Americans as our society exists today. Financial products were made decades ago. Our generation is very different and has different needs than ever before. For example, there are 55 million Americans who don’t have 401K retirement benefits through their job, because they are part of the gig economy, and they must figure out investments and insurance when they don’t get it from their employer. That never needed to be created fifty years ago. There are also double the number of women in the workforce. There are a lot of ways we can create more access for people, adapt financial services to society as we see it today, and change the financial system in the process.


What has your experience been like being a student entrepreneur? Do you have advice for other students?

My co-founder and I have a thesis that founding a company in school is the best time to start a company because you really don't have anything to lose. Being at a university is like a living lab where you don't have to pay for anything besides what you already would be paying for, and you have amazing resources available to you, and you are surrounded by really intelligent people. It's pretty much the perfect place to test an idea, even if it doesn't become a company. For us, we found an interesting topic that we wanted to explore and it started gaining traction really quickly.

There are so many more resources to start a company now, like Rough Draft Ventures or Dorm Room Fund.


What has been really surprising to you as a founder?

One misconception that I had is that when you start a company, there's one big problem that you'll encounter that you have to get over and that's not really how it is. Instead, it’s like a thousand little problems that just happen every hour, every day that set you back a little bit. And they add up. People ask what is the one huge challenge- there isn’t just one.

Also, when you're a founder, all of your flaws are magnified in front of you. If something isn’t being done, it is because you can’t do it or you’re not doing it.

There's a very glorified, glamorous idea around starting a company. In reality, it is 99% dealing with everything that has to get done. You have to love what you are doing in order to run a company. Eventually, you get out of the honeymoon phase and realize this has to be a huge thing, and that we are going to be the team to make it happen.

You have to figure out what your flaws are, how to build around that, and how to bring people on to fill those gaps.


How has your view on entrepreneurship changed over the past few years as you have worked through LearnLux’s journey?

Two things.

It's a long game. Everyone knows each other in the startup community. Everyone is hyper-connected (Boston, New York, San Francisco, etc.) and so it's just a matter of figuring out how to get to the people you need to get to.

What you start to learn about entrepreneurship is that:

The world's a huge place and every place is very different. A lot of people go into this starry-eyed thinking you can make this huge change. And you can, but it's really about starting small and then creating this ripple effect that can just perpetuate because you can't attack everything at once. The biggest thing for me that changed is going in with the mentality that I can change everything really fast. But then I realized that there are 7 billion people in the world pushing one way and I'm one person pushing the other way.

That's what entrepreneurship is- you have to love it so much that every time you hear no and every time 7 billion people are pushing against you, you're still pushing the other way. You realize that you have to start small and grow strategically over time.


What do you find most challenging and exciting as an entrepreneur?

Challenging: I never really expected what it was like to surround yourself with the right people- building a team, hiring. It is the most important thing. What you cannot plan for is how humans interact. There are dynamics you can’t plan for. If you have 20 people on your team, and you are hiring 5 more, do you let everyone interview? At some point, someone has to make a decision. Do you at some point just have to say, they fit this role and if there are these other dynamics that you two have, you're going to have to figure it out. Human dynamics is the one thing you can't plan for as you build your team.

Exciting: When we started the company, I was a twenty-year old woman in fintech, one of the most male dominated spaces. Initially, I would go to events and it would be all 60-year old men, and no one looked like me, or thought like me. At first, you try to assimilate to what the existing culture is and I think early on I discovered that's not who I am. I am not going to be able to think like them. I knew I already thought differently about the industry and I think the reason we're so successful and will beat incumbents in the market is because we come from such a different perspective. And don't have analysis paralysis of working in the industry for thirty years.

People are different today than what used to exist. We can change the market because of all this data that looks at how people today make financial decisions. Ultimately I'm just excited about creating more pattern recognition for women, especially in fintech, because right now there just not enough people to look up to as role models in this industry. As a company we will be able to change the industry because we think differently and I also think we'll be able to change society because more and more people will have someone to look at and say there's a positive pattern here of women being successful in the space.


How has your view of leadership changed since being an entrepreneur? What is your leadership style as a CEO?

The one thing that I believe is that you should always hire people smarter than you. Being a young founder I always want to surround myself with people who are world class, people who know their stuff and know how to get work done.

My leadership style is the idea that I'm not hiring you to tell you what to do, I'm hiring you to help you understand the vision of what we're creating and then you're going to be able to run your team and run your own projects.

It’s definitely evolving over time.


On the topic of being a boss without ever having a boss, how did you get scaled up to being a CEO?

You make a ton of mistakes. To learn, I read a lot. I am very interested in behavioral economics. I read a lot of Adam Grant. I love to think about how people think, how people take in information, how people make decisions.

I'm a big believer in, you can make the right decision or you can make a decision right. Within a startup, you have so few data points to make a decision, that you really have to just make a decision and then make it right because at the time you have no idea how that is going to play out.
I kept getting the advice to wait until you are ready. People always say, oh you should work for a couple years and get experience. You are in school and have no time, no money, no experience, why don’t you wait until you have those things? But you can make those excuses every single year.

You can always have more time, more money, more experience. I always say if you wait until you are ready, you will be waiting for the rest of your life.


Switching gears to diversity and inclusion. You host monthly women-in-tech dinners. What inspired you to do that?

Most of the events I go to, no one looks like me. It started with the idea, “can we trick women into getting into tech.” A lot of people that I talked to would put deterrents in their way, “I don’t know enough yet,” “I don’t have enough experience.” We actually started it as a way of bringing people together and as we hear about opportunities, can we get more women in, because their friends will already be in tech. I also wanted to be around people who were also ambitious but weren’t triple my age.

I love the idea of helping other women, because why do I not want all of my friends to be the most successful women? In ten years, all of my best friends should be the most successful women because we are creating this network effect. The largest community of women supporting other women.


To that point, do you think there is a way that women can foster better community and networks?

There is so much we can do. Jennifer Hyman from Rent the Runway actually talked about this- changing the wording that both men and women use to talk about women in tech. The words “visionary” are always used for male CEOs, but rarely used for women.

Whenever I talk about other women, I'm very aware of the wording that I'm using to make sure that it is this powerful, ambitious, visionary type of wording that people use for men who don't know what they're doing but not for women who have a plan.

Change the way you talk about people, change how you interact, and want to support other people because it will only benefit society as a whole. There is a lot of overt sexism and inherent biases against women. Things that you say that you would never say to a man, but don’t realize you are saying. There are deterrents, but we are at a point where we have a huge opportunity to change that. We are at a point where we can create more pattern recognition for women.


Fire Round:


What is an industry trend you are most excited about?

I see a huge trend of investors, even SF investors, seeing value in companies outside of SF. Steve Case has been a huge leader in this!


What is your favorite book or article you have read recently?

The Harvard Business Review article on how investors talk to men and women differently. The idea of preventative versus promotional questions. After I read that I started seeing and hearing it everywhere.


Who is a female entrepreneur or investor that you'd most like to meet?

Julie Rice from Soul Cycle. She built a brand that people will fall on a sword for.


What is your spirit animal?

Giraffe- because I am tall on the inside. It’s funny because I am short. I always feel like I am at the same level as someone if I can just see their eyes. We are the same height!


What is the best piece of advice you have ever received?

What you worry about isn't what happens and what happens isn't what you worry about.


Want to learn more about Rebecca and the LearnLux team? Check out their website.


Samantha Kaminsky