The power of mentors: Alex Rodriguez, Angela Duckworth, and more

0:00Scaling a business in the US can feel like a maze. Each state has its own payroll, benefits, and compliance rules, pulling your focus away from growth, which is why founders use Deal. Deal is the professional employer organization, or PEO, that gives you a dedicated HR expert, plus Fortune 500-level benefits for your team. The National Association of PEOs says businesses can grow twice as fast if they use one. So, if you're scaling, make it simple with Deal. Go to deel.com. slash MOS and get up to three months free. If you're in private capital, you understand that your next great deal starts with who you know.

0:41That's why over 3 ,000 firms trust Affinity, the CRM platform purpose-built for private capital. Affinity's relationship intelligence reveals your team's strongest paths to founders, investors, and decision makers using insights It's hidden in emails, calendars, and meetings. With powerful AI tools like Affinity NoteTaker and Deal Assist, you'll spend less time managing data and more time closing the right deals. Learn more at affinity.co slash marketplace.

1:18A mentor is going to tell you the truth. It's going to kick your ass. And it's going to want you to be the best version of yourself. What makes a great mentor? Mentors really kind of teach me about how to win, how to avoid losing, how to avoid some of the bumps they've come through. How do you get a mentor? How do you even become one? When you listen to people talk about their mentors, it's like a thing that falls out of heaven. But they're not just falling out of heaven. You have to proactively make them.

1:55you gotta have incredible talent at every position it's like this huge push there are fires burning when you're going out can you believe it such an idiot and then you go back to this is totally going to be amazing there are so many easy ways i have no idea what to do sorry we made a mistake but you have to time it right oops working out of a three-bedroom apartment stuff that just seems absolutely nut balls. Ten years later, we're like, well, that's just how you do it. We haven't made it just how you do it. This is Masters of Scale.

2:31I'm your host, Jeff Berman. So many business leaders recognize the importance of mentorship in their journeys. This is something we hear again and again in our interviews with exceptional founders and thought leaders. Behind every star solo player, there's a strong coach or several coaches. I've certainly experienced the power of a great mentor more than once in my own career, and I've seen their influence in nearly every organization I admire. But these relationships often only appear as footnotes in the longer stories of successful companies. So we're putting a spotlight on mentoring and its relationship to scaling an organization.

3:10We dove into the pantheon of masters of scale, all-star guests to do it. There's always an opportunity to build or rekindle a relationship with a mentor who can have a life-changing impact on you and your business. And if you're interested in playing that role yourself, well, there's plenty here for you too. Let's get into it. Luke Skywalker needed Obi-Wan Kenobi, right? The modern day Luke Skywalker For me, it's Diana Nayad. This is the amazing woman who swam from Cuba to the shores of Florida, a feat that had never been done without a shark cage. Angela Duckworth is a psychology professor at Penn and the Wharton School and the author of the bestseller Grit.

3:54On her last and successful attempt that she had made after decades of trying and failing to do this, she heaves herself onto shore and she says this. And I'm going to quote you. I'm going to read it to you so I don't get it wrong. She says, I have three messages. One is, we should never give up. Two is, you're never too old to chase your dreams. And three is, it looks like a solitary sport, but it takes a team. In our conversation, Angela emphasized mentorship while describing the missteps she's seen so many successful people make, including herself. When I was growing up, so much of what I accomplished was really trying harder.

4:38You know, like sitting there in my BC calculus class and I'm like, I know, I know that Darshak got it faster and, you know, Chan Kim got it faster, but they can't outwork me. Like, I am going to learn BC calculus. Right. And I felt like that for, I don't know, 40 years. And even in my own marriage, I thought to myself, wow, you know, my husband is a real estate developer. Well, if you put two and two together, you realize he was a young real estate developer in 2008. It was a very, very stressful time. He was working some weeks, 100 hours a week. I was on tenure track at an Ivy League institution.

5:14We had two young children who had to be taken care of. Like, there was so much stress. And the only trick I knew was try harder. The only trick I knew was grit. I was like, you know, I'm going to wake up earlier. I'm going to stay up later. I am going to use every ounce of my will to make the life that I need to make for my children and my husband and my career. And I'll tell you that that led to a real crisis. It almost broke our marriage. There were just an unbelievable number of therapy hours that we logged trying to rescue ourselves from the precipice. And what has struck me now and what I'm writing about is that grit is not enough.

