NYLP: Welcome to the New York Launch Pod, a podcast highlighting new start-ups, businesses, and openings in the New York City area. I’m Hal Coopersmith, and this is our ninth episode. And we are not going to be talking about a business in this episode, but a book. Before we start, I never thought that we would do a book. But I happened to read it this summer and really loved the book. And I thought it would be appropriate for the podcast. And I reached out to the author, and she has done so many media appearances but was willing to come on. I’m very excited about it. So stepping on to the Launch Pod, we have Gillian Zoe Segal. The book is “Getting There: A Book of Mentors.” Welcome to the podcast, Gillian.
Gillian: Thank you so much for having me.
NYLP: So what is Getting There about?
Gillian: I photographed and interviewed 30 people who are all famous at the top of their fields. And I talked to them about the road they took to get there, focusing on failures and obstacles that they had to overcome and the lessons they learned from their journey. So each essay, there’s 30 people in the book, and they range from Warren Buffett and Michael Bloomberg to Jillian Michaels, who’s a trainer, and Rachel Zoe, who is a stylist and fashion designer. There are 30 essays, and they are each in the subject’s own words. And I put them together from interviews that I did. So there are about five or six pages each, super easy to digest.
NYLP: How did you come up with the idea?
Gillian: You know what? Growing up, I never had a mentor and . . .
NYLP: Never had a mentor?
Gillian: I never had a mentor. I always used to look at people who were in diverse fields, and I would wonder, “How did she figure her path out?” and “How did he become so successful?” It was something I wanted to know, so what a great excuse to find that out is to write a book about it. And it was a good excuse to sit down with a lot of these people that I really admired and asked them everything I wanted to know.
NYLP: So you were looking for a mentor, or you just were curious about how everyone became successful?
Gillian: I was curious about their secrets to success. Basically, it’s called “A Book of Mentors” because they’re virtual mentors. I guess I was looking for mentors. But what is a mentor? I wasn’t looking to have lunch with each of these people once a month and talk to them every week. But I was looking to learn from them.
NYLP: So you came up with the idea and then what did you do?
Gillian: And then I went out to try to get subjects, which was the really, really hard part, because I was going for an A-list of people. And I got rejected a lot and ignored a lot. And it took me five years to put this group of 30 together.
NYLP: Did you come up with the people that you wanted first? How did you select the people?
Gillian: I wanted to get a diverse group of people because I thought it would just be interesting to see what the themes were between successful people from a broad spectrum of fields. And that’s what I was going for. So it wasn’t like I had to have anyone in particular. Once I would get somebody in a certain field, then I’d think, “Okay, that box is checked off.” And I wanted to make sure I got a diverse group.
NYLP: Who was the first person that you got?
Gillian: The first person that I interviewed was Craig Newmark, who was the founder of Craigslist.
NYLP: How did you get him?
Gillian: Actually, my brother knew his publicist. So I went through his publicist. I contacted her, and she liked the idea. I did have another book under my belt. This was my second book. And my first book was called “New York Characters,” and it had some notable New Yorkers in it like Spike Lee, John McEnroe, Ed Koch, and a bunch of people who were only famous in their own little subcultures. But I did have something on my resume to show my work. So it wasn’t so hard to get somebody.
NYLP: And how much time would you spend with everyone?
Gillian: As much time as they would let me. But usually, it was under an hour. Sometimes, it was around a half an hour. I had to photograph and interview them during that time.
NYLP: And you did the photographs yourself?
Gillian: Yes, I photographed everybody.
NYLP: How long did it take to photograph?
Gillian: Well, it just depended. I knew how much time they had given me. I always got the photograph out of the way first, because that was something I couldn’t follow up with on the phone. So I had to make sure I got the photograph, and then I would interview them. But if we had to go, we had to go. And sometimes, I would ask a couple of follow-up questions via the phone.
NYLP: So what were the interviews like?
Gillian: They were just like intimate conversations, basically. I had to psych myself up to not be intimidated of asking anything. I knew that if I left the interview and hadn’t asked something that I was truly curious about, because I was afraid to ask, I knew that I would be really upset with myself. So I just went in there and asked all of the things that I was interested in. And I hoped that other people would be interested in the same things, as in readers.
NYLP: Did you vary up the questions? You must have done a little bit of background research.
