Creating Confidence with Heather Monahan
Confidence Classic: Unlock an Unstoppable Mindset & Marriage with Sarah Blakely & Jesse Itzler
Wed, 07 May 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
Chapter 1: What are common signs of hormonal imbalance?
Tell me if this sounds familiar. Some things change, and you can't seem to put your finger on it. You're experiencing brain fog, hot flashes, night sweats, and mood swings. Or you just feel heavy and bloated. You're trying to do all the right things, but nothing's working. Basically, you don't feel like yourself anymore, right? It could be your hormones.
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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, I couldn't run 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.
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.
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Chapter 2: How do Sarah Blakely and Jesse Itzler handle self-doubt?
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 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's 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 cue this video up, the Instagram stories.
Lovely.
Yeah. Oh, great. Okay.
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Chapter 3: What is the 'Last Man Standing' race?
Yeah. I would just put an asterisk next to that because, you know, I just ran this race, and 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 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 Roctane, which was the drink that I was drinking. I had 200 calories, 70. 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 are.
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, 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?
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