5:58We needed to reach out to our friends and actually be vulnerable and not just have small talk, but actually tell them that we were in crisis. He needed to change his work situation. He has an advisory board now of mentors who, you know, kind of help him prioritize in ways that he would never be able to do on his own. I reached out to mentors to, you know, help me figure out my research program and help me accomplish it in more effective ways. And so to me, you know, grit is great, but grit is not enough. And you absolutely need to make your situation your ally if you're ever going to, you know, run the marathon of success.

6:33But I think one of the mistakes that I see founders make is because they've had this trick that has gotten them really far in life, like try harder and be independent, right? You know, to not be a slacker, right? To not like whine and get other people to solve your problems. I think the double-edged sword of that is they don't ask for help. When I look back at the mistakes that I've made in advising young leaders, it was to not tell them that first. I'm like, oh, wait, who are you talking to? Like, what's your AA group, essentially? Right. If you don't have one, you need to get one right now. What I would say is a number one action step is like you should be in a formal community of other founders, right?

7:13I think this is why I'm a big fan of incubators, especially the ones that are, you know, well, well designed, like Y Combinator. Like there's a power in the solidarity, the accountability and the peer learning of a group. You know, you want to be in a flotilla, not like off sailing on your own. So that's number one. And the second one is related, which is I think you need to make mentors. When you listen to people talk about their mentors, it's like a thing that falls out of heaven. You know, like, oh, I'm so grateful that this person came into my life and, you know, they put me on the straight and narrow.

7:45Right. But they're not just falling out of heaven. You have to proactively make them. It's a relationship. And you need to start at the beginning and cultivate and so forth. And I think if we are honest with ourselves, when we think about our most meaningful mentorships, we did have a role in holding up our end of the relationship and even in initiating the relationship. So those would be my two pieces of advice to founders. You know, go find another founder. It doesn't have to be your co-founder for your startup. It could be somebody who's doing something totally different. But you should be meeting regularly, trading stories, crying on each other's shoulders.

8:22And then you should go and very proactively cultivate mentoring relationships.

8:32Like Angela says, it's important to be proactive in seeking out a mentor. But sometimes an opportunity presents itself and the right mentor chooses you. That's what happened to Jimmy Iovine, renowned founder of Interscope Records. Before he produced albums for icons like Bruce Springsteen, Patti Smith, Eminem, and Dr. Dre, he worked as an assistant in a recording studio. He did the dirty work so many of us have done, mopping floors, literally, on his way to the top. Jimmy was waiting for a moment to be invited into the studio to learn the trade. And when that moment arrived, it came with one of the biggest names in music history.

9:15Basically, I walk into the studio, and there's my boss, Roy Ciccala, and John Lennon. And obviously before that moment, Roy decided he was going to teach me and take me inside and through those sessions, teach me how to be a recording engineer. He asked me to come in with the intention of me working with John. And Roy, through me, by working through me, taught me how to engineer records. I had a mentor, and he thought I was strong enough to go in there and deal with it. And it was the greatest two years I could ever, ever possibly want. Roy was very, very stern, a very tough guy, but he loved teaching.

10:02And he gave me a safe place to be in there. Now, if I screwed up, he'd be the first to crack me over the head. but he was incredible at teaching young people how to become engineers, which makes the idea of a mentor so important that to make yourself useful and to be of service to that mentor in order for you to get somewhere and not think that you actually belong there. You don't belong there, but somebody can help you feel like you belong there. My first mentor was my father, who was a longshoreman and a very, very modest guy. But he told me growing up, he said, you know, you're a special kid.

10:45Every room you go into will be better just because you're there. Now, was that true? I don't know. But I love my dad. If someone believes in you, and if you could be of use in that room, that's a very very important thing it's do not breathe your own exhaust no matter what room you get to go into stay humble and keep focused and drive jimmy's boss who had produced a score of platen records by the way opened the door to a life-changing hands-on experience it was mentorship with apprenticeship built in. But not all mentorship appears so overtly supportive at first. Mentors can give brutally honest advice.

11:34That was true for Allison Kluger. She's a Stanford business professor and former media executive whose broadcast career includes stints at Good Morning America and The View. Allison says that sometimes mentors take you by surprise. My first mentor was the woman who I was most frightened of. She was the mentor I didn't know was going to be my mentor. And the reason she became my mentor is that she gave me some radical candor about something that she felt was going to influence my career. I was 21, and I was at Good Morning America. And basically, I was crying one day at work. I was new to the job, and I wasn't crying about something that had to do with work.

