On December 9, we wrapped up our Table Stakes Summit with a conversation between Kirsten Green, founder and managing partner at Forerunner Ventures, and Serena Williams—tennis superstar, entrepreneur, fashion designer, and founder and managing partner at Serena Ventures. They chatted about Serena’s investing philosophy, diversity and inclusion, and more:
(This transcript has been edited and condensed for length and clarity.)
Juggling a million things
Kirsten: You wear many hats on a regular basis, and you do it all to such incredible accomplishment and with so much grace. How do you prioritize things in your life? And how do you enable yourself to be as successful as you are juggling all those things?
Serena: Prioritizing is super important. You have to decide what you want to focus on and what you want to do. For me, it’s about being super, super organized. I know that tennis is first in my life, outside of my family and God of course. Everything else works around that.
But it’s easy because my job is such a blessing. I get to train first thing in the morning, I wake up at eight, finish everything by 10, and I have the rest of the day to focus on other things that I want to do or that I’m doing.
Kirsten: Being an athlete at a professional level, being an investor at a professional level, being an entrepreneur, and running your own businesses—those are really different activities. How does Serena show up in each of those? Is it the same Serena, or do you think about putting a different hat on at different times?
Serena: It’s definitely the same Serena. I feel like being an athlete and playing at such a high level has really prepared me to be able to play in the new field of being an entrepreneur. It’s really the same thing. My whole life, I’ve been wanting to be an entrepreneur, and by playing tennis, I am an entrepreneur. I’ve always been an entrepreneur because I’ve had to grow my own game. I had to do everything to grow. So it’s such a natural transition because I’m still doing things on my own. I’m still building on my own, and I’m still learning—taking all the lessons that I got from tennis and incorporating them into entrepreneurship.
I’ve always been an entrepreneur because I’ve had to grow my own game.
Entering the business world
Kirsten: What do you think of as the inflection point when you felt like you were taking your game off the court into business? What was the first foray that led you there?
Serena: That started for me over a decade ago. My dad always told myself and my sister to prep for after tennis. He always said, “Serena, you’re an athlete. Anything can happen on any given day. So you always want a plan B.”
That stuck with me for many years. So when I was a teenager, I ended up going to fashion school. I always joke that in between winning Wimbledon and the US Open, I would be in school. That set me up to be able to multitask at a high level because fashion school is one of the hardest things I’ve ever done in my life. Everyone had a meltdown at some point. It was super intense—the curriculum we were on was insane.
But I’ve always been setting myself up for what I wanted to do after. And even with investing, something I’m doing now, I’ve been doing it for nearly seven years. So it isn’t something where I decided now’s the time to change. For me, it’s always about:
- What do you want to do?
- Have a plan.
- Do it way ahead of deciding to do it full time.
So obviously I’m still playing tennis, but at the same time, I’m building the best teams and making the best decisions and joining great boards that are going to be able to help me continue to be the best leader and CEO and entrepreneur that I can be.
Kirsten: You launched Serena Ventures in 2014, and your mission is to invest in companies that embrace diverse leadership, individual empowerment, creativity, and opportunity, which are worthy missions in their own right. Your focus is on early-stage, about 60% of the companies you’ve invested in have diverse founders, your portfolio has a market cap of $14 billion, which is crazy impressive, and you have over 50 portfolio companies, including Daily Harvest, Billie, Lola, Noom, Masterclass, Neighborhood Goods, and Little Spoon.
You really have built a tremendous portfolio. Talk to us about your investing philosophy beyond what I just shared and how you’ve approached building that portfolio of companies.
Serena: It took me a while to get here. When I first started seven, eight years ago, I started by taking on different mentors, and a mentor a long time ago told me, “you need to have a philosophy and a plan if you’re going to set this up.” So I thought about what makes sense to me. Early on, I realized that I loved being a part of companies that were able to shape your lifestyle and how you think and approach different things. And I realized at the same time that my life has been shaped by technology and being creative.
I also wanted to make something super authentic. And people—LPs as well as consumers—see through something not real. So I wanted to make sure that it was really authentic. All that came together and I realized I want to invest in women. I want to invest in people that look like me—people of color. And I want to be able to highlight that. At times, we’re not able to use my money or our money at the firm, but we want to be able to at least help them meet other people.
I want to invest in women. I want to invest in people that look like me—people of color.
Kirsten: You’re such a role model as an athlete, and being able to help promote role models in business is so powerful and important. And there’s been a lot of conversation, particularly as we’ve had more outward conversation about the need for more female participation in the venture and startup community, as well as just more diversity in general. A big part of the effort of fostering that is having role models and being able to shine a light on people and start to show success in those lanes. So I think it’s an incredible mission to be able to do that.
