Drybar Founder Tells ALL Her Secrets! “Trusting My GUT Made Me $255 Million” | Alli Webb

Alli Webb 0:00 I think delusion is maybe ignoring red flags. Like, "No, no, it's gonna be fine." What are you doing? Why are you not listening? Those mistakes and those red flags actually are really great gifts. Afterwards, you're like, "Oh, I needed to learn this."

Jay Shetty 0:12 Entrepreneur Alli Webb.

Alli Webb 0:13 The co-founder of Drybar.

Jay Shetty 0:15 The $100 million empire.

Alli Webb 0:18 I've had this shame. I didn't want to be divorced once, and now I'm heading into divorce twice. Can I be in love with a person and myself and what I'm doing? I haven't been able to figure that out yet.

Jay Shetty 0:30 Before we jump into this episode, I'd like to invite you to join this community to hear more interviews that will help you become happier, healthier, and more healed. All I want you to do is click on the subscribe button. I love your support. It's incredible to see all your comments, and we're just getting started. I can't wait to go on this journey with you. Thank you so much for subscribing. It means the world to me. The bestselling author and host. The number one health and wellness podcast. On Purpose with Jay Shetty. Hey, everyone. Welcome back to On Purpose, the number one health podcast in the world, thanks to each and every one of you that come back every week to listen, learn, and grow. Now, you know that our community's all about becoming happier, healthier, and more healed. And whether it's your career, whether it's your relationships, whether it's your personal life, we try and focus on all aspects on On Purpose. Today's guest is someone who's excited to share with us what I believe is the truth, and it's called The Messy Truth. Alli Webb, who I'm gonna tell you about in a second, this book is all about how she sold her business for millions but almost lost herself. The Messy Truth is available right now. We're going to put the link in the caption so you can order it while you're listening to this conversation. And for those of you that don't know, Alli Webb is the founder of Drybar, New York Times bestselling author, Canopy president, co-founder of Squeeze, Brightside, and Beckett & Quill. In 2010, Drybar exploded into a nationally recognized and highly sought-after brand, growing to over 150 locations, and highly successful product line which sold for $255 million in 2020. Staying true to Alli's signature approach to beauty and self-care, Squeeze followed suit as an innovative massage concept. Alli joined forces with LA-based jewelry designer Meredith Quill to build yet another new company, now known as Beckett and Quill. Most recently, Alli joined the Canopy team as president, and I'm excited to talk to Alli because we bumped into each other recently-

Alli Webb 2:35 [laughs]

Jay Shetty 2:35 ... at a soccer game, football game, uh, for Angel City FC. Please welcome to the show Alli Webb. Alli, thank you for being here.

Alli Webb 2:43 Thank you. Thanks for that introduction.

Jay Shetty 2:45 Of course. You had to live it all, as I always tell my guests.

Alli Webb 2:47 [laughs] I try.

Jay Shetty 2:48 And, and I love this.

Jay Shetty 2:50 You know, the title of your book just immediately captured my attention because I couldn't agree more that every success story is underpinned by the messy truth, and we often don't hear about the messy truth. We often don't see the messy truth. Sometimes we don't even want to know about the messy truth.

Alli Webb 3:11 Yeah.

Jay Shetty 3:11 We'd rather believe in the facade or the beauty or the perfection or the perfect image that we see, and I'm really glad that you're sharing this. So I have lots of things I want to ask you from the book today. I highly recommend everyone goes and buys the book, especially if you're on your entrepreneurial journey. Maybe you want to be an entrepreneur. You're thinking about it, and you're thinking about, "How do I figure out all of this stuff?" So, so let's start with this idea, Alli, that a lot of our audience, a lot of our community wants to be entrepreneurs.

Alli Webb 3:39 Yeah.

Jay Shetty 3:39 They may already be entrepreneurs. Some of them are struggling. Some of them are winning. Some of them are still figuring out what they're even gonna do. What is the messy truth about starting that no one tells you about starting specifically?

Alli Webb 3:53 Well, you know, I think that we

Alli Webb 3:55 live in a generation now where we are finally at the point, which wasn't the case when I was starting out, where it is accessible to get to hear what's really going on. There's so many panels and so many conferences where, you know, entrepreneurs are talking about more of the real stuff, which I'm super grateful for. Like I said, 13 years ago when we started Drybar, that didn't exist. Like, nobody was talking about anything. You know, you didn't have access to founders or CEOs the way you do now, and it's such a beautiful thing that there's [laughs] podcasts like this and there's places where people who are thinking about starting a business can go. Like, I have a mastermind that's launching next week where it's, like, for entrepreneurs. Like, there's so much access out there now. But, you know, I think there is still, understandably so, it's like, I mean, everybody wants to look good, and everybody wants to, like, show their best side. And for me, it's like I, I've always just been drawn to the, like, you know, the realness, and maybe it's because I've always been a bit of an underdog. You know, I mean, starting from the time I was, like, a kid, my, my older brother, Michael, who's my business partner in Drybar, you know, he was, like, the overachiever in our family, like very, you know, kind of more book smart and just, you know, was kind of either always in trouble or always doing something really amazing. There wasn't really a lot of in between.

Jay Shetty 5:09 [laughs]

Alli Webb 5:10 And I was kind of a w- bit of a wallflower, which if you know me now, that is not my personality at all, but back then I was just kind of observing my brother in trouble or doing something great. I grew up in this, with this, like ... I, I was just in the background. And I think that as, as I've gotten older, I have felt like more wanting to, you know, talk about, you know, m- my story and, like, how I was, like, a, like, a bit of a ... I think I have a chapter in the book called, like, "The Unlikely Entrepreneur," something like that. I should probably know all the chapters in my book.

Jay Shetty 5:41 [laughs]

Alli Webb 5:41 But, but I- I've always considered myself, like, kind of this underdog and, like, not who you'd expect to succeed. And I think, I guess I f- have felt called to shine light on that because There are a lot of us out there, you

Alli Webb 5:55 know? And I don't have a traditional path, and I think that at one point it was like there was this societal like you have to go to college, you have to have a business degree if you want to start a business. And now, you know, there's so many- I've spoken at so many colleges that have entrepreneurial programs, which I'm like, I always get a chuckle out of 'cause I'm like, "I didn't even go to college. Like, do you want me to not mention that?"

Jay Shetty 6:13 [laughs]

Alli Webb 6:13 You know? But I think it's just good to show that like you can find success and have success no matter who you are, whether you went to college, didn't go to college, like graduated [laughs] high school, didn't graduate, whate- whatever. You know, so I've, I've just felt really drawn to that kind of like underdog, like the person that you just wouldn't expect, you know, to be successful. And so I try to, you know, highlight that. And there's good there, too, and there's a lot of things that I am, you know, I am really good at. But showing like a peek behind the curtain to people that it's not... I mean, we- I think any entrepreneur who's listening to this knows it's not easy. Of course it's not easy. I feel like I just wanna talk about and highlight more of the hard stuff than just the good stuff, you know? 'Cause it's, it's completely a mixed bag. It's not one or the other. It's usually like one minute to one minute. Like, you're like, "Oh, this was amazing," and then you're like, "The whole thing's falling apart," you know? I mean, it's literally like that crazy. So my mission with the book was like to highlight both. Like it c- it's really amazing and it's the greatest journey, and it's also incredibly hard and taxing and like you don't realize how much it's gonna change your life. And I don't- I think that's good that you don't know that. You know, I'm a little bit of like the ignorance is bliss mentality because I feel like the less [laughs] you know about what you're getting yourself into... And I think just that whole mindset of like if you can accept you don't what you don't know, you go into things a little like not as freaked out, [laughs] you know?

Jay Shetty 7:37 Yeah. Well, in the book you go into in detail, give us a snapshot for everyone

Jay Shetty 7:40 who's listening of what your life looked like when you even thought about starting this, because that will give us a picture of this-

Alli Webb 7:45 Yeah

Jay Shetty 7:45 ... underdog, unlikely entrepreneur.

Alli Webb 7:47 Yeah. I mean, you know, I got married to my first husband when I was 26. I moved to New York City when I was 18 'cause I didn't wanna go to college. And I was like, "I'm gonna move to New York City. I feel like that will be good college." [laughs] And that's what I did. And I, you know, I jumped around from job to job, and I would eventually go to beauty school when I- in South Florida, and then I moved back to New York and, and then I got married and moved to LA and had two babies and was like, thought I'd like hit the jackpot. Like, I loved being able to be a stay-at-home mom. I really felt so blessed and lucky that I got to be home with my boys, and I was home for like, you know, about five years before I started Drybar, and that was such an amazing time. But I did get that itch to get back out there and start doing something for myself, which was really just like a feeling that I had. I mean, I really wanted to have kids and I really wanted to be a stay-at-home mom, and part of me thought I'd get really involved in the school and stuff like that. And as I kind of approached that, I was like, "No, I don't think I wanna do that." And not n- there's no right or wrong, right? It just wasn't for me, and I've always really trusted my gut and my feeling. And I, and I p- I stay very close in to what feels right. And I- and after staying home with my kids, it was about, they were about two and four when I started Drybar. And about a year before we started Drybar, I got that kind of itch to do something and I started a mobile blowout business which was, again, just like a way to get out of the house for a few hours, get away from my kids who I loved, love, loved, the whole thing. But just wanted to do something for myself, and I knew having done hair for so many years that I could do that pretty easily. I also, you know, had this like intuition on that that if I were to only charge $40, which was like, oh, 220, super easy, I'll come over while your baby's sleeping, that was it, you know, that maybe that would be fulfilling for me to get out of the house, talk to adults. I mean, that's the other thing is like when you have two little kids and you go to the park all day and you're, you're in like kidville all day. I just, I wanted a little bit of a break from that, and not just from my husband. So I started this, and it was so perfect at the time, and I remember telling people that. Like, I remember it was, I mean, it was 15 years ago but it feels like yesterday 'cause I was like, "Oh, this is great. I love this." Like, I'm getting out into the world. It was a great way for me to meet other women, and I would... It also informed a lot of the things that we would eventually instill in Drybar, like not doing someone's hair in front of a mirror 'cause I was doing their hair in their living room. And so it was just perfect at the time. I wasn't really making any money, but I didn't g- it w- I've never been like driven by money, so I was like, "I'm just happy to do this and make a little extra cash. I go and do this thing that I really love doing. I get to talk to these amazing women." And it was kinda like wildfire. I, you know, women would tell their friends and then their friend group, and so

Alli Webb 10:30 it would just grow and grow, which, which is eventually why Drybar came to be because I was getting so busy operating this mobile business by myself that I was like, "I think I need to start having them come to me instead of me come to them," and that's really how Drybar was born. But I was just this like one-woman show, driving my Nissan Xterra around LA with a, like a duffle bag full of tools and hairspray and... You know, it's funny 'cause it's like I remember it so well. Like could, could have never guessed it would turn into the life that I have now. I mean, not in a million years. I was just happy to be out of the [laughs] house for a couple hours, you know?

Jay Shetty 11:05 Thank you for sharing that. I know you've probably had to share that so many times.

Alli Webb 11:08 No, but I love it.

Jay Shetty 11:08 But I wanted you to because I just, I mean, to me I'm hoping that so many people are listening and watching going, "That's me, Alli," right? Like-

Alli Webb 11:16 I bet

Jay Shetty 11:16 ... I'm someone who like, I, I love my family but I, I wanna do something. I have this instinct that I have something inside of me. I don't know what it quite is yet-

Alli Webb 11:26 Yeah

Jay Shetty 11:26 ... or by the way, I'm doing something on the side and my friends all tell each other that I'm good at it and-

Alli Webb 11:30 Yeah, exactly

Jay Shetty 11:31 ... I, I think I could build something but I'm not sure. Like-

Alli Webb 11:34 Yeah

Jay Shetty 11:34 ... what was it that made you feel This is real and it could be bigger versus actually, uh, this is great and it fulfills my needs of getting out the house and giving me an little bit of extra cash. 'Cause what, you could argue that already felt like success-

Alli Webb 11:51 It totally-

Jay Shetty 11:51 And it can be success for a lot of people. What was it for you that said, "No, this should be bigger. I can be bigger and I want it to be bigger," yeah.

Alli Webb 11:58 Yeah. Well, it's funny how, and I'm sure you've experienced this too, when you're doing something and it feels really right, and then there's like these rumblings and this like inner knowing of you're like, "Wait a second, I might be onto something here." And that's really how I started to feel because I realized I was saying no more than I was saying yes. And I was like, you know, scratching my head going like, "I'm getting so many calls," and I was pretty good at what I was doing. And so I was like, there's gotta be something else here. And, and at the time my kids were really little, and my, my mom, who passed away eight years ago now, but she was... We used to move her everywhere we moved, like at an apartment down the street, and she loved being near my kids, and so that was really helpful and she was, you know, in our lives. And I remember being like, I, I wonder what would happen if, if we had a location, one location. You know, I'm like, "My mom could help. I could get my kids after, you know, preschool, like around 3:00 or 4:00. I think I could still make this work." And a- a- and again, still thinking pretty small. You know, that like, let me just go from like the next step from going to people's-

Jay Shetty 12:59 I love that

Alli Webb 12:59 ... homes to like opening a store. And it, and it was so ex- exciting, you know? And it was just like, I tell people this all the time, that, you know, if you're chasing the money, like, [laughs] I mean, maybe that works sometimes. In my experience, most businesses that I know of, like it's like you're chasing something that you love. And I never, I never thought

Alli Webb 13:20 about selling the business. I never thought about making a ton of money. I was like, I never even thought about money. We didn't, I mean, for years I didn't take much money as a salary from Drybar. I just loved it, you know? And I, and, and when you, you know this, when you love your passion and like the thing that you, it's, and you get to do it every day, you know? It was like I just felt like this is the coolest thing ever. And I couldn't believe like, you know, when we first opened Drybar and so many people were coming and, and, and, you know, again, it was like it just felt so meant to be because this mobile business that I had built and these women that I had come to know in LA, and some of them were like, I mean, it's LA, you know, it's like producers and actors and celebrities and like, you know, I was a little thrust into that world. And, and, you know, beyond like the celebrity, just, you know, there was just so many women who were really connected. And when I started talking to my clients, which by the way, were the first people I talked to about Drybar, I was like, "What do you think of this idea?" And they're like, "Oh my God, it's the best idea ever. But how do you make it work?" And there was like certainly naysayers, but it was such a cool, exciting opportunity. And to have women like being like, "You should totally do this"-

Jay Shetty 14:21 Yeah

Alli Webb 14:22 ... and then we opened that first store and it was so busy and crazy

Alli Webb 14:26 and I, and I just l- I loved every second of it, you know? I couldn't get enough of it.

