Image by Greg Betza

Alison Rapaport (MBA 2018) has always been passionate about sports, both as a spectator and a participant. “I love being part of a team and I’m super competitive, so I like to win,” she laughs. Rapaport grew up in Los Angeles playing soccer (she named her car for English footballer Michael Owen) and rooting for the Denver Broncos (her mom is a native, she explains). After completing her undergraduate degree at Wharton, Rapaport took on a range of investment banking roles. “I learned that I loved the challenge of learning but I wasn’t passionate about markets,” she says. Her interests leaned more in the direction of strategy—and sports.

Rapaport found plenty of outlets in both areas at HBS, where she was president of the Business of Sports Club. She also volunteered for Crossover into Business, an HBS program launched in partnership with the NBA. While she stands just over five feet tall, Rapaport was the number-one draft pick of Orlando Magic forward Al-Farouq Aminu, who saw her experience at Jefferies, JP Morgan, and Goldman Sachs as a definite plus in helping chart his own financial future. Rapaport mentored Aminu in the semester-long program—led by HBS professor Anita Elberse—that develops the business skills of highly paid professional athletes, who all too often make questionable investment decisions. (It has since expanded to include athletes from a variety of disciplines, including skiing and ballet.)

She also made an invaluable connection while working on an independent project with NBA All-Star Carmelo Anthony, an investor in Andreessen Horowitz’s Cultural Leadership Fund. “Chris Lyons, who oversees the fund, told me, ‘The number of people who understand how to work with talent and have an investing mind is very small. You should lean into that.” Lyons offered to send Rapaport’s resume to some of the investors in the fund, including Serena Williams. After much due diligence, multiple pitches, and a well-timed taco lunch (Rapaport brought the fixings to the tennis great’s home), Rapaport won a coveted role overseeing investments at Serena Ventures, a fund backed by Williams with an emphasis on startups that make diverse leadership and inclusivity a priority.

Rapaport manages a portfolio of close to 60 early-stage investments focused on companies in the health, lifestyle, and fintech sectors. To date, Serena Ventures has a market cap portfolio of $14 billion, with 60 percent representing diverse-founder investments. “Venture is a network-based community,” Rapaport observes. “If you’re not building your network to be reflective of the country that we live in, you’re not giving the opportunities to everyone who deserves them.”

Is there a particular skill set involved in working with celebrities and professional athletes?

You need to do well with ambiguity. It’s not a situation where the CEO has a five-year plan to execute. Most talent hasn’t worked in a professional setting. There aren’t OKRs [objectives and key results] or job descriptions. Every day, new opportunities are coming up at Serena Ventures; we’re thinking of multiple timelines and different lines of business. I might get a text from Serena about a deal we haven’t talked about in a while, but now it’s top of mind. The ability to jump from one thing to the next and be organized while doing so is super important.

How would you describe your working relationship with Serena?

It takes time to build trust with someone who is a celebrity, so I definitely think my first year and now, my third year, are very different. Serena isn’t a micromanager, but she knows every company in the portfolio, and we talk all the time. She’s very funny and disarmingly authentic.

I would also say that our skill sets are different and super complementary. I’m more on the analytical side, the portfolio-construction side. She can get an amazing read on a person and see the big picture really quickly, whereas it takes me longer. I think celebrities don’t always experience pushback, but I give that, which she respects, and she does it with me.

What happens when you disagree about an investment’s potential?

We’re very different. We don’t always see eye to eye. Sometimes I go to her and I’m super passionate about something, and she just doesn’t see it. And vice-versa. Those situations can go a couple of ways. Sometimes, I’m going to push through because I think it’s important. We’ve both done that, and have companies in the portfolio where we say, “Look, this is on me. I really believe in this company.” But for the most part, we don’t invest if we can’t both get there. We don’t make decisions lightly. It’s an iterative process. We just invested in one company that I think we first met a year and a half ago. While we don’t always agree, I would say we get there with 90 percent of the companies in the portfolio.

What has your work been like during the pandemic?

Not that different, in the sense that Serena is never, never in the same place for more than a week or two at a time. I’m based in San Francisco, she’s based in Florida, and we have an associate who also is in San Francisco. We’ve always been a quasi-remote team, so we’re used to texting, FaceTiming, and Zooming. I moved from a coworking space, which I loved, to my dining room table, which I don’t love as much. At the beginning of the pandemic, Serena wasn’t competing, so it sped up some things we were trying to get done, which was great. In that sense, I think it was almost a net positive for us, which is a rare thing to say during the pandemic.

Do you feel like you can get a sense of a team when you’re doing (virtual) due diligence on a potential investment?

Most of the deals we’ve done since the pandemic started were ones that we’d been tracking for a while, and we’d met them in person before. But we did just do a deal in where we’d never met the team in person. It’s harder for sure—particularly when it comes to getting a sense of company culture—and it takes longer; but I think everyone’s at a point where we’ve gotten better at communicating and reading people via Zoom.

How would you describe your investment strategy at the moment?

Broadly speaking, it’s about making everyday life easier for the everyday person right now. Our whole world revolves around our homes at the moment because we’re not going anywhere, for the most part. COVID-19 is going to fundamentally change some aspects of our lives. People are cooking more and creating new spaces for themselves to work from home. I have 24 plants in my apartment that are still alive because I’m here every day to take care of them. We like to think of ourselves as investing for the future, and home is part of that. But we’re generalists, investing across multiple sectors, including health care, environmental sustainability, and fintech.

Can you give a few examples of recent investments?

Pachama, a startup founded by Diego Saez-Gil, is leveraging data and AI to create a carbon-offset marketplace for companies through reforestation projects. Another I’d mention is Every Mother, which offers exercises, education, and support for postpartum women who are experiencing diastasis recti, or abdominal-wall separation. This company has created a medically and scientifically proven approach to help repair the condition, which can cause issues with internal organs and other complications for years.

Does the Black Lives Matter movement have the potential to accelerate change in venture capital?

I’m cautiously optimistic. I think investors are seeing their portfolios in a way they haven’t seen or thought about it before. Some of the work comes from investors putting pressure on the companies; when we’re meeting with a company with a customer base that is 70 percent women and there’s not a single woman on the executive team, we’re going to talk about that and ask the hard questions. The founder is important, but so are the first 10 employees. They set the culture, and it’s also where the wealth creation comes from.

We don’t approach it as an “us-versus-them” situation; Serena has always fought for inclusivity. We have a conscious bias toward companies with diverse leadership and companies focused on solving problems that disproportionately affect women and people of color. Both are systematically overlooked by venture capital, so that’s just good business.

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