Coffee Meets Bagel CEO on turning down $30M on Shark Tank, working with family, and pursuing her dream

Before she headed one of Millennials’ top stops for dating, Coffee Meets Bagel CEO Dawoon Kang took a gamble. She didn’t have to, but an inner calling was urging her to do something different with her life. Coming from a family of entrepreneurs, Kang was working for JP Morgan when she wanted to start her own business. Together with her two sisters, they started Coffee Meets Bagel, the Millennial dating app that stresses slow dating compared to hook-up counterparts like Tinder and Bumble.

Kang recently visited Ladders’ offices in Manhattan to speak at length about her experience as CEO, the dynamic of running a company with her twin sister, why she left JP Morgan to chase her dream job, and what would she do if two employees met using her app.

Career pivot

You worked at Avon and JP Morgan before leaving and starting Coffee Meets Bagel with your sisters. Some would say that’s a risk. What influenced your decision in changing career fields?

“I grew up in an entrepreneur family. My sisters and I always knew that we wanted to start a business together. It was very inspiring, particularly my dad, because he ran a pretty sizable business which he built from ground up with his brother. It was a recycling metal business which had different factories. He actually built a lot of the plants himself. He was an engineer and patented a lot of them. He went through hiring and firing, sometimes going through layoffs — that was his baby. Sometimes he would just wake up and start talking about work. He probably didn’t really care that we didn’t really understand the things he was saying, but I think just the energy was very contagious.

Follow Ladders on Flipboard!

Follow Ladders’ magazines on Flipboard covering Happiness, Productivity, Job Satisfaction, Neuroscience, and more!

“It became something that we knew we were going to do. We just didn’t know when. Of course, we all had our own interests as well. For me, particularly in finance, I went to Penn. Wharton has a very strong presence on campus. I majored in psychology, I was a Liberal Arts major. I think part of me always saw finance as this mysterious power and intelligence. I kind of wanted to try it for the sake of finding out what it’s like to be in it. I was partially interested in the field of micro-finance for economic development and knew that in order to get into something like micro-finance, like private sector finance, experience only helps. I never really saw that as my calling or anything. It was very intellectually stimulating. There’s always something exciting happening and you’re surrounded by colleagues who are really driven and ambitious. I knew very quickly that this wasn’t something I wanted to do for the long term because it doesn’t feed my soul. I did it for three years and then at the time, my twin sister graduated from school. She said we always talked about starting something together, why don’t we just try it now. That’s when I moved off.

“A lot of people ask me, ‘Was it hard?’ I think because I grew up in an entrepreneur family it didn’t seem that crazy to me. Jeff Bezos talks about this a lot because he also comes from Wall Street. He talks about how he started Amazon where he was packing boxes on the floor and what not. He uses this framework called regret minimization model. It’s basically like imagine yourself when you’re 60 looking back, what decisions will you regret making the least? “I think that’s where you don’t want to be for yourself, no matter what the outcome is. I thought that was such a no brainer because I got to work on something that I wanted to do since I was little with two really awesome people. Being able to give it a go and create something that could impact millions of peoples lives, I mean, it just really felt like a no brainer.”

dawoon kang coffee meets bagel

Making a name for yourself in a crowded space

What about joining the dating app landscape? I feel like it’s always changing with what’s hot and popular while others die off.

“It’s never really changed. A lot of people really think dating just heated up recently, but it’s actually not true. It’s always been like this, just not in mobile space. There’s never been a shortage of dating services. The competitive dynamic is still the same. The reason why we landed on dating because we think it’s an interesting problem. If you’re going to do something for a long time, you better make sure it’s something that you’re really passionate and invested in. It has to be really meaningful to you. We said, ‘Hey, what’s more meaningful than enabling people to find someone significant in your life?’ It really does have a transformative impact on you. That felt really good for us. It was an interesting but very hard problem.

“We also saw market potential. There are millions of singles coming online globally. It’s growing 15-20% every year. It’s a very huge market. We also saw white space in this sea of dating services. We didn’t really see a dating service that took this slow dating angle that focuses on quality. We really thought that was the best — and better way — to actually create real connections that add something more to your life instead of just swiping all day.”

The leadership transition

What’s the most surprising aspect of being a CEO for you?

“One thing that I didn’t realize starting off when you get to a company of 20-25 size, that’s probably the biggest transition for a CEO who’s a founder. When you’re starting small as a founder, you’re basically a product person. Your vision, and the problem you wanted to solve, you brought the product into life and you’re just building it. You’re the product manager basically. Once your team becomes bigger, you actually become a manager and a leader. That transition is actually the hardest and the most jarring for a lot of founders because we start off as a product person and we feel like that’s what we need to be doing. But you kind of start having to let go of that and you need to think about how to build an organization. That takes a lot of investment and work. That’s something that should be talked about more.”

Was it difficult for you?