Gillian: I did. There were certain questions that I asked everybody. And there were a lot of questions that were more pointed that I asked specific people. But I made sure to ask open-ended questions, because if you go into an interview and you know all the questions already, you’re not giving that person a chance to open up and tell you something new. So if I was only going to ask somebody about an experience that I’d read about, I might miss out on something they’d never talked about before.
NYLP: So you photographed and interviewed in an hour’s worth of time. How long did it take . . .
Gillian: Or less, a lot less, like 45 minutes might have been the average.
NYLP: How long did it take for you to write an essay about each of the people?
Gillian: It took about a week! And when I say a week, I mean a week of waking up and sitting in my pajamas writing all day long. I am surprised about this too, because I thought, “All right, it’s going to be in their words. I’ll just have to edit this.” But when people talk, they talk all across the board. So you talk a little here, you talk a little there, but it’s not like an essay. It’s just a big mess. We would talk about . . . And so basically, I had to clean up the mess. I would have about a 20-page transcript from each interview. And I would take a sentence from here, from the end and move it to the first. We would start with that. And then I would add things together and make sense of it. It was like doing a puzzle, basically, from a messy conversation into an organized essay.
And then I would send every essay back to the subject for their approval, because I wanted to make sure that I didn’t mess up or make some wrong juxtapositions or change a word I shouldn’t have or anything. So every single essay in the book was sent back to the person who said it. And as a result, the essays really do feel like you’re having an intimate conversation, and everyone stands behind everything they said.
NYLP: Were there any edits by any of the people?
Gillian: Well, afterwards, I handed it over to everyone, and I said, “I want to make sure you’re completely happy with this and happy with how you came across and feel free to change or add or delete anything.” There might have been some small edits, but not really big ones, which I was happy about. It was maybe like “My daughter’s name Sarah is spelled the other way” or whatever. But there really weren’t any major edits.
NYLP: What was your pitch to get people on the book?
Gillian: Well, basically, I feel that this book is a celebration of every subject who’s in it and what that person has to offer. And I truly feel with all my heart that anyone who reads this book is going to benefit from it. And I just thought it was a chance for all of the people who participated in it to give back and help others. So that was my pitch. I just said, “I know people will be so inspired by your story.” And a lot of people feel alone in their own career struggles. And it’s just incredible for them to hear that the people they admired most also had failures and setbacks and had to overcome obstacles. So basically, I pitched it that way and that is not BS.
NYLP: I read at one point, you only had just a brief moment with some of your subjects to get them as a interview, and you had an elevator pitch. What was your elevator pitch?
Gillian: When you approach somebody, sometimes, I would approach my subjects live. And you really want to take up as little time as possible. You don’t want to be annoying. No one wants to hear a mouthful from a stranger going on and on. You just have to get to the point quickly, like “I’m here to ask you about this. Who should I contact, and I’ll send all the information tomorrow?” Basically, I would give a 15-second or less pitch to the person. That’s what I was talking about.
So I didn’t go up and say, “Hey, I’m doing this book and blah, blah, blah, blah, blah, blah, blah, blah.” I would just say, “Hi, I’m doing this book. It’s celebrating the lives and careers of successful people,” or whatever. I would say, “And I would love for you to participate.” I might have dropped a name or two. “Warren Buffett is in it. Michael Bloomberg is in it. I’d love to include you as well. Let me know who to contact at your office tomorrow, and I’ll send all the information. That’s all.”
NYLP: One of the things that I thought was interesting and just talking to you now, I get a better sense that it might have been more self-selecting. But Warren Buffett called it an “internal scorecard” and that a lot of the people that you had as subjects were successful but also seemingly good people. They don’t have a bad reputation. Was it self-selecting? Or did you go out and say, “I want these type of people”?
Gillian: I wouldn’t put anyone in the book whom I didn’t personally admire. So if there was somebody who was slimy or whatever, I just wouldn’t ask them. I wanted people who I really could look up to. They had to be at the top of their field, and I had to admire them.
NYLP: So after writing the book, what do you think success is?
Gillian: Success is something different to everybody. And you have to just know yourself and know what success means to you and go for that, and there should be no judgment. So what I might think success is could be different from what you might think success is. So if success to Warren Buffett means making a lot of money, all the power to him. There’s nothing wrong with that. Nothing wrong with that. And if success to someone else means doing something else, helping a lot of people, getting a lot of fans, whatever it is, all the power to that person.
