Gillian Zoe Segal is the Author of Getting There: A Book of Mentors where 30 luminaries share their secrets to navigating the rocky road to the top. She received a Bachelor of Arts from the University of Michigan and a law degree from the Cardozo School of Law.
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Worst Entrepreneur Moment
- Gillian had an idea for Tinder 4 years before Tinder, but her friends talked her out of it. Fire Nation, we describe what crabs in a bucket means, and we talk about the tall poppy syndrome. Don’t miss it!
Entrepreneur AH-HA Moment
- Don’t take a “no” from someone who can’t give you a yes. Sounds obvious, but we do it EVERY DAY.
What has you FIRED up?
- Getting There by Gillian Zoe Segal
Small Business Resource
Best Business Book
- Stand Out by Dorie Clark
John: Gillian is the author of Getting There: A Book of Mentors, where 30 luminaries share their secrets to navigating the rocky road to the top. She received her BA from the University of Michigan and a law degree from the Cardozo School of Law. Gillian, take a minute, fill in some gaps from that intro and give us a little glimpse in your personal life.
Gillian: All right, well, I have sort of a nonlinear career path in that I went to law school and just as I was about to graduate, I realized I did not want to practice law and so I went through a little lost phase and then I came across a commencement address that someone had given at my alma mater at the University of Michigan and it was actually the cartoonist, Cathy Guisewite and she suggested that everyone graduating take the classes, the friends and the family that have inspired them the most and remember what they love and if they remember what they love they’ll remember who they are and if you remember who you are you can do anything. So, I literally did that.
I made a list of everything I loved and I decided to pursue photography, a big change from law, and that led me to my first book which was called New York Characters and I photographed and interviewed the people who made New York such an incredible city. And that eventually led me to my current book which just recently came out which is called Getting There: A Book of Mentors.
And the way I got to that was I still even though I was doing photography, I wasn’t really sure where I wanted to end up and I’d never really had a mentor growing up and I used to find myself looking at highly successful people and thinking how did he figure his career path out and how did she become such an incredible success.
So, I basically created the book that I wanted. I was fulfilling a need that I had and I sat down with 30 leaders and I got as personal with them as they would let me get and I asked them to just let their guards down and tell me their stories and tell me about their lowest lows and the lessons they learned from their journey and then I asked them to basically distill the best advice and wisdom that they had to offer.
John: I love that scratching of your own itch, that filling a void that you see. I love this quote by Gandhi, “Be that change you wish to see in the world.” If it’s not actually a change that you’re seeing or something that you see exist that you think should, get there and create it, like stop whining and complaining that it doesn’t exist or it’s not there and be that person to make it happen.
So Gillian you’ve done that, you will continue to do that over and over again. Fire Nation, that’s why you’re listening right now because you are a change maker, a void filler, and Gillian, let’s just break this down. You’re at a networking party and someone walks up to you and they say, “Gillian, what exactly do you do?” How do you respond in 10 seconds?
Gillian: You know I’d say No. 1, I hate being pigeonholed.
John: Ah oh, boom! But if you’re gonna pigeonhole me –
Gillian: Yeah, I just wrote a super inspirational career book and I am currently looking into several entrepreneurial ventures.
John: Nice. I hate being pigeonholed. I think that’s a great start to any conversation to be honest because that’s the antithesis of being an entrepreneur is being pigeonholed.
Gillian: That’s true.
John: It’s so true.
Gillian: We all have a lot of chapters in us.
John: Yeah, a lot of chapters, a lot of pivots, a lot of just different directions that we can go, grow and expand as entrepreneurs. And Gillian you’re doing a lot of things, you know, but the reality is life ain’t cheap, you need to find a way to put food on the table, to pay the rent and that’s what we’re doing as entrepreneurs, we’re growing viable businesses. So, how are you currently generating revenue today?
Gillian: Get some revenue from book, some from speaking engagements and most is from real estate investments that I’ve made.