Jay Shetty 14:30 That's such a, I, I love that and I want to pull from it for our listeners. So something Alli said that stands out to me is this idea of she was taking baby steps. It was just about the next step. It wasn't like, "I've come across a-

Alli Webb 14:42 World domination

Jay Shetty 14:43 ... a million dollar idea, a hundred million." It wasn't like this-

Alli Webb 14:45 Yeah

Jay Shetty 14:45 ... crazy thought process. It was like, "I do something. It makes me happy. Clients are happy. Let's get a store." And I think sometimes we kind of go from, "Well, I have a really good idea. It should be a million-dollar business, a billion-dollar business," or whatever it may be, and we don't get that next step right. So that's one thing I want to share. The second thing that really stood out in what you said is you asked the people you are serving, your clients-

Alli Webb 15:10 Mm-hmm

Jay Shetty 15:10 ... for what they thought of the idea. A lot of us ask our friends, we ask our family, we ask people around us who don't actually know how skilled we are at this thing-

Alli Webb 15:19 Right

Jay Shetty 15:19 ... and we're not asking the people who are actually going to be our potential clients.

Alli Webb 15:23 [laughs] Yeah.

Jay Shetty 15:23 And so the fact that you were asking them and they were saying, "Oh, I'd turn up there. Oh, I'd recommend all my friends"-

Alli Webb 15:28 Right

Jay Shetty 15:28 ... "We're in," that's a much better person to talk to when you're sharing a new idea. What's the difference, Alli? Because you've talked about now and in the book, you talk about this idea that you've always been pretty decisive, but more deeply when you go into it, and, and I know you have a, have a, have a deeper side to you, and when you're thinking about things like intention and intuition and instinct, and you said, "I always knew, like I was always listening for that inner voice."

Jay Shetty 15:56 What is the difference between intuition and delusion? If you had to think about how you notice the difference, what would that be for you?

Alli Webb 16:05 I think intuition is like versus delusion, 'cause I feel like I'm well acquainted [laughs] with both of them.

Jay Shetty 16:10 [laughs]

Alli Webb 16:11 I mean-

Jay Shetty 16:12 That's good.

Alli Webb 16:12 Yeah. Because like delusion is like something to me, at least how it lands for me, is like something that's like, you know, a, a delusional view back then of Drybar would have been like, we're gonna grow this thing to 150 locations and we're gonna sell it for $255 million. Although I did say early on that I thought we would've e- but not early, like in a year in, I was like, "I think we're gonna sell the business for 250 million." Isn't that crazy? I, I mean, I feel like I manifested that. It, I think it kind of goes back to what you're saying about baby steps. It's like is we're doing ourselves a disservice of, you know, moving in this like, you know, in a delusional path I, I think I would say, you know, versus like staying close in. And, you know, and I have gotten very into spirituality in the last few years, and one of my very best friends, and, and I talk about her in the book, her name is Pa- Paige, and I always say I'm riding her spiritual coattails 'cause she's always in Tellus in some retreat and, you know, I'm just kind of like trying to pick it up of what she's doing and, and she always says to me, "Stay close in." You know, and, and you have to really think about that and like what that means, and it's like, oh, for me anyways, it means like pay really close attention, and I've really started to think about that more and more, especially having had a, you know, rough couple months recently. It's like, how does this make me feel in the moment? And I don't think I ever could have articulated that the way I can now, and I think we get older, we're wiser, we go through more things, we read more books, we do all the things. I meditate a lot more now. I do all that stuff now and, and I pay really close attention. I don't think I did the way I do now back then. But I think I had it instinctually in me, I just didn't know how to like pick up on it, you know? Whereas like now I can, I can almost like I can read something or have a thought and like immediately get a ping in my body of like, "No, this does not feel good," or get a like, "Oh yeah, this feels really good." And it's fascinating. And it, and it, and the thing is, and I'm sure you f- being who you are would agree with this, it's like if you get really quiet and you pay attention to that stuff, it's pretty clear.

Jay Shetty 18:10 Mm-hmm.

Alli Webb 18:10 You know, I have definitely been known to purposely ignore red flags in situations, which have gotten me into some bad situations, and it's, it's really funny the awareness that we get as we get older and wiser and we make some mistakes and we learn from them. And so I, I guess, you know, delusion is like a, I think delusion is maybe ignoring red flags, you know?

Jay Shetty 18:30 Mm-hmm.

Alli Webb 18:30 It's like, "No, no, it's gonna be fine," besides the fact that like you know it's not, but you're gonna... It's like y- what are, what are you doing? Why are you not listening? I heard something, um, Brene Brown said, I'm sure she's been on the show.

Jay Shetty 18:42 She has not, no.

Alli Webb 18:43 She hasn't?

Jay Shetty 18:43 No, no, no, yeah.

Alli Webb 18:43 Oh, you have to have her on.

Jay Shetty 18:45 Yeah.

Alli Webb 18:45 She's amazing, and she was really there for me in my first divorce, which is crazy. But she, um, I just saw something recently where she was like, "Every, every once in a while the universe taps you," or w- not every once in a while, "When you get to mid-age, the universe like taps you on the shoulder and is like, 'You can't run anymore.'"

Jay Shetty 19:00 [laughs]

Alli Webb 19:00 And I was like, "Is she talking to me?"

Jay Shetty 19:02 [laughs]

Alli Webb 19:03 You know? And it, but it was a, it's a fascinating thing, 'cause I think at some point in our lives, and it seems to me like it's more midlife, you get that tap and you're like, "Yeah, I gotta, I gotta be really like, I gotta pay attention to what's happening." Like I, you just c- you just can't get away with it anymore, you know? And I think as we're, when we're younger, we can. I don't know why that is, and I think maybe we're just ignoring the red flags and thinking it can just all work out. And I'm such a like it all works out kinda gal anyways, which I think is true. And now I'm, I've come to realize that those mistakes and those red flags and the things that we don't pay attention to when we should actually are really great gifts, not in the moment. In the moment you're like, "Why is this happening to me?" But then afterwards you're like, "Oh, I needed to learn this," you know? A- again, my friend Paige always says, "It's the medicine," you know? She's like, "This is the medicine that you need." I'm like, "It's always about the medicine," you know? But it's really true.

Jay Shetty 19:56 Yeah. Absolutely. Thank you for, thank you for doing that thought experiment with me.

Alli Webb 19:59 Yeah. [laughs]

Jay Shetty 20:00 I- intuition and delusion.

Alli Webb 20:02 Yeah. Yeah, it's a g-

Jay Shetty 20:02 I, I really loved your take on it. Yeah.

Alli Webb 20:04 It's good. It's good.

Jay Shetty 20:04 I loved your take

Jay Shetty 20:05 on it. I wanna pick out some moments from your book, because I love some of the quotes in your book, and things that stuck with me. And so I'm gonna start with this, because it really, you know, enhances the conversation we're having right now about your work, and you says, this is page eight, "Though entrepreneurs today face different challenges, more noise, more competition, et cetera, it still always starts with you, your idea, your skill set, your purpose, and your gut instinct." And you say, "What is the thing that you just can't stop thinking about?" Which, which I love that. I love that language to it. But you talk a lot about this finding your skill set as an entrepreneur.

Alli Webb 20:43 Mm-hmm. Mm-hmm.

Jay Shetty 20:43 And I think there could be nothing more true about, than that. Like, I'm, I'm so aligned with you, and I think often we're doing things we're passionate about that we're not skilled at, or if we are passionate, we haven't thought that we need to be skilled at it. And obviously you could be doing the opposite, where you're doing-

Alli Webb 20:59 Yeah

Jay Shetty 20:59 ... something you're skilled at that you're not passionate about, sure, and that's what a job is pretty much.

Alli Webb 21:03 Yeah.

Jay Shetty 21:03 But how do people discover what they're skilled at? Because what I've found is that most of us, when we're skilled at something, we devalue it as a skill-

Alli Webb 21:14 Mm

Jay Shetty 21:14 ... because it's so easy to us.

Alli Webb 21:16 Mm-hmm. Mm-hmm.

Jay Shetty 21:16 And we see someone else with another skill, and you talk about this a lot in the book, about don't become someone else's story, don't chase another entrepreneur, don't try and-

Alli Webb 21:24 Yeah, yeah

Jay Shetty 21:24 ... imitate. But we look at someone, so for example, people will look at me and be like, "Oh, Jay, like you're really good at XYZ," but then if I'm not aware of that skill set, I'll be like, "No, no, no, but you're really good at ABC," and then we play this kind of tag of like, "No, I don't have your skills," but we rarely sit and go, "No, I'm actually really good at that," I'm, because we devalue what we find easy.

Alli Webb 21:46 Yeah.

Jay Shetty 21:47 And-

Alli Webb 21:47 God, it's so true

Jay Shetty 21:47 ... right?

Alli Webb 21:48 I, I think it was really highlighted in, in my business with my, my brother and my first husband, Cam, who Cam was the creative genius behind Drybar, and my brother was like more the behind the scene business side of it, and I was like, you know, the hairstylist and

Alli Webb 22:04 like the experience. And everybody always asks us like, "Is it really hard to work with your brother and well, now ex-husband?" And that's not why we got divorced and whatever. But I was like, "No, it was great," because we were all very clear on what we did and what we did well, and what our highest and best use was. I had that conversation so many times. I still, I still go back to that, what's my highest and best use, always in life, because I think it's like-

Jay Shetty 22:25 Mm

Alli Webb 22:25 ... really like think about it, you know? And we had really almost no conflict. And if we ever, I mean, we all talked about all things together, but if there was ever like a, a questionable thing, it, whoever would decide was like whose lane that was, you know?

Jay Shetty 22:38 Mm-hmm.

Alli Webb 22:38 And that was, we were all very okay with that. And I think when you do run into problems with business partners, it's often because you guys think you have the same skill set, and then that's such a, it's like five-year-olds playing soccer. Everybody's kicking the ball.

Jay Shetty 22:50 [laughs]

Alli Webb 22:50 It doesn't work, you know? So I feel like it is, it's, it's like the old cliche, like y- it doesn't feel like work if you're doing something you love, which I know has been said eight million times, but like it is so true. And, and, and I think it's like almost feels too easy, to your point, so people are like, "Well, I've gotta challenge myself." And of course, like you do, and you wanna keep challenging yourself, but like what a gift in life to like be able to do what you love to do, and I think, I think there's this misconception that like you shouldn't do that, you know? It's like, you know, f- for me, like when I told my parents I wanted to go to beauty school, they were like, "Really?"

Jay Shetty 23:25 [laughs]

Alli Webb 23:26 "Are you sure?" You know? And like very like looked their nose down on it, like, "You wanna be a hairstylist?" And they also had, I grew up in South Florida, and my parents had, were entrepreneurs, which definitely informed a lot of my, or who I became. But they had this like old lady clothing store, and it was right next to this like old lady hair salon, and they were, and I think in their mind they were like, "You wanna work there?" And I was like, "No, I'm gonna move to New York City. I'm gonna do editorial and like fashion shows." And I had these like grand ideas. I didn't have Drybar at the time. You know, but it was like- That's what I loved. Like, I grew up in South Florida. I have naturally curly hair, and my hair was just massive and frizzy all the time, and I was just fascinated by hair. I loved hair. It's just what I loved, you know? [laughs] And so it took me a long- it would take me many years to finally, like, get the courage to say, like, when my friends were going to college and they were studying whatever, and I was always like, "How do you guys know what you want to do?" Very confused by that whole notion of college and majors and all that. And I just loved hair, and that was the thing that I really loved, and it w- you know, and I talk about it in the book, that it took me a while to, to figure out, again, c- comes back to, like, being close in. Like, I always loved hair. I would spend hours in the bathroom in high school, and I was just so... I worked at a hair salon as a receptionist when I was in high school because I wanted, well, to get free blowouts-

Jay Shetty 24:37 [laughs]

Alli Webb 24:37 ... and 'cause I loved being around hairstylists, and I was like, "This is the thing that I love," and I ignored it for so many years.

Jay Shetty 24:43 Mm.

Alli Webb 24:43 You know? And it's like, to be able to tap into that thing. And, and you can't find a person.

Jay Shetty 24:48 Mm.

Alli Webb 24:49 There's nobody you can meet and say, "What do you really love to do?" And sh- and they may not tell you because they're embarrassed, or they don't do it as a job because they, like, "My parents won't approve, my husband won't approve," my whoever won't think it's a good idea. My parents did not think it was a good idea to go to beauty school, but I had enough, like, chutzpah to be like, "I hear you, but it's what I wanna do," you know? And I had no idea it was gonna turn into, like, this beautiful life that it did for me, uh, but I was just like, stay really focused. And I, and I talk about that a lot to entrepreneurs that I'm mentoring. It's like, "Don't, you know, shut all that out. You know, listen to what really feels like is, is good for you, not what everybody else ar- around you wants," you know?

