Creating Confidence with Heather Monahan - Confidence Classic: Unlock an Unstoppable Mindset & Marriage with Sarah Blakely & Jesse Itzler

Episode Date: May 7, 2025

If you’ve ever felt like self-doubt is slowing you down or wondered how the most successful people keep showing up with grit, resilience, and fun—this episode is for you. I had the honor of sitting down with power couple Sarah Blakely and Jesse Itzler for a live conversation that will completely shift the way you think about mindset, momentum, failure, and chasing your dreams your way. From Spanx to ultra-marathons, reality TV to billion-dollar exits, this one is packed with real talk, hilarious stories, and life-changing insights on how to create confidence that lasts. In This Episode You Will Learn How to spot and protect your billion dollar idea. How to build momentum (that leads to unstoppable success.) The direct connection between your mindset and how far you’ll go. 2 ways to create deeper customer connection. Your “why” sells more than your “what.” Be different—your uniqueness is your biggest business asset. Resources + Links Sign up for a one-dollar-per-month trial period at shopify.com/monahan Download the CFO’s Guide to AI and Machine Learning at NetSuite.com/MONAHAN. Want to do more and spend less like Uber, 8x8, and Databricks Mosaic? Take a free test drive of OCI at oracle.com/MONAHAN. Get 10% off your first Mitopure order at timeline.com/CONFIDENCE. Get 15% off your first order when you use code CONFIDENCE15 at checkout at jennikayne.com. Call my digital clone at 201-897-2553!  Visit heathermonahan.com Sign up for my mailing list: heathermonahan.com/mailing-list/  Overcome Your Villains is Available NOW! Order here: https://overcomeyourvillains.com  If you haven't yet, get my first book Confidence Creator Follow Heather on Instagram & LinkedIn

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even as a parent, as an entrepreneur, as a marketer, someone's, I'm not good enough. I don't have what it takes, whatever. We go through this period of self-doubt. I had it in my race. I started off, I was like, who'd run four miles? And once you get momentum and you start to believe and you can, you can have something that you

can build on, that's super powerful. Come on this journey with me. Each week when you join me, you're going to chase down our goals, overcome adversity and set you up for a better tomorrow. I'm ready for my closeup. Tell me, have you been enjoying these new bonus confidence classics episodes we've been dropping on you every week? We've literally hundreds of episodes for you to listen to.

So these bonuses are a great way to help you find the ones you may have already missed. I hope you love this one as much as I do. I'm so excited for you to hear this interview. This again, literally is an interview of a lifetime and I'm going to cut right to it because you're going to be blown away by Sarah Blakely, the founder of Spanx and her husband, Jesse Itzler, a serial entrepreneur. And I got the opportunity to interview Sarah and Jesse live on stage.

And now you get the chance to hear it. Can't wait to hear what you think. As was just mentioned, you guys have had a lot going on in the last week. Yes, that's definitely true. Not much sleep. Not a lot going on in the last week. Yes, that's definitely true. Not much sleep. Not a lot of sleep. In case some of the people here don't follow you on Instagram,

can you kind of break down what Last Man Standing was all about? Yeah, so that's the reason why I'm wearing flip flops. I just got back from a race called the Last Man Standing, you guys see me okay? Cool, okay, I feel like an operator. And the format of the race is you run a 4.2 mile loop, you have an hour to do it, and if you finish earlier you can rest. Finish in 15 minutes, you have a 10 minute rest, and then they line

you up again at the top of the hour, and you do it again, and you keep going until one person is left. So my wife was in Maine, and when I Googled it, it said that there was moderate elevation. Yeah, if you live in Maine. It was crazy terrain. So I ended up, I just got back. I did 20 hours, 80 miles, and I came in fifth. I think that deserves a round of applause. And my wife was the last wife standing. Yes, I win last wife standing. I didn't sleep for 35 hours so I was

supporting him and it's really challenging. I said at one point I had a breakdown I think at like four in the morning where I just started crying because it's I said marriage is hard when you have to really support each other's dreams and especially if you have to watch the person you love suffer and Jesse had a pep talk with me before it he said no matter what tell me I look good tell me I look strong don't pull me out of the race don't tell me that you're worried about me. So I didn't say to say like this, you look good. That's true. But it was really a wild experience of just human spirit. You know what we all have inside of us, that grit and determination and there were 112 of really intensely impressive ultra runners there.

And wow, I was just blown away by mindset really because I asked Jesse after this. I mean Jesse's 51. So I said, honey, even though you didn't get the last man standing, you definitely won the oldest man standing. Because he was 10 to 20 years older than every other racer in this race. And yeah, so I said to him, I was so curious because I knew mindset, I'm a huge believer in mindset, and I said, what was your mindset and what were you thinking during the race? And he looked at me with laser focus after it and he said, I was saying repeatedly to myself, I push my body and my body responds. And boy did

it ever. I mean, because his knees, his ankles, I mean, the rest of his body really, I mean, was shutting down. But his mindset was there. And that pushed him. I would say, I mean at mile 47, I thought you were done. I love you, but I really don't. I was like so worried, and then like, you know, you just can't ever doubt the mindset. If the mindset of the person's in the right place, then they just go way beyond what you expect. What's interesting about this race is, you know, you can get lost in how long it's gonna be or what the distance is, and it's like anything you're doing in your entrepreneurial

journey or any challenge, any goal, it's really just being laser focused on what's happening right now, what's the most important thing, and not getting, not patting yourself on your back for all your achievements, like, oh, I got to mile 25 or whatever, and not thinking about how far you want to go. It was literally just saying super present, and I always say, be where your feet are, and right here I'm in this loop. I'm in this loop right now. Let me get back to the chair, get my little rest, and go on the next loop. Right now, this is my job to get to the loop, and that was the focus. Wow, it's very, very impressive.

