Serena Williams’ Winning Formula: From World Champion to Elite Business Leader

Summary

Podcast Summary: Living The Red Life

Episode: Serena Williams’ Winning Formula: From World Champion to Elite Business Leader

Host: Rudy Mawer
Guest: Serena Williams
Date: December 19, 2025

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Episode Overview

In this insightful episode, Rudy Mawer sits down with tennis legend Serena Williams to explore her journey from groundbreaking athlete to venture capitalist and business leader. The conversation centers on Serena’s sources of self-belief, her approach to leadership, team building, entrepreneurship lessons, and the crossover between athletic and business mindsets. Serena also reflects on her relationship with her sister Venus and the power of resilience, discipline, and positive affirmations in achieving world-class success.

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Key Discussion Points & Insights

1. The Power of Self-Belief and Family Influence

• Serena credits her self-belief to her parents, especially her father, who filled her environment with positive messages and confidence boosters.
  • Quote: “My parents really instilled, you're good, you're going to be great, you're great. Even down to having signs around, positive affirmations, telling us all the time how good we are.” (03:05)
• Her sister Venus played a pivotal role at a critical time, reinforcing Serena’s sense of worth and pushing her forward.
  • Quote: “I think my sister saw that I was going through it at that moment and she said these words that I will never forget, which is why I wanted it in the movie, in the script. I think she saw something in me that no one saw, not even my parents.” (04:16)

2. Sibling Dynamics: Tag Team and Rivalry

• On Doubles Success and Sisterhood:
  • Playing together as sisters was a joyful experience, making their doubles victories and shared time particularly meaningful.
    • Quote: “My fondest memories are definitely on the Doubles Court...The best times is winning gold medals with her or winning Grand Slams with her.” (04:54)
• On Competing Against Venus:
  • Serena is candid about the challenge and discomfort of playing against her sister, emphasizing their resolve to put family before rivalry.
    • Quote: “It was something I never really enjoyed playing against my sister, but...at the end of the day, tennis would only last so long and we would be sisters forever.” (05:29)

3. Life After Tennis: Parenting & Serena Ventures

• Transition to Business:
  • Serena divides her focus between being a mother, running Serena Ventures, and other media projects. She shares her passion for investing in underrepresented founders.
    • Quote: “We invest in women, we invest in underrepresented founders and ideas and products that are helping underrepresented people through technology, fintech, AI, B2B, SaaS stuff…I try to think that [being a mom] is my number one job right now.” (06:26)
• Building and Leading Teams:
  • Serena draws parallels between managing tennis teams and leading business ventures, stressing the importance of learning to hire, manage, and inspire others.

4. Leadership, Team Building & Entrepreneurial Mindset

• Leadership Lessons from Sport:
  • “It became a completely team sport, whereas you needed a team…leading that team really helped me as an entrepreneur and understanding like, who to hire, how to hire, how to be.” (07:24)
• Entrepreneurs Need a Strong Team:
  • Rudy notes that like pro athletes, entrepreneurs need a robust team, not just go it alone.
  • Serena’s Practical Tips:
    • Trust your gut.
    • Hire slow, fire fast:
      • Quote: “If it's not working, it's not going to work next year, next month, it's never going to work.” (09:00)
    • Don’t take hiring or firing personally—uplift and respect people, but don’t force fit.

5. Mindset and Transferable Skills Between Sport and Business

• Entrepreneurs & Athletes: Shared DNA:
  • Both require resilience, discipline, belief, and learning from setbacks.
    • Quote: “I always feel like athletes make great business people and you can see nowadays that they really are.” (10:55)
• Belief Is More Than Words:
  • Actions must back up ambitions. Serena stresses that conviction is what separates those who reach their goals from those who don’t.
    • Quote: “Words are words, but words are followed by actions…they make you act harder, they make you work harder, they make you dream more.” (11:47)
• Self-Affirmation:
  • If support or affirmation isn’t coming from others, build it yourself.
    • Quote: “You don't have to have. And you can give them to yourself.” (12:47)