Jay Shetty 25:30 Yeah. It's

Jay Shetty 25:31 almost like that question that's come from what you're saying is, what's that voice you're ignoring on the inside?

Alli Webb 25:37 Yeah.

Jay Shetty 25:37 Or what's that idea that you keep kind of putting away because you're like, "That's ridiculous-"

Alli Webb 25:42 Yeah

Jay Shetty 25:42 ... or, "That's stupid," or-

Alli Webb 25:43 Yeah

Jay Shetty 25:44 ... and you've heard that voice before where someone looked at you weird because you actually shared your intention-

Alli Webb 25:48 Yeah

Jay Shetty 25:49 ... or your excitement-

Alli Webb 25:50 Yeah

Jay Shetty 25:50 ... and everyone looked at you like, "That's not real. Get over it."

Alli Webb 25:52 Yeah.

Jay Shetty 25:52 It's s-

Alli Webb 25:52 And by the way, people did that at Drybar because, I mean, like I said, it was in, it was in the middle of a recession, and people were like, "How do you make this concept work?" It's like, you know, we were starting at $35 a blowout, and it was like, you have to do a lot of blowouts to make that business work, and I was like, "Yeah, you know, but I think we can do it." And I, and, like, I literally, not, not great at math, but I was like, "I think if we can do, like, you know, 10 blowouts an hour and we're open, you know, 10 hours the d- like, I think it'll work," you know? And I remember my brother started, like, putting an actual spreadsheet together and running the numbers. It was like, "Yeah, if we do 30 or 40 blowouts a day, we'll have a nice business," you know? And of course we, we never did that little. We always did, like, 70, 80, 100 blowouts a day, which was just bananas. But it was like, people were the ones who put it in my head that, like, maybe, maybe this idea doesn't work. I mean, so many people. And then we started raising money and, you know, that's a whole other conversation of, like, raising money with, like, walking into these rooms with men in suits who, like, did not understand the concept of Drybar and were like, "What?" You know, like, "How does this work?" And just didn't believe in it. So many people didn't believe in it. And it, and it did seem like a tough... You know, how do you make this work, like, on a large scale? Is there enough [laughs] women who want to do this? Is the price, the price point is really low. Like, margins are really thin. How does it work? And, you know, and I just, I'm like, "I'm just telling you, I really, you know, from a gut level know that this is gonna work." And then you're like, "Oh, shit, this better work," you know? But it, it did. And, and, and I always felt like

Alli Webb 27:21 there was money on the line, for sure, and that's not a small thing. But, you know, I remember when I started cutting hair, and I mean, when you're starting to cut hair and you have really sharp scissors in your hand, it is very scary.

Jay Shetty 27:33 Mm-hmm.

Alli Webb 27:33 And, like, and you know what's so funny is, like, the very first haircut I-

Jay Shetty 27:35 I would never trust myself-

Alli Webb 27:36 Oh my God, it's-

Jay Shetty 27:37 ... with scissors in my hand with my own hair or anyone else's hair.

Alli Webb 27:39 No, it's the worst.

Jay Shetty 27:39 For that matter.

Alli Webb 27:40 And they're sharp.

Jay Shetty 27:40 Even if my wife says, "Will you s-" I'm like, "Nope."

Alli Webb 27:42 [laughs]

Jay Shetty 27:42 Like, I'm not going anywhere near that. Yeah.

Alli Webb 27:44 Well, the first haircut I ever did in beauty school, I cut someone's ear, and I felt like I was gonna die, and the ears bleed so much, and I thought I was-

Jay Shetty 27:53 When you say cut someone's ear, how much?

Alli Webb 27:55 Just, like, a m- just a little nip on the... I mean, it was-

Jay Shetty 27:58 Oh

Alli Webb 27:58 ... it was, I, I rememb- it was so traumatizing. I mean, sure, for them, but for me. And also, in beauty school you're doing, like, $2 haircuts, and it's where you're learning, you know?

Jay Shetty 28:05 Yeah.

Alli Webb 28:05 I still have, like, nightmares about that because it was, like, the worst thing that can happen. But beside that weird story, which I don't think I've ever talked to anybody about-

Jay Shetty 28:13 [laughs]

Alli Webb 28:13 ... um, I [laughs] it was very traumatizing for me. But I always felt like at the end of the day when I was on the floor cutting and when I was doing all that and, you know, and then when we were starting Drybar, I was like, "No one's gonna die if this business doesn't work," like, which is, like, the worst possible outcome. It's like, we're not doing [laughs] surgery. We're not, we don't... You know, and, and I, and I always, like, found [laughs] comfort in that 'cause I was like, you know, there's always a chance that we're gonna lose money. In my case, it was gonna really be my brother's money and my b- [laughs] you know, my, my husband at the time and I put in our life savings, which wasn't really that much, but a lot to us at the time.

Jay Shetty 28:45 Mm-hmm.

Alli Webb 28:46 And, you know, and I was like, "It's gonna really suck and we're gonna lose money," but we're like, "We're really smart, capable people, and if this idea doesn't work, like, we'll figure something else out." And I think that that mindset of, like, y- you gotta just, like, put it on the line is, like, it is really why I think I've been successful, is, like, not holding anything too tightly of, like, "Yeah, I really hope this works and I really think this is gonna work, but if it doesn't, like, we're all gonna be okay," you know? And I think that's, like, you know, I think a lot, a lot of entrepreneurs I talk to are like, "I have to have this much money saved, and I have to do this-"

Jay Shetty 29:19 Mm-hmm

Alli Webb 29:19 ... "and I have to do this, and I have to do this," and I was like, "Yeah, prepare,

Alli Webb 29:22 for sure, but, like, at some point you're gonna have to just jump, you know-

Jay Shetty 29:25 Mm

Alli Webb 29:25 ... and, and hope for the best." [laughs]

Jay Shetty 29:26 Yeah.

Alli Webb 29:27 You know?

Jay Shetty 29:27 There is, there is a moment for that leap.

Alli Webb 29:29 Yeah.

Jay Shetty 29:29 I wanna dive into a couple of things here that you've mentioned that I think really stood out, and you talk about this, and we would talk about this a bit offline. It was this idea of page 13, you say, "If you feel like an imposter, embrace it."

Alli Webb 29:42 Yeah.

Jay Shetty 29:43 And I feel like imposter syndrome has been something that a lot of people are talking about.

Alli Webb 29:47 Yeah.

Jay Shetty 29:47 I think it's something that- There are even more people that are feeling than are talking about it, and it seems to be a recurring feeling-

Alli Webb 29:54 Yeah

Jay Shetty 29:54 ... whenever you're in a new room or a new league or a new zone. When you say embrace it, what does that mean?

Alli Webb 30:01 Well, I think to your point of people talking about it a lot, they talk about it like it's a bad thing, and I think I think of it as a good thing. If you're embarking on a position in a new job or you're starting a company or whatever you're doing that's new to you, like, that's amazing. Like, you're starting something new. You're- you're taking that leap of faith. You're, you know, putting yourself in a situation that you've not been in, and that's really scary-

Jay Shetty 30:26 Mm-hmm

Alli Webb 30:26 ... for sure, but it's also really exciting and exhilarating and it means you're growing and you're in this next new phase in your life. And so this- this negative association with imposter syndrome as if it's, like, a bad thing, it has definitely happened to me be- and I think maybe 'cause I had never had any real formal training in anything other than hair where I would start a job and I was like, "I know I'm under-qualified for this job-"

Jay Shetty 30:47 [laughs]

Alli Webb 30:47 "... but I'm gonna, like, figure it out." And I- and I would, you know? And I guess that was part of it, like, yes, I am an imposter technically. I don't know how to do this job, but you better believe I'm gonna figure it out and do it well. And it's no different with entrepreneurship. I mean, when we started Drybar, I had never, like, been in charge of that many people. I'd never managed a l- a salon. Like, I'd never... My parents did and I watched them, and I worked for owners of hair salons, and I've been a stylist for years. Like, I had a lot of the things that I think I needed to have, but I had never actually done it.

Jay Shetty 31:18 Mm.

Alli Webb 31:18 And so I was learning it as I went, which was scary, but also amazing. And I also think when you come in, again, nothing I could have articulated then, but a- a term I think we're hearing more and more now is this, like, l- beginner's mindset. You know, and I had that when I was- when we were starting Drybar because I was quite literally a beginner and running a business, and I made a lot of mistakes, and I had to figure out a lot of things. And that's- that's also the beauty of this book is that I feel like I got an education in this. I lear- I got, like, a, you know, a business degree while I was running a business because I was having to figure all these things out, and I made tons of wrong decisions and bad choices [laughs] .

Jay Shetty 31:55 Yeah.

Alli Webb 31:55 You know, I also think I felt, it's not necessarily imposter syndrome, but I think I felt this, like, immense pressure because I was the boss. Like, I had to know all the answers and I had to, like, if you came to me and asked me a question about the business, I had to be like, "Well, here's what I think," even though it wasn't always right. It was just, like, me ha- And I- I used to think that that was like, oh, you're just the boss and you just, you, the buck stops with you and you have to. And now I feel like, and- and how I- how I approach th- that question now is like, "Well, what do you think?"

Jay Shetty 32:25 Mm-hmm.

Alli Webb 32:25 Which is not something I would've said, and that's, like, I think that was all ego 'cause I was like, oh, I feel this pressure like I'm supposed to know the answer because I'm sitting where I'm sitting in this company. And now I'm like, "Well, what do you think about that?" And then people are like, "What?"

Jay Shetty 32:37 [laughs]

Alli Webb 32:37 You know? And I'm like, "Well, I don't... I actually don't know the answer, but I'd love to hear what- what you think." But I- I didn't have enough, like, you know, I was- I was too focused on, like, feeling like I had to be, and maybe that does go back to imposter syndrome. I had... I felt like I needed to know all the answers because I was the boss and this was my company and blah, blah, blah, where now I'm like there's so much freedom-

Jay Shetty 32:58 Mm

Alli Webb 32:58 ... in saying, "I don't know." You know?

Alli Webb 33:00 Like, let's talk about it. And then- and then the culture that you create in a company when you're, like, the kinda boss that's, like, not a know-it-all and people aren't afraid to be like, "Hey, Jai, you know, I actually think that if we tried this, this, and that..." Like, we do- I'm sure people do that in your company. Like, I'm... When someone comes up to you and they're like, "I actually think if we try blah, blah, blah," and your response is like, "No," you know, they're n- they're never coming to you with something again.

Jay Shetty 33:21 [laughs]

Alli Webb 33:21 But if your response is like, "Oh, that's interesting," you know, and you may not always take it, but that beginner's... That feels to me like a beginner's mindset of like, "I'm open to other ways of..." And- and I think that there's a part of... I know there's a part of me that gets a little like, "Huh," you know? And it's also like, "I- I feel like I know best," and we go into our- our ego of like, "No, but I know what I'm doing." How... But- but embracing what somebody else is bringing to you I think is really powerful, and that's something that took me a long time to get comfortable with.

Jay Shetty 33:51 Yeah. There's- there's something that you've reminded me, and you talk about this on page 52. You're saying, "Being open to feedback, personal or professional, is a practice, a learned intention to stop, take in the information, maybe go on a walk, take some deep breaths, and come back open to hearing what someone else is feeling."

Alli Webb 34:06 Mm-hmm.

Jay Shetty 34:07 And I wanted to ask you, what's been the best or most memorable piece of feedback that you gained on your professional journey that's kind of stuck with you where maybe even in the moment it was so painful to hear-

Alli Webb 34:20 Yeah

Jay Shetty 34:20 ... but you now look back and go, "I- I believe that"?

Alli Webb 34:23 Well, I think thinking of feedback as a gift, which I- I learned pretty early on, and I remember, you know, somebody in our company who said it. I heard her say it once and I was like, "Wow, that's so profound," because if you can be open to what someone is telling you, which is so hard, and it is painful. And- and you know, I remember my brother saying to me once, like, [laughs] "People are scared of you," and I was like, "What?"

Jay Shetty 34:50 Mm.

Alli Webb 34:50 You know, just no awareness on my part. Like, I was like, "What are you talking about?" You know, "What are you talking about? What do you mean people are scared of me?" Like, and he was like, "Well, because..." [laughs] You know?

Jay Shetty 34:59 [laughs]

Alli Webb 35:01 But yeah. It was a joke.

Jay Shetty 35:02 Yeah.

Alli Webb 35:02 Um, I, [laughs] you know, I was... I, but- but in the moment I really was taken aback by it and I was like, "I'm so nice. What do you mean?"

Jay Shetty 35:09 Mm-hmm.

Alli Webb 35:09 And he was like, "Well, you know, you walk in the stores and you lose your mind." And I was like, "I do that because I'm so passionate," you know? And I- and I was covering it up with, like, I'm so passionate and I want things to be perfect and- and I did, but I- I would learn over time that that walking in and, like, you know, I would- I would... You- you could see it all over my face-

Jay Shetty 35:31 [laughs]

Alli Webb 35:31 ... 'cause I was like, "Why are the floorboards dirty? Why is the music not up? Why did this person not get greeted that way? Why..." I mean, just for me it was like, you know, it was like sensory overload-

Jay Shetty 35:39 Yeah, yeah

Alli Webb 35:39 ... of everything that was wrong, which I think is a blessing and a curse 'cause you're like-

Jay Shetty 35:43 Yeah

Alli Webb 35:43 ... "Well, I am the person. This is my baby." Like, I am the person who has to be the one that's like- This is not working and, and we need to fix this. But I also would learn that I kn- I, I... People were excited when I would come in the store, and they wanted to tell me the good things.