John: Good, good, there we go, diversifying across the stream and growing different areas. Now Gillian you have some stories. Some are good; some are bad and we’re not gonna any corners here, we’re gonna go right to the bad and not just the bad but what I would call the worst entrepreneurial moment you have experienced thus far in your entrepreneurial journey. So, take us there Gillian. Tell us that story.
Gillian: Okay. So, I think the worst; it’s not just one, it’s a few. And basically, it’s giving up on an idea that I had that was a good idea or, you know, not even pursuing it because someone I ran it by had something negative to say about it. And I look back on things that I had dropped in the past and I regret it.
John: Let’s get specific.
Gillian: Okay, I had an idea a long time ago for a dating service. It was kind of, you know, all that was out there at that time was Match and JDate basically and my idea was a little bit more like Tender, but I ran it by some people that said oh, that’s gonna be really hard and this and this. And I ended up just dropping it and I think the lesson I learned from that, and especially from making my book, is that no matter what your idea is, even if you invented the Internet before it existed, there’ll be people out there who say that’s a bad idea, that’ll be too hard or you’re gonna be spinning your wheels.
And no matter how good your idea is, it’s not gonna be easy executing it no matter what it is and really, you know, the most important factors for success and to be an entrepreneur is to be determined and resilient and without that you’re not gonna get anywhere. And at those times in my life when I gave up on things, I think I didn’t have the confidence to be that way. And there’re a lot of examples in my book of people who were that way and that’s why they’re in my book.
And Ian Schrager who is an amazing entrepreneur and he says a quote and he says, “In the end, there’s so little that separates people. Those who want success the most and are relentless about pursuing it are the ones who get it.”
John: I love that quote and Gillian let’s be honest, Tender, I don’t think is gonna work out anyways, I mean the founder might make a billion dollars and do you really want that kinda stress in your life?
Gillian: Yeah, who wants to be responsible for so many marriages, right?
John: And kids and babies and all these things.
Gillian: Yeah, it’s a big responsibility.
John: Oh, so there’re a couple things that I wanna talk about. Have you ever heard of the crabs in a bucket theory Gillian?
Gillian: No, tell me.
John: So, I’m from Maine so this is kind of a Maine thing, but I mean it’s definitely applicable across the world. But when fisherman get in or lobster men or crab men, whatever they wanna call themselves, and they have all these crabs in a bucket, they just put the buckets on the dock and they don’t even have to put a cover on the bucket that’s full of crabs because when there’re multiple crabs in a bucket and they’re gonna not stop by the way trying to get out. Crabs are always gonna try to get out, but the thing is whenever a crab is about to get out, all the other crabs that are still in the bucket pull it back in 100 percent of the time so much so that you don’t even have to put a cover on the bucket.
And that’s the world that we live in which is unfortunate. Hopefully, things are changing as we move into a mindset of abundance with entrepreneurship, etc., but we live in the crabs in a bucket society where people wanna drag you down. They don’t wanna see you fly. In Australia, they actually call it the Tall Poppy Syndrome which is when you have an actual flower that grows higher than rest, it gets chopped off by other people because they don’t want somebody to outshine them, to out accomplish them in different ways.
So, just think about that Fire Nation, realize if you are surrounded by people who are crabs in a bucket that are pulling you back down or they’re chopping off your flower as soon as its rising above the rest, you need to find other people to hang out with; you need to find the average of the five people that you wanna spend the most time with, be sure it’s people that’s going to encourage you, that are going to be pushing you out of that bucket and then say hey, give me a hand, grab me as well, let’s get out of here together and that is so critical across the board.
Gillian: First of all, my mouth was open when you told me that crab story because I think it’s incredible. But also sometimes people pull you into that bucket not because they don’t want you to succeed but because of their own issues. So, one example of this is that Sara Blakely, who is the billionaire founder of Spanx, she told me that when she told her friends and family about her big idea that she was working on, which is basically footless pantyhose, that’s what Spanx is. It’s like control-top pantyhose that you can wear underneath your clothing.
John: Just like a solid improvement off of something that already existed by the way.