And if any of you guys want to be super entertained and inspired, it's on my Instagram page at Sarah Blakely and it's in one of those, you know, I put it in a permanent circle in the bar below the descriptor of my name and it's called The Last Man Standing and it's really, it is very... Yeah. You have to check it out. Her Insta stories are really funny. So Sarah, you mentioned mindset and the importance

and effect that mindset has, not only for Jessie, but people look at you and your company today and they think you're enormously successful and it was probably always that way. However, you were a salesperson at one point in time and had a very different life. Do you attribute the things that have happened in your life to mindset,

or what do you attribute that success to? Yeah, definitely mindset. I mean, I sold fax machines door to door for seven years after graduating from college. And I, you know, for 20 years, Spanx is gonna be 20. I started it in the year 2000 and the sound bite in the media has been Sarah cut the feet out of pantyhose and solved an undergarment issue and you know now Spanx is here and and while that is true there was so much more about

the behind the scenes of why this happened and people have asked me can I have 10 minutes 15 minutes of your time I want to pick your brain on how Spank started but that real answer is it started way before I cut the feet out of my pantyhose and it it started when I was much younger and I had a series of kind of tragic events happen to me when I was in high school and it led me to Wayne Dyer who is a motivational inspirational speaker he passed away about two years ago but I got exposed to him and I listened to his cassette tapes over and over and over

again to the point that I had his one series called how to be a no-limit person memorized all ten cassette tapes front and back and try living with that yeah that's funny because in high school no one wanted to get stuck in my car like after a party they're like she's gonna make you listen to the shit I would take simple things like I'm just gonna do the laundry tomorrow, and she'd be like, do you know the ramifications of waiting until tomorrow? So but then fast forward, you know, I think it was 10 to 15 years after high school that I ended up on the cover of Forbes, and the texts I got in my phone were so funny. I mean, literally all my friends were like, damn, should have listened to that shit.

So but I'm a big believer in it. I learned early on about manifesting law of attraction, not caring what other people think about you, which is a really big one for an entrepreneur or in life really. And I'm a work in progress on that. There are times where I do care and I check myself and say, let's work on this. But it's very freeing to not care what other people think. You'll take more risks to not really focus on the outcome and be so afraid to fail. So all of that is a big part of my journey and thanks for sure. So I think mindset is... I work on it daily.

We all need to. I need to get those cassettes. Jesse, you didn't start out an MTV rapper. You didn't start out owning an NBA team. You were sleeping on couches for quite a while with people I probably find hard to believe. Do you attribute your success to mindset or what do you attribute it to? I think, well, I definitely have my own version of mindset. When I have a goal, I like to say that's the end of the movie. I go to the end of the movie first, where I want the outcome to be. And that's unwavering. I don't negotiate that.

I don't try not to ever negotiate my goals. The script changes, the plot changes, how you get there. You have all kinds of obstacles. But the end of the movie really never changes for me. So that's my form of visualization and how I kind of attack it. Sari, you mentioned that you didn't share your invention with anyone for that first year. Why would you take that approach instead of enlisting others to help you or support you through that? That really came from a gut feeling.

I really honor my gut and intuition a lot and still do through the journey that I'm on. But when I cut the feet out of my pantyhose and started Spanx, I had actually asked for the idea two years prior. So I was selling fax machines. I had one really bad day. I'd been kicked out of an office again. I mean I got usually business cards ripped up in my face about once or twice a week. I got escorted out of buildings all the time and this day was just hard. I mean I'm

seven years into 100% cold calling to sell people a fax machine and I pulled over and I said I'm in the wrong movie. How did this happen? Call the director, call the producer. This is not my life. Like I'm redirecting my life. And I went home and I wrote down a list of what I'm good at in the positive column

and strengths, and I saw sales. And I thought, okay, well, what is it about sales that I'm good at? And it led me to the fact that I like to offer people things that they may not know they need and then really makes a difference for them. And I wrote down in my journal that night, I'm going to invent a product that I can sell to millions of people that will make them feel good. And then I looked up in the air in my apartment and I said, I'm ready for the

idea, if you give it to me I won't squander it. And two years later, I cut the feet out of control top pantyhose one night to wear white pants to a party and not have a panty line or anything show, because guys, you're out there in the audience. I don't know how many of you struggle with what to wear under white pants. But it's a legit problem that we have. And so I cut the feet out of my pantyhose one time and I thought this could be the idea because I had already set the intention for the idea to show up. So, but as soon as I started on the path of it I thought, okay I don't want

