Working with the GOAT: An Interview with Alison Rapaport, Partner at Serena Ventures
Alison Rapaport is a Partner at Serena Ventures, an early-stage venture capital fund founded by tennis superstar Serena Williams in 2014. Serena Ventures has made investments in over 30 companies across multiple industries, including Coinbase, Daily Harvest, and Billie to name a few. Previous to Serena Ventures, Alison worked in investment banking at Goldman Sachs and JP Morgan Chase, as well as in talent management for several athletes.
We had the pleasure of hearing from Alison on advice she would give to her younger self, her path to VC, and how she has stayed motivated during this time.
This interview has been edited and condensed for clarity.
Dana Iverson: What got you into venture, and what is keeping you here?
Alison Rapaport: I never thought I’d pursue a career in venture. However, I’m a firm believer that success comes from focusing on the skills you want to develop and the people you want to work for rather than fixating on job titles.
My path to Serena Ventures started with another sports superstar, ten-time NBA All-Star Carmelo Anthony. During my time at Harvard Business School, I had the opportunity to work with Melo7 Tech Partners, where I was exposed to the world of VC. During this time, I got along really well with Carmelo’s business manager, Stuart Goldfarb, who saw that I understood how to work with sports talent and also had a deep understanding of the investment world, a rare combination of two very different skills sets. He then introduced me to Chris Lyons at Andreessen Horowitz’s Cultural Leadership Fund, who encouraged me to lean into my skill set to support world-class athletes who would like to get into venture but don’t have the investment background.
One meeting led to another and the next thing you know, I’m working at Serena Ventures.
There are so many things that keep me in venture. Each day is a learning experience, I’m learning all the things that I would have had I taken venture classes at school. It’s incredible working with founders to help them solve everyday problems as well as find new companies along the way. We’re working on a mission that is bigger than any one of us and that makes me feel excited to do my job.
I’m a firm believer that success comes from focusing on the skills you want to develop and the people you want to work for rather than fixating on job titles.
Abena Anim-Somuah: Tell us how you met Serena and what drew you to work with her?
Alison: I took my first call with Serena from a bridal store while trying on bridesmaid dresses for a friend’s wedding. I hurriedly picked a dress, which luckily fit, and jumped on the call. We had great chemistry on that call. A week later, she asked me to come to her house and present some ideas to her.
As the famous story goes, I came over with tacos and a binder of pitches. With my little experience in venture, I knew that I had to go in prepared and used all of my resources to get ready. So I spent the week practicing my pitch with friends. My first time pitching was terrible. My friends were asking questions that I didn’t have the answers to, but I got better with time and more practice. When I eventually presented the pitches to Serena, she asked the same questions that I had worked to prepare for.
Serena is such a smart and driven person. She is also disarmingly authentic. She makes you feel comfortable, as if you’re not talking to the greatest athlete of all time. While interviewing for jobs, she was the only person who I felt would empower me to succeed. I felt that it was an opportunity to combine my skill set with a mission and make a difference.
Dana: The goal of Serena Ventures is to “make everyday lives better.” How does this manifest in the companies that you choose to invest in?
Alison: There are a lot of different ways to think about making everyday lives better. It can be as simple as making products more affordable or accessible. We also think about products that are creative, fun, and make life more enjoyable. Inclusivity is a key factor for us, we analyze all aspects of a business with that lens, including who is on the team, who the target customers are, and what the price points look like. This mindset allows us to have a broad and holistic approach to invest in FinTech, Wellness, and everything in between.
Each day is a learning experience, I’m learning all the things that I would have had I taken venture classes at school.
Abena: What traits stand out to you in a founding team?
Alison: We invest early in a market and a founder. We understand that what we see in the pitch deck is not what the product will look like later, and the product will go through a hundred iterations before it is out in the wild.
Sitting in a room for six months brainstorming to find a white space with a huge market opportunity is not the way to build a company. It is important to us that the founder has a personal connection to the problem and is uniquely positioned to solve it.
We also want to see a founder who is self-aware. A founder should hire a team around themselves and hire for what they are not. It can be hard for founders to delegate. The company is their baby! But it is important to have a founder who can be self-aware, handle feedback, and build a team to help them be successful. The founder should find people with experience or a particular skill set to offer advice to prepare them for the ups and downs.
Abena: What is motivating you right now?
Alison: We are in a moment when people have finally realized that inequity exists in all aspects of life — what many of us have known for a long time. Venture is one of the most inequitable places to work. It is dominated by men who try to solve problems and fund innovation for a nation that is rich in socioeconomic diversity yet neither funders nor founders adequately represent our nation.
It is not us versus them. However, we need to acknowledge there is a problem and strive to fix it. We can’t resort to a theater allyship, you have to do the work — write the checks and make the hires. We have been trying to do this for a long time and I’m excited to see the current momentum.
I want to highlight that we do not invest in women and people of color to simply check a box. We invest in diverse teams because we stand by the belief that diverse leadership and diverse thoughts have the best returns, both financially and socially.
What motivates me is our mission to make lives better and ensure that others in the venture industry and ecosystem see the value in innovation for all by all.
I recently had to question a founder at a company because they were building a product for women and did not have any female or non-white representation at the executive level. By highlighting this behaviour and offering support, we are drawing awareness to the systemic issues at hand and showing people in the industry how it can be done.
We are in a moment when people have finally realized that inequity exists in all aspects of life — what many of us have known for a long time. Venture is one of the most inequitable places to work. It is dominated by men who try to solve problems and fund innovation for a nation that is rich in socioeconomic diversity yet neither funders nor founders adequately represent our nation.
Dana: What trends are you excited to see in the world of consumer?
Alison: I’m excited about the refocus on the home. There has been a lot of innovation outside of the home, but now with consumers spending most of their days at home we have the opportunity to think through how to make home life better. The food we eat, the space we live in, and the tools we use at home are all getting a second look.
We’ve made some investments in the food and beverage space but are interested in the holistic wellness space as well. I am excited about companies that are focused on natural ways to get healthier, supporting the postpartum journey, and mental health services for younger women.
Abena: What advice would you give your younger self?
Alison: Don’t get bangs — it is not worth it!
Also, invest in a few good people and don’t try to please everyone. I spent my teenage and college years trying to be liked and now I talk to three people from my high school. In hindsight, I did not need to worry about the other people who barely thought of me.
Try not to control everything. I was someone who lived my life to be on a conveyor belt. I thought I’d work in banking, then work as an associate and go to business school, but my best work has happened when I have hopped off the conveyor belt and took a risk.
Dana: Fill in the blank: “I wouldn’t get through quarantine without…”
Alison: Skincare. I’ve been on a bit of a skincare kick so I have been trying a lot of Kate Somerville’s products.
Television. I’ve been watching a lot of reruns of reality shows. I’ve watched all of Face Off, a show where people go head-to-head with special effects and makeup. It has been fun to watch creative people in that setting because I’m not a creative person.
My puppy Zoe. My fiancé and I have had her for about two months. She has brought so much joy to our family and is a living reminder that there is a world beyond my screen. Zoe is the best decision that we have made in quarantine.
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Abena Anim-Somuah is a contributing writer at All Raise. When she is not working on the Business Development team at Ada Support, she is avidly baking and elevating Black culinary creatives on Instagram , listening to a podcast, or digging into a good book. You can find her on Twitter.
Dana Iverson is a contributing writer at All Raise. She is a student at Princeton University in the School of Public and International Affairs with Minors in Entrepreneurship and Urban Studies. She is currently on a gap-year and works on the Public Policy and Business Development Team at Tesla. You can find her on Twitter.