Anyway, meanwhile, Warren Buffett doesn’t think that success in life means making a lot of money. He’s very wise and deep and has incredible values. But as far as his business is concerned, he’s out to make a lot of money, not at the cost of his reputation or being a good person or anything like that.
NYLP: One of the reasons why I wanted to have you on is that this is an entrepreneurship focused podcast, and when I was reading the book, there seemed to be a lot of lessons that were in the book that could be transferred to entrepreneurs. Before I’d say what some of the themes are, in your introduction to the book, you talk about some of the themes. Do you want to say, specifically, what themes might be applicable to entrepreneurs?
Gillian: Well, first of all, I want to say that almost every single person in my book is an entrepreneur. Basically, what they did is they took something, an interest that they were passionate about and good at, and we can talk a little bit about that, and made the most of it. Jillian Michaels, who is a personal trainer, she has a health and wellness empire. There’s Laird Hamilton who’s a surfer, and he’s got a whole surf world. He’s an entrepreneur. He creates different products. So whatever someone’s passion is, they made an entrepreneurial venture out of it and a big one.
So basically, the main themes are that you should start by doing something that you’re passionate about and something that is within your “circle of competence,” as Warren Buffett puts it. He says that it’s very important to know your strengths and weaknesses and do something that you’re good at. He says, “Knowing what to leave out is as important as knowing what to leave in.” And he actually quotes a friend, his, and I love this quote. It’s his friend, Tom Watson, who’s the founder of IBM, and he says, “I’m no genius, but I’m smart in spots, and I stay around those spots.”
So not everybody has the potential to be a huge success in every single field. If you took Warren Buffett and you put him in Jeff Koons’ shoes or Hans Zimmer, he wouldn’t . . . Hans Zimmer is a famous composer who’s in the book, who did the music for “The Lion King.” He wouldn’t do it and vice-versa. But they’re all doing something that they’re passionate about and that’s within their circle of competence.
NYLP: Well, one of the interesting things that I thought was once you’d find a passion is not quitting, and a lot of the people that you interviewed were very resilient, for lack of a better term, about what their pursuit was.
Gillian: If I had to say what the most common thread between all of my subjects is is that they are all determined and resilient people, because I’ve compared life to a game of Whack-a-Mole. You know that game in the carnivals where the moles put their heads up out of the hole, and you whack it with this big hammer that looks like a microphone?
NYLP: Love the game.
Gillian: Yeah, well, that’s what life is like. I think life whacks everybody on the head in big ways and in small ways and in personal ways or ways that just have to do with your career. But there’s things that get you down, and you just want to get in bed for a year.
Everyone in my book, they might have gotten in bed for a little while, but not that long. And they learned from their mistakes. And they get back up. And they try again or they try something new. And like what Mayor Bloomberg says, “The harder you work, the luckier you get,” if you keep at it, something will hit. So don’t underestimate the role of determination in success.
NYLP: And one of the other things that’s somewhat of a contrast to it is that your subjects were very resilient. But they also kept their eyes open for new opportunities. They weren’t necessarily on the path that they were destined for.
Gillian: Yes. That is something . . . another theme, which is that you don’t need to have everything all figured out. If you were to interview any of my subjects, they wouldn’t know if you got them at a young age where they were going to end up. They couldn’t have scripted it out. But they all started doing something and then kept their eyes open for new possibilities.
So an example of that is Leslie Moonves, who’s the President and CEO of CBS. And he started out, he wanted to be an actor. And after years of really being a bartender to make ends meet, he decided to try things out on the other side of the camera. And he became a tremendous success, obviously. If you’re too rigid, you’re just going to miss out on opportunities. And you have to be fluid and open to change.
Jillian Michaels, who we were speaking about, she became famous for being on “The Biggest Loser” as the trainer. Well, she only devoted herself to her field after being fired as a talent agent. Ian Schrager is in the book. He became famous for starting Studio 54, the famous disco in New York City. And he actually ended up going to prison for tax evasion. And then when he got out, he saw a new opportunity in the hotel world, and he became a hotelier. He is responsible for the boutique hotel revolution. But anyway, he couldn’t have told you that he was going to do that when he was a young lawyer, which is what he started out as.