to tell anybody my idea because I feel that ideas are the most vulnerable in the moment that you have them. And it is our human nature that the minute we have an idea, we tell our friend, our co-worker, our wife, our husband, boyfriend, girlfriend, and in those moments out of love and care and all the right intentions half the time, the person might say something that completely squashes it or makes you not pursue it. So I didn't want to tell my friends, family and friends, and I have very supportive family and friends, but I didn't want ego to have to get involved too early on in the process. I wanted to

spend my time pursuing it and not defending it. So at night and on the weekends for two years I would sell fax machines during the day and then at night I would stay up and I was working on the patent and I was doing all my research and taking vacation days to drive to North Carolina where the manufacturing plants weren't begging them to help make the first prototype. But that is really why. And I have to say, I mean, everybody in their life has a million dollar, even a billion dollar idea. I mean, we do. They come out... I haven't had mine yet. Everybody in their life has a million dollar, even a billion dollar idea. I mean, we do. They, they kind of- I haven't had mine yet.

Well, well, you do. And I feel like recognizing it is a big one. And then also, you know, holding it sacred for me. And I'm glad I did because I sent my family down a year later and all they knew was Sarah's working on some crazy idea. And a year later I sat him down and I said okay guys are you ready? It's footless pantyhose and I mean they were like so sweetie if it's such a good idea why hasn't anybody else created it? And then someone else in my family was like

well honey you know and even if this is a good idea the big guys are just gonna knock you off in the first six months and you will have spent your savings on this. And if I had heard those things in the moment that I had it, I probably would still be selling fax machines or something like it. So I really, I really believe that. I believe that you got to, you got to really protect it. Now, it didn't mean I didn't tell people that would help me pursue it. I was telling lawyers, having them help me try to write the patent.

I was cold calling manufacturers and talking to them. I just didn't seek out people simply for validation until I knew I'd put enough of my own sweat equity into this idea that no matter what the validation came back as, I wouldn't waver. That was a tweetable moment for me. I'm gonna spend my time and energy pursuing it, not defending it.

I think that's really powerful. Do you see ideas the same way that they need to be nurtured and protected, or were you more, I mean, because you created a lot of different companies and concepts over your career and life, did you bring people in earlier on, or did you take that same approach?

Well, I have to agree with everything we're married. So, of course I agree. No, I think one of the most important things as an entrepreneur, I found, is figuring out how to get from point A to point B the fastest. And if that is telling someone or if that, in my case, maybe it was getting a key investor, getting a celebrity as part of Zico, one of our brands, whether it was a key partnership. I think that's been a critical part of my journey because when I started out, I did

sleep on 18 different couches. The one thing I needed that we all need is we need a story. We need momentum. People buy into stories and momentum more than they buy into products. Like we're the business plan. And when I started out, I started out in the music business. I had a record out on a label called Delicious Vinyl. And right when my album came out, I did Club MTV,

which was a big show on MTV at the time. I was 21 years old, and I thought like, wow, man, mom, I made it, I'm on MTV, this is unbelievable. And I did my first show in Pittsburgh, and I got off the airplane in Pittsburgh. And when I got off the airplane, there was a huge newsstand and on the cover of this big magazine called Rap Pages at the time was my picture. And I'm like, holy shit, I'm on the cover of Rap Pages. And I'm like, this is unbelievable. I was like digging on fours for the Sarah, I'm like, I'm on rap pages. And I go in and get the magazine and the cover of the magazine with my picture on it was,

are white rappers ruining hip hop? That wasn't the- I have not heard this story. Why would I tell you? With the married me. So, I'm kidding. So I needed a story. I needed a story. So for me, at that age, it wasn't about when I had an

idea of telling people, it was about getting momentum. And I went to the New York Knicks with an idea to do a theme song for the Knicks. I was 22 years old. And I said, you know, sports is changing. People sit in seats for three hours in an arena but the game is only 48 minutes so you have to entertain him for over two hours let's do a song and a video and we'll get all the celebrities in New York the song was called go New York oh and the Knicks paid me $4,000 for the song and by the time I paid the studio the engineer the singer the producer the drummer it cost me $4,800 to do the song so is that a good business model? No. Right they paid me $4,000 they paid me $4,800 to do the song. So is that a good business model?

No. Right. They paid me $4,000. They paid me $4,000. It cost me $4,800. You guys think that's a good business model? Wrong. That's an amazing business model because I would have paid the next $5,000 to do the song for them to help me get to point B faster because now I had a story and I could call up the Bulls and be like I did the Nick song and every team that came into Madison Square Garden was like why don't we have a song like that and that was what really jump-started my career so for me it's like how do you get from A to B the fastest and then you wrote and produced a song for the NBA

that actually won an Emmy. I did. And then you created a company, another company, out of this concept, right? So it actually was a good business model losing $5,000. Yeah, well I mean we figured out the business model after that. It wasn't sustainable, but it got me in the door and it got me momentum. And you know, I always tell people that ask me if they're stuck, if they're overwhelmed, small wins, just, you know, even in this race I just ran, they were, we all go through this period in any part of our journey where we're overwhelmed with self doubt. Anybody, no matter what you're doing, even as a parent, as an entrepreneur, as a marketer,

someone's bad, I'm not good enough. I don't have what it takes. Whatever. We go through this period of self-doubt. I had it in my race. I started off, I was like, who runs four miles? And once you get momentum and you start to believe and you can have something that you can build on, that's super powerful.