“I think it caught me by surprise. It wasn’t difficult. Luckily, I enjoy both — not every founder is like that. But I think I was caught by surprise by how I was spending too little time on leadership and managing and recruiting and retaining. Those all take a lot of time. There was a period of time at CMB that I saw some turnovers very unexpectedly that made me realize what should I be prioritizing at this juncture of this company. I realized I wasn’t spending enough time at this area of my job which has now become more important because, in order for my company to be successful, I need have to succeed through my team. I can’t be the one who is actually doing things anymore.”

Being that you run a dating app, what’s your stance on inter-office dating?

“Our teammates use CMB and other dating services because we can always learn to go on dates. A lot of us are single and very much like our target user base. We actually have a singles channel on our Slack for all our singles and we have conversations like these. They are the first people our product and marketing team go to to get immediate feedback. In terms of office dating, we don’t encourage. We don’t have a specific policy on it.”

But, hypothetically, what if a coworker were to match with another coworker through CMB, would you encourage the relationship”

“I wouldn’t encourage it like, ‘Oh, I think you guys should date.’ We’re very small so everyone knows each other. If they were to see each other on the app and something starts happening, I think that’s great but I’m not going to encourage that, per se. It’s their personal thing. We encourage everyone to use CMB because they are single and dating. But if they are single and not dating, I don’t want anyone to feel pressured to use it.”

Swimming with Sharks

In 2015, CMB went on SharkTank and turned down reportedly the highest offer ever ($30 million) on the show. What were you hoping to accomplish on SharkTank?

“We were looking for a deal and exposure. Shark Tank is great because it gives you both.”

If Mark Cuban were to offer you $30 million today for CMB, would your answer be different?

“No, I don’t think. The problem that we set out to solve which is dating is such a hard, exhausting thing. It’s honestly gotten worse with the rise in Tinder and mobile dating apps that emphasize and causes all this swipe fatigue. There’s actually is even more and a real desire and real awareness with this not being the right model here. Years later now, I don’t think there’s better timing for a service like CMB because of how the dating industry has evolved.”

Coffee Meets Bagel had a big year last year. The app doubled its user number and raised $12 million in its Series B in 2018. The app underwent a redesign and introduced a ton of new features. Is there anything else on the horizon to look out for?

“We have so much stuff coming out that I’m super excited about like our subscription [program]. We haven’t even rolled out the actual product because it’s still being built into a package that we want to present. But the experiments we have done have been extremely successful, but we want to make it into this ultimate dating hack where it’s a super no-brainer. I’m sure Ladders’ audience falls into a similar category: they want to be super productive and whatever they do, they want the biggest bang for their buck. If you’re that person, it’s no brainer — you’ll become a CMB premium member because it’s a great way to get results fast. We are adding things like priority likes where you’ll always be the first to be seen by your potential matches. There will be unlimited likes. We give our users a limited amount of matches because if the user is actually exposed to too many, they are just going to be swiping. But if you’re someone who’s willing to prioritize and commit to dating and making a lot of room for it if you’re becoming a premium member, obviously you’re not going to swipe and you’re going to still be thoughtful, so we’ll give you more. You have access to activity reports, where you’re with more data from your matches so you’re not left wondering if they saw your chat, how likely are they to respond, do they actually typically initiate chats? It’s kind of like your superpower.

“We’re actually creating a section called ‘Likes you for you’, where you’ll actually spend only time on people that actually liked you. It’s just going to power-boost your dating life which comes out in July. It’s our way to fight to ghosting. Besides the subscription package, not everyone is going to have this approach of wanting the best bang for their buck. A lot of users are not going to want to do that. We want to make sure our basic service is still really good and differentiated and delivering our mission. There are features for everyone. My philosophy with how dating apps have evolved in the last few years is about swiping and what not.

“We get a lot of inspiration from other dating services like matchmakers like how can we bring in some of their ideas instead of being just a regular dating app. There’s going to be a lot of those features coming up in the summer.”

What’s the most enjoyable part about being a CEO?

“There are two things. If I think about the stakeholders of my company, it’s our customers, my team, and then my shareholders, which actually include my team and investors. What gives me joy the most is when I’m able to make them feel joyful and fulfilling. Nothing makes me happier than that. For our customers, when we hear from them about what kind of impact Coffee Meets Bagel has had on them when they share photos or stories or their babies. Even if they didn’t get married, they still learned something through the people that they met on Coffee Meets Bagel. Nothing makes me happier or more fulfilled than thinking my time was worthwhile.

“I would say my team has a higher impact on joy than even the customers. That might sound weird, but I work with my team on a daily basis. I come into the office and see them working so hard, building and making our vision come true. Seeing them with each other really gives me a lot of joy. Recently, we celebrated the anniversary of an employee. Any time there’s an anniversary, we celebrate together. My teammate was celebrating his four-year anniversary with us. In the Valley, the average tenure is not even one year. This was a big milestone. He wrote me such a nice email about his reflection on the last four years and what kind of impact working at Coffee Meets Bagel and with me and the teammates has had on his life. It brought me to tears. That’s hands down the most fulfilling part of my job, making an impact on my team and working with my team.