Jay Shetty 35:57 [laughs]

Alli Webb 35:57 And I did start to perpetuate this reputation of like, "Alli's coming. Watch out." And you know, part of me was like, "I think maybe that's a good thing." But then I was like, "No, it's, it's not." And, and I would learn eventually to, you know, like I would take notes, and I would then like, you know, not like ruin everybody's day when I would come in [laughs] the store, you know? And I, and I had to learn that the hard way. But it really did take my brother, probably one of the only few people in our company who felt comfortable enough to say to me, 'cause he wasn't scared of me, you know, he'd be like, "People are scared of you." And I, again, at first I was very defensive and I told him he was wrong, and you know, and it was also my big brother. But it really like sunk in and I was like, "Man, I don't want that. I don't want people to be scared of me. I want people to be able to talk to me. I don't want people to feel like they have to protect me either," which was also another thing that drove me crazy, and still does to this day. Like, I don't, you know, and I'm sure you agree with this, like you don't wanna be surrounded by yes people. Like, please no. Tell me. Tell me the truth. Tell me what people are saying. I wanna know what people are thinking if I, if I can't ascertain that on my own, you know? So if you have people around

Alli Webb 37:00 you who are willing to give you like the feedback, it's like you're only gonna be better for it, you know? It st- it stings in the moment, and it still does. Like, you know, sometimes someone will tell me something and I'll be like, "Oh, gosh." Like, "I can't believe that." And then if you're open to it and then you, you, then now you have the awareness about it... And, and I'll tell you, I'm like, I don't think you have children, right?

Jay Shetty 37:21 No.

Alli Webb 37:21 You know, for me, I have a 16 and 18-year-old, two boys, and like talk about honesty. I mean, I'm really, really close to my kids, but they will tell me things like that are very hard to hear. And it, it, it is a real practice, a mental exercise for me to not, you know... And my kids used to say to me, like [laughs] 'cause I've, 'cause during the Drybar era when I was, I guess, a little scary, you know, my, my kids would even say to me like, "We don't know what version you're gonna, of you we're gonna get."

Jay Shetty 37:49 Mm.

Alli Webb 37:49 Which is like, oh.

Jay Shetty 37:50 Oh, yeah.

Alli Webb 37:51 Yeah, and I was like, "But I know that now." And now, like the power is in, in my control. Like, I can be like, "Okay." And it, it literally just happened. I was with my son is at Denison, an university in Ohio, and he's playing football, and we went out to see him. And this, you know, he, he like came off the field, you know, and he was like, he didn't really wanna talk about some of the stuff that we wanted to talk about. And my younger son said to me like, "Just give him a minute, Mom." And I was like, "What?" He's like, "Just give him a minute." And I was like, "Oh, right." You know, 'cause as a mom, and anybody listening to this who's a mom, you're like, when your kid isn't like perfect and happy you're like, "What's wrong? What's wrong? What's wrong? How can I fix it? What can I do?" Da, da, da. Like, you know, we get, we go into that like mama bear protective mode, and my younger son looked at me and he's like, "Mom, give him a minute." And I, I do get defensive with him for a second, and I was like, "W- what are you talking about?" You know? And he's like, "You know." And I was like, "You're right," you know? And I was like, "Okay, th- " And I thanked him, you know, and I backed up and I was like, "When he's ready to talk to me about it, he'll talk to me about it." And sure enough, he did. Couple hours later, talk- he opened up, and it was like such a great lesson and reminder of like sometimes, you know, you need to give people space and you can't just have what you want when you want it. And, and that's been a really hard lesson for me, and I think it's also like being at the, at the helm of a company and, and having this like mentality of like, "I can do and say whatever I want 'cause I'm the boss, and blah, blah, blah. You can just do whatever," that bleeds over into your real life, which, you know, my kids are kind of a living example of that, of like, you know... And I used to say things to my kids like, "I've been around longer than you guys and I just know." And they're like, "You don't always know, Mom," you know? And it's like, you know, your, so your kids are like [laughs] talk about mirrors, you know? And, and they've, they've, all of that awareness I think has been such a gift to me. And, and that, you can get that anywhere in your life, from your best friend, from your spouse, from someone who works for you or with you. It's like if you ask genuinely, they're gonna tell you, and like what a gift to like get that awareness, you know? And it does sting for a second, and then you're like, "Oh, okay. I'm gonna take that and, and be better." My best friend tells me stuff, too, you know? It's like, "Oh, thank you," you know?

Jay Shetty 40:03 Yeah. Yeah, and it requires that beginner's mindset, that humility to accept and receive it. I know, I know my wife does it with me all the time, and-

Alli Webb 40:11 [laughs]

Jay Shetty 40:11 ... it's so much easier to defend yourself, to mask yourself, to shield yourself in a false sense.

Alli Webb 40:19 Yeah.

Jay Shetty 40:20 And what you don't realize is every time you pretend to shield yourself from good feedback, you're just setting yourself up for more downfalls-

Alli Webb 40:27 Yeah

Jay Shetty 40:27 ... and it happens again and again.

Alli Webb 40:29 Yeah.

Jay Shetty 40:29 And the ego is so well-equipped to keep drawing the sword and-

Alli Webb 40:36 Gosh, it's crazy, isn't it?

Jay Shetty 40:37 ... cutting down everything in its way, and it's perfect at it because that's its job.

Alli Webb 40:42 Yeah.

Jay Shetty 40:42 But it's not protection. It's actually your resilience is getting thinner and thinner and thinner-

Alli Webb 40:47 Yeah

Jay Shetty 40:47 ... and you're getting weaker and weaker and weaker. I wanted to ask you, because you're

Jay Shetty 40:50 shifting into that, you know, the, I love how honest you were about the kind of feedback you get from kids. I think people often talk about, "Oh, you know, my kid said I'm not cool anymore. I can't..." Whatever, that kind of stuff, and like that doesn't sting. But hearing this kind of stuff, do you think it's, because you, you definitely have a take on this in your book, like do you think it's possible to be really materially successful and have a happy marriage? Like, are those two things possible?

Alli Webb 41:15 My, my first marriage, which was like 16 years, didn't, didn't work, not because of the business, and I think that it's like I, I joke a lot that like people are like, "You know, it, it must have been hard to work with your husband." I was like, "Yeah, we got divorced," you know? But that's not really-

Jay Shetty 41:30 Mm-hmm

Alli Webb 41:30 ... you know, it's a joke. Um, which of course is like a deflection. But, but more true was that like we probably never should have gotten married in the first place. Like, I, we met when we were 26, and I'm pretty sure I put this in the book that he tried to call the wedding off a month before the wedding. And I was like, "Oh no, we are not doing that." Like, and he had some real good reasons for that. Like- You know, the relationship was really hot and heavy in the beginning. It had faded quite a bit. Like, the intimacy wasn't really there, but we were best friends. And, and I would later learn that, like, my parents had that marriage, which they ended up getting divorced too, and I, I think I definitely emulated my parents' marriage, which is just wild when you read all that about how we do that, 'cause I didn't see it-

Jay Shetty 42:12 Mm-hmm

Alli Webb 42:12 ... at all. But, you know, we, we had kids very quickly, which I really wanted. I was very, like, I'm very [laughs] driven, and I was like, "I want children." And so we had kids a year after we got married, and then, you know, like I said, we started the business Drybar when my kids were three and five, so it was like boom, boom, boom. And Drybar felt like a third baby, and then h- you know, Cam was doing all the creative and I was doing all the other stuff. And so, you know, we're on this path and, and I knew all along, and so did he, even though we didn't want to admit it, that, like, this wasn't, like, this can't be it.

Jay Shetty 42:43 Mm.

Alli Webb 42:43 This can't be, like, what it's supposed to be. But, you know, we didn't want to, like, disrupt our lives, and we d- you know, it's just like it's a lot to get divorced, and I didn't want to be a divorced person, and I liked the facade that I had. These two really cute boys with great hair and this amazing husband, and he was like the, you know, the brainchild of the creative of Drybar, which was amazing. I was like, I loved the way the package looked.

Jay Shetty 43:05 Mm.

Alli Webb 43:05 But I knew it wasn't right. You know, the material success, I didn't, I didn't wanna shatter the whole image, you know? And, and obviously, like, I've, you know, come to realize that, like, you just, you, you have to, and that's the messy truth of it all. And, and then it was, then I, I made the really hard decision to end the marriage, and then my son, who's now 18 and doing really well at Denison, he went into rehab because he started doing drugs, and there's a whole chapter about that.

Jay Shetty 43:30 Mm-hmm.

Alli Webb 43:31 And just my life completely unraveled, you know? And, and, and to your question, it was like I, on this hand, I had all this success and I was, like, doing all this cool stuff. And, like, anybody who didn't know me, I was like, I w- I was a guest on Shark Tank, like, coolest thing ever. I was, like, on Inc. Magazine on the cover. I mean, it's just like all these really cool things were happening, and you look at my life like, "Wow, what a cool life she's got, and, and she..." Then all this success, and I was being, you know, praised, and it was great. But then my life was falling apart, you know? And, and so no, I didn't ha- I wasn't able to, like, hold both. And then I come out of, Grant, after about two years, like, it really worked, all the treatment we put Grant through, and he, he really came out on top and he really did the work, and he's such a... I mean, he ended up in a couple different programs. One of them was an outdoor wilderness program in Utah, which I actually think every human should probably have to go through. We went to visit him once, and he was, like, making fire out of like, you know, two sticks, and he was, like, learned how to... I mean, the thing, it, it was amazing.

Jay Shetty 44:30 Wow.

Alli Webb 44:30 And I was like, "This is really profound." And, and he really came out such a better person on the other side. And it, it also brought me and my ex together, because we had to, like, do group fam- group therapy and family ther- and all the things. And it, it, it was also one of those things that I, I actually thought might kill me, 'cause it was so painful, but it actually was a blessing in disguise. I mean, g- the, the insight and the person that Grant turned into and the other side of that is just remarkable, and it brought me and my ex back together as friends, and, like, we learned how to co-parent because of all that. And even my younger son really be- I mean, it was all, like, such an amazing blessing. At the time, I wouldn't have ever a- [laughs] I mean, asked

Alli Webb 45:10 for that, you know? And so it was like the, the both/and, and the odds, and the dua- duality of what, what I was living. And then I came out of that situation, you know, and rushed back into another relationship that was like, now I'm, now I'm looking for, like, real love, because I didn't feel like I had it the way I wanted it in my first marriage. And then I jump into that, you know? And at that time we were like, you know, it was right before the... I met him, like, five months before the pandemic, and I was already kind of, like, transitioning out of Drybar in a lot of ways, 'cause the company was so big and we had so many people running it now, and what I was doing on a day-to-day basis wasn't really there anymore. And, and now I was like, you know, just looking for love, and, like, and then I found it, and I was like, "Oh, I think this is what it's supposed to be." And, and I was, you know, madly in love with this man, and I wasn't paying attention to anything else, you know, and to any of the red flags that were there that I now really see were there. And so I, again, to your question, which is such a good one, like, I d- I couldn't hold both, you know? It was like I, now I was, like, stepping away from Drybar and now I was stepping into just love, and I lost, completely lost myself on that side. You know, it was like I lost myself in the Drybar world and put my love life, and even my kids a little bit, on hold. And now I was in th- the other side of it, where I'm madly in love, and I lost the, the other side of my own personal purpose.

Jay Shetty 46:32 Mm.

Alli Webb 46:32 You know? And I kind of enmeshed into his world, and I was like, [sighs] oh my God. And now, as you know, we're, we're going through a divorce, and I g- could never have imagined that would happen. But on the, on the other side of it, I'm like, oh yeah, you know? It's like, what I haven't learned yet, which I'm hoping I get now, is that, you know, I have to keep myself intact. Like, what do I love, and what do I wanna be doing, and can I love somebody else while I'm in that place? 'Cause I would throw everything else out the window. It was like when I was building Drybar, it was like only Drybar. When I was, like, falling in love with this new man, it was only him, and I lost myself. And, like, he was building a business, and he was really busy, and he had little kids and whatever, and so I threw myself into his world and, like, kind of forgot about myself. And even now, and it hasn't been that long, but I'm, like, coming back into my own, and I'm like this book, and I have all these projects, and I'm like, oh, I'm getting back to myself. And I would like to have love too, but, like, also. [laughs] You know? And I've n- so to, it's such a good question. I love that you asked it, because I, I haven't been able to find it yet. And I get it now. Now I'm, like, anxious to, like, try it out, you know, and be like, "Can I be in love, madly in love, have the right kind of love with a person and myself and what I'm doing?"

Jay Shetty 47:51 Mm.

Alli Webb 47:52 I haven't been able to figure that out yet.

Jay Shetty 47:54 Mm.

Alli Webb 47:54 And I think, you know, I think a lot of us It falls, one of those things inevitably fall by the... I guess. I don't know. I don't know how other people's lives-

Jay Shetty 48:02 [laughs]

Alli Webb 48:02 ... are like. You know, I, I just... You know, it's funny, I was, we, we were talking to a couple recently, I, and they were s- the, the wife said something like, "You know, our marriage is good enough." And I was like, "Oof."

Jay Shetty 48:12 Mm.

Alli Webb 48:13 You know? And, and she said it in front of her husband, and the husband was like, you know. And I was like, "Ooh, there's definitely some stuff to unpack over there."

Jay Shetty 48:19 Mm-hmm. Mm-hmm.

Alli Webb 48:19 But it is interesting, and it's like w- how do you do that? I mean, I don't know if you guys

Alli Webb 48:25 have figured it out. [laughs]

Jay Shetty 48:26 No, no. I mean, I, I don't... The first thing is, the challenging thing about any relationship, whether it's business or marriage, is that there's two minds, and as we know, our mind is always changing and growing and evolving. Now imagine that times two. Are they changing at the same time in the same way?

Alli Webb 48:45 Yeah.

Jay Shetty 48:45 No. Are they having the same thought at the same time every day? No.