Yeah. I mean, you got to create your own hype. Small wins. For sure. Meet a different guest each week. Paying on it's a change. Confidence created. Meet a different guest each week. Paying on it's a change.

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SPANX ironed onto it that I went to one of those t-shirt shops and took a white leather and ironed on Spanx and cream pants, but I was the advertisement. So I wore that everywhere I went. And then when I got a chance to sell it in Neiman Marcus I would bring my friends to the store to act like excited customers and they would stand around my display table and go oh every time we'd like cue it we'd like customer coming and this like really fancy lady you know perfectly dressed would be walking up and my friends would all go tell me more what is this I can't believe I'm just finding out about this and it would always cause

the customer to go, what's happening? And then I'd be like, yes, I get an opportunity to explain it to her. I love that you brought that story up. Would you mind sharing that story of how you sold it into Neiman Marcus? Because that is such a great face-to-face,

and it just pulls on that past track record that you had with the cold calling and how it paid off for you. Yeah, so when I first landed landed Neiman Marcus was my first account and two things about that that are just something that I reflect back on. One is everybody in the industry after I landed Neiman's came up to me and said how in the world did you land Neiman Marcus? And I would look at them and I'd say I called them what do you do

and they'd say oh my god we go to trade shows and we set up a booth and we've been doing it for seven years and everybody says around year six or seven that you get a chance with Neiman's I didn't even know there were trade shows so I often say what you don't know can be your greatest asset if you let it if you're not intimidated by the self-talk of, I have no idea what I'm doing, and that shuts you down. So if you can power through the, I have no idea what I'm doing, and actually see it as a positive and go, that means I'm gonna do it different, and that's where you break real ground. It takes a lot of courage and a lot of willingness to look stupid

and potentially fall on your face, but that's where the magic is. So anyway, I got a chance to go and cold call Neiman Marcus. I flew on a plane from Atlanta where I lived to Dallas, and I met with the buyer, and she was impeccably dressed. I'm in the intimidating Neiman's headquarters. I had my lucky red backpack from college. I had the prototype in a Ziploc bag from my kitchen and a color copy of the packaging that I had created on my friend's computer. And halfway through my pitch, I was telling her what it is and I could tell I was losing her. You know, after seven years of cold calling and trying to sell things to people, you get really good at reading

nonverbals. And I always say nonverbals tell you way more than the verbal. You know, when people sit there and shake their head and say, I love it and I'll call you tomorrow, you're like, oh my god, mayday, you know, that's when you pull the chute, say I've got to like try everything. And so she was kind of doing that. She was like, okay, thanks. And I just stopped and said, you know what, Diane, will you come to the bathroom with me? And she literally was like, excuse me? I'm like, I know it's a little weird, but can you just follow me to the bathroom and I'm gonna actually show you what my product can do? I'm gonna go in the stall. And she was like, oh okay. And she walked down the hall and

I went in the stall and I put it on under my white pants and I came out. So I showed her before and then I showed her with the product on and she just sat there and she goes, I get it, it's brilliant, and I'm gonna try it in seven stores. And I was like, that deserves a round of applause. I love that story. So you guys talk a lot about humor and embarrassing yourself, poking fun at yourselves in business and in life, and have a lot of fun with that. And we mentioned specifically on Instagram, can you talk a little bit about what that looks like?

I just think we both, you know, don't take ourselves super seriously and humor works. Humor's fun. I think one thing we've both had in our entrepreneurial journey is we've had fun. And I think a lot of people forget how fun it can be and you know and we work on making it fun. We try to do fun things, incorporate fun things into our household with our kids, with our cultures and our companies and it's an important part of the process. I mean I would say to add to that I recognize that the two biggest fears that we all have as human beings are basically the fear of public speaking and the fear of being embarrassed.

And so I want that to lose its power over me. So I will intentionally embarrass myself, or I will intentionally find scenarios where I'm not good at something. And then I go through it. And it usually ends up making me laugh. Or if something ridiculous happens to me, I immediately want to share it with people. Because then I start to find that it loses its

power over me. And then you also find that when these things happen, if you can make somebody else laugh or smile, then it wasn't all in vain. And that's where real human vulnerability and connection happens, especially even with your customers. So I learned that from selling fax machines. I mean, anytime I tried to act perfect or put on the perfect pitch, I got kicked out time and time again. You know, if I walked in and was like, look, I'm, you know, I'm nervous. It's hard for me to walk through

your door. I'm sorry. I know there's no soliciting sign. I mean, I would get farther with that, but just calling out the humanness and the real of what we're all dealing with and not being afraid of it. So we do that at Spanx, too. We have oops meetings at Spanx where we have the whole company get together and we stand up and we share what we failed at or an oops or a mistake that we made and everybody claps and it just like diffuses it. That's such a great culture.