NYLP: One of the things that was interesting are a lot of these subjects, they had an opportunity to explore themselves in childhood. It seems in our culture that . . . At least in your introduction, you mentioned that you were set on a certain path, or we have a certain impression as to what success is but don’t necessarily let children explore. And that was something that a lot of your subjects brought up.
Gillian: Yeah, a lot of my subjects credited not being over-scheduled as a child, for allowing them to get to know themselves and having free time to explore. One of my favorite stories is Craig Venter. And he is a scientist, and he was the first person to sequence the human genome. And before anyone turns this podcast off, I’ll explain that in a super easy way.
Sequencing the human genome, all that means is looking at a human’s DNA to see what it says. And once you can read a human’s DNA, you can know from the genes they have what their future holds. You might say you have the gene for breast cancer or whatever it may be. And now, all of the medicine that’s going on now is based on that knowledge. So he was the first person to do that. And he was a terrible student. This is what was so surprising. He almost failed out of high school. He slid by on a D-minus because they forced him to write an extra paper that no one else had to write because he was such a hellion that they didn’t want to ever see him again. Anyway, he did terribly in school. But he says that he survived the school system because he escaped it. And he had a lot of free time, and he would go and be creative. He would build boats and just run around his neighborhood creating things out of plywood. And that’s what allowed him to develop into the person he is. And that’s what allowed him to eventually provide us with all this incredible knowledge that’s helping us all with our health and our lives.
NYLP: After writing this book, do you think that anyone could be successful like the people that you interviewed or that there are people that could be successful that aren’t? What’s your takeaway?
Gillian: I don’t think you’re born with something. It’s not like you’re born with it or you either have it or you don’t. I think that things can be learned. So I think that if you can find something you’re passionate about, that will give you the motivation to persevere and jump all of the inevitable hurdles that are going to be in your way, because nothing’s easy.
I do think that success is something that anyone can achieve. But I don’t think anyone can achieve it without doing the work necessary to get there. It’s not easy. It’s not easy, but you can learn a lot from others. And that’s what the book provides. It provides an incredible . . . It’s like business school in a book.
NYLP: And another common theme to that point was that almost everyone said that they weren’t afraid to fail and that people can be afraid or people can have paralysis by fear and not do the venture or something that they were meant to do because they are afraid of failing for whatever reason.
Gillian: Yes, that is a huge theme. I could give you so many examples because basically, everybody in the book fails. But they say that if you’re not . . . This is a quote from Kathy Ireland. She says, “If you’re not failing, it means you’re not trying hard enough.” And I’m going to tell you Kathy’s story. She became famous as a Sports Illustrated swimsuit model. And as she grew older, she wanted to do something that wasn’t dependent on her looks. And she failed for years at launching her own brand. She wanted to launch her brand, and nothing worked. She tried a beer company, skincare line, arts and crafts projects. Nothing worked. She finally launched her own brand with a line of socks, of all things. And how did that happen? Some guy offered her the opportunity to model a pair of socks, which wasn’t something she was really psyched about doing. But she said, “You know what? I’ll do it if we can go into business together.” So she had a pair of Kathy Ireland socks, and that’s what launched her brand.
But even when she started this brand, it wasn’t easy. And she almost went bankrupt. She talks about sleeping in airports to save money and having to downsize her office space and everything. But finally now, her brand has taken off. It’s a $2 billion business. And her name is on over 15,000 products. So when she says, “If you don’t fail, you’re not trying hard enough,” she knows what she’s talking about.
NYLP: And I was also thinking about Sara Blakely who said in her essay her father would go around the dinner table and ask everyone how they failed that day.
Gillian: Yes. She said that growing up, her father would do that. And it basically taught them that what’s important is to go out there and try things, and he just wanted to guard against them being paralyzed by the fear of failure.
NYLP: So talk a little bit more about Sara Blakely.
Gillian: Well, Sara Blakely is the billionaire founder of Spanx. And for those of you who don’t know what Spanx is, it’s basically footless pantyhose. It makes women’s tummies and butts look good under the clothing. And she has a really interesting career path. Her whole life was geared towards being a lawyer. She wanted to be a lawyer. That’s what her father was. She would take off from school to watch him in court and take notes. And that’s what she wanted to do.
