Justine Lee started her career as an M&A lawyer advising multinational corporations, was part of the leadership team that built Citi Bike, and led its acquisition by Lyft. Now, as a partner and Chief Operating Officer at fast-growing early-stage venture firm 25madison ventures, she’s reached unusual heights as a woman in venture. And yet, having just joined the firm’s Board of Directors, as a general partner of its newest venture fund, and with her eye on how emerging technologies and innovation can solve global challenges, it seems pretty clear she’s just getting started.
“Building expertise is important and you need to be good at what you do, but don’t let people put you in a box.”
—Justine Lee, Partner and Chief Operating Officer, 25madison ventures
Jessica Pliska: You’ve worked in public policy, government and as a corporate M&A lawyer, but your defining career turn was when you took a hard left to get involved in launching a little start-up called Citi Bike. It’s hard to imagine Citi Bike as a start-up.
Justine Lee: Yes, when Citi Bike first launched in New York, people were very suspicious of it. Property owners were up in arms, worrying that it would destroy our neighborhoods and create chaos on the streets. It’s funny to look back at now, since Citi Bike has become part of the fabric of the city. It’s viewed as such an attractive amenity by condos and businesses looking to draw people to neighborhoods and has transformed transportation in our city.
Pliska: What was it like being in the trenches there?
Lee: We started out on folding tables in a warehouse in Brooklyn. We had an amazing team of true believers, and I loved it, but I’ve honestly never worked harder. I led corporate strategy for our team, acquiring our key technology provider, spearheading how to expand into e-bikes, building our relationship with the Department of Transportation in New York and negotiating expansion into new cities. We negotiated exclusivity in our contracts with New York, San Francisco and other key cities, which gave us access to all-important street space and helped shelter the company when venture capital-fueled dockless bikes and scooters emerged on the scene in 2017.
Pliska: How much of this did you know how to do before you did it?
Lee: Not much! But I’ve always been game to learn new things as I do them. It’s what energizes me.
Pliska: Why was the job so exciting―and worth such grueling personal investment?
Lee: Because what we were doing was incredibly innovative. Bicycles are an age-old form of transportation, but the technology of shared mobility, finding a bike or dock on your phone, was new. And that stage of growth through acquisition is a singular experience. I loved the all-consuming aspect, being in the trenches with a close-knit team, the tunnel vision to make the company succeed, and the intensity of every high and low. But nothing beats the pride of seeing Citi Bikes on the street. In marketing, there is this concept of ‘how do you “surprise and delight” the customer?’ There’s literally nothing more surprising and delightful than the boost of power you get from the pedal-assist motor the first time you take an e-bike for a spin.
Pliska: What were strategic challenges in that frenetic phase?
Lee: It was a wild time. Dockless bike companies were launching in China and quickly growing to billion+ valuations. One night, we heard that a copycat company in stealth mode was on the eve of launching in one of our cities, with 10,000 bikes, in violation of our exclusive right to operate. We’d been through a massive strategic review of whether to put out a dockless bike product, and had instead decided that electric pedal-assist bikes were going to be the technological game-changer. We’d gained the trust of the city regulators by committing to a responsible program with sustainable funding, and on the strength of those partnerships we kept those companies at bay while we improved our technology.
Pliska: What happened from there?
Lee: We had big vision and ambition for the company. We had started talking to capital providers and corporate strategics like Lyft, in an effort to find a partner who could help accelerate our growth and make the technological investment to bring thousands of e-bikes to the streets. Then Uber announced it was acquiring Jump, and the company Bird launched e-scooters, and suddenly the whole venture capital world was pouring money into micromobility. And then Lyft came on board.
Pliska: Well, that’s glossing it over a bit. You led that acquisition from the Citi Bike side, yes?
Lee: Yes. I had always been a huge fan of Lyft. It has a unique culture and a genuine commitment to shared ridership and the reduction of personal vehicles. To me―riding to work every day on a Citi Bike, and often taking a Lyft home―the convergence of bikeshare and ride-hail felt inevitable. I got an introduction to Lyft in the fall of 2017, and a few months later John Zimmer, the co-founder, flew to New York and we had our first in-person meeting.
Pliska: How did he respond?