6. Final Advice and Takeaways

• “Work Hard and Try a Lot”
  • Serena notes the reality that overnight success is rare; persistence and ongoing effort are crucial.
    • Quote: “It's cliché. It's not going to happen overnight. And for every story that it does happen overnight, there's billions that it doesn't. So you have to work hard.” (13:38)
  • She prefers “try a lot” over “fail a lot,” reframing setbacks as lessons and reminders to keep trying.
    • Quote: “I like to say try a lot because it might not work out, but just keep trying. Don't stop trying.” (14:02)
• Be the Best Version of Yourself:
  • Serena hopes listeners will draw inspiration to become their best selves and to seek inward success as much as outward achievement.
    • Quote: “Being the best version of yourself. A little inspiration on inside success.” (14:24)

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Notable Quotes & Timestamps

• On Positive Affirmation:
  • “My parents really instilled, you're going to be great…positive affirmations, telling us all the time how good we are.” — Serena Williams (03:05)
• On Difficulties Playing Venus:
  • “It was something I never really enjoyed playing against my sister…but we would be sisters forever.” — Serena Williams (05:29)
• On Team and Hiring:
  • “Trust your gut. Hire slow, fire fast.” — Serena Williams (09:00)
  • “It could be someone that you really respect…but if it's not working out, don’t feel guilty.” — Serena Williams (09:43)
• On Mindset:
  • “Words are words, but words are followed by actions…they make you act harder, …work harder, …dream more.” — Serena Williams (11:47)
• On Trying vs. Failing:
  • “I like to say try a lot because it might not work out, but just keep trying. Don't stop trying.” — Serena Williams (14:02)

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Key Timestamps

• 03:05: Self-belief and positive affirmations from family
• 04:16: Venus’s pivotal encouragement
• 04:54: Joys of playing doubles with Venus
• 05:29: Emotional challenge of playing against her sister
• 06:26: Serena’s ventures and balancing motherhood
• 07:24: Leadership lessons from tennis applied to business
• 09:00: Advice on hiring and firing in business
• 11:47: Actions over words; authentic belief
• 14:02: Reframing "failure" as ongoing effort and learning
• 14:24: Encouragement to pursue inner and outer success

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Memorable Moments

• Serena clarifies a semi-fictional moment from the "King Richard" movie: It was really Venus who first told Serena she’d be the greatest of all time, which was pivotal for Serena’s self-confidence. (04:00–04:44)
• Candid talk about firing in business, equating personnel decisions with dating: if it’s not a fit, keep searching, don’t take it personally. (09:00–09:43)
• Distinction between merely saying and believing your ambitions, and how daily repetition and discipline cement conviction. (11:47)

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Conclusion

This episode offers a rare, candid look into Serena Williams’ mindset both on and off the court: the value of belief, leadership evolution, team building, and learning from experience are woven throughout her advice. Serena’s humility and practical wisdom stand out, providing actionable insights for entrepreneurs, athletes, and anyone pursuing major goals. Her journey from tennis stardom to business is both inspirational and instructive—urging listeners to persist, uplift others, and never stop striving for their best selves.

Transcript

[A]

You may know who I'm sat with today. I just actually finished giving her a few tennis tips on the court behind us and now we're going to chat a little about business and her career.

[B]

Glad to be here.

[A]

She's so strong. She hits the ball so well with a brownstone. Her hands are just unreal.

[C]

Greatest of all time, Serena Williams.

[D]

Serena Williams is a relentless, record breaking and iconic champion whose career reshaped the standards of greatness in global sports. Today. She brings that same vision to business through Serena ventures, building companies and investing in founders who are shaping the future.

[A]

The power of belief, we talked about it. Yeah, you said it's very important.

[B]

Yeah, listen, belief is important and I think believing in yourself is important. It's great for other people to believe in you and pat you on the back, but at the end of the day, in particular as an athlete, in particular as an athlete in a solo sport, you really need that self belief. But where do you get it from?

[A]

How have you had to evolve as a leader as you've gone into the entrepreneur side?

[B]

I was able to evolve as a leader in tennis. It is a start.