I believe we actually may have a video or two that we can share. I happen to be a huge fan of this one bird video. If we could queue this video up, the Instagram stories. Lovely. Yeah. Oh, great. Okay. I see him. I see him looking at me. My husband has been running every day on this island and says a bird attacks him. So I'm on the walk with him where his jaw cut this because I don't believe him. Well honey, where, how bad can it be? Come on! How are you going to get past this walking spot? Nothing's attacking me.

He's fine. I see him and he's fine. See, the bird's there. He's not going to bother you, Jess. Oh, oh, oh, oh, oh. That bird, that bird, no Heather, that bird was not raised properly. That verb was ridiculed as a kid. I have to tell you, I'm so happy that you shared that video. I had shown it to my son after I'd gone to interview you and I said, you know, Jesse said a great guy, and I was showing it to my son.

He said, Mom, I thought he was a really strong kind of guy until right now. I ran the same route every day, and I would come home, and Sarah would say, how was the run? I was like, the run was great, but I got attacked by a bird. Every time. And she's like, it's impossible. I said, no, you've got to come with me. And she walked by, and the bird didn't care.

I walked by, and the bird went bonkers. It was very personal, obviously, for the bird with Jesse. I don't know. Maybe they thought your hair was a nest, honey. I don't know. Meet a different guest each week. What do you know about the change? If you're anything like me,

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Sarah, you actually spent some time doing standup comedy. Were you petrified to do that? Because now it seems natural. I feel like you could just grab a mic and walk around and do it. I was so petrified. I did it when I was selling fax machines door to door. And I just, I have this thing where I don't, if something terrifies me or if I think I would never do that and the answer is because I'm scared, it kind of becomes something I really want to try to do. And that was one of those things.

And I just did open mic mostly around, I did it around the country for two years while I was a trainer for the company that I worked for. But it was terrifying. I mean, I was so nervous and I wasn't that good. It sounds like the hardest job in the world. It's the hardest, well, it's, I mean, it's taking the number one fear in America, which is public speaking, to the next

level because you can be in front of an audience and be bombing and not really know, you know, like the whole back section could be asleep or on their phone and you still ramble on. But if you're doing stand-up comedy, I mean, you get validation or you get crickets every 15 seconds. So it's like the most immediate, like you're failing, you're not failing, you're failing, you're not failing. And the only way to test it is in front of an audience. So you have to be so willing to bomb in front of a group of people. So please laugh at our jokes. Yeah, exactly. Or to learn what's funny or not funny. So I am, yeah, it was, it was, but you know what, I didn't know it at the time.

This combination, see I wanted to be a lawyer, but I'm a terrible test taker. I'm not good in, like I have trouble with reading comprehension, so I'm sure I have some sort of undiagnosed learning disability. But anyway, so I did debate all through high school and college, and then I get to the LSAT and I bombed it, not once but twice. So it derailed my whole vision of being a lawyer and that was really depressing at the time. And then I naturally then went to Disney World and tried out to be goofy. And you have to be, you have to be 5'8 in order to be goofy and I'm only 5'6. So I'm the height of a chipmunk.

So like this was rock bottom for me. I mean my family, everyone's like what's happening? I said I'm too short to be goofy and I don't want to be a chipmunk. And so I just started selling fax machines or to door because it's really, I mean you needed a pulse to be hired there. And so anyway, but the stand-up comedy I did, but life has a weird way of giving you these experiences because when I started Spanx, the combination of the amount of rejection I had had was perfect to start a company because I was told no every day for two years.

The idea is no good, no thank you, we don't want to help you, we think this is stupid, whatever. And it didn't really faze me. And then the writing comedy for two years while I was doing that helped me do all the writing for Spanx and the marketing. And Spanx didn't advertise for 16 years. We became a household name and a household brand around the world without ever advertising. And I believe we did so much of that through humor and through the connection that we had with our customer and storytelling. Jesse mentioned it.

Lead with story. Your customers are so much more interested in why than they will ever be interested in what? What you're selling, why you're selling it, why you're doing it, who are you in the world, what matters, what's your why? That is what people really respond to. So, and if you can do it and make somebody laugh or smile, it's so much better. I mean you then you have a chance of them telling five or smile, it's so much better. I mean, you then, you have a chance of them telling five other people, which is what happened

with Spanx. You know, it became a word of mouth brand. Jesse, did you have that same experience that Sarah had getting into standup comedy, being afraid of it when you became a rapper? Was it that same, you know, you were petrified of it? Did you gravitate towards it? Well the first, right when I got signed to my record label, Delicious Vinyl, they had two huge acts at the time. One was a guy named Tone Loc, some of you might not remember Tone Loc, yeah, wild thing, funky cool Medina.

