#179 Focusing on the Four Main Buckets with Sara Blakely and Jesse Itzler
#179 Focusing on the Four Main Buckets with Sara Blakely and Jesse Itzler
One of the youngest self-made billionaires and an entrepreneur/author/ultra marathoner get married and have four kids, yet they still manage their own businesses and try new adventures daily. How do they manage it all?
In this from-the-vault episode of Seeking Wisdom, DC sits down with founder of Spanx, Sara Blakely, and author, entrepreneur and keynote speaker, Jesse Itzler, to talk prioritization, marriage and extreme sports. DC and Jesse bond over big calendars, and DC learns how Sara and Jesse’s whirlwind love story still works today.
DC: And we're back. One of the most exciting interviews that I've ever done. I cannot tell you how nervous I was for this interview. Now, this was an interview that happened in 2019 at our conference, HYPERGROWTH. And I've been sitting on this one because this one is pure gold, and I've been waiting for the day to finally release this. Now, this is with two of my virtual mentors, two people that I've looked up to for a long time, and they just so happened to be married. It's with Sara Blakely, who's the founder and CEO of Spanx, and who's the youngest ever female billionaire, and Jesse Itzler, who's her husband, who's an entrepreneur, author, keynote speaker, has written amazing books. If you haven't read Living With SEAL, you need to read that book. Living With SEAL. It's an amazing book. So in this episode, we talk about Jesse's insane appetite for long- distance endurance ultras, and all the crazy stuff that he does, this calendaring system that is mental, and I've adopted, how Sara and Jesse met, and all of the amazing stuff on how they make this work, as two superhuman people. Now, don't forget to leave a six star only rating for this episode. This is one of my favorite ever interviews. I'm so lucky, so fortunate to have done this. Peace. Alright. So we are here with Sara Blakely and Jesse Itzler. Two people who I have... I don't know who I have a bigger crush on, actually. I have super crush on both of you. Yeah.
Sara Blakely: That's so nice.
DC: But I think it started with Jesse.
Jesse Itzler: Thank you. Thank you.
DC: It started with Jesse. Jesse, you grew up in Long Island, right?
Jesse Itzler: I did.
DC: Yeah. Where in Long Island?
Jesse Itzler: Roslyn.
DC: Yeah. See, the way he said that, that's true Long Island.
Jesse Itzler: Yeah.
DC: That's the true test.
Jesse Itzler: Coffee.
Sara Blakely: It's in the jaw.
DC: Yeah, yeah. Jaw.
Sara Blakely: And he calls me" Sa- ra", instead of" Sera".
DC: Sara. I love it. Yeah. Actually, I heard you speak somewhere, and I can't remember where it was. I heard you narrate your books later on, like Living with SEAL, which I had given to everyone. But the first time I heard you speak, I was like," There's someone like me. There's someone that talks like me." Yeah. This is water. This is amazing. I'm freaking fired up.
Jesse Itzler: Good.
DC: And I can't remember the first time. It's incredible. So you just got through this race. What's this race that the two of you were at?
Jesse Itzler: Yeah. So the race is called the Last Man Standing. And it's got a really interesting format to it. You have to complete a 4.2 mile loop in under an hour. If you finish in 50 minutes, you've earned a 10 minute rest, because at the top of the next hour, they line you up again for another 4. 2 mile loop. And that continues till one person's left. So yeah.
DC: And this is the first time this race has been done or is this an annual thing?
Jesse Itzler: The format's relatively new, but they've done races like this before.
DC: Because you've done ultras like Badwater.
Jesse Itzler: There's not a lot of people that sign up for these races.
Sara Blakely: Actually there were 112. Super intense, impressive ultra runners there. And he said a 4.2 mile loop, but he's leaving out how intense the loop was.
DC: Yeah, that's what I was just going to figure out.
Sara Blakely: Super hilly.
Jesse Itzler: Yeah.
Sara Blakely: A super hilly loop on a dirt trail with rocks and debris. And it wasn't as super carved out. And 10 of the hours that he ran, out of 20, were in total darkness with a headlamp.
DC: That's crazy.
Jesse Itzler: Yeah. When I Googled the race, it said" moderate elevation". So moderate elevation. So I was like," I'm going to go get the mail. I'll come back." And if you live in Maine, moderate elevation means severe mountains.
DC: So I'm just trying to figure that out. Because I saw 4. 2, and I was like,"It doesn't seem like that much." Right, obviously, I can't do 4. 2. But it didn't seem, for you, like that much.
Jesse Itzler: Well, I was anticipating coming in, based on months of training, around 52 minutes, having an eight minute rest. But the course was so challenging. I got in around 57 minutes. So it did give me a lot of rest.
DC: When did you start this whole ultra kind of racing thing?
Jesse Itzler: Well, I was a runner. I ran marathons since my twenties. But once we had four children under 10, that stopped. And I would get a four mile run, a three mile, whenever, here and there. So I recommitted to this about three or four months ago.
DC: Mm- hmm(affirmative).
Jesse Itzler: Yeah.
DC: And do you do this too?
Jesse Itzler: Sara recommitted with me.