Gillian: Exactly. And when she told her friends and family, they all laughed at her. They thought she was joking and they tried to discourage her from pursuing it, not because they were jealous but because they thought it was a waste of her time. And they’d say, you know, if it was a good idea wouldn’t the big guys have already done it, stuff like that. So, sometimes crabs pull you in out of love.
John: Out of love. Oh, we did not even plan that. We both said out of love Fire Nation because it is true. Your friends, your family, oftentimes they do want the best for you and entrepreneurship is risky and it is scary and you might fail and they don’t want to see you fail because they don’t wanna see you hurt. And so realize that it’s not always out of jealously or spite but sometimes it is out of love and just realize, hey, say I love you too, but I’m gonna do this anyways so now I’m asking for your support. I’m not asking you for your guidance, I’m not asking for anything except your just support; just be there for me if I fall because I might fall and I know you don’t wanna see me fall or fail but I might.
And Gillian, I wanna move into another story because you have so many. And this one I want it to be an ah ha moment, an epiphany that you’ve had along your journey, which you’ve had a lot of, but share one, one moment in time where you just had this great idea that you put into action. Tell us that story.
Gillian: My biggest feat recently was getting this book created. And in order to do it, I really set my sights high. I wanted to get A list subjects and I did. I ended up having, you know, I have Warren Buffett and Michael Bloomberg and everybody in between. And it was really, really hard to do this. It took me five years to put this book together. And at one point when things weren’t going so well, I went out to lunch with a friend of mine and I was telling him how I was getting bounced by everybody’s bouncer out there, no one was saying yes to my interviews.
And he said to me, “Don’t take a no from someone who can’t give you a yes.” And basically, there are a lot of gatekeepers out there and your job is to just get through them. So, when he said, “Don’t take a no from someone who can’t give you a yes,” that really fired me up to just keep on persevering even when I got rejected. And I think that no matter what business you’re in, you’ve gotta do that because nothing is easy.
So, I use this metaphor now that I say, you know, if you try to get in the front door and it’s locked, try a side door. If that’s locked, try the backdoor. If that doesn’t work, just try crawling in a window and if that doesn’t work, try the front door again, you never know, someone may answer it this time.
John: There’s always the chimney too.
Gillian: Yeah, and I can give you a specific example which is so one of my subjects is this incredible architect, Frank Gehry. He’s widely thought of as one of the most important architects of our age. And I tried; I got rejected by his office twice. Then my friend’s father was dating someone who said she knew him so she contacted his office for me and she got ignored twice.
And then one day I thought, you know what, emails are free, I’ll just ask again and I sent an email just to his office and whoever the assistant was that day decided to answer my email and I jumped on her basically via email.
John: I got you.
Gillian: Yeah, got you, can I send you this, can I send you that, okay, when, you know, and he’s in the book.
Gillian: So, I tried a few different avenues, but I love my friend’s words, “Don’t take a no from someone who can’t give you a yes.”
John: Yep, and that’s what I just wanna reiterate Fire Nation. Do not take a no from somebody who isn’t even able in the first place to give you a yes because of course you’re gonna get a no from that person because they can’t do anything but say no. And there’s actually a great quote that I heard from Mark Cuban which actually allowed me to get a response from him. As he said he doesn’t even respond to people until they’ve emailed five times because he said if they don’t really care enough to try that hard, five times, they’re not worth my time.
Gillian: I love that.
John: So, I just kept emailing and, you know, I got a one-sentence response from him and it wasn’t a yes but it was a response and that was pretty cool. So, I mean –
Gillian: Can I tell –?
John: Yeah, let’s hear it.
Gillian: No, I’m in your boat or bucket because I get responses from him but he hasn’t said yes but at least he writes me back and says no personally.
John: Yeah, all lowercase, no punctuation, just I get it though, I mean the guy’s doing hundreds of emails a day, etc., but it’s key, so yeah, we’re persistent, make it happen. And Gillian, what’s your biggest weakness as an entrepreneur?