Alli Webb 48:49 [laughs]

Jay Shetty 48:50 Do they have the same dreams and aspirations every day? No. And so we should be more surprised when people get together and stay together-

Alli Webb 48:59 Yeah

Jay Shetty 48:59 ... than when people separate and move apart. It's actually remarkable that anyone could spend their life [laughs] with another person for a long amount of time than it is that people find it hard to stay with people.

Alli Webb 49:09 I mean, that statement in and of itself makes me feel so good because it's like I've had this shame. I've, I didn't want to be divorced once, and now I'm heading into divorce twice, and I really, I think a lot of my sadness and grief when this first happened was because I was, like, embarrassed, and I was like-

Jay Shetty 49:27 Of course. I get that

Alli Webb 49:27 ... I, what? Like this second marriage I'm getting divorced again. Like, holy shit. You know, and just all the like shame-

Jay Shetty 49:34 What's wrong with me? Yeah

Alli Webb 49:35 ... what's wrong with me? But it's such, I, which is why I really love, and I hope people who are listening to that, like feel that too, because, and I, I was telling you before, like I get a lot of people who now reach out to me, and they're like, "I'm really unhappy in my marriage. Should I leave my husband?" I'm like, "I don't know. Don't ask me." But, like, it's a good thing to ask yourself.

Jay Shetty 49:53 Yeah.

Alli Webb 49:53 You know?

Jay Shetty 49:54 Yeah.

Alli Webb 49:54 And, and I do think you're right. It's like we grow and change, and, you know, and in my case, I don't think we were having the right conversations enough-

Jay Shetty 50:01 Mm-hmm. That's, yeah

Alli Webb 50:02 ... of like, and we ignored a lot of things. And granted it was, like, a really weird time, and our relationship got very fast-tracked because of COVID, and, like, we moved in together after five months. I don't know that we would have done that had COVID not thrust this, like, very crazy change into all of our lives.

Jay Shetty 50:18 Mm-hmm.

Alli Webb 50:18 And, you know, I think it all happened the way it was supposed to, but it is a like, yeah, we're always growing and changing, and how do you do that together?

Jay Shetty 50:27 There's two kind of thought experiments that I think can help people with what we're talking about, not as solutions, but as... And it's what you just said. If you're not having the right conversations with yourself, and if you're not having the right conversations with that person-

Alli Webb 50:39 Yeah

Jay Shetty 50:40 ... everything's gonna feel like a surprise.

Alli Webb 50:42 Yeah.

Jay Shetty 50:42 And everything's going to kind of be a random event.

Alli Webb 50:45 Yeah.

Jay Shetty 50:46 And all you can do, you can't make someone stay with you, and you can't make something work. All you can actually do is track whether you're getting closer or moving further apart.

Alli Webb 50:55 Mm-hmm.

Jay Shetty 50:55 That's actually all you can do is track and monitor because, like I said, so much is changing all the time, and so all you can do is track change.

Alli Webb 51:04 Yeah.

Jay Shetty 51:04 You, you can't force a result or a direction.

Alli Webb 51:07 Yeah.

Jay Shetty 51:07 You can only track change and try and move closer together or move apart. And it's what you said, like I think when we think about the word balance, if you think about it, we all have a finite

Jay Shetty 51:15 number of hours. We have a finite number of resources, and we have a finite number of amount of energy. So if you had 100% and you said you've got yourself, you got your partner, you got your work, you got your kids, and then you got your family, and you put 20% into each of those, now you're gonna get a 20% result on each of those. That's a balanced life if we look at it in that way. So if you-

Alli Webb 51:39 That doesn't work. [laughs]

Jay Shetty 51:39 It doesn't work.

Alli Webb 51:40 Yeah.

Jay Shetty 51:40 Or, or it may work for someone, but-

Alli Webb 51:42 Yeah

Jay Shetty 51:42 ... the idea then being, okay, well, now you got like a 80% return on your career, which means 80% of your energy was going into the work part, which means then 5% was going to all the others.

Alli Webb 51:53 Which was me.

Jay Shetty 51:53 So you've got a huge 80%... Uh?

Alli Webb 51:54 Yeah. That was me in the Drybar era, yeah.

Jay Shetty 51:56 Right. And, and, and so when we look at that, we just go, well, how can any human ever achieve-

Alli Webb 52:02 Right

Jay Shetty 52:02 ... perfection? Any human, including me, including everyone. We're so, everyone is so limited that our ability to make everything and everyone happy and successful is mathematically impossible.

Alli Webb 52:16 Yeah, it's so true.

Jay Shetty 52:17 So if it's mathematically impossible, let's stop pretending that we're able to nail every part of every life-

Alli Webb 52:23 Yeah, yeah

Jay Shetty 52:23 ... and let's be honest and say, "I'm focusing on this in this era or this phase or this month or this year. That naturally means I can't focus on these three areas."

Alli Webb 52:35 Yeah, yeah, yeah.

Jay Shetty 52:35 And I think people who stay together or adapt or whatever in a healthy way are people who found a way of saying, "I understand what you're focusing on, and I get that, and I respect it. But guess what? When you're back and you have time, I may be focusing on something else."

Alli Webb 52:51 Yeah, yeah.

Jay Shetty 52:51 And so I think anyone who's navigating their relationship in a healthier way, there's no better or worse, but in a way that we would consider healthier is only because two people are communicating, as you said, enough-

Alli Webb 53:02 Yeah

Jay Shetty 53:02 ... where they're just having conversations.

Alli Webb 53:04 Yeah.

Jay Shetty 53:04 It doesn't mean there's a perfect standard or there's complete intimacy at all times or they're having the best, you know, sex or relationships at all times while everything else-

Alli Webb 53:14 Yeah

Jay Shetty 53:14 ... is going on. Like-

Alli Webb 53:14 It's not possible

Jay Shetty 53:15 ... it's mathematically impossible.

Alli Webb 53:16 Yeah. Yeah.

Jay Shetty 53:17 And-

Alli Webb 53:17 It's, it's so interesting too because I think you don't want, you're avoiding dealing with something that you know is there. It's like you said, you're not always gonna be on the same page. You're not gonna, you're gonna grow differently and, and whatever, and it's like, y- you know, in our case, it was like we weren't... You have to, uh, again, not, I don't mean to be like a broken record, but going back to like your in- that inner voice of like for, you know, for me, I knew there were things that weren't right. And I think now, and, you know, I work with therapists and coach, and I have lots of people, [laughs] you know, 'cause I love getting as, I love getting as much... I mean, now I'm like, "I love the feedback. Give me all the feedback." Like, I really want to hear as many perspectives as I can, and from people that, like, I really trust and admire.

Alli Webb 54:01 And, and, you know, one of the things that I was talking to, uh, my coach about recently was like 'Cause I've, I've been trying to like put a bow on this, to like make myself feel better about it not working, and I've come to realize, like, if... Well, I'm like, if we had had the conversation that we weren't having, you know, the g- right. I mean, you're shaking your head-

Jay Shetty 54:18 [laughs]

Alli Webb 54:18 ... 'cause you know what I'm gonna say. What if we had talked about the thing? Maybe it would've worked, maybe it wouldn't have worked. Like, obviously nobody is, nobody knows, you know? And, and, and he and I had that conversation in, in the aftermath of all of this. Like, had we called out, you know, one of the big things that wasn't working for us early on that we both did not wanna call out because it would've pr- potentially probably meant the, the end of the relationship, and we didn't want that, you know? We were very, like, wrapped up in like the excitement, and the newness, and the lust, and the chemistry, and the passion, and all the things that happen when you're brain... I mean, I'm sure, I'm sure there's some science on like what happens to your brain.

Jay Shetty 54:53 Yeah, it's all in my book, yeah. [laughs]

Alli Webb 54:54 Yeah.

Jay Shetty 54:55 There's loads, yeah.

Alli Webb 54:55 Yeah, but you know, and so we weren't, we didn't have those conversation, and perhaps had we had it, maybe it would've shifted and we could have figured something out that would have changed the trajectory of our relationship, and it maybe it had worked and maybe it wouldn't have. But we didn't even have the conversation, you know? And that, and that's the thing. It's like you have to have those honest conversations in work, in busines- you know, in business, in your personal life, and if you're avoiding them-

Jay Shetty 55:20 Mm

Alli Webb 55:21 ... it's gonna come back around.

Jay Shetty 55:22 Yeah.

Alli Webb 55:22 Like, you can be sure of that, you know?

Jay Shetty 55:24 Yeah. I always say there are like, there are four check-ins that I do with my wife regularly. And so every day I try and ask her a simple one, "What was your highlight of the day?" or, "What was exciting today?" Which is-

Alli Webb 55:36 I love that, yeah

Jay Shetty 55:36 ... an easy one. Anyone can ask that. Very simple. Uh, every week or month I'll ask, you know, "Is there something coming up that I can help you with?" Like, "Is there something you're struggling with or something that's on your mind that I need to be aware of or conscious of?" Every quarter I'll ask, "Is this relationship going in the direction you want, or is it going in the direction I want? If it isn't, what are we both willing-

Alli Webb 56:02 Yeah

Jay Shetty 56:02 ... to do to put it in the right direction?"

Alli Webb 56:04 Yeah.

Jay Shetty 56:05 "Are you willing to do something, and am I?" And then every year a simple one of like, "Well, what's your goal this year?" or, "What, what are you pursuing this year?" And those four questions d- or check-ins don't save a relationship, they do what I was saying earlier, is they help you track-

Alli Webb 56:19 Mm-hmm

Jay Shetty 56:19 ... whether you're on the same page or you're completely on another page, and if you're even aware and conscious. And the reason you have to do that is those should be four check-ins you do with yourself, coming back to your point.

Alli Webb 56:30 Yeah.

Jay Shetty 56:30 Like, checking in with every day and going, "Myself, what's my highlight today?" Checking in with myself every week or every month-

Alli Webb 56:35 So good

Jay Shetty 56:35 ... and going, "Hey, what do I need help with this month? Have I asked for that?" Every quarter, "Is my life going in the direction that I want it to go in?"

Alli Webb 56:42 Mm.

Jay Shetty 56:42 And every year, "What am I pursuing?" Like-

Alli Webb 56:44 I love that

Jay Shetty 56:44 ... if I'm not checking in that with myself and I'm not checking in that with my wife, then how can I know myself and how can I know this human? And I think the assumption that I know someone, like, I've... You know, me and my wife have only been together for 10 years, but it's... All I know is that she's a constantly evolving, growing human.

Alli Webb 57:04 Sure.

Jay Shetty 57:04 Just 'cause she's over 30 doesn't mean that she's fully formed and done.

Alli Webb 57:09 Oh, God no.

Jay Shetty 57:10 And n-

Alli Webb 57:10 Yeah

Jay Shetty 57:10 ... and neither am I. And just like your s- children are growing up, your sons are changing and growing, I think we assume that kids grow and adults stay the same.

Alli Webb 57:17 Yeah, yeah.

Jay Shetty 57:18 And it's like, well, wait a minute, that's so untrue.

Alli Webb 57:20 Yeah.

Jay Shetty 57:21 And, and I think that's what I'm always trying to stop my mind from normalizing, that, "Oh, I know her now. Oh, I know how she's gonna react."

Alli Webb 57:28 Yeah, isn't it s- it's such

Alli Webb 57:30 a like that fixed mindset, and I'm so guilty of that because I'm such a like-

Jay Shetty 57:33 Me too

Alli Webb 57:34 ... I want everything wrapped up in a pretty bow. I'm like, I like things like really neat and clean and tidy, like physically, you know? That I'm like, I just wanna know what's happening, and like, you know, accepting uncertainty and, like, life is completely uncertain. And if you can surrender to that, like... But I, it's just, it's hard, you know?

Jay Shetty 57:54 It's hard, yeah.

Alli Webb 57:54 It is really hard to be like, "Okay, I'm gonna, like, go with the flow." And I read that, uh, who is it? Um, Bruce Lee's daughter wrote a book called Be Like Water.

Jay Shetty 58:03 Oh, yes, yes, yes, yes.

Alli Webb 58:03 You know? And I was like, I l- and I, I, I love when I remember it because I feel like I need like posters all over my house-

Jay Shetty 58:09 [laughs]

Alli Webb 58:09 ... of like all the thing that you just said and all these things, and you're like, oh yeah, y- you can't fight the current. Like, you can't, you know, you can't fight it, and it's like if you can e- surrender to it and like, you know. And that, the fact that we are always changing and growing, and it... And I love that what you said about tracking it. And, and I think there was a phase in our relationship when we were doing more of like check-ins, and we probably had listened to something like this and we're like, "Oh, we should be checking in more," and then eventually we stopped doing that.

Jay Shetty 58:32 It stops, yeah.

Alli Webb 58:33 Yeah, and you're like, oh man, we lost, we lost our way, you know?

Jay Shetty 58:36 Yeah.

Alli Webb 58:36 And it's just so easy to do that. And, a- a- you know, and it, and it really does like straddle the fence on business and personal because I did it all the time in, in the Drybar era when I would like, you know, stop paying attention to what was going on, people around me, and stopped having, you know, all those conversations like I really needed to be having, and just like would get all like sulky and, you know, why, why wouldn't, why wasn't I having those conversation?

Jay Shetty 58:58 Mm.

Alli Webb 58:58 I was, I was causing my own suffering, you know?

Jay Shetty 59:00 Mm-hmm.

Alli Webb 59:00 And it's like we just as humans do that, which I, you know, which I think is like the, the self-awareness piece. It, it's like the things that we use to nurture ourselves, like what we're listening to, what we're watching, what we're reading, you know, if you kinda... Sometimes I'm like, especially in the last few months having gone through, going through my divorce and being so sad, and I'm like ingesting so many books and so many things, and I'm like, "Okay, I've read enough. I'm done. I'm good." But then I'm like, no I'm not.