And when it finally came time for her to take the LSAT, she bombed it. And so she picked herself up. She took a review course. And she did one point worse when she retook it. And she was totally depressed. And she went off and drove to Disney and got a job loading people on rides at Epcot Center. And after that, she spent eight years working for a company that sold fax machines door to door. And she would literally drive around, knock on doors, and say, “Can I sell you a fax machine?”
And one day . . . She would do, actually, stand-up comedy at night, which is interesting. But . . .
NYLP: And for those who don’t know, a fax machine was the thing before email.
Gillian: Yeah, exactly. A fax machine is not even a Xerox machine. That’s a high-end thing. Fax machines cost nothing. Anyway, so one day, she was really unhappy with how her butt looked in her pair of white pants, and she wished she had pantyhose without the feet, because she wanted to wear sandals without covering her feet. And she thought, “This is what I have to invent.”
So she spent a year working on this idea. And when she finally told her friends and family what her big idea was, she said, “It’s footless pantyhose,” they laughed at her. They thought she was joking. When they realized she wasn’t joking, they tried to help her out by getting her to stop working on this because it was a waste of time. And they would say things like “This is a good idea. The big guys would have done it,” or “They’ll just knock you off if it really is a good idea.”
Anyway, she stuck to her guns, and now, she’s a billionaire from footless pantyhose. And she has incredible lessons in the story. She talks about the importance of keeping a young idea secret. She also talks a lot about how her training selling fax machines door to door equipped her with the skills necessary for her ultimate success.
NYLP: It seems like a sales is a common theme, and I’m thinking about John Paul DeJoria.
Gillian: Yes, he also has an incredible story. He was fired from four different jobs, and he ended up living in his car on $2.50 a day. Now, he’s worth billions. One of his jobs early on was selling encyclopedias door to door. And he also says that that training equipped him for his ultimate success. And his first successful company was called John Paul Mitchell Hair Systems. And it’s a line of hair care products. And he had to go from beauty salon to beauty salon convincing people to buy his product. And from his years selling encyclopedias, he knew that after being turned down from four out of five salons, he knew not to let that discourage him. He knew that that’s just part of the process.
NYLP: I loved his little anecdote where he was selling encyclopedias and he said, “If you get turned down from 15 consecutive people, you have to go to the 16th door just like it’s your first.”
Gillian: Exactly. You have to show up all bright-eyed and bushy-tailed, because if you’re acting all defeated, people will think you’re selling a bad product if you’re saying “Oh, I’m sure you don’t want to buy this encyclopedia.” You have to be like “I have the greatest product.” You’ve got to show completely excited.
NYLP: So was there someone that you wanted to interview that you didn’t get a chance to do?
Gillian: Name any power woman. It was hard to get people in the book . . .
Gillian: Yeah, I tried her.
NYLP: You tried Oprah?
NYLP: What happened?
Gillian: Said, “No, thanks.” I had to throw a lot out there to get the people in the book. And I wanted to get more women in the book. I’m a woman, and I would love to be supportive of women. But it was hard. So there’s a two to one ratio of men to women in the book.
NYLP: Would you do a sequel?
Gillian: I don’t think I’m going to do a sequel, because I think that this was a perfect number, and I think that . . . I don’t know. It might just get old for me.
NYLP: It took you five years to do?
Gillian: It took me five years, yeah.
NYLP: What was that like?
Gillian: What took so long was really getting people to say yes. Like I said, I was ignored a lot. I was then rejected a lot. I would get a no from somebody, and I’d find another way in. Very early on, a friend of mine said to me something that stuck with me. He said “Don’t take a no from someone who can’t give you a yes.” And basically, what that means is don’t let someone’s gatekeeper get you offtrack, because a lot of times, the person who you’re after, the person who I wanted to interview might not have even known I was knocking on their door, because everyone, all of these luminaries are super-busy. And they can’t field every request that comes their way. So they have gatekeepers, assistants, managers, agents, publicists, who make decisions that they don’t even know about. That’s how it has to be. Otherwise, they would have no time in their day to run their business.
So basically, I say, “If the front door’s locked, try the back door. If the back door’s locked, try the side door. And if that doesn’t work, try crawling in the window. And if you can’t do that, then wait a little while and try the front door again. You never know, someone might answer.” So basically, that’s how I did it. And I have stories of being . . . Frank Gehry was one of the toughest, the architect, Frank Gehry, who has an incredible story, by the way. Do you know about . . .