DC: Yeah. Yeah.
Sara Blakely: Do I do it?
DC: Do you do these kind of races?
Sara Blakely: No.
Sara Blakely: No.
DC: Me neither.
Sara Blakely: I am doing a challenge though in Switzerland. I'm going to swim, bike, and hike through the Swiss mountains. And I'm doing that with Richard Branson and about 35 other entrepreneurs, and it's to raise money for education. So I'm not like my husband. What happened is I had had too much tequila when Richard asked me if I would do it. And I said," Sure." And now, I'm like," Okay."
DC: When is that?
Sara Blakely: So I leave this Friday.
DC: What? It's coming up right now?
Sara Blakely: Yes. I know. So I leave this Friday. And I had to read the list of what I need. I need a wetsuit to swim in a glacier lake.
DC: It's crazy. Are you going to be tweeting this?
Jesse Itzler: Oh yeah, absolutely.
DC: Yeah. Yeah.
Jesse Itzler: I mean, I'm not going with her, but I'll be following it from afar.
DC: You're supposed to stay up the whole time.
Jesse Itzler: Yeah, exactly.
Sara Blakely: I was thinking about it. I didn't tell you this, but in the car ride here, I was like," What are things I should do for 20 hours, and have Jesse have to tag along?" Maybe I should shop for 20 straight hours, and you have to go with me. Or maybe we should just listen to really sappy love song and talk about emotional stuff for 20 hours.
DC: And film it, and put it on Instagram. It'll be amazing.
Sara Blakely: If I could make him stay up for the whole thing.
Jesse Itzler: Very funny.
Sara Blakely: I'll come up with something good.
DC: How do you two manage to do all the things that you do, like watching your Instagram? I think that's part of the question that everyone asks, that I ask myself, and other people ask when I showed them, because I show everyone both of your Instagram accounts all the time. And I'm like,"Look at the mystery wagon." It is on your Instagram. Yeah.
Jesse Itzler: Well, for me, I prioritize it. I really only have four main buckets- my family, my business, my wellness, things that are important to me- friends, charity. And if something doesn't fit into one of those buckets now, I'd really say no. And I eliminate all the stuff, as much of the stuff that was a time suck for me. When I was single, I could watch TV, go to sporting events. And that's changed for me. So as you get older, you have to change your system a little bit.
DC: Yeah. And does this segue into your big calendar?
Jesse Itzler: Very much so. Don't make fun of my big calendar.
DC: I love the big calendar. Yeah. I remember we had a... I don't have a big calendar myself. I need a big calendar. We started this business a little less than five years ago. One thing when you have sales teams, they would always come and they'd be like," Oh, this week's a little slow. It's 4th of July." And I was like,"4th of July is on a calendar." The 4th of July happens every year. Or it's like Memorial Day, and it's like... So I got everyone giant calendars. And we just put all the dates on the calendars, and it's like," Look, we have the same holidays every year." But that was our version of the giant calendar.
Jesse Itzler: In all seriousness, though, creating a system to optimize... Here you go, Sara.
DC: There we go.
Jesse Itzler: There you go.
Sara Blakely: This is Billy.
Jesse Itzler: Creating a system to optimize, get the most out of the time, is so important. And that calendar helps me. I'm visual. I need it.
DC: Yeah. How did you two meet?
Sara Blakely: I mean, he does not leave home without that calendar. It's just outrageous, for real. I mean, he's carried it through airports. It's always in the hotel rooms. I just cannot stop laughing.
Jesse Itzler: It's efficient for me. I didn't bring it on this running race, because why would I need my big calendar on the running race? And on the way there, Sara was like," When I'm in Switzerland next week, how many days you wait for speeches or whatever?" And I'm like," I have no idea. I don't have my calendar."
DC: Is there digital form of the calendar? inaudible.
Jesse Itzler: When you get to be 51, the digital thing becomes out to here, and it's just like," You can't inaudible" I'm not exactly sure it even says, so I need the calendar.
DC: It's crazy. And how did you meet? I know this story, but it's a funny story.
Jesse Itzler: Sara was a customer of mine at a company I had, called Marquis Jet. And we were having a customer appreciation event, a poker tournament in Vegas. And each rep was allowed to invite one person in their territory to this event. And the Georgia rep sent a picture of Sara. And I was like," No applicants."
DC: You're like, crosstalk.
Jesse Itzler: Make sure she's there. We were married a year later.
DC: Get out of here. A year later?
Jesse Itzler: Basically. A year and a half later?
Sara Blakely: Yeah. Yeah.
DC: And how did that work?
Sara Blakely: What?
DC: How did he manage to convince you to date him?
Sara Blakely: Oh, he did some funny things. I mean, first of all, he was about to run a hundred miles. And he called Spanx and said to somebody that he got in touch with, which was my PR person at the time, he said," I'm Jesse Itzler, and I'm going to run a hundred miles in Spanx." And literally, this girl came down to my office and said," Sara, I have a lunatic on the phone, who's claiming he's going to run a hundred miles in Spanx."
Jesse Itzler: Did you want me to send an email?" You want to go out for dinner?"