Gillian: I think my biggest weakness has to do with the times when I have given up, you know, when I haven’t had the confidence to keep going in things. So, that’s basically it, but I really have been fired up by my book and by all of the stories in my book to sort of stay strong and keep at it because that’s the name of the game.
John: What’s your biggest strength?
Gillian: My biggest strength would be that now when I’m after something, I get laser focused on it and I don’t give up until the curtain closes. So, I think out of all the people in my book, the most common thread was that determination because every single person gets knocked down repeatedly, but the people who end up rising to the top are the ones who just sort of get up, dust themselves off and try again or try something new. You can learn from your mistakes or rejections, but you just have to keep at it.
John: Perseverance, persistence Fire Nation, two words you need to keep close to your heart. And I’m paraphrasing a little bit but there’s a great quote by Rocky, one of my favorite all time movies. I can’t stop rewatching those Rocky 1 through 4s. And it’s, “It’s not who hits the hardest; it’s who get ups after getting hit the hardest who wins,” something very close to that and it just really makes a lot of sense to entrepreneurs because we’re gonna get hit hard and we’re gonna get knocked down but keep coming back. Now, Gillian you have a lot of things going on, but what is the one thing that you are most fired up about today?
Gillian: I am still fired up about my book because you can read it and read it and it feels like – each essay in it is in the subject’s own words. So, you feel like you have Sara Blakely talking to you, Michael Bloomberg talking to you and they all, you know, I edited the essays down from about 20 pages to about five or six super easy, digestible pages so it’s sort of chockfull of great inspiration and anecdotes and advice.
John: Love that. Well, Fire Nation, don’t go anywhere because we’re about to enter the lightning round but before we do let’s take a minute to thank our sponsors. Gillian, are you prepared for the lightning round?
Gillian: I think so.
John: What was holding you back from becoming an entrepreneur?
Gillian: Fear, fear of failure, and so I let the smallest things knock me off course.
John: What is the best advice you’ve ever received?
Gillian: Okay, it’s gonna have to do with what was holding me back and this comes from Kathy Ireland. She became well known when she was a Sports Illustrated swimsuit model and now she runs a $2 billion business. She brands over 15,000 products with her name and you might think okay, if I was born looking like she did it would be easy, but that is not the case.
She failed for years at starting her own brand. She tried a beer company, a skincare line, you name it, she lost a lot of time and a lot of money and eventually she was able to start her own brand with a line of socks of all things.
Gillian: So, yeah, they’re Kathy Ireland socks. She actually got an offer to model these socks and she said you know what, I won’t model your socks but I will if we can partner up and go into business together and that’s how she started it. And now back to the quote. She says, “If you never fail, it means you’re not trying hard enough.”
And I love that because if you can just, you know, get knocked down and think all right, this means that I am part A team and that I’m doing my job then you have a huge leg up on everybody else who sort of let’s failure discourage them or get them off track.
John: I love it, I mean Fire Nation, it is not going to happen overnight for anybody so why should we think it’s gonna happen overnight for us? I mean it’s just the reality and Gillian, what’s a personal habit that you believe contributes to your success?
Gillian: Lists. I know that if I don’t write something down, I will forget it; it won’t happen. So, I keep lists and I just go over them. It’s sort of like with a fine-tooth comb and I make sure that, like I said, I keep dancing until the curtain closes so if there’s something I have to follow up on, you’ll be hearing from me.
John: What’s an Internet resource like Evernote that you can share with our listeners?
Gillian: Okay, posting on LinkedIn, now I was a member of LinkedIn. I had a profile on LinkedIn and I knew nothing about the power of LinkedIn until my book came out. And can I tell you that when I post a good article on LinkedIn, it gets way more traffic and has a bigger impact on my book sales than anywhere else, than Fortune, Forbes, can you believe that?
John: It’s shocking, but I’ll tell you, I do believe it because a good friend of mine, James Altucher, huge blog, great guy, he posts on LinkedIn because that’s where all the interaction happens for him.