12:21It was personal. And she said, Allison, I don't want to ever see you crying again. Do you know why? And I intuitively knew why. But she told me anyway. She said, you're young. You're female. You're attractive. No one is going to believe you can do your job. No one is going to trust you. No one is going to think you're reliable. If someone says to you, how's your day? You say, I'm having a great day. And if you want to come cry somewhere, you come in my office and close the door. And so she said, do you understand? And I said, I do. And she then kicked me out of her office. And all I wanted to do was cry.

12:58I was so mortified. One, that I had been caught crying. And two, that I didn't figure out that it wasn't the right thing to do. But what she did for me is she made me realize the kind of leader that I wanted to be. And I decided that I want to be reliable. I want people to give me work. I want people to trust me. And so the evolution of my personality started then. I was the person everyone went to for help. I got along with everybody. I was unflappable. You know, if something bad happened, I'd go hide in a corridor and just get all the stress out, and then I'd go back to solving the problem. And then she gradually became my mentor.

13:37And the fact that she was so honest with me and was willing to tell me something that was hard to hear, that was really the start of me understanding the power of a mentor. And a mentor isn't someone who's going to flatter you and make it easy for you. A mentor is going to tell you the truth, is going to kick your ass, and is going to want you to be the best version of yourself. I spent nearly five years in my first job out of school before I was hired to be chief counsel to a member of the Senate leadership. Before I took the job, I went to one of my mentors, a man named Robert Rabin. He is as brilliant as he is kind as he is wise.

14:17And Robert had also worked on Capitol Hill. He told me that most Fridays, my boss would head back to his state and that most of my colleagues would probably take a light day to catch up, socialize, do whatever, and that I could do that if I wanted to, but that by virtue of the senator's name on the door, I could reach out to almost anyone in America and they would want to talk. Robert asked me, do you know what most people like to talk about more than anything else? And before I could answer, he smiled with sort of a Yoda-like smile, which you would recognize if you knew Robert. And he answered his own question.

14:52He said, themselves. And it was obvious once he said it. And Robert told me that my new job was coming with something of a cheat code. And that if I used it, I would have access to the world's treasure trove of knowledge and insights and ideas. And that advice has really helped shape what I think would generously be called a nonlinear career, jumping from industry to industry and role to role. It's been a journey that I've really loved and that I continue to love. And that one bit of mentorship from Robert has really helped shape the past two plus decades of my life.

15:34After the break, how to be a great mentee and how to build a network of mentors among your peers.

15:56real leaders don't back down when the stakes are high they innovate they push forward and then they take the stage at the masters of scale summit join us in san francisco october 7th to 9th to hear from the CEO of the New York Times, scientists using cutting-edge technology to find cures, the leader of crypto powerhouse Coinbase, a retired four-star general, and many, many more. Apply now at mastersofscale.com slash apply25. That's mastersofscale.com slash apply25. If you're ready to take your startup from idea to impact, then AWS is your launchpad. From data storage to machine learning to secure app hosting, AWS gives you the tech trusted by the world's fastest scaling startups.

16:46And here's the best part. Join AWS Activate today and you could score up to$100 ,000 in AWS credits tailored to your stage and network. Go to aws.amazon.com slash activate and start building. Expanding your business in the U.S. can feel like a maze. Every state has its own payroll, benefits, and compliance rules, which can pull your focus away from growth. That's why founders use Deal. Deal is the professional employer organization, or PEO, that gives you a dedicated HR expert plus Fortune 500 level benefits for your team. The National Association of PEOs says businesses can grow twice as fast if they use one.

17:30So if you're scaling, make it simple with Deal. Go to deel.com slash mos and get up to three months free. Welcome back to Masters of Scale. We're exploring our favorite lessons on mentorship from the legendary leaders who've told us their stories. One field where mentorship is key to top performance is sports. We had Major League Baseball superstar Alex Rodriguez on Masters of Scale to share insights on how his all-star baseball career relates to his successful business ventures. And he told us he counts one of America's true sports luminaries among his long list of mentors. Magic Johnson started mentoring me about 20, 25 years ago when I was a really young player in the league.

18:18And I thought, wow, if Magic can play for the Lakers and win championships, and he can also be a Hall of Fame businessman in the boardroom, I said, well, I can do it too. And he's got brown skin like me. If he can do it, I can do it. That was the start of it. And I saw how powerful that was. When I transferred to business, I've had some of the greats not only be my friends, but mentors and really kind of teach me about the ins and outs, how to win, how to avoid losing, how to avoid some of the bumps they've come through. You know, from Barry Sternlitt to Mark Mastro from who started 24 Hour Fitness to Mark Laurie from Jet and the big one, Warren Buffett.