Lee: We met him at a hotel in Midtown and gave him one of our test e-bikes to demo on Fifth Avenue in peak-hour traffic, just praying that nothing would go wrong. Fortunately, he loved it and he saw our company as a beachhead from which Lyft could expand into bikes, scooters and transit. In 2018, we merged and our team moved over to Lyft to build out that vision of a broad micromobility platform in the Lyft app. In 2019, the company went public.
Pliska: You’ve said that’s when ‘swim lanes’ came into play for you. What do you mean?
Lee: I was suddenly no longer working for a start-up and we were all growing into more siloed, functional roles. I was told I needed to pick a swim lane but I realized I didn’t want to. I loved having my hand in multiple areas. That’s when I started thinking about going back to earlier-stage companies, where I could continue to do that. It was bittersweet, but it was a moment of clarity for me.
Pliska: I’m sure it surprised them, coming off this tremendous success. Did it surprise you?
Lee: I’ve always had difficulty picking a swim lane. I don’t think people should feel pressure to specialize. I interned at the U.S. Senate and the State Department and practiced corporate law for a number of years at Davis Polk before moving to the business side. I see a continuum between strategy, business development, partnerships, and deal-making, where the same instincts and similar skill sets come into play. My advice to others starting their careers is, yes, building expertise is important and you need to be good at what you do, but don’t let people put you in a box.
Pliska: Then you did what few people do: “I was good at xyz. Let me now try my hand at something brand-new”―in your case, venture capital. Because you had the confidence you could do it.
Lee: I enjoy extending boundaries beyond my comfort zone. My first exposure to venture capital was when we were in discussions to raise outside capital at Citi Bike. Building a relationship with investors, learning to tell our story, and having them in our corner as we encountered challenges shaped my view of the role good investors can play in supporting portfolio companies and being true partners to start-ups. So when I started to think about what I wanted to do next, I thought it would be interesting to see more of the investing side.
Pliska: And to say you’ve landed on your feet is an understatement. You’re COO of a fast-growing venture firm, and you’ve now joined its Board of Directors and its investment committee. Tell me about the firm.
Lee: At 25madison, we both build and invest in early-stage companies. As a venture studio, we back start-ups and entrepreneurs at the earliest stages and we build companies from the ground up. We help entrepreneurs with everything from finding product-market fit and developing a go-to-market strategy, to helping them fundraise and scale. We recently announced a strategic partnership with the private equity fund Apollo, which led our most recent capital raise and gives us access to their portfolio companies, who help us identify the pain points of more mature companies, and often serve as beta or distribution partners to our start-ups.
Pliska: What do you see as a unique asset you bring?
Lee: Neither of my parents is American, and I think I will always see the world through the lens of an outsider looking in. I see things naturally that others may miss about where bias might come into play, whether in recruiting talent or investing in entrepreneurs. And at the same time, I think I have an ability to relate to different types of people and understand how people have different world views. There’s value in the ability to traverse what I see as porous boundaries between different languages, cultures and socioeconomic backgrounds, to highlight areas of commonality rather than difference.
Pliska: On that note, you are one of very few women of color in your field, especially to have risen to these heights. What are the root problems?
Lee: How network-driven VC decision-making is. If investors have insular networks then it’s self-reinforcing. I’m proud of where I sit, because having more women and more diverse perspectives at VCs is going to expand the networks from which we’re sourcing and will diversify the voices and perspectives in the room when we are assessing a deal. We also have to intentionally look outside our networks to build relationships with talented entrepreneurs. And finally, we need to adopt structural changes and policies, like posting job opportunities openly, so that we are not just mining our own networks.
Pliska: What’s ahead that you’re excited about?
Lee: We’re gearing up to raise a new Seed to Series A venture fund. We’re also exploring the possibility of healthcare- and climate-focused funds in the future. The latter is particularly exciting to me because there’s been an explosion of activity in the climate-tech space, and it is a huge passion of mine. I’m excited to have recently joined the board of Aquapao, a company dedicated to access to clean water via a proprietary technology developed by Princeton Professor and Vice Dean of Innovation, Rodney Priestley, that supplies a low-cost way to purify water. And through The Friends of Governor's Island, I’m involved in the effort to build a new Center for Climate Solutions on the island. There’s just so much good stuff ahead.
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