DC: So good. If you're listening to this and you need game, get at @ jesseitzler on Instagram, and ask him for advice. That move is legend.
Jesse Itzler: Thank you.
Sara Blakely: It worked. Whatever he did worked.
Jesse Itzler: Four kids later, man. Four kids later.
DC: Does he still have great stuff like that? Does he still surprise you?
Sara Blakely: Yes, definitely.
DC: Yeah. Yeah. It never ends?
Sara Blakely: Yup. I mean his whole life is a surprise. He's very adventurous to be married to. There's never anything boring. It's very exciting. He's a fascinating guy because a lot of people who've become top in their game are typically interesting by nature. But he's been top in the game in so many different sectors. I mean from rap, to jets, to coconut water, to ultra marathon. So it's really cool.
DC: Have you done the 290, 229?
Sara Blakely: Yes, I did the first one in Vermont. But I timed out, so I didn't get a chance to finish it in time. So it's still on my bucket list. When?
DC: This year.
Sara Blakely: In Vermont?
Jesse Itzler: Unbelievable.
Sara Blakely: Oh, amazing.
DC: So I'm doing it, Dave Gerhardt, our VP of Marketing. And we haven't told him this. I hope it doesn't air. My co- founder, we just told him that we're doing it, but we haven't told him what it is yet.
Sara Blakely: Oh, nice.
DC: And we're going to film the whole thing. Because he is the kind of person that... He spoke earlier. I sent him to Jocko's Bootcamp. You know Jocko? It was four years or five years ago, before it was much... A lot of people knew about Jocko. And he's the kind of guy that I sent him there, and I knew he was not going to research what it was about. He just shows up. And he shows up late, and he walks into one of the Jocko's bootcamps, and he has no idea what this is about. So I know he's going to show up in Vermont, and not have any idea what to do about it.
Jesse Itzler: Wow. How did he do at that bootcamp?
DC: He's one of those, he can befriend anyone. He's kind of like Jesse. He didn't know what it was. Jocko's making fun of him in front of everyone within 10 minutes, because he doesn't know what this is. And then, within 20 minutes, he's sending live video that he's part of the band of brothers, he's with Jocko, and all these Navy SEALs, and that they're blood brothers now, and they're going to go do this. And that's the kind of guy he is. He can talk himself into anything, which I suspect Jesse can.
Jesse Itzler: I want to see how many laps he can talk himself into.
DC: Yeah. That's going to be amazing.
Sara Blakely: That is going to be amazing.
DC: That's going to be amazing. Are you doing it this year?
Jesse Itzler: Yeah. Yeah.
DC: You do every single one?
Jesse Itzler: Yeah. I didn't do the last one in Utah because I had my race, but I've done them all. Absolutely.
DC: I think Sara's the most amazing person, for letting a SEAL live with you, in your book, Living With a SEAL, doing that race that you do at Connecticut, right at the backyard.
Jesse Itzler: She is.
DC: How do you do all this?
Sara Blakely: Let me tell you something. When I first was dating him, it's right when the 100- Mile race was happening. And everybody that I would say," I'm dating this guy, and he just ran a hundred miles without stopping." Everybody would always ask me the same questions or have the same response. Everyone would look at me and go," No way. What did he eat? How did he pee?" And I was filming something with George Foreman. And I said," George, I'm dating a guy. And he just ran a hundred miles without stopping." And he looked at me, dead in the eyes, so serious, and he said," Sara, don't try to understand a man like that." And he goes," Just love him."
DC: Wow. Was that the best advice ever?
Sara Blakely: Best advice ever.
DC: Yeah. Don't dig in. You don't want to dig even a little bit.
Sara Blakely: And I was like," Got you." And he was speaking for you. He's that kind of guy that's got whatever that chip is.
DC: Yeah. He's like," Don't even scratch a little bit into that."
Sara Blakely: He goes," Don't try." And I was like," Whoa." And it was such good advice. So I mean, we got married late enough in life. I was 37. He was 40. For the first time ever, getting married. And I think marriage is all about just supporting who that person is. And I knew who I was marrying and what he...
DC: There was no surprise. You start with a hundred miles.
Sara Blakely: Yeah. So, and that's what it really is about. So I'm on the journey with him. And every chance I get to support what he wants to do and where he's headed, I do it.
DC: And how do you push him to the limit?
Sara Blakely: How do I push him to the limit?
Jesse Itzler: Sara?
Sara Blakely: I don't know. He doesn't really... He pushes himself. And I might push him to the limit sometimes in other ways, drive him a little crazy.
DC: That is amazing.
Jesse Itzler: We're married.
DC: You're married. Yeah.
Jesse Itzler: It is what it is.
DC: Yeah. That is life. Well, thank you so much for spending time with us today. Let me know what you thought of this episode by texting me at 1- 212- 380- 1036. Again, 1- 212- 380- 1036. Now, if you're looking for more leadership insights, sign up for my weekly newsletter, The One Thing, at drift. com/ dc. Every week, I'll share a habit, tool, or mental model that's helping me reach my goals. Hope to see you there. Text me, hit me up.