18:56And I saw how powerful mentorship was in my life. As a mentee, I benefited from that. Now, as a mentor, I have so many young athletes reaching out saying, I want to get involved in investing. How do I do it? How do I do it? And it's hard to pick them all, but I have at least a dozen that I'm constantly talking to and saying, maybe think about it this way, maybe think about it that way. The very best are the one that has the most questions. They're enthused. They lean in. They're very inquisitive. Don't think of mentorship as a transaction. Think of it as a relationship and building bridges. One of the things I've applied to my life is the 10 touch rule.

19:35I would try to touch bases 10 times before asking for any single thing, whether to be my investor or my partner. I wanted to build real credibility. And how you do that is by going narrow and deep and figuring out creative ways of can I send an article? How do I celebrate? How can I give credit? How can I make a connection? Everybody can be helped in some way. and it's your job as a mentee to create that and just be humble, grateful, and appreciative for their time. Humility and gratitude. Both are important qualities to bring to your relationship with a mentor to be sure they feel how valuable they are to you.

20:15And sometimes mentors become more than that. With a foundation of mutual interests, respect, and admiration, a mentorship can become an active partnership. That's what happened with Alexa Von Tobel. She's the founder and CEO of the personal finance platform LearnVest. Literally all of my closest friends are fabulous humans, many of them big entrepreneurs. And we always not only rooted for each other, but really in the moments that mattered were red phones saying, how on earth do you find engineers when the only engineers here work for Goldman Sachs and Bank of America? How do we get them to come learn this new way of the internet?

20:56you know, really building very honest, close friendships. And people always are like, how do you approach networking, Alexa? And I'm like, I don't think I network at all. I just, I build friends. And then I try to do two favors for somebody else before they can do something for me so that I can just be helpful. But that's how I've always approached it. Penny, my business partner, was my mentor. And now she's my business partner. And Lucy Deland, My best friend of 20 years, who I met under God at Harvard, she was a co-founder of Paperless Post. And I don't think mentors is like, you know, older people to younger people.

21:30It's dual. Some of my 80-year-old mentors would tell you I'm mentoring them. And I'm like, a 20-year-old who's my mentor teaching me about what the next generation cares about. And so I just approach it as friendship. And I'm happier because of it. Alexa's point is an important one, that there's no single template for mentorship. Learning can happen across industries, across generations, and across geography. And I return to our first insights from Angela Duckworth about how these beautiful relationships only become possible when you first acknowledge that you're stronger with help, instead of putting it all on your back and trying to go up the mountain alone.

22:13Mentor relationships showcase generosity and they offer us great capacity for change. They're clearly worth celebrating. If you have a mentor, this is the moment to reach out to them. And if you're looking for mentorship in your life, we hope this episode inspires you to continue that quest with some practical ways to go about doing it. Oh, and if you have a mentor you'd like to shout out, we'd love to hear about them. You can email us at hello at mastersofscale.com or the rest of our contact info is in the show notes.

22:57Meet Nicole Nicholas, Capital One business customer and co-owner of Ansett Uncles, a plant-based restaurant and community space in Brooklyn, New York that got its start from a need for unity. The inspiration, it was born from the desire to create a space that felt like home, where we can connect community culture, good food, and come together with family and friends. That's how we birthed aunts and uncles. Nicole and her husband, Mike, were fulfilling their dream of bringing people together out of their home kitchen. But they soon learned that the demand for community was greater than they knew.

23:28It became overwhelming and we were like, we need home, but not in our actual home. We realized that there was also a need in our community for something bigger in our neighborhood. So we had to find a place. Moving from a home operation into a storefront was a huge next step. But Nicole and Mike were able to take it on with the help of Capital One Business. It's not for the weak as a small business. Finding resources is super important because that's the way you'll be able to manage and scale. We would have never done that without having Capital One to be able to help us along the way. The cashback rewards are very helpful.

24:03you know, it just gave us that runway to be able to breathe a little bit. Then you get to focus on the cooking of the food and making the experience great. To learn more, go to CapitalOne.com slash business cards. Masters of Scale is a Wait What original. Our executive producer is Eve Trow. Our senior producer is Tricia Bobita. The production team includes Tucker Ligurski, Masha Makatonina, Brandon Klein, and Timothy Lou Lee. Additional production by Juliette Luini. Our senior talent executive is Stephanie Stern. Mixing and mastering by Aaron Bastinelli and Brian Pugh. Original music by Ryan Holiday.

24:44Our head of podcasts is Lital Mollad. Visit mastersofscale.com to find the transcript for this episode and to subscribe to our newsletter.