[A]

Yeah, yeah.

[B]

You know, and as I started to build other companies, I understood leadership. Leadership is so important.

[A]

Leaders lead if someone's listening. Now, as a, you know, female, male, as a founder, do you have some tips on like getting, you know, you work with a lot of early stage. Right.

[B]

I think it's important to, you know, have.

[A]

It spans the globe like a super high Internet Elvis.

[C]

Brent, for me today, Apple is going.

[B]

To reinvent the phone.

[C]

It's not over until I win. The living your legacy podcast. For those who live to leave a legacy that's extraordinary. The impossible. Oh, that is sensational. Jordan Open Chicago. With the lead, Usain Paul is the fastest man on the planet. You can live your dream.

[A]

Hello and welcome back. You may know who I'm sat with today. I just actually finished giving her a few tennis tips on the court behind us and now we're going to chat a little about business and her career. I'm sat with Serena Williams, someone that I've always admired. I came from a sporting background and one of the greatest athletes of all time. So welcome.

[B]

Glad to be here, you know, greatest.

[A]

Athlete of all time. I, I think is a statement I've always said about you as one of the greatest athletes of all time.

[B]

Whoa, okay.

[A]

And I don't think I'm the first to say that, but, but you really are, you know, and you, you, you know, you and your sister, but you Guys had the most amazing career. You inspired, you know, millions of people. Right. And you've just got such an epic story behind it all too. And you know, I've watched the movie many times because I, I grew up with a family of pro athletes and I, I think I became successful because of my parents just taught me I could do whatever I wanted to do and believed in myself. And I see so much of that in, in you and your dad too. Right. So I'd love to start there. Like the talked about it.

[B]

Yeah.

[A]

You said it's very important.

[B]

Can you. Yeah. Listen, belief is, is important and I think believing in yourself is important. It's great for other people to believe in you and pat you on the back. But at the end of the day, in particular as an athlete, in particular as an athlete in a solo sport, you really need that self belief. But where do you get it from? I say I got it from my, my dad, he and my mom, obviously. I, I, my, my parents really instilled, you're good, you're going to be great, you're great. Even down to having signs around, positive affirmations tell us, telling us all the time how good we are.

[A]

Yeah. And there's one, you know, I don't know exactly how, how true to the core it is, but there's a moment in the movie, right, where, you know, right near the end, Will Smith, right, plays it, comes over and says, you're going to be the greatest of all time. Do you remember times where like. Because that's a bold statement to say to anyone as a kid, right. Do you remember the being told that.

[B]

That was so we produced the movie, so we, everything we wanted it to be? Very true. My sister actually said that we thought it would be a better moment to have my dad say that in the movie, obviously Hollywood, but that's one of the few things that we changed. But that moment actually did happen, which is why the line even existed. I was feeling rather down at the time because I felt like everyone was talking about Venus and I'm like, hey, I play too. You know, I'm actually really good. And I think my sister saw that I was going through it at that moment and she said these words that I will never forget, which is why I wanted it in the movie, which is why I wanted it in the script. I think she saw something in me that no one saw, not even my parents. And it was amazing that she saw it.

[A]

Talking about her briefly like, you two are such a powerful tag team too, right? Like how fun I Just gotta ask, like, how fun was it to be playing together, winning the doubles?

[B]

You know, I think out of my career, when I look back at some of the memories, my fondest memories are definitely on the Devil's Court. And it was mostly laughter. And I think it was fun because it was just a time where we ended up not even spending a ton of time together because we were both playing so much and always playing each other. And you know what it was really the best times is winning gold medals with her or winning Grand Slams with her. It was great. It was fun.

[A]

And what about the flip of that, playing against each other? How was that?

[B]

Yeah, you know, I'm very candid about how I feel about that. It was something I never really enjoyed playing against my sister, but it was also something that I knew was going to happen again. When I was younger, we always knew that we would play each other in the finals of Grand Slams. You know, we just never knew how hard it was going to be mentally, physically, emotionally. But we always knew that at the end of the day, tennis would only last so long and we would be sisters forever. And so we wanted to make sure that we always had that bond. But, you know, it wasn't very easy playing her. Sure.