Gillian: Yeah, okay. So, so many people didn’t know that and so I think if you have a business or something you wanna promote, start posting on LinkedIn. It’s just the most incredible resource and anyone can do it. That’s what’s great like not anyone could have an article written in Forbes or Fortune or whatever, but anyone can post on LinkedIn.
John: If you could recommend one book for our listeners Gillian to join Getting There on our bookshelves, what would that book be and why?
Gillian: Okay, it’s a good compliment to Getting There and the author is someone who you have had on as a guest, Dorie Clark.
John: Oh, she’s been a repeat guest. That’s how much I love Dorie.
Gillian: Yes, she’s awesome and so her book is Stand OUT: How to Find Your Breakthrough Idea and Build a Following Around It.
John: Love Dorie, she does amazing work on so many different levels and Fire Nation, I know that you love audio so I teamed up with Audiobooks and if you haven’t already, you can get an amazing audio book for free at eofirebook.com. Gillian, do you have an audio version of Getting There?
John: Naughty, naughty, I mean you’re on a podcast girl. These are listeners of audio.
Gillian: I know. I’m gonna get to my publisher right now when we hang up.
John: Add this to your list. No, don’t even wait until after the interview.
Gillian: Get on it.
John: I want you typing right now on your list.
Gillian: It’s on my list; it’s on.
John: Okay. Gillian, this is –
John: – the last question of the lightning round, but it is a doozy. Imagine you woke up tomorrow morning in a brand new world, identical to earth but you knew no one. You still have all the experience and knowledge you currently have, your food and shelter is taken care of but all you have is a laptop and $500.00. What would you do in the next seven days?
Gillian: You know what I would do? That is a tough question, but I think the most important thing in the whole wide world, more than entrepreneurial success, is having success in your personal relationships. If I knew no one, I would want to meet people. I would wanna have friends that were like family to me. I assume my family’s not in this world.
John: You don’t know anybody girl.
Gillian: But I don’t know anyone. I’d wanna meet people. I think that if you have good relationships that’s the most important thing in the world. So, if I knew no one, I would surely want good friends around me. I’d wanna make good friends.
John: Gillian, let’s end today on fire with you sharing one parting piece of guidance, the best way that we can connect with you then we’ll say goodbye.
Gillian: Find me on LinkedIn; that’s a good way.
John: Yeah, good one, and a parting piece of guidance.
Gillian: This is something Warren Buffett told me, and I love it because it’s applicable to all aspects of life. He told me that you can always tell someone to go to hell tomorrow and basically what that means is that if something bothers you, it could be in your personal life or your business life; just try to control your temper, sit on it. If it still bothers you tomorrow, you can tell that person to go to hell then but if you spout off in a moment of anger, you could do or say something that you’ll regret.
John: Yeah, let me even add to that, and you can tell me Gillian what you think about this, but if you’re really furious about something and you just need to get it out, write the email and just write it out and just say everything that you wanna say and then use a tool like Boomerang to send it to yourself 24 hours later. And then read it and then see if you still want to send that email.
Gillian: I love that and it’s pretty much the same thing Warren’s saying, which is just sit on it and you could always tell someone to go to hell tomorrow but you can’t take it back if you said it in a moment of anger.
John: So good, and besides LinkedIn, any way that you want us to connect with you?
Gillian: Facebook, LinkedIn and I have a website or I have an email. How about this?
John: Ooh, you have an email? Girl, you are an entrepreneur.
John: Okay, I thought you were gonna say something like aol.com the way you were excited about email, but I’m glad we got you a Gmail girl. So, email@example.com and Fire Nation, you’re the average of the five people you spend the most time with and you’ve been hanging out with Gillian Zoe Segal and JLD today so keep up the heat and head over to eofire.com, type Gillian in the search bar, her show notes page will pop right up with everything that we’ve been talking about today.
You can email her directly at firstname.lastname@example.org, connect with her on LinkedIn, that’s where she does and posts her best work. And Gillian, I just wanna thank you for sharing your journey with Fire Nation today. For that, we salute you and we’ll catch you on the flipside.
Gillian: Thank you so much for having me.
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