Serena: Thank you. That’s what we want to do, and we want to continue to do that and encourage other people to do it as well because I feel like having a diverse portfolio and having diversity on boards really makes for a better company.
Having a diverse portfolio and having diversity on boards really makes for a better company.
Kirsten: 100%. That’s what the country looks like, that’s what the world looks like, and that’s who the users of all these businesses are. It makes so much more sense to have diversity represented across the spectrum of management in business—everything from founders to employees to board members.
You mentioned that you were on a couple of boards of companies—which companies are you most closely involved with?
Serena: I’m closely involved with SurveyMonkey as well as Poshmark. And I sit on the board of Spring Hill, which is a very interesting company. All of them are amazing, and you learn so much, and now I’m able to contribute a lot. I’ve been on the board for a few years now at the first two; Spring Hill just started their board. But it’s also been really cool to be a part of something that just started. And again, that’s really what we want to do—we want to be able to shape companies and people and innovations and products. So that fits right in with what I want to do and what I’ve been doing.
I bring that championship mentality into everything I pursue. You can’t be a champion without taking risks and having different challenges. Nothing I ever set my mind to is easy or risk-free.
Kirsten: We’ve been talking a little bit about lanes of opportunity in investing. How do you think about risk as an investor and also just as an entrepreneur in your life?
Serena: On the court, being fearless is crucial for success. I remember one of the big moments in my career was just saying, “close your eyes and hit the ball as hard as you can.” And I won the US Open. From that, it always made me feel that I have to be fearless and take chances. You definitely have initial fear, but you have to harness it and realize that sometimes fear can hold you back. So I bring that championship mentality into everything I pursue. You can’t be a champion without taking risks and having different challenges. Nothing I ever set my mind to is easy or risk-free.
That said, investing is really about taking calculated risks and preparing yourself. So whether I’m looking at an investment or a new business venture, I’m really a student of the game. Risk-wise, I try to make sure I’m super well informed. We do our due diligence, to a level where sometimes even if we’ve done tons of due diligence, I decide to make a couple more calls. And we literally are ready to invest, but we pull the money because we realized that one extra call made all the difference in the world and opened our eyes up to so much stuff. So it’s also about taking that calculated risk and setting yourself up by doing as much due diligence as you can.
Kirsten: Yeah. That really resonates with me. I started out investing in later stage companies where I think it was much clearer to evaluate what the risks were. I felt comfortable being able to do an analysis, see a full picture, and debate where the risks were.
With early-stage companies, you can do a certain amount of diligence. But at some point you just have to say, “I’m all in on the opportunity” or “I’m all in on the founder” or “I’m all in on the mission of this company.” And you have to remind yourself that we’re the business of taking risks and you should be taking some risks. Calculated risks.
Serena: And how low can you get that risk? The only way to do that is by doing all the due diligence that you can do.
Kirsten: And having all the lessons you learn over time. You’ve been navigating your career for a couple of decades, you have a tremendous amount of experience in the driver’s seat and on the supporting seat, and you try to bring all of those lessons to bear and hopefully be a good partner and offer guidance or support to companies.
Another important thing in all of this is preparation. Diligence is research work you can do. But another aspect of it is thinking about how you can come to a meeting with a prepared mindset. How do you think about preparing yourself for another journey? Obviously you do that well—what’s your philosophy or effort on that end?
Serena: I think you’d be surprised how similar the preparation is to what I do playing tennis. I feel like that’s really prepared me to be ready for entrepreneurship—in particular with Serena Ventures and our company. For me, it’s really about being prepared. I try to surround myself with experts who drive and try to excel but also ask a lot of questions.
Preparation is super important. I don’t go into a match unprepared, and I don’t go into any meetings unprepared. I usually have my computer and all my notes together. And I do study sessions before. I want to know who I’m talking to. What do they like? What do they dislike? Where are their strengths, and do they have any weaknesses? For me, it’s really good to go into a meeting knowing that.
Especially on Zoom, you’re not going to get to know the person as well because you’re looking through a screen. So I want to know them very well before I get there. And I want them to be able to believe my vision. It’s something we do internally. We want to make sure we go to each meeting knowing as much as we can. We want to make sure we’re super prepared.
I don’t go into a match unprepared, and I don’t go into any meetings unprepared.
Kirsten: You touched on something unique about this year—we’re all communicating differently. What has been the most different for you as it relates to the different business ventures you’re in, in operating through this environment?