Jay Shetty 59:30 [laughs]

Alli Webb 59:30 I gotta keep re- I mean, I gotta do at least a couple things a day that like keep me on that spiritual path, you know? And it's like, what's the word I'm looking for? I don't wanna say it's like a job or responsibility.

Jay Shetty 59:40 A habit?

Alli Webb 59:40 Habit, you know?

Jay Shetty 59:40 Yeah, daily practice, daily habit.

Alli Webb 59:41 Daily practice, yeah. It's like it's so important. It's so easy to lose track of that, especially when like something you get really excited or you meet somebody new and you're like, which is exactly what I do. I'm like, "Oh, I'm so happy now." I'm like, "I got it. I'm, I'm good. I don't need to do any of that stuff anymore." Like, you know?

Jay Shetty 59:56 Yeah.

Alli Webb 59:56 And then I remembered.

Jay Shetty 59:57 And, and we're all then, I wanna thank you for being so like honest about it, and so real, and being so messy about it because I think that's all of us, right? Like, that's what we're all looking for, and we're all looking to have a perfect start and a perfect end.

Alli Webb 1:00:11 Yeah.

Jay Shetty 1:00:11 And we're all looking to have like the perfect person and the perfect relationship with ourselves and-

Alli Webb 1:00:15 Yeah

Jay Shetty 1:00:15 ... none of that exists. Talk me through this because I have so many friends who Like you would feel shame and guilt for getting divorced, and so they never will. Or I have a couple of friends that have kind of had the courage to

Jay Shetty 1:00:29 get to the other side, but they now experience the judgment, or they feel the shame that comes from other people's projection of it.

Alli Webb 1:00:37 Yeah.

Jay Shetty 1:00:38 What is the hardest thing about getting divorced? Like, what's the toughest part about it?

Alli Webb 1:00:43 I've been on both sides of it now. You know, where the first divorce after 16 years, you know, feeling like I di- the love that I wanted and intimacy that I wanted wasn't there, so I was like... It's, it was funny 'cause I, when I first left the marriage, I was like, you know, like, r- raring to go, and I was, like, dating really quickly and all of that. And then very quickly, my s- the thing happened with my son, and then I realized that, like, dating wasn't so easy, and now I'm a single mom, and at the time my ex didn't really wanna be talking to me. And so it was like my world spun out of control, and I fell into a bit of a depression. And I remember people telling me that, like, even though you're not in love with your ex-husband anymore, he still held, like, a space and energy that is no longer there.

Jay Shetty 1:01:27 Mm-hmm.

Alli Webb 1:01:27 And it's like a death. And I've, for months and months and months, I refused to believe that. I was like, "It's, it's not a death. Nobody died." Like, I took it very literally, and I was like, "He's, uh, he's alive." Like, I co- would not allow my brain to, like, understand that, you know, until I finally did. And it's like, you know, when you, it's like when the student's ready, the teacher appears mentality. And I was like, I'm sure a lot of people said it to me, but it was like, I m- I was on some show with this guy who wrote a book called Energy Speaks. I don't know if you've ever heard of it.

Jay Shetty 1:01:54 Hmm.

Alli Webb 1:01:54 And he was talking about energy and whatever, and after the show, I pulled him aside and I, like [laughs] very quickly told him what was going on and I was, and how, like, I was, you know, coping with my divorce, and I was in this depression. And he was like, "Listen, your husband, even though you don't love, like, love him like that and wanna be with him, he still held an energy that's gone, and that is a very big hole, like black hole, for you to fill in your life, and it's just gonna, you know, take some time," which isn't rocket science, and I'm sure other people said it to me, but at that moment, I was like, "Oh, my God."

Jay Shetty 1:02:21 Yeah. When it hits, it hits.

Alli Webb 1:02:21 It hits, right. And so that change of life, of, like, your whole life being one way and then it becoming another way, and on a, in my case, like, my son going through rehab and that, like, very hard time. So it was all rolled into, like, just being hard, and I was really sad and, and I, and I was really struggling and, you know. And then the identity stuff started to kinda creep in, too. And so that was, that was hard I think from, like, more of an identity, like a personal identity standpoint was hard and, like, a rebuilding my life after so long. This divorce was l- was quite different. It felt just m- much more like heartbreak. Like, I was heartbroken. Like, just heartbroken, and I'd never experienced that kind of heartbreak. I, I, I recognize now truly that it's, it's for the best, and, and I think f- um, for, for both of us, for all of us, it's for the best. But it just hurt so bad that, like, to experience heartbreak like that where you're like, "Ugh." Someone just put it really well that, like, trauma is the intersection of unexpected and overwhelm.

Jay Shetty 1:03:30 Hmm.

Alli Webb 1:03:30 And I think that's such a simple way to understand trauma.

Jay Shetty 1:03:34 Hmm.

Alli Webb 1:03:34 It's like this thing you didn't see coming really, and then the overwhelm of it and, like, the boom.

Jay Shetty 1:03:39 Hmm.

Alli Webb 1:03:39 You know? And that's kind of what it was for me. I was like, "I may never recover from this." Like, that's how, like, devastating it was. I mean, I think you know 'cause I think I talked to you right around the time it was happening and, and I was so sad. [laughs]

Jay Shetty 1:03:52 Hmm.

Alli Webb 1:03:52 I was like, "I'm never gonna be okay," you know? And I'm, you know, it's, a- and I'm okay.

Jay Shetty 1:03:57 Hmm.

Alli Webb 1:03:58 You know? And I've, and I've... When the fog starts to clear, 'cause it's like it's real muddy when you're in it, and you know, I mean, quite literally when you're in fog you can't see, and it's the perfect analo- analogy to me is, like, I was in so much fog around it, and, like, my ego was all, like, bent out of shape and I was, you know, and I was worried, like, my kids were gonna be mad at me, and I was worried what the world was gonna think and all this stuff. And then I was like, now a- as the clouds and the fog started to clear, I'm like, "Oh, no, this was not ultimately the right thing," you know? And maybe in some universe, like had we had these conversations and we'd done this thing and da da da da, maybe it would've been right, but it just wasn't, and this was the way it all went down.

Jay Shetty 1:04:41 Hmm.

Alli Webb 1:04:41 And I realized that, like, oh, this, there's a lot of lessons here, and there's a lot of medicine, and I've learned so much, and I'm so grateful for it now. You know, like, I'm still coming out of the anger of it a little bit, but I am ultimately just really grateful for

Alli Webb 1:04:58 all the lessons that I've learned. And, and I think I said this earlier, I like who I am on almost every level now more than I did then. I had a, it was a lot of tough lessons I had to learn, and I was looking at myself in this lens that I had not looked at myself through of, like, why he made that decision and why he didn't want the marriage anymore, which is just, uh, I mean, you can ima- I mean, you put yourself in th- those, in that for a second. If your wife was like, "I want a divorce right now," you-

Jay Shetty 1:05:28 Mm-hmm

Alli Webb 1:05:29 ... y- you would just be like, it's devastating-

Jay Shetty 1:05:31 Mm-hmm

Alli Webb 1:05:32 ... if you're, you know, in love [laughs] with somebody.

Jay Shetty 1:05:34 Of course, yeah.

Alli Webb 1:05:34 But then when sh- and so I was like try, I've tried to now put myself in the very painful place of, like, why?

Jay Shetty 1:05:40 Hmm.

Alli Webb 1:05:40 Why didn't he want to be with me? And, and sure, like, I, not, not to go down the rabbit hole of, like, I'm a terrible person and I'm not worthy. It's not that. It's more of, like, let me see what, what the things were that I didn't like about myself that I can now see through his eyes.

Jay Shetty 1:05:57 Hmm.

Alli Webb 1:05:57 And this is not a conversation with him. This is a conversation with me and how I perceived a lot of things and the way I acted and the way I showed up a lot that I don't like.

Jay Shetty 1:06:06 Hmm.

Alli Webb 1:06:06 You know? That I'm like, oh, I don't ever wanna show up like that again.

Jay Shetty 1:06:10 Hmm.

Alli Webb 1:06:10 And what a gift and what a lesson to, like, be this better version of myself now.

Jay Shetty 1:06:15 Hmm.

Alli Webb 1:06:16 So to answer your question, those were, like, the hardest things of it, but it is- I'm literally living proof that you can, you will get through it, and everybody kept saying that to me, and I would grasp onto that. Like, when people would say, "It's- you're gonna be okay. It's gon- I promise you're gonna be okay," and I would, like, hold onto that. Like-

Jay Shetty 1:06:32 Mm

Alli Webb 1:06:32 ... "Thank you." I needed other people to say it to me 'cause I couldn't find it in myself. I could- I didn't believe it, but if enough people said it to me, like, "I promise you-"

Jay Shetty 1:06:42 Mm.

Alli Webb 1:06:42 And so many people said that to me, "I promise you you're gonna be okay."

Jay Shetty 1:06:45 Yeah.

Alli Webb 1:06:45 It's, you know, it's, it's a beautiful thing-

Jay Shetty 1:06:47 Mm

Alli Webb 1:06:47 ... to have, like, a community of people around you that will tell you that and that you... And I'm like, "Are you, are you sure? [laughs] Like, do you know?"

Jay Shetty 1:06:53 Mm.

Alli Webb 1:06:53 And they're like, "I know." You know? And it's lofty, but it's true.

Jay Shetty 1:06:57 Yeah.

Alli Webb 1:06:57 You know? So.

Jay Shetty 1:06:58 Well, you know what I find so hope-giving about your choices is that you turn towards people, things, ideas that would help and support you.

Alli Webb 1:07:08 Oh, yeah.

Jay Shetty 1:07:08 And I think that that's the hard part. Like, it's so easy-

Alli Webb 1:07:12 Yeah

Jay Shetty 1:07:12 ... and it's natural and should not be judged at all, but it's so easy for you to go off the rails and go in a different direction.

Alli Webb 1:07:19 Yeah.

Jay Shetty 1:07:20 And the fact that you had the inner wisdom and the intuition to say, "Actually, I'm gonna turn towards advice, and therapy, and coaching, and insight, and learning, and reading-

Alli Webb 1:07:29 Yeah

Jay Shetty 1:07:29 ... and hearing this message from a supportive community," like-

Alli Webb 1:07:32 Yeah

Jay Shetty 1:07:32 ...

Jay Shetty 1:07:33 that's what I want people to take away, is I want you to hear that, that that's the choice we have to try and make. And something you said, this concept you were talking about, the intersection, something sparked for me as you said that, and I was gonna complete your sentence, but I didn't want to because-

Alli Webb 1:07:46 [laughs] You knew what I, you knew what-

Jay Shetty 1:07:47 No, I didn't know what you were gonna say-

Alli Webb 1:07:48 [laughs]

Jay Shetty 1:07:48 ... and that's why I waited, because I didn't know what you'd read or heard. But I was thinking about it, that when I heard the word, when you think about trauma or even, like, a trigger that eventually leads to trauma, it's actually the intersection between an unexpected event-

Alli Webb 1:08:05 Mm-hmm

Jay Shetty 1:08:05 ... but a familiar feeling.

Alli Webb 1:08:07 Mm.

Jay Shetty 1:08:08 And so there's what you were talking about earlier as well, like how you repeat your parents' marriage.

Alli Webb 1:08:12 Mm-hmm.

Jay Shetty 1:08:13 Like, the idea that it's an unexpected, because you didn't think you would ever do that-

Alli Webb 1:08:16 Right

Jay Shetty 1:08:16 ... but then it's a really familiar feeling and you're like-

Alli Webb 1:08:18 Yeah

Jay Shetty 1:08:18 ... "Oh, I s- I feel that."

Alli Webb 1:08:20 Yeah.

Jay Shetty 1:08:20 Or, like, I'm going through a divorce, someone's asked me for a divorce, it's an unexpected event, but it's a familiar feeling of I don't like myself already, and this is a reminder of something I know deep down.

Alli Webb 1:08:29 Yeah. Oof.

Jay Shetty 1:08:30 And it's that familiarity with the unexpectedness that completely-

Alli Webb 1:08:34 Yeah

Jay Shetty 1:08:34 ... converges to create such disharmony and misalignment internally.

Alli Webb 1:08:38 Ugh. Yeah, it really does.

Jay Shetty 1:08:40 It's so painful.

Alli Webb 1:08:40 You know, because you're like... And it's amazing when you have, like, a great support system around you telling you that, no, you're a good person. It's like, y- you know, m- my best friend, she would tell me, like, we would, "Yes-

Jay Shetty 1:08:52 Mm

Alli Webb 1:08:52 ... s- you have culpability here."

Jay Shetty 1:08:54 Mm.

Alli Webb 1:08:54 You know? And we would... She knew it, my relationship, very well, 'cause she's my best friend. "But no, you're not a bad person."

Jay Shetty 1:09:01 Mm.

Alli Webb 1:09:01 You know, there are things that you had to learn about yourself, and there are things that, you know, you want to change, but there, it doesn't mean you're a bad person. And it's hard to live in that duality of, like, beating yourself up and the shame that we can put on ourselves because this marriage failed. And I'm like, 'cause i- in the beginning, I was like, "This marriage failed, I'm a ter- you know, I'm a terrible person. No one's ever gonna love me again. Any, any man I'm gonna date is gonna be like, 'Oh, you were married twice. Sorry. See ya.'"

Jay Shetty 1:09:28 Mm.

Alli Webb 1:09:28 You know, which isn't true, you know? But it's, it, it is the things that, you know, we do, which, you know, I, I have spent a lot of time, a lot of the stuff that I read is on, like, you know, mindset, and the brain, and how powerful the brain is, and how we can change our thoughts, and h- and that stuff's all so fascinating to me. You know? Like, that you can, we have control. I didn't believe that until now, like, until [laughs] very recently. I was like, "It is what it is." You know? But now I'm like, oh, we can change our thoughts, and we can, you know, decide. And, and it's like, there's a, to me, there's, like, a, well, you still gotta grieve the thing.