The other was a guy named Young MC who won a Grammy for his song called Bust a Move. And I was one of the next artists signed to the label. So before my album even came out, I got a call from the owner. Wait, Jesse was best known for two songs shake it like a white girl and college girls are easy please Google it please Google it so nervous I get a call which I had a lot of fun telling my dad you know I was like dad dad I think I met the one he's like nice buddy what does he do like he's a rapper that's known for shake It Like a White Girl, College Girls are easy.

People buy into stories. This is all part of the plan. Anyway, before my album came out, I got a call from the owner of the record company who said that they're having this huge concert in Atlanta where we live now at the Georgia Dome and they were busing in 36,000 inner city kids from all over the state of Georgia for this concert that they coined the Increase the Peace concert, because they were going to have black artists and white artists come together in this community bonding event. And the day before the concert, Vanilla Ice canceled, and they needed a white rapper,

so they volunteered me to be the white act. So I get to the venue, and as soon as I get there, I recognize immediately like the place is unruly. There's fist fights going on, they're putting the house lights on and police are everywhere and the kids are booing. Every single act that came on stage, they booed them off stage. So the first guy up was like LL Cool J and his prime and they booed LL Cool J off the stage.

I'm sitting over here in the green room about to go on next to sing my song called Shake It Like a White Girl. So I called my mother and I said, Mom, I got a really big problem, man. They're booing LL. And she was like, sweetie, just be yourself. They're going to love you. And I get up on stage and the MC is like, you know, all the way from California, give it up for my man Jesse James, which is my stage name, do not Google it.

And as I'm going on stage, the record company gave me some t-shirts, like promotional t-shirts, so I grabbed them and as I come on stage, I'm like, I'm looking at the kids in the front row and they're pissed off that I'm even invited to the venue, but I have these t-shirts. So I'm like, does this section over here want some free t-shirts? And the kids go crazy. I threw them out. I'm like, this section over here to my right, you want some t-shirts? They went nuts.

I threw them out. I'm like, middle section, you want some t-shirts back there? They went bonkers. I threw them out. I said, thank you very much. Salt and pepper's up next. I got the fuck out of there, man. Never let them boo you. Never let them boo you.

Never let him boo you. It's like the first rule I got in business. No, I'm not doing standup. How animated is this man? Oh my gosh. I can't take it. Okay. So Sarah, after you had made it, you made a very shocking decision, in my opinion, to

really put yourself out there and go on Richard Branson's reality TV show. Why did you make that decision? You know I read his book in college and I really thought he was seemed like such an interesting guy that I would like to know and so I that was the start of it and when he declared that he was doing his own version of The Apprentice, his own reality show, I just thought this was a great opportunity to meet him. And he started Virgin overseas in London.

He's just a really colorful, fascinating, adventurous guy. Spanx was four years old at the time and my lawyers literally begged me not to do it. They're like, why would you ever do a reality show? You're the face of this brand and you're putting your reputation over to Fox and you have no idea how they're going to edit you or what they're going to do. And I just, I just had confidence that Richard from what I'd read about him wouldn't wouldn't be a part of something that would wouldn't edit me the way that I am but I got a 27 page contract before I

did this and it was the most insane contract it literally said we can burn you we can submerge you underwater we can drop you in political unrest I mean it was like insane so my dad is a lawyer and I emailed it to my dad and I said, Dad I'm thinking about doing this reality show, can you help me edit the contract? And all he wrote back was no sane person would sign this love dad. And I signed it and I went and... Which is a great influence on our kids. Yeah we have not let the kids see the video footage, but it was two months of the most intense stuff.

What they didn't tell me, but I should have figured out and put the two and two together from the contract, was that if you lost the business challenge, each business challenge took place in a different city around the world. So instead of every challenge being in New York City, one was in Hong Kong, one was in Africa, one was in Tokyo. So it was wild. We were traveling all around the world. But if you didn't win the business challenge, instead of going to a boardroom and just being fired, you had to do a world record breaking death-defying stunt with Richard.

And two days into filming, I literally was in Atlanta in the Starbucks line like the day before, and then the next day I'm in England, and they woke me up at 3 in the morning and handed me a helmet and I said I'm an entrepreneur why do I need a helmet and I had to scale the side of a hot air balloon at 10,000 feet in the air and have tea on top of the hot air balloon with Richard. And you're afraid of heights. And I'm so afraid of heights. Like I cry on planes, I cry during takeoff. I don't like heights. Yeah.

So that was crazy. And that was the first day of filming. But Jesse can't even watch it. Jesse's watched like half of the first episode. The stunts got so ridiculous. It was like, Sarah, climb the scale of the top of the building and jump in this glass of water, you know. And then when you're in the water, we're going to throw you in with the sharks and then you swim around and come up and I was like, what? This is crazy.

So you guys weren't married back then? No. He didn't know me then. But yeah, so. Was it worth it now when you look back? Are you glad that you did that? I'm so glad I did it. I mean, I think that I don't think I would have done the challenges if I was a mother at the time, but I wasn't. I was single and... Definitely not. Yeah. But yes, I'm so happy I did.

I mean, Richard's actually a great friend. I'm actually going to Switzerland this Friday with Richard and about 35 entrepreneurs from around the world and we're doing a physical challenge through the Swiss Alps to raise money for education. And I'm not like my husband. I'm not this physical, you know, challenge person, but I had had too much tequila when Richard asked me if I wanted to go and I said yes. And so now I'm going.

