The power of mentors

ALLISON KLUGER: 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.

JEFF BERMAN: What makes a great mentor?

ALEX RODRIGUEZ: Mentors really teach me about how to win, how to avoid losing, and how to avoid some of the bumps they’ve come through.

BERMAN: How do you get a mentor? How do you even become one?

ANGELA DUCKWORTH: 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.

[THEME MUSIC]

BERMAN: I’m your host, Jeff Berman.

Many business leaders recognize the importance of mentorship in their journeys. This is something we hear again and again with our exceptional founders and thought-leaders. Behind every star, 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 mentorship and its relationship to scaling an organization. We dove into the Masters of Scale pantheon of 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 your business. And if you’re interested in playing that role for someone else, well, there’s plenty here for you, too.

Let’s get into it.

Copy LinkGrit is not enough without support

DUCKWORTH: Luke Skywalker needed Obi Wan Kenobi, right? The modern-day Luke Skywalker for me is Diana Nyad, the amazing woman who swam from Cuba to the shores of Florida, a feat that had never been done without a shark cage.

BERMAN: Angela Duckworth is a psychology professor at Penn and the Wharton School, and author of the best-seller “Grit.”

DUCKWORTH: On her last and successful attempt that she made after decades of trying and failing to do this, she heaved herself onto shore and said this, and I’m going to quote it so I don’t get it wrong.

She said, “I have three messages. One, we should never give up. Two, you’re never too old to chase your dreams. And three, it looks like a solitary sport, but it takes a team.”

BERMAN: In our conversation, Angela emphasized mentorship while describing the missteps she’s seen so many people make — including herself.

DUCKWORTH: When I was growing up, so much of what I accomplished was really trying harder. Like sitting there in my BC calculus class and thinking, “I know Darshak got it faster and Chang Kim got it faster, but they can’t outwork me.” I am going to learn BC calculus, right?

And I felt that way for, I don’t know, 40 years. Even in my own marriage, I thought to myself, “Wow, 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, right?

It was a very, very stressful time. He was working, some weeks, a hundred hours a week. I was on tenure track at an Ivy League institution. We had two young children who had to be taken care of. There was so much stress. The only trick I knew was to try harder. The only trick I knew was grit. I was going to wake up earlier.

I was going to stay up later. I was going to use every ounce of my will to make the life that I needed to make for my children, and my husband, and my career. And I’ll tell you, 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.

We 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 help him prioritize in ways that he would never be able to do on his own.

I reached out to mentors to help me figure out my research program and accomplish it in more effective ways. To me, grit is great. But grit is not enough, and you absolutely need to make your situation your ally if you’re ever going to run the marathon of success.

But I think one of the mistakes 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? To not be a slacker, right? To not 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 not to tell them that first. I’m like, “Oh wait, who are you talking to? What’s your AA group?” Essentially, right? If you don’t have one, you need to get one right now.

A number one action step is you should be in a formal community of other founders. This is why I’m a big fan of incubators, especially the ones that are well-designed, like Y Combinator.

There’s a power in the solidarity, the accountability, and the peer learning of a group. You want to be in a flotilla, not sailing off on your own. So that’s number one.

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, like, “Oh, I’m so grateful that this person came into my life and put me on the straight and narrow,” 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 create a relationship, cultivate it, and so forth. 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.

Those would be my two pieces of advice to founders: go find another founder. It doesn’t have to be your co-founder for your start-up. It could be somebody who’s doing something totally different, but you should be meeting regularly, trading stories, crying on each other’s shoulders, and then you should very proactively cultivate mentoring relationships.

BERMAN: Like 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.

Copy Link“You have to make yourself useful”

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. When that moment arrived, it came with one of the biggest names in music history.

JIMMY IOVINE: I walked into the studio, and there’s my boss Roy Cicala and John Lennon. It’s a session being run by my boss. 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 working with John and him and Roy. Through working with me, they 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.

It was the greatest two years I could ever want. Roy was very stern, a very tough guy, but he loved teaching, and 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. You have to make yourself useful and 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 modest guy. But he told me growing up, “You’re a special kid. Every 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 can 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.

BERMAN: Jimmy’s boss — who produced a score of platinum 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.

Copy LinkThe truth about what a mentor really does

Mentors can give brutally honest advice. That 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 sometimes mentors take you by surprise.

KLUGER: My first mentor was the woman I was most frightened of. She was the mentor I didn’t know was going to be my mentor.

The reason she became my mentor is that she gave me some radical candor about something she felt was going to influence my career.

I was 21, and I was at Good Morning America.

One day I was crying at work. I was new to the job, and it wasn’t about work — it was personal. She said, “Allison, I don’t want to ever see you crying again.”