Jay Shetty 1:10:05 Yeah.

Alli Webb 1:10:06 But I can also... 'Cause I was like, you know, I was, I started s- listening to Joe Dispenza.

Jay Shetty 1:10:10 Yeah.

Alli Webb 1:10:10 You know him?

Jay Shetty 1:10:10 Of course. Yeah. He's been on the show four times or something like that.

Alli Webb 1:10:12 I... Oh, right. I think I might've discovered him-

Jay Shetty 1:10:14 Yeah, yeah, yeah

Alli Webb 1:10:14 ... through your sh- your show, actually. I love that guy.

Jay Shetty 1:10:17 Mm-hmm.

Alli Webb 1:10:17 And I love what he says. You know, and I... But I, I had the people be like, "Yeah, his stuff is great, but, like, you still have to grieve the stuff."

Jay Shetty 1:10:24 Mm-hmm.

Alli Webb 1:10:24 'Cause I was like, "I'm just gonna believe this," you know? And it's like, but there's still the grief over there.

Jay Shetty 1:10:29 Yeah.

Alli Webb 1:10:29 And I think that's another challenging part of, like, anything. Like, dying is, like, the grief your body physically needs to go through if you change your mindset too fast. And like, y- you know, so it's kind of an interesting, I think it's a little of both.

Jay Shetty 1:10:43 Yeah.

Alli Webb 1:10:43 I'm really fascinated by, by the whole thing the brain [laughs] can do.

Jay Shetty 1:10:47 Yeah.

Alli Webb 1:10:47 You know?

Jay Shetty 1:10:47 Yeah, absolutely. When you look at grief and loss, it's like there's the grief and loss of that person-

Alli Webb 1:10:54 Right

Jay Shetty 1:10:54 ... and then there's the grief and loss of the person you were with that person.

Alli Webb 1:10:58 Yes.

Jay Shetty 1:10:59 And they're two different things, because you were a particular type of yourself.

Alli Webb 1:11:04 Yeah.

Jay Shetty 1:11:04 There was a part of yourself that was connected to that individual, and now not only is that person gone, that part that you'd created with them-

Alli Webb 1:11:12 Yeah

Jay Shetty 1:11:12 ... has also gone.

Alli Webb 1:11:13 Yeah.

Jay Shetty 1:11:14 And is no longer existent.

Alli Webb 1:11:15 Yeah.

Jay Shetty 1:11:15 And so there's so... Identity-

Alli Webb 1:11:18 So layered

Jay Shetty 1:11:19 ... is such a fascinating-

Alli Webb 1:11:21 Yeah

Jay Shetty 1:11:21 ... subject in and of itself, and it's like you weren't complete in the first place either. And so there's, there's just so many layers to it that are so challenging, and all of these things that you're talking about, whether it's your work, your marriage, your kids, they put a spotlight onto-

Alli Webb 1:11:36 Yeah

Jay Shetty 1:11:36 ... all of this-

Alli Webb 1:11:37 Yeah

Jay Shetty 1:11:37 ... and all the gaps. What would you say was the most important

Jay Shetty 1:11:41 lesson you took away from your first relationship and then your second relationship? I- because you've just, you were talking so much about it was all about lessons, I'd tell them. What would you say was the first one that you took away from the first, and then from the second, what have you taken away? What's been the big-

Alli Webb 1:11:54 Um

Jay Shetty 1:11:54 ... lesson that stayed with you?

Alli Webb 1:11:56 You know, I think for me, and it's, it's pretty vulnerable to say, but, like, it was like, oh, I, I think I rushed into both of my marriages because I didn't want to be alone, and I wanted to be in a relationship, and I just wanted to be in a relationship.

Jay Shetty 1:12:06 Mm.

Alli Webb 1:12:07 They were right enough. I don't think anything's ever perfect, of course, but you know, I realized there were things in both of my marriages that weren't, like, exactly what I wanted them to be. And, and again, it's a hard thing to say 'cause it's like nothing's ever exactly what you want it to be.

Jay Shetty 1:12:22 Mm-hmm.

Alli Webb 1:12:22 With some of the things that were happening with us, I think I actually was pretty open and honest about them, but we, what we weren't open and honest about was, like, what I actually needed it to be-

Jay Shetty 1:12:30 Mm

Alli Webb 1:12:30 ... and if it wasn't gonna be that, like, then it probably wasn't gonna work.

Jay Shetty 1:12:34 Mm.

Alli Webb 1:12:34 And we both needed to, like, come to terms with that. So you know, I think the lesson is, like- ... really level setting what you need and what that other person needs, not just what you need.

Jay Shetty 1:12:44 Mm-hmm.

Alli Webb 1:12:44 Like, sometimes you have to be the one that's willing to say, like, "I don't think this is gonna work because blah, blah, blah." But, like, to me, I don't think I've ever been strong enough to be like, "I'm completely in love with you, but I don't think this relationship is gonna work."

Jay Shetty 1:12:59 Mm.

Alli Webb 1:12:59 Like, who can do that?

Jay Shetty 1:13:00 Mm-hmm.

Alli Webb 1:13:01 That's so hard. I'm sure people do.

Jay Shetty 1:13:02 Mm-hmm.

Alli Webb 1:13:03 You know, it's like [laughs] I think about it, like, so silly. I think just 'cause I've watched so many movies in my life, like Legends of the Fall.

Jay Shetty 1:13:09 Oh, me too.

Alli Webb 1:13:09 Did you ever see Legends of the Fall?

Jay Shetty 1:13:10 [laughs]

Alli Webb 1:13:10 You know, I mean, it's like it just, it just ha- it came to me recently. I was like, you know you watch one of those movies, and, like, you want the, like, the love story to work-

Jay Shetty 1:13:17 Totally

Alli Webb 1:13:18 ... and then it doesn't, and you're like ... And you, you walk out of that movie f- like so sad, and you're like, "I just wanted them to be together."

Jay Shetty 1:13:25 Yeah [laughs]

Alli Webb 1:13:25 You know? And that's how I feel-

Jay Shetty 1:13:27 Yeah

Alli Webb 1:13:27 ... in this second marriage. Like, I really wanted it to work.

Jay Shetty 1:13:30 Mm-hmm.

Alli Webb 1:13:30 And as the viewer watching the movie, you're like, "I know it wasn't right, and it wasn't supposed to be," and it's like, you know. And that's how I felt like Legends of the Fall.

Jay Shetty 1:13:37 [laughs]

Alli Webb 1:13:37 You know, where it's like Brad Pitt-

Jay Shetty 1:13:38 I feel like that in La La Land.

Alli Webb 1:13:40 Oh, yes.

Jay Shetty 1:13:40 Yeah, yeah, yeah, yeah.

Alli Webb 1:13:41 Oh my God, that's even better. La La Land, like, why weren't they together at the end?

Jay Shetty 1:13:44 Yeah, yeah, yeah, yeah.

Alli Webb 1:13:44 You know, and you're, and, and you watch that movie, and I've watched it a couple times, such a great movie, and you're like, you know, she marries another guy, and you're ... Sorry for anybody who hasn't watched La La Land.

Jay Shetty 1:13:53 [laughs]

Alli Webb 1:13:53 It's been a while though.

Jay Shetty 1:13:54 Yeah [laughs]

Alli Webb 1:13:54 Yeah, and it's, that is h- really how it's, like, landed for me in this, like, sometimes, like, what we want to work just doesn't, you know? And you have to just learn to accept it, and I think that's, that's been the big lesson for me, is like-

Jay Shetty 1:14:07 Mm-hmm

Alli Webb 1:14:07 ... you know, a lot of people, and people close to me know a- and have said to me in the aftermath of this, like, "You've, you've had things work out for you pretty well most of your life," you know, and I have. And I'm really blessed and lucky in that way. And this has been, like, one of the first things that, like, didn't work out the way I wanted it to, and I couldn't-

Jay Shetty 1:14:25 Mm

Alli Webb 1:14:25 ... control it.

Jay Shetty 1:14:26 Mm-hmm.

Alli Webb 1:14:26 You know, no matter what I did, I couldn't change the outcome, and, like, oof, that's rough.

Jay Shetty 1:14:32 Mm-hmm.

Alli Webb 1:14:32 You know, and I'm sh- and I know a lot of people have dealt with that on a much bigger and l- harder scale than me, and, and so that was a real lesson of, like, sur- surrender, of like you just don't get control, you know?

Jay Shetty 1:14:42 Mm-hmm.

Alli Webb 1:14:43 I look at my first marriage and think that, like, we were married for so long, and for so long I didn't have that, like, electric chemistry love that I wanted, but yet I had these two amazing kids, and I built this great business. And so, like, that was enough for me.

Jay Shetty 1:14:55 Mm-hmm.

Alli Webb 1:14:56 You know, in this stage of my life, I feel like I actually want more of it all now. You know, where I was always like, "Well, I have this. I don't have that, but I have this," and now I'm like, "I wanna do something that I really love and feel passionate about for myself, and I wanna have a great love too." And now I'm trying to find both. [laughs]

Jay Shetty 1:15:15 Yeah. Yeah, absolutely. And, and you know, Alli, like what I really appreciate about you, honestly, this conversation, the book, is, like, you're the real deal. Like, a lot of people will say they wanna share their messy truth, and they want to tell what's really going on, and I think it's almost like we're still trying to do it because it sounds and looks vulnerable, but it isn't.

Alli Webb 1:15:39 Yeah.

Jay Shetty 1:15:39 And that's not, you know, and I think that hearing from you today, all I've heard is the messy truth.

Alli Webb 1:15:45 [laughs]

Jay Shetty 1:15:46 And, and it's not been ... I can't think of anyone who's listening to this that isn't gonna feel comforted, supported, held, and feel connected to your journey in some way.

Alli Webb 1:15:58 Mm.

Jay Shetty 1:15:58 I don't think it's mathematically, spiritually, emotionally possible for someone to master every area of their life-

Alli Webb 1:16:05 Yeah

Jay Shetty 1:16:06 ... perfectly at all times.

Alli Webb 1:16:08 [laughs]

Jay Shetty 1:16:08 I just, I just wanna throw-

Alli Webb 1:16:09 Yeah

Jay Shetty 1:16:09 ... that out there because-

Alli Webb 1:16:10 Yeah

Jay Shetty 1:16:10 ... we still keep putting it up when we th- say things like power couple, when we say things like, "Oh my God, the perfect match," when we say things like, you know. We don't realize how many ideas we put into the world-

Alli Webb 1:16:22 Yeah

Jay Shetty 1:16:23 ... that, "Oh my God, did you know they're both billionaires now, and they're both..." And it's like you have no idea just how many ideas you're, we plant seeds in people's minds that these headlines exist in reality.

Alli Webb 1:16:36 Yeah.

Jay Shetty 1:16:36 And if you're someone who knows anyone, you know that the headline is so untrue-

Alli Webb 1:16:41 Yeah

Jay Shetty 1:16:41 ... about everyone, and that doesn't mean people can't have healthy relationships. It doesn't mean people can't have happy relationships, but do people have perfect relationships? No. And do people have perfect businesses? No. And do people have perfect anything? No. And so-

Alli Webb 1:16:54 Yeah

Jay Shetty 1:16:54 ... it's, it's a mindset that we've all been so conditioned to believe. It's why we feel sad when Ryan Gosling doesn't end up with Emma Stone.

Alli Webb 1:17:01 [laughs]

Jay Shetty 1:17:02 Like, it's, there's a, it's because we've been taught that that is the perfect ending.

Alli Webb 1:17:05 Yeah, the Disney, yeah.

Jay Shetty 1:17:06 That is the perfect ending, and there's so much wiring that we have to uncross, and that's the work you're doing. And I think that that, that's what I'm so appreciative of watching and observing you on this journey, is you're so courageously and bravely doing the hard unlearning.

Alli Webb 1:17:28 Yeah. There's, uh, it reminds me of, you know, I'm sure you're familiar with Michael Singer and, you know-

Jay Shetty 1:17:32 Of course

Alli Webb 1:17:32 ... Untiling the-

Jay Shetty 1:17:32 Untiling the Soul, yeah.

Alli Webb 1:17:33 Yeah. There have been a few books that I'm like I've listened to on repeat.

Jay Shetty 1:17:36 Mm-hmm, mm-hmm.

Alli Webb 1:17:36 You're just like, I just gotta keep listening to this to get, like-

Jay Shetty 1:17:39 Mm-hmm

Alli Webb 1:17:39 ... through the day. [laughs] It didn't sink into me until I started thinking about the whole movie thing, which was like he was like, you know, if you're in heartbreak or you're in sadness, he's like he equated it to, again, it, it only connected for me recently, not when he said it, but this, like, idea of when you watch a movie and you get sad about something, it's like you al- and but then you tell all your friends about it and you talk about it, it's like you almost like the sadness and the emotion-

Jay Shetty 1:18:04 Mm-hmm

Alli Webb 1:18:04 ... that it brings in. But it's just like when it happens to you, you don't like it quite as much.

Jay Shetty 1:18:09 Mm, mm.

Alli Webb 1:18:10 But if you can put yourself in that, like, it's just your movie.

Jay Shetty 1:18:13 Mm-hmm.

Alli Webb 1:18:13 You know? And you're just watching it, and you're not-

Jay Shetty 1:18:15 Mm

Alli Webb 1:18:15 ... gonna feel sad forever.

Jay Shetty 1:18:17 Mm-hmm.

Alli Webb 1:18:17 You know, it's such a good perspective of it.

Jay Shetty 1:18:19 Yeah.

Alli Webb 1:18:19 And it's funny how it's, like, come full circle for me of like, oh, this is my sad movie, and it's sad, and then it's go- and but it's also okay, you know?