[A]

And talking about tennis only lasting so long. Now you're obviously focused, being a great mom and family, you know, part of the family and the venture side. Right. Serena Ventures and the investments. And you have a podcast now and, you know, a new show on Amazon. Can you talk a little about, you know, how you're doing all those things and what inspires you to do all of those things?

[B]

Yeah. So for me, when it comes to investing, ventures is super important. And that's what I do every day is ventures. And Serena Ventures is a company that I built. And we invest in women, we invest in underrepresented founders and ideas and products that are helping underrepresented people through technology, through fintech, AI, B2B, SaaS stuff. And that's something that I've always enjoyed. But my biggest joy is definitely being a mom. I love being a mom. It's something that I truly love. And I try to think that is my number one job right now. And, you know, just always want to just continue to build my team out to do their best job so I can be the best mom that I can be.

[A]

Well, I was going to ask you. You said that earlier. That's the leadership side. Right. You know, I have 100, about 140 employees and staff, and it becomes a whole different ball Game from when you start with 5, 10, 20. Right. So how have you had to evolve as a leader as you've gone into the entrepreneur side?

[B]

Yeah, no, I feel like I was able to evolve as a leader in tennis. And when tennis first started, I wasn't a leader. My dad was on the team, then I had a coach. But then it became a team sport. Even though it's a solo sport and it's one person out there, it became a completely team sport, whereas you needed a team. And nowadays I understand tennis players have at least 10 people on their team now. When I retired, it was like at least four. It was like five to six people, and now it's doubled. And leading that team really helped me as an entrepreneur and understanding like, who to hire, how to hire, how to be and how to be. Of course, it's not 140 people, obviously, but it is a start, you know, and as I started to build other companies, I understood leadership. Leadership is so important. Leaders lead.

[A]

And I think it's so key for entrepreneurs because I actually, when I speak on stage, because I came from a family of athletes, I show a graph of a pro athlete and the eight or nine or ten people around them.

[B]

Yeah.

[A]

And then most entrepreneurs, it's just them, and they try and build this company and it's just them. And it's like, no, you know, a pro athlete has the physio, the nutritionist, the masseuse, the mindset. You as an entrepreneur, you need the tech people, the designers, the marketers, the finance, the hr.

[B]

Right.

[A]

So if someone's listening. Now, as a, you know, female, male, as a founder, do you have some tips on like getting, you know, you work with a lot of early stage. Right. So any tips on getting. That's the hardest part. Right.

[B]

Trust your gut.

[A]

Yeah.

[B]

You know, hire slow, fire fast, you know, don't have regrets. It sucks. Firing sucks, Hiring sucks. Hiring and firing sucks. But you know what? That's one thing I've learned is like, fire fast. If it's not working, it's not going to work next year, next month, it's never going to work.

[A]

Well, and you said also I laughed earlier because I teach my team all the time. You use this kiss in the frog analogy with business ideas. I use it with team members all the time. I'm like a lot of entrepreneur. A lot of entrepreneurs hire. One person doesn't work and they say, well, I'm not going to have that role anymore.

[B]

Yeah.

[A]

I'm like, well, you wouldn't say that about dating. You went on one day and then said, I'm going to be single forever. Yeah, well, yeah, but yeah, give it up. You have to believe, right? And keep testing people.

[B]

Keep learning. Yeah, you have to believe. You have to keep testing. You have to keep high. That's why I say hire slow but fire fast. You know, you take that dating for a long time, but if it's not working out, also don't feel guilty about it, you know, Cause it's nothing personal. It could be someone that you really respect. And I always say have that respect for people. Like, I always try to uplift people and I always try to be positive and I always try to help people. But that doesn't mean I don't like you. It just means it's not working out for this. It's absolutely nothing personal. And that's how you just have to think about it.

[A]

Yeah, I think that's great. It's like even dating, you're not a fit for me. Doesn't mean you're not fit for someone else.

[B]

You're a bad person. It just like. And I, for me, I'm always wishing people well, but like that, it just means it didn't work out for us and that's okay.