Serena: We’re really fortunate. I love technology, and I’ve always liked being ahead of the curve. I’m not trying to toot my own horn here, but I built our fashion company years ago to be all remote. Everyone thought it was crazy. We have a team in New York, and we have a team in Florida. I built a team to have our own warehousing where we did our own shipping. So when Covid happened, we didn’t have a third party shipping company, so we were fine. And we could have one person in the warehouse go in and still ship things and make fulfillments. It was perfect. Our COO called me and said, “I’m so sorry I doubted you—this is brilliant.” We’re able to keep everything going because of everything I set up.
It’s the same with Serena Ventures. My team is out in San Francisco, but obviously with me traveling with tennis, it was really important for us to build a great working relationship, and a great way to do that is to always have meetings. We’re always on camera and on our computers talking to each other through our screens. So it was kind of natural. And then with board meetings, I decided we can save a lot of our time if we had our board meetings virtually. We can do a lot more. We can get a lot further. We don’t waste money. We can invest that money somewhere else.
I think this time has helped people realize that you can do a lot of things virtually and from a distance. There’s a lot of things we do miss, but at the same time, there are companies canceling their leases for millions and millions of dollars just to stay virtual. So, I think it has been a big lesson for all of us.
Kirsten: Yeah. I think everybody has learned to be flexible this year. From the startup standpoint, flexibility is such an incredible trait and strength to have. And this year, people’s need for flexibility has been challenged and stretched. But I think people feel mostly empowered by it. And I don’t think that’s going away.
This year, we’ve obviously had a lot of board meetings remotely and found that it’s very productive because there’s structure to the meeting—there’s an agenda. And we try not to talk over each other anyway, so you can balance and have a conversation on Zoom. So that feels like it makes a lot of sense. I think, though, that you need to think about new ways to introduce opportunities to make sure you’re fostering personal relationships and finding in-person touch points too. 2D is good—it’s efficient—but in-person is a whole nother dynamic that adds to it.
Serena: And I think that’s important, especially with teams because you want your team to always be able to function together and be together and work together and have that harmony. Particularly with VC, you really need your team to work together. So for me, it’s super important. I think there are different ways to do these things. Zoom is great, but I feel like we have to figure out how to be together, just to make sure the company and everyone still feels good and is able to face the challenge as a team.
Diversity and inclusion
Everyone should have a seat at the table. And by the way, it’s large enough.
Kirsten: Another topic that feels important in every conversation this year is inclusion. Can you talk to us about your experience talking with other people about inclusion as it relates to startups and business?
Serena: I built Serena Ventures to be inclusive because I felt like that’s what we need. When I started investing, I wanted to invest in people that didn’t have opportunities—that weren’t included. I wanted to invest in women. I wanted to invest in people that look like me, I believe everyone should have a seat at the table. And by the way, it’s large enough.
For me, inclusion goes beyond just being in the room. It’s about making sure all the voices heard include people from all different types of backgrounds. Talent does not discriminate. I feel like my portfolio includes founders from all walks of life. And we range in different markets, too. We really try to continue to keep going and make goals everyday and make people better.
Kirsten: What are some best practices or some things that, if you came into a company that needed help fostering inclusion, you would suggest to them or advise them on?
Serena: When we’re talking to companies in the beginning, we say, first of all, who are your founders? Who are your first employees? Because that’s really important when you’re building a company and you’re talking to these young founders. You have to realize that you are a part of shaping that company for the best. So you want them to know that if you only have people that look a certain way, you’re going to get a certain result. So what result are they looking for? Does that result work with what we look to invest in? And how does that fit for us? We really try to talk and help everyone understand that inclusion really doesn’t miss out on anything.
Inclusion goes beyond just being in the room. It’s about making sure all the voices heard include people from all different types of backgrounds.
Looking forward to the future
Kirsten: We’re coming to the end of a rough year. What are you excited about as you think about being able to turn the page on a pandemic in the next few months? There’s certainly a lot of problems, but problems are opportunity.
Serena: One thing I learned is don’t make future plans, but I’m excited just to get back to normal and see people. Business-wise, I’m excited about the companies that’ll come from this. From every low, that’s usually when the biggest investable companies come. I’m excited to see how that plays out and how we can be a part of it.
Kirsten: In closing, what would you like to share as words of wisdom or advice or inspiration?
Serena: Stay committed, and stay strong. Everyone is going through the same process right now. I’ve never been through this, but no one else has either. So we’re all just taking it step by step, taking the process day by day, and seeing where it leads. That’s the only thing we can do. So just stay strong, and if you’re making a product, believe in it—stay with your team. Just work hard—work harder than the person next to you.