siheun song


Sometimes the best business ideas are personal. When Siheun Song and her partner tried to organize a bus trip in college, they needed a simpler way to let people to chip in. That’s how the rideshare service, Rally, was born. Siheun gives us the real scoop on how to start a company (hint: lots of fundraising!), and shares the highs and lows of connecting strangers together.


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When did you move to New York?

I was born in Korea, and we moved to New York when I was four years old. I’ve lived here since then, except for when I attended Yale for my master’s degree. I did my undergraduate degree at Columbia University studying comparative literature and society.

What does that mean?

It means I studied two foreign languages, Spanish and Korean. I spent my entire junior year in Buenos Aires!

Did you know yet how you’d use that degree in your career?

When I was in high school, someone gave me this advice: “If you go to Columbia, it doesn’t really matter what you major in.” [Laughs] So I decided to study what I love: people, culture, and languages. I’m interested in what drives people. When I went to Yale, I did a master of arts in religion.

How did you decide on that focus?

Three members of my family were ministers, so I grew up around religion. I would play piano and organ at church. I actually studied organ at the Juilliard School as a pre-college conservatory student. When I lived in Buenos Aires, I was a music director of a Korean-Argentine church.

In terms of my career path, I always thought of myself as someone who would be in business in some way. Not necessarily by taking economics classes, but by really understanding culture and people, history and motivations. When I went to get my master’s, it wasn't about connecting my studies to a career. It was something that would serve me for the rest of my life in terms of understanding the “why.”

You have to keep seeking advice

What was your next step after you graduated with your master’s degree?

In grad school, I started to become interested in the startup world, and I wanted to see what kind of resources were available to student entrepreneurs. My life partner Numaan and I incorporated our startup, Rally, while we were at Yale. We met on OKCupid—and we love to add that we were a 99 percent match on the site. Yes, algorithms do work! [Laughs]

So that summer of 2014, we were accepted into the Yale Entrepreneurial Institute, which is a program that teaches the basics of fundraising, talking to investors, and getting financials in order. Yale became our first investor—they wrote a $100,000 check for us at the end of that program, which allowed us to go full time and launch Rally in 2015.

Can you describe Rally for someone who’s never heard of it?

Rally is a bus rideshare. It's a platform that aggregates like-minded individuals to take productive, dynamic trips together. We help them organize trips to all kinds of events—football games, concerts, festivals—anytime you have a lot of people getting together at the same place. We create pop-up mass transport around events and venues.

Can you give us an example?

People will usually Google how to get to a certain event. We built our site with very strong SEO, so Rally actually shows up at the top of the search results. For example, let’s say you’re looking for “bus to Kentucky Derby.” You’ll then land on the Kentucky Derby Rally page, where you choose where you want to come from, or you can add your own stop. Rally’s business model is all about sharing, so you have to share in order for this trip to happen. It has to reach a tipping point—essentially, it's a like a Kickstarter for each bus. The bus has to be 40 percent full in order for the trip to be confirmed.


How did you think of this idea?

Numaan was actually the one who thought of it. We had five weeks to arrange our transportation to a political rally in DC, so he thought, “Okay, let me help charter a bus for people.” But then we found out that chartering a bus from New York to DC cost a few thousand dollars. I didn't want to put my credit card down and hope to fill the bus up! We needed enough people to commit to the bus in order for me to put the money down. So within that five-week lead time, we built a crowdsourcing product and had 5,000 paying customers.

How did Rally grow from your first bit of funding to where you are now?

Through a convertible note, we were able to raise an additional million dollars in about three months through the Yale network. I recommend that you set a minimum check size when raising from angel investors, such as $50,000. You have to pitch each angel individually, so setting a minimum reduces the number of conversations you have to have. We were willing to engage with up to 20 angel investors in that round, but many wrote larger checks, so we didn’t have as many.

With the first million, we were able to really figure out what it costs to acquire a customer. We don't want to reach all the millions and billions of fans of all the different kinds of events—we want the ones who have the tickets in hand and are actually going to the event.

In 2016, we became part of another business accelerator called Techstars Mobility, which is based in Detroit. We were able to start thinking about the future of transportation. Why are car makers like Volvo, Volkswagen, and GM investing in rideshare companies like Uber and Lyft? What’s the meaning of a rideshare? And that's where we started to develop a sense of ourselves as a bus rideshare.

Rally is so satisfying, though, because it helps small businesses. There are 4,000 bus operators in the US and Canada alone. That's a lot of companies that own giant 55-passenger buses. They don't have much marketing or the technology to promote their services, and that's where we come into the picture. We built all the apps to digitize the antiquated process of booking a bus: creating dynamic routes, processing payments, procuring the vehicles, and communicating with all parties.

When did you feel sure you were on the right path?

I’d say the turning point was the 2016 presidential election. On the Saturday after the election, we were on our way to work. I looked on Facebook and saw that there was a lot of activity online about a women’s march happening. So I got to the office and immediately created a Rally page for the Women's March and started spreading the link across Facebook. Then, I introduced myself: I'm an immigrant woman founder, this is what my company does, and let me help you. It went viral within a few days, and thousands and thousands of people booked from as far away as Maine, Florida, Minnesota, Texas—cities that were 20 hours by bus in some cases. It was their passion that was driving them, so we ended up moving nearly 50,000 people to DC and simultaneous sister marches. It was the largest mobilization by any transportation company for a single day event.


Wow, that's incredible! Was it challenging to bring that many people together?

Very few companies are in that intersection of politics, transportation and culture. Who else can say, "We're here to support our constitutional right to free assembly?” It got really difficult at some points when women were getting upset that we had sent buses for groups that they don’t support. There were a lot of conversations around, “What's our role as a startup? Do we support this cause and not that cause?” Ultimately, it really helped us understand our values. Obviously, we're going to be led by the things that we're personally passionate about. Those events will probably thrive because of that personal passion, but it doesn't mean we have to be censors.

How big is Rally now?

Right now, we have 10 people in the core team. We also work with of lot of distributed team members who are doing technology, marketing, design. With everyone, it would be closer to 30 people.

What events make up most of your business?

About a third of our trips are for sporting events. We just signed a contract with the Buffalo Bills, for example. The second largest percentage would be festivals and music concerts. The other third is smaller groups: wedding parties, schools, and, of course, political rallies. Our mission is to unite people with their passions.

Do you have a goal for Rally?

Yes. It's to become the brand that is synonymous with buses. When you think of buses, you're going to think of Rally.

I think sometimes people are also curious about what it’s like to work with your life partner. Can you talk about that?

I think Numaan and I are very fortunate that we both grew up in immigrant households where we watched our parents work together. My dad is a Methodist minister but my mom’s role is minister's wife. She supports him through every facet of the church life. But if you look back just a few generations, that was kind of the norm. Parents worked together in a farm—there was division of labor and they were working towards the same ends. That's kind of how we are, too. He takes care of the technology and business side. I'm taking care of the creative, marketing and the business development side.

What's the best piece of advice you can give?

You have to keep seeking advice. Set up your own personal board of advisors. The people who you look up to can give you very different and contradictory perspectives, because nobody really knows the answer.

What does New York mean to you?

New York is home right now, it’s where my friends and family are. It’s important to me to be surrounded by people I love.

Learn more about Rally here


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Photography by Stephanie Geddes ©


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