NYLP: I read the whole book.
Gillian: Yeah . . . He was told in architecture school to get out, to drop out because he would never make it. And he actually failed his first perspective drawing class. And now, he is considered one of the most important architects of our age. And he’s got famous buildings like the Guggenheim Museum in Bilbao, the Walt Disney Concert Hall in Los Angeles. He’s got two great buildings here in New York City, the Spruce Street and the IAC Building on the West Side Highway that’s got those white cloudy windows and looks like a ship, sort of.
Anyway, so he was the hard person to get. I was rejected twice from his office. Then a friend of mine said that her dad was dating someone who knew him. And I had her ask, and she was ignored twice. And then I just figured, “Okay, e-mails are free. I’ll send another one to his office.” And that one got some attention from whoever that assistant was that day, and I got in.
NYLP: And you just thought, “I have to have Frank Gehry.” You just kept on trying?
Gillian: I was very passionate about the project. So that gave me the fuel to just want to keep on trying. And I was basically dancing until the curtain closed, until it was like “All right, this book has to come out. Hand it in.”
NYLP: So Frank Gehry was the hardest. What about Warren Buffett?
Gillian: I loved Warren Buffett. He is exactly where he is today because he deserves to be. He has so much wisdom. And what I love about my book is that you can have no interest in somebody’s field, like you don’t need to be a value investor or want to even invest in anything to get something from Warren Buffett. You can be an entrepreneur with a bagel store and get so much out of him.
So one of the favorite things that he taught me is he’s had this quote, which is “You can always tell someone to go to hell tomorrow.” And this is a piece of advice he actually got about 50 years ago from a friend of his. And he says it’s one of the most useful things he’s ever learned. And basically, what it means is it’s a lesson in controlling your temper. When something bothers you, just try your hardest to refrain from spouting off in a moment in anger because you might say or do something that you’ll regret and you can’t take back. He says, “Whatever it is, just sit on it for a day. And if you still feel the same way, you could tell them to go to hell tomorrow. You haven’t lost your opportunity.”
I just love that because it’s just such a universally applicable advice. You could use that in your love relationship. You could use that if you’re a parent and have children. And you could certainly use that in any business relationship.
NYLP: You dedicated this to your daughter in terms of finding a mentor. And you talked about finding success. Who was the target audience for your book, aside from your daughter?
Gillian: Well, really, originally, I dedicated it to her. But really, I was the target audience. It was something that I wanted. I ate up every single essay, and that’s really what kept me going to make this book. But I figured that if I was so interested in this and so inspired by what all of these luminaries had to say, that other people would be too.
And what I think was so special about the book is that people really just opened up. The people who I interviewed really opened up. They let their guards down, and they didn’t sugarcoat their careers. That’s what’s important. That’s what we need to not feel alone and to feel inspired and to feel like we could do it too.
NYLP: But you’ve had this book out for a little while now. Is there a portion of audience that is surprising to you that’s picking up your book and you thought, “Boy, I’d never thought that this book that interested me would be appealing to this group”?
Gillian: Well, the one thing that does surprise me is that when people say their kids are so into it, because I’m thinking, “Really? Your 12-year-old is so into the book?” I just didn’t think anyone that young would be, but I get that. But meanwhile, anyone who’s listening, please don’t go give it to a 12-year-old because that . . . It surprises me.
NYLP: Well, I love this book. I thought there were a lot of great lessons that came from it as I was reading it this summer. I’m so glad that you came on. It’s also beautiful. The photos that you took are great. You can read it on your Kindle, but also, you can get the hardcover. You can display it. People will love flipping through it. At least everyone knows someone who’s in the book. And you’ll learn a lot of lessons. And if you mention “New York Launch Pod,” Gillian will sign the book for you.
Gillian: Yes, I sure will.
NYLP: Well, Gillian, thanks for coming on the New York Launch Pod and sharing your time with us.
Gillian: Thank you so much for having me, Hal.
NYLP: If you want to learn more about the “New York Launch Pod,” you can follow us on social media @NYLaunchPod. You can also visit nylaunchpod.com. People may not know this, but there are transcripts of every episode up on the website. So if you don’t want to listen again and there’s something that’s interesting to you, you can go to the website and read all about it.