Do you know why? I intuitively knew why, but she told me anyway. She said, “You’re young, you’re female, and 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 asks you how your day is, you say, ‘I’m having a great day.’ If you want to come cry somewhere, you come in my office and close the door.” She said, “Do you understand?” I said, “I do.” She then kicked me out of her office, and all I wanted to do was cry. I was so mortified — one, that I had been caught crying, and two, that I didn’t realize that it wasn’t the right thing to do.

But what she did for me was make me realize the kind of leader I wanted to be. I decided that I wanted to be reliable. I wanted people to give me work. I wanted people to trust me. The evolution of my personality started then. I became the person everyone went to for help. I got along with everybody. I was unflappable. If something bad happened, I’d go hide in a corridor, get all the stress out, and then go back to solving the problem.

She gradually became my mentor. The fact that she was so honest with me and willing to tell me something hard to hear was really the start of me understanding the power of a mentor. 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, kick your ass, and want you to be the best version of yourself.

BERMAN: 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 U.S. Senate leadership. I went to one of my mentors, Robert Raben, a man who is as brilliant as he is kind and wise. He had also worked on Capitol Hill and told me that on most Fridays, my boss would head back to his state and most of my colleagues would take a light day to catch up and socialize. I could do that if I wanted, but he told me 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?” He smiled a Yoda-like smile and answered his own question: “Themselves.” Robert told me that the job came with a cheat code, and if I used it, I would have access to the world’s treasure trove of knowledge, insights, and ideas.

That advice helped shape what would generously be called a non-linear career, jumping from industry to industry and role to role. It’s been a journey I have loved and continue to love. That one bit of mentorship from Robert has helped shape the past two decades-plus of my life.

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

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Welcome back to Masters of Scale. We are exploring our favorite lessons on mentorship from the legendary leaders who’ve shared their stories with us.

Copy LinkA-Rod’s key to being a good mentee

One field where mentorship is key to top performance is sports. We had MLB Superstar Alex Rodriguez on Masters of Scale to share insights on how his all-star baseball career relates to his successful business ventures. He told us he counts one of America’s true sports luminaries among his long list of mentors.

RODRIGUEZ: Magic Johnson started mentoring me about 20 or 25 years ago when I was a really young player in the league.

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 can do it too.” He’s got brown skin like me. If he can do it, I can do it. And that was the start of it. I saw how powerful that was.

When I transitioned to business, I’ve had some of the greats not only be my friends but mentors. They’ve taught me about the ins and outs, how to win, how to avoid losing, and how to sidestep some of the bumps they’ve gone through.

From Barry Sternlicht to Mark Mastrov from 24 Hour Fitness to Mark Lore from Jet, and the big one, Warren Buffett.

I saw how powerful mentorship was in my life. As a mentee, I benefited from that.

Now, as a mentor, I have many athletes reaching out, saying, “I want to get involved in investing. How do I do it?” 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 ones have the most questions. They’re enthused, they lean in, and 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. I try to touch base 10 times before asking for anything, 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.

Figure out creative ways of saying, “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.

It’s your job as a mentee to create that and just be humble, grateful, and appreciative for their time.

BERMAN: 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.

Copy LinkRethinking the roles of mentor & mentee

And sometimes mentors become more than that. With a foundation of mutual interests, respect, and admiration, mentorship can become an active partnership. That’s what happened with Alexa von Tobel, founder and CEO of the personal finance platform LearnVest.

ALEXA von TOBEL: Literally all of my closest friends are fabulous humans, many of them big entrepreneurs. We always not only rooted for each other but were also Red Phones in the moments that mattered, 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?” Building very honest, close friendships.

People always ask, “How do you approach networking, Alexa?” And I’m like, “I don’t think I network at all. I just build friends.” Then I try to do two favors for someone else before they can do something for me, so that I can just be helpful. 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, whom I met during undergrad at Harvard, was a co-founder of Paperless Post.

I don’t think mentors are just older people mentoring younger people. It’s dual. Some of my 80-year-old mentors would tell you I’m mentoring them, and I have a 20-year-old who’s my mentor teaching me about what the next generation cares about.

So I just approach it as friendship, and I’m happier because of it.

BERMAN: Alexa’s point is an important one — that there’s no single template for mentorship. Learning can happen across industries, generations, and geography. 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 going up the mountain alone. Mentor relationships showcase generosity and 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 more mentorship in your life, we hope this episode inspires you to continue that quest with some practical ways to do it.

Oh, and if you have a mentor you want to shout out, we’d love to hear about them. You can email us at [email protected]. Or, we have contact info in our show notes.