“Of course, if something doesn’t really go well, that’s also the most stressful.”

Keeping it in the family

What’s the dynamic of running a company with your twin sister, Arum? I’d have to imagine there are times when you butt heads.

“It’s not easy. The great thing is we have a level of trust and respect for each other. That’s something that needs to be talked about more. I feel it’s the most critical attribute you need to find in your partner or co-founder because even if there’s a little bit of dent in trust, it causes a ton of dysfunction in your company between you and your co-founder. Even if she does something I don’t understand, she has the best interest in the company and the best interest in me. She would put that ahead of her own needs or visa verse. I have no doubt in my mind about that which is really awesome.

“On the flip side, there’s a lot of things we have to deal with being sisters, having that baggage and growing up as sisters when we were little. We started as co-founders. My older sister [Soo] left because she started a family and wanted to focus more on the family. My twin sister and I run [Coffee Meets Bagel]. Being twins, you get compared a lot growing up. You self consciously compare yourself to the other person. There were certain levels of a competitive dynamic that have gone on and on throughout our lives. We do butt heads from time to time, actually pretty frequently [laughs]. The good thing is we have the tools now to be able to work things out because sometimes it gets heated. I think it’s very important for our roles to be clearly defined such that whenever there’s an issue that can’t be resolved, we have to differ it to the other person when it comes to their own domain as long as we stick to that. In the very beginning, it was very hard to stick to that but now whoever owns that domain owns the ultimate call.”

5 questions

What’s the best advice you never listened to?

“I didn’t ‘never listen’ to it, but I definitely didn’t get it. The value of relationships. Really, that’s everything. Not only for the success of your business but for your life. At the end of the day, that’s what matters. If you actually got something at the expense of the relationship, you’re going to regret it.”

What’s the last book you read?

“I’m currently reading “A New Earth” by Eckhart Tolle. He’s a really amazing philosopher who really talks about the new earth. This might be a little bit out there [laughs] but people’s conciseness wakes up and we become aware of who we are as ourselves versus our ego. A lot of times we think its the same but it’s actually not.”

Are you a podcast listener? Have any you’d like to share that impact you?

“One of my favorites is “Impact Theory” by Tom Bilyeu. I look up to him so much. A lot of things I share are tidbits that I get from him. He talks a lot about dating because he and his wife actually starting a company together and in the “Impact Theory,” he interviews a lot of great people. Sometimes, he has podcasts that are focused solely on relationship because of both of them on. He’s my hero.”

Do you have a morning or nightly routine you try to stick by?

“I have a set routine. It’s nothing innovative that I do, but I have a gratitude journal. Sometimes I write or if I feel lazy or too tired, I actually tell my partner. In the morning, I do the same thing every single day. It’s by this guy named Hal Elrod called The Morning Miracle. It’s six things: you meditate, exercise, visualize, you have affirmation and you read and write.”

Would you say this is your dream job?

“This is my dream job! It’s funny — I also went to business school and in the last semester, we have a seminar dedicated to life outside of school. I remember one of the alumni coming and he was talking about his job saying how he wakes up every day to go to work and how he feels grateful for having this job. He said he couldn’t believe he got paid to do this. After he left, we were having discussions with our classmates, asking each other, ‘Is that possible?’ We all concluded that wasn’t possible and it was BS. It’s so funny looking back on that because I’m in the same position. Certainly there are days when I don’t feel like this, but usually, I wake up feeling super energized and really lucky to do what I do. I feel really lucky for the team that I have and really humbled and honored by the opportunity. I think it’s a privilege to run Coffee Meets Bagel and I can’t believe I get paid to do it.

“I could say I wish I could work a little bit less and that’s something I’m working on. It does sometimes get overwhelming.”

If someone is in your similar position thinking about leaving a solid, safe job to chase a dream, what would you tell them?

“This may sound out there, but take time to listen to yourself. That requires sitting still and listening to yourself. When it comes to a dream job that actually not in the realm of what you’re used to, there’s a lot of skepticism and doubts. You fear that’s going to be there. It’s going to sway you the other way. It’s going to confuse you and you might end up believing that this isn’t what you want to do. It’s very important you create room to listen carefully about what your mind and body is telling you. Keep inquiring. Figure out what the fear is and keep asking. That’s really an important element.

“I also think creating support is also very important. Of course, if you have more support, it’s going to feel less scary. If you have a supportive family, supportive friends or finding someone who’s actually done this, it’s very important.

“I guess this is all mitigating fear so that you can actually just listen to what you really want. This also helped me out a lot. Imagine your worse scenario. For me, it was starting this thing and it not going anywhere. We said we were going to do this for a year. A year in the grand scheme of life isn’t a whole lot of time. We invested our own money and I invested the money I was comfortable losing. After a year, if it doesn’t take off we move on. It’ll be a good experience and I could go back to doing what I was doing before. When I positioned it that way, it didn’t feel like a big deal. To think it’s a choice I have to live with for the rest of my life is really scary. But that made it easier for us to make that change.”