Jay Shetty 1:18:29 Mm-hmm. Yeah. And it's almost like just like a movie when you walk in and watch one part of a movie, you don't get the full picture.

Alli Webb 1:18:36 Yeah, yeah.

Jay Shetty 1:18:36 So you walked in on a sad scene-

Alli Webb 1:18:38 Yeah

Jay Shetty 1:18:38 ... or you walked in on a scene where one guy's chasing another guy, and you think the guy being chased is the bad guy, but actually it's the good guy.

Alli Webb 1:18:45 Ah.

Jay Shetty 1:18:45 Like, there's just so much.

Alli Webb 1:18:47 Right.

Jay Shetty 1:18:47 We, we look at people's lives in snapshots.

Alli Webb 1:18:49 Like a, yeah, yeah.

Jay Shetty 1:18:50 And-

Alli Webb 1:18:50 It's fascinating

Jay Shetty 1:18:51 ... you can't tell ... who's what and who's who and who's the villain and who's the hero.

Alli Webb 1:18:56 Yeah.

Jay Shetty 1:18:56 And, uh, yeah, becoming an observer in our own life is so hard to do,

Jay Shetty 1:19:00 but-

Alli Webb 1:19:00 Yeah

Jay Shetty 1:19:00 ... Alli, we end every episode of On Purpose with a final five.

Alli Webb 1:19:04 Okay.

Jay Shetty 1:19:04 And so these are your final five. They have to be answered in one word to one sentence maximum.

Alli Webb 1:19:09 Oh, I love stuff like this.

Jay Shetty 1:19:10 And I will ask you to go off if I feel like it. So-

Alli Webb 1:19:12 [laughs]

Jay Shetty 1:19:13 [laughs] Question number one, uh, what is the best entrepreneurship advice you've ever heard or received?

Alli Webb 1:19:20 Progress over perfection. You know, I think that we as entrepreneurs, we get stuck in this, and I see it all the time, of like, "Oh, I can't start this because I don't have this, and I don't know this, and I don't have enough money, and I don't have this." But, like, just start and, you know, you'll... It's n- it's never gonna... I mean, we've just been just talking about this. It's never gonna be perfect, but just, like, just go. It'll, you'll, you'll get it. You'll figure it out as you go.

Jay Shetty 1:19:40 And I think that's what people don't realize, that I fully agree with you, and that's where the mistakes are made, but the problem is there's no other path.

Alli Webb 1:19:46 Yeah.

Jay Shetty 1:19:47 So if you just waited, waited, waited-

Alli Webb 1:19:48 You never get anywhere

Jay Shetty 1:19:49 ... you never make any mistakes-

Alli Webb 1:19:50 No

Jay Shetty 1:19:50 ... but you never get anywhere.

Alli Webb 1:19:51 Yeah.

Jay Shetty 1:19:51 And if you start and you stumble, you will make loads of mistakes, and that's what kind of exposes you, and there's all these flaws and everything, but you got somewhere.

Alli Webb 1:19:58 Yeah.

Jay Shetty 1:19:58 And it's that w- awkward messiness that-

Alli Webb 1:20:00 Yeah, and it's like you, y- it- it's hard in the moment. Like, anything that's, like, worth anything is hard in the moment, you know? It's like the mistakes are hard, it sucks, but you learn from them, and it's very cliche, but it is so true. You know, f- and you're right, if you don't get into a relationship... Like, you know, I have a friend who, like, is like i- hasn't gotten into a relationship 'cause she's kind of scared. I'm like, "You just, just, just go."

Jay Shetty 1:20:22 Yeah.

Alli Webb 1:20:22 And even if it's not a good one, just go and, like, learn from it, you know?

Jay Shetty 1:20:25 Yeah.

Alli Webb 1:20:25 Go on that date, you know?

Jay Shetty 1:20:27 [laughs] Absolutely. Second question, what is the worst entrepreneurship advice you've ever heard or received?

Alli Webb 1:20:33 It's interesting that w- earlier you pointed out how I, you know, I, I took the advice from the women that I was serving in my mobile business. What, what I didn't do was take the advice from, like, a bunch of men who didn't understand this business, you know?

Jay Shetty 1:20:47 Mm-hmm.

Alli Webb 1:20:47 And I'm not a big fan of, like, decision by committee.

Jay Shetty 1:20:50 Yeah, yeah, yeah.

Alli Webb 1:20:50 Not, and not to say that I don't want, like, trusted people around me to help me make decisions.

Jay Shetty 1:20:53 No, no, I get what you're saying.

Alli Webb 1:20:54 Yeah, it's like I don't, I don't believe in this, like, "Let me just ask a million people and then figure it out." Like, I, I love using, you know, Steve Jobs, obviously a brilliant, brilliant man. It's like nobody knew that we didn't know we needed iPhones, and, and maybe we don't need iPhones, but, like-

Jay Shetty 1:21:10 Mm-hmm

Alli Webb 1:21:10 ... we sure love them.

Jay Shetty 1:21:11 Mm-hmm.

Alli Webb 1:21:11 But, but we didn't know we needed them.

Jay Shetty 1:21:13 No, I know what you're saying.

Alli Webb 1:21:13 Yeah, like, even the, the... I feel like I saw a preview of, uh, the new movie coming out about the founders of BlackBerrys.

Jay Shetty 1:21:19 Oh, I wonder what's that? I didn't know that.

Alli Webb 1:21:21 Yeah.

Jay Shetty 1:21:21 Oh, cool. Okay.

Alli Webb 1:21:21 I, I know I saw it. I'm pretty sure I didn't dream it. And it, because, you know, the story, the story is really fascinating.

Jay Shetty 1:21:26 Mm-hmm.

Alli Webb 1:21:26 It's like, uh, like, I think the premise of it is that the founder of BlackBerry, this is so apropos to what we're talking about, it's like the f- people in his company came to him and said, like, "I think I, there's something coming out. We need to change from the, what we're doing and, like, go into this smartphone world." And, and he was like, "No, that's not gonna work. That's not gonna happen," and everybody in com- the company was like, "No, this is gonna happen."

Jay Shetty 1:21:48 Mm-hmm.

Alli Webb 1:21:48 And obviously we know what happened-

Jay Shetty 1:21:49 Yeah

Alli Webb 1:21:49 ... and BlackBerry went away, which by the way, my brother, like, had the last BlackBerry standing as he loved the little buttons. And-

Jay Shetty 1:21:55 Yeah. [laughs]

Alli Webb 1:21:56 A lot of people did, and the BlackBerry-

Jay Shetty 1:21:57 Yeah

Alli Webb 1:21:57 ... was, like, revolutionary.

Jay Shetty 1:21:58 I had one, yeah, yeah, yeah.

Alli Webb 1:21:59 Of course. They, they were amazing. We, they were the first thing, you know? But this, this, the story, as, as I believe it's set up in the preview, is like that company could have taken the p- similar path as, as iPhone did, but they didn't. And-

Jay Shetty 1:22:11 Mm-hmm

Alli Webb 1:22:11 ... and again, I'm loosely remembering the story, but I just think it's really fascinating that y- you got, sometimes you gotta just, like, try something and see if it's gonna work and see if people are gonna want it, and I, and I'm, I've always been a massive fan of Steve Jobs, and I'm, like so many others, and the iPhone, and, you know, it's like, it's just so cool, like-

Jay Shetty 1:22:28 Yeah

Alli Webb 1:22:28 ... this, you know, like, he invented this thing that became this thing, you know? And, and so y- you know, I feel like don't ever get too caught up in what people think of your idea.

Jay Shetty 1:22:37 Yeah. Yeah, there's, you remind me of a famous quote from Henry Ford. He said, "If I would've asked people what they wanted, they would have said faster horses."

Alli Webb 1:22:44 Yeah.

Jay Shetty 1:22:45 And, and, like, that was the mindset.

Alli Webb 1:22:46 Oh, my God. I'm gonna steal that.

Jay Shetty 1:22:46 Yeah, yeah, yeah.

Alli Webb 1:22:47 It, I mean, that's great.

Jay Shetty 1:22:48 Yeah.

Alli Webb 1:22:48 Yeah, 'cause that is what it is. It's like-

Jay Shetty 1:22:49 Yeah, if you do that committee and that focus group, it's-

Alli Webb 1:22:51 Yeah

Jay Shetty 1:22:52 ... you can't necessarily think beyond-

Alli Webb 1:22:53 Yeah

Jay Shetty 1:22:54 ... what you see.

Alli Webb 1:22:55 Yeah.

Jay Shetty 1:22:55 Um-

Alli Webb 1:22:55 And, and, you know, and so many ideas don't make it and so many ideas fail, and lots of them don't work, but, like, might as w- somebody's gotta try or we wouldn't get anywhere, you know?

Jay Shetty 1:23:03 Absolutely. All right, question number three, what is one habit, mindset, or practice that you believe every entrepreneur should try to develop?

Alli Webb 1:23:12 Some sort of awareness practice.

Jay Shetty 1:23:14 Mm.

Alli Webb 1:23:14 You know, whether it's through entrepreneurship... Like, I, I listen to your meditations all the time, yeah, and-

Jay Shetty 1:23:21 Thank you

Alli Webb 1:23:21 ... I've gotten into this place of every morning before I, not, not always, but most of the time, I c- before I, like, get on my phone and check all my stuff and do all the things, like, I tr- I, like, keep my phone on sleep mode and get into a meditation while, like, I'm still in bed. And I think that, like, quiet time in the morning, and then I'll usually, like, write for a little while. Not even, like, a page, you know-

Jay Shetty 1:23:41 Mm-hmm

Alli Webb 1:23:41 ... just something to get, like, like, the cobwebs out almost, you know? And I think it's, I think it's just important as a human, but y- you know, as a, as an entrepreneur just to, like, [exhales] you know-

Jay Shetty 1:23:52 Mm-hmm

Alli Webb 1:23:52 ... like, level set yourself. And I, and I really try to do it before I go to bed at night, too. You know, I always go to sleep now, whether I'm really tired or not, to, like, some sort of, like, sleep meditation.

Jay Shetty 1:24:03 Mm-hmm.

Alli Webb 1:24:04 I think I only catch, like, the first, like, five or 10 minutes of it.

Jay Shetty 1:24:06 That's, that means it's good. [laughs]

Alli Webb 1:24:07 Yeah, but I, I really love that, and I, I never had a practice like that before. And I'll tell you, I never had a practice like that until my, my separation happened, and I was like, "Huh, you know, I'm by myself." We used to, like, watch TV and then fall asleep, and, like, again, that was a, that's, like, one of those things that I'm like, "I'm so glad." I, I almost never turn my TV on in my bedroom anymore. I am, and I know that probably a lot of people don't believe even in that, and I'm actually about to move, and I'm like, "Do I want to put-"Put a TV in my bedroom because I feel like I almost never watch TV in my room anymore 'cause by the time I get in bed, I usually wanna read, I wanna do my meditation, I wanna write, and by the time I do all that, I'm so tired and I also, I don't know, I pick up so much random information, but I, I heard somewhere and somebody said it, maybe it was you, who knows, 'cause I watch so much of your stuff [laughs] , but like by 10:30 you should be off screens. I think it was maybe Huberman who said it.

Jay Shetty 1:24:57 Mm-hmm.

Alli Webb 1:24:57 And 'cause from 10, 10:30 to 4, he's like y- your brain starts to go into to depression. Again, I don't remember the science.

Jay Shetty 1:25:04 [laughs]

Alli Webb 1:25:04 But I was like, whether it's true or not, I like this. Like, I wanna, I wanna be off my devices by 10:30, and so that's really my goal now, which I used to stay up and watch TV till, like, midnight. You know, I'm so glad I don't do that anymore. I feel so much better. I mean, I was also on a mission to, like, I gotta feel better here, like, I gotta get out of this depression and this sadness, so I better do everything I can do, and now I'm like, "Oh, I'm not really that sad anymore. I'm not really, I'm not sad anymore, but I think I should still keep doing these things," you know?

Jay Shetty 1:25:30 Mm-hmm. Mm-hmm.

Alli Webb 1:25:30 And so that, I think, is important to have that kind of practice, and I really have come to love it.

Jay Shetty 1:25:34 That's beautiful. I love it. All right, question four and five. Uh, question number four: how would you define your current purpose?

Alli Webb 1:25:45 That's very clear to me right now, is, like, giving back, being of service. Like, I feel really called to, like, help others in lots of ways. Like, I'm, I'm starting this, um, volunteer program at CHLA, which I feel really called to. I'm looking at doing some stuff with animals, and I do a lot of mentoring for other entrepreneurs. And, you know, in some things there's, like, you know, m- money involved and I'm speaking at things and I, you know, and I think that that's okay and good.

Jay Shetty 1:26:10 Absolutely, yeah.

Alli Webb 1:26:10 And then there's some things I'm just donating my time, but it's all in, like, in the name of service-

Jay Shetty 1:26:15 It's beautiful

Alli Webb 1:26:16 ... for sure right now.

Jay Shetty 1:26:17 I love that. All right, fifth and final question, which we ask to every guest who's ever been on the show: if you could create one law that everyone in the world had to follow, what would it be?

Alli Webb 1:26:26 Oh, to be kind.

Jay Shetty 1:26:28 Mm-hmm.

Alli Webb 1:26:29 We're just so divided because of, you know, it's like, I mean, I think it's deeper than that-

Jay Shetty 1:26:35 Mm-hmm

Alli Webb 1:26:35 ... but it's like this notion of, like, you know, even I, I s- I read something the other day that was like, "Anger is just grief."

Jay Shetty 1:26:42 Mm-hmm.

Alli Webb 1:26:42 We had to, like, it was just, like, innate in us to be kind to other people. Like, can you imagine-