[A]

Yeah, love that. So next question I have is the mindset I talked to you a bit earlier about. Like, I see so many similarities because I came from a family of pro athletes and Now I last 10 years, all my friends are millionaires, ultra millionaires, some billionaires. And there's so much overlap. Right. And then even filming these segments, like different pro athletes, different billionaires, lots of.

[B]

Crossover entrepreneur and athletes have so much in common. Right. I feel like, I feel like it's the same thing. You've had these conversations, you know, so you know, by listening to this, like, wow, that and with you having your background with your family too, you can probably see all the similarities and it's, it's interesting. I always feel like athletes make great business people and you can see nowadays that they really are. That they really do. Yes.

[A]

And one I think difference with you though is like just. And I'll come back to it because we started there, I guess, as we finished today, that power, belief. Right? Like the big difference I, I've seen chatting with you is your dad just did such a great. And you guys too, because you had to also consume it and believe it yourself. But you guys did a better job than anyone I've ever met up actually believing the dream would come true because a lot of people, like, they kind of set the Goal. I want to be an Olympic gold medalist or whatever. Right.

[B]

But they don't really mean it. No.

[A]

Until they say it.

[B]

They're words. Words are words, but words are followed by actions. And so I think that we had those words. But when those words are engraved in you every day, then they start. They make you have these actions even more. And so they make you act harder, they make you work harder, they make you dream more about eat, sleep, breathe. Like that's the thing.

[A]

Conviction. Like there's. So you guys had. Like there's a scene in the movie where, you know, they go, venus, are you going to beat whoever's on the other side of the net? Absolutely. Right. That's. That was real. You guys were exactly like that growing up.

[B]

I wasn't. She was. He believed more than me. But as I got older and I was younger too, so as I got older and as I got more experience, I was like, okay, I can do this too. But it took me a little to get there, to have that self belief. I think that just comes with the territory when you're growing up behind someone named Venus Williams. But I think it's important to. I think it's important to, you know, have a lot of positive affirmations. And if no one's given it to you, you don't have to have. And you can give them to yourself.

[A]

Yeah. And I think that that's what made you guys so great. Like you could. You always would have probably been great tennis players, but just take it to the next level. That made you, well, like the most famous tennis players in history, basically. Is that difference there? I think, you know.

[B]

Yeah, I think my dad was really smart about it because I think if we were basketball players, maybe he wouldn't have done that because it was, okay, you can be a basketball player. It's probably. We were taking a route that wasn't normal. So I think he knew that he needed to give us more affirmation than normal because we were gonna face things that no one literally at the time or still have ever faced. So I think it was a lot of his genius behind that.

[A]

Love it. Good. So last closing comment. Any tips for entrepreneurs or people trying to achieve a massive goal in life, whether it's business, sport, work hard.

[B]

It's cliche. It's not going to happen overnight. And for every story that it does happen overnight, there's billions that it doesn't. So you have to work hard. You have to work hard. You can't expect someone to give you handouts or you can't expect it to.

[A]

Just come and fail a lot. I hear that like, you know, I.

[B]

Hear that so much, but I don't even like the word fail because it just seems like it to me. That seems. Just try a lot.

[A]

Okay, Try.

[B]

I like to say try a lot because it might not work out, but just keep trying. Don't stop trying.

[A]

Yeah. Just lessons. They're lessons along the way.

[B]

Exactly. Exactly.

[A]

Good. And any. Any big takeaways people will get from watching the full. You know what? We just recorded the full. The full part.

[B]

Hopefully. Just a little inspiration on, I don't.

[A]

Know, being the best version.

[B]

Being the best version of yourself. A little inspiration on inside success.

[A]

Yes.

[B]

And what does it take to be a successful inside.

[A]

Good. Love it. Well, thank you so much. Thank you, guys. I hope you enjoyed that. You know, this is really, like I said, one of the people I look up to the most. I know so many of you do, too, and such an amazing story. So thanks again.

[B]

Thank you so much.

[A]

See you guys. Take care.