I hate it when that happens. I'm slightly terrified. But we're going to swim, bike and hike through Switzerland and it starts with a glacier lake swim in a full body wetsuit. Well just in case you guys haven't, can't picture this or haven't seen this show, we brought you a clip. Oh you have a clip? Which clip is it?

Is it of the balloon? Next challenge is that we're gonna go up into the top of the balloon. Something I've never done. It's not gonna be easy at all on the top of the balloon. We're gonna have a tea party and have a discussion Being hoisted out on the ladder suspended at 10,000 feet on the side of a hot air balloon is sweat. I'm in a full sweat. I'm in a full sweat. I don't want that. Did you just watch it? I'd rather run for 20 hours. That was so intense. There were so many things about that, but it took me 48 minutes to climb.

It was a dangling rope ladder, so there was nothing anchoring it. So I spent the first 25 minutes of the climb just flailing around in the air. And then the last 20 minutes, I kept saying, just get to the balloon. Get to the balloon. Get to the balloon. Get to the balloon. Get to the balloon. Get to the balloon.

Get to the balloon. Get to the balloon. Get to the balloon. I spent the first 25 minutes of the climb just flailing around in the air and then the last 20 minutes I kept saying just get to the balloon get to the balloon but once I got to the balloon the balloon was hot and the rope was very taut against the balloon so I'd nowhere to put my fingers anymore around the rungs of the ladder so I'd use my fingertips and then once I did the little tee thing and was like, whoa, that was great. I started bawling because I'd realized I had to climb down. use my fingertips. And then once I did the little tea thing and was like, woo, that was great, I started balling because I realized I had to climb down.

Oh my gosh. I was like, wait, how do we get down? So we had to go back down the ladder. It sounds horrific. Yeah. Thank God you're here. Listen, I'm here and what an experience. So Jesse, you have an online community, Build Your Life Resume Community, which is really

amazing. Check it out if you guys haven't seen it. Awesome. So some of the feedback Jesse that really pops out at me the things that people like the takeaway is the brownie the you know what is your unique brownie can you share what that means and how you develop that? It's just a reference to a story when I was in college I took was a crossroads in my senior year of college. I was either going to the music business, which I loved, or I was going to sell a product called Aunt Franny's

brownies. I had a roommate in college that had an Aunt Franny. And every month she sent us a shipment of brownies. And I don't know what she put in the brownies, but they made everybody happy. I can market these. This is going to work. So for my advertising class senior year, we had to create a fictitious brand from scratch. Soup to nuts, like, you

know, jingle, which I was good at, billboard, slogan, packaging, everything. So I said, I'll use this advertising class as my R&D department and if they like my Aunt Franny's brownies presentation, I'll just roll it out and I'll sell brownies. So the way that the final exam was set up, there were 100 kids in the classroom, it was small, and everybody had a hand in their campaign, but five people were gonna get picked at random to present a 30 minute state of the union

of the business they were going into, the industry they were going into in front of the class. So like I'm a senior in college, there's a 5% chance that I wanted to get picked, like nobody prepared for the oral presentation, You didn't want to get picked. And sitting to my right in the classroom was a guy named Ronnie Cohn. Ronnie Cohn was a professional jackass. No, Ronnie Cohn bullied half of the class for four years of college. So when the professor said, we're going to do this the democratic way, everyone write down your name

and I'll put, take off my hat and I'll pick out the name. When he came to me, I took 25 pieces of paper and I wrote Ronnie Cone's name down and I stuffed him in the hat. And when he picked out the name, this is a true story, sure enough, the first name that came out was Jesse Itzer, the jackass did the same thing. He's such an asshole. So I went up there and I pitched Aunt Franny's brownies in 30 seconds into my presentation. By the way, the tuition at American University is $40,000 a year.

That's where I went. So for four years of tuition, $160,000 of my parents' money. This is literally the only thing I remember. The professor stopped me. For $160,000, he stopped me in the middle of my presentation, 30 seconds in, and he said, son, I want to know what is your point of differentiation? And I was like, what does that even mean? He said, what makes your brownie different than all the other brownies on the market? And I was like, well, they're moist and delicious.

They could be gluten free. They're home baked, blah, blah, blah, blah. And he was like, well, they're moist and delicious, they could be gluten-free, they're home-baked, blah, blah, blah, blah. And he was like, no, he said, son, there's a thousand brownies that come out every year. And substitute them for marketer, for restaurateur, for advertising, for lawyer, for whatever you do, there's a thousand of you that come out. And if you want to make it, your brownie, whatever it is, has to be different than all the other brownies. Sit down. And he made me sit down. And I realized at that moment, like it was a real powerful moment for me because I asked myself at that moment, like, and since then, as an entrepreneur, I've always asked myself, like, how am I different? You know, what makes my product stand out? How can I treat my customers differently than everybody else?

Zara mentioned it early, but like if you, if you rip up the playbook that everybody in the industry is Using and you say like well, how would I do it if I never was taught how to do it? That's where innovation comes from so I always ask myself in an authentic way You know if you're quirky be quirky if you're this be this but what makes you different? I just remember not to belabor this point But I remember when we started marquee jet which is a private jet company that I started with my partner. We had no aviation experience, we had no airplanes, we didn't know a lot of rich people, and

we started this company that had, and not a great formula for a private, but we ended up building a company that did $5 billion in sales, and we sold it to Warren Buffett's NetJets. And I remember sitting with our sales sales team and I would go in and I would listen to pitches and they would pitch the way Kenny and I, my partner and I were pitching and I'd be like what are you, you can't, what are you doing? Like you're a single mom, tell, be who you are, you know, and be unique for you and be different for what you are. You can't, you're not the co-found, so it's always been a mantra of mine to just kind of like what makes you uniquely

different. And I was a question Sarah asks all the time to her team and to her employees, you know. She always asks employees if no one taught you how to do your job, how would you do it? Yeah, because we're on autopilot as human beings. I mean think about it almost every single thing that we do, someone taught us how to do it or we observed how it was done. So I like the space of closing your eyes and saying if no one showed you how to do this, how would you do it? Like would you be doing it differently? Oftentimes you will and the answer or the vision comes to you and then that's a real nugget for yourself. Yeah. I would just put an asterisk next to that because, you know, I just ran this race

and I did, I'm a big believer in becoming the expert in the space you're going into. So before I approached this race, I called everyone that I could find, anyone I could find that did this race and asked them a lot of questions. How many calories you have to take? How many ounces of fluids you have to take? How many ounces of fluids do you have to take every hour? How much sodium do you need every hour? And in a very, very short amount of time, I became what I believe in my own head was an expert. And I would come in every station and say to my pit crew, I'd be like, I had one goo, half a bottle of racten, which was the drink

that I was drinking. I had 200 calories, 70, you know, I need 350 milligrams of soda. I was very aware of it. So in certain circumstances, you want to become the expert and follow the advice, but in others, you want to stand out for what you know, what you want. Please do not get mad at me, but unfortunately we have to move to the lightning round of questions and we're about ready to wrap up and even though no one wants these two to leave. Okay, what's happening in your life right now? I'm going to Switzerland on Friday, which sounds very fabulous. That sounds very exciting. Okay,

how do you feel when you're in a room with Richard Branson Microsoft Giving Pledge? How do I feel when I'm in the Giving Pledge room? Super humbled and you know, like kind of like, how did I get in this room pinched me kind of feeling. Sarah's agreed to give away half of her wealth to charity. Amazing. What would your career be if you didn't start Spanx? I mean, I'm a frustrated beautician. I might have my own salon or I was someone who did everyone's hair for prom and I always like doing makeovers and things like that.

Oh, that sounds fun. Theme song for your life. Your speed round, sweetie. Gosh. Theme song for my life. Look, either one of you can answer. Baby Got Back. Yes! Excellent marketing. Excellent marketing.

I'm in the butt business, okay? Wow, that's good. That's good. Oh, there's a song called Here I Come. It's a reggae song. That's one of my mantras, like, here I come. So, it's my personal thing. Nice.

Okay, favorite party trick. There's a song called Here I Come. It's a reggae song. That's one of my mantras, like Here I Come. So it's my personal thing. Nice. Okay. Favorite party trick? I can make people say no. I have this crazy thing I could do with you after, Heather. Have you ever heard it before? No. All right. that was good. Weird trait about you.

Weird what? A weird trait about either one of you. I mean, this is so weird, but I can vibrate my eyes. What? What does that even mean? What did you say? I can vibrate my eyes. You learn something new all the time.

We met for 10 years. I've never seen you vibrate your eyes. I can vibrate my eyes. And the weird thing is Charlie just looked up at me and vibrated his eyes the other day. Our little boy. So apparently it's genetic. I've only had fruit until 12 o'clock noon for 28, 29 years now, unwaveringly. Fruit till noon, brother. And I didn't like that smoothie that you gave me. It's pretty nasty. Listen. Okay, what's your biggest pet peeve? Pet peeve? Oh, I know what

yours is. Oh wait. Oh this is like the newlyweds game. What do you think mine is? Well, I mean, you're probably about to answer something different but running water. Absolutely. Don't get me started on running water. Yeah. Did anyone notice the clock is now going the opposite direction? A little confused. Okay. My pet peeve is when the windshield wipers are going more than they need to. That's a fair one. Believe me, I get the, I mean, she'll be driving and say, I'll be like like shut the window lower the wipers I'm like based on the wind raise the wipers lower the wipers okay here's a good one Sarah shut the wipers off who is your celebrity crush

well growing up my celebrity crush was Gene Wilder. I'm not kidding. My celebrity crush was Wonder Woman. Guess I love that! I love that! Thank you, sweetie. Please join me in thanking these two amazing human beings. Thank you. Thank you. I couldn't be more excited for what you're gonna hear. Start learning and growing. Inevitably something will happen. No one succeeds alone. You don't stop and look around once in a while. You could miss it. I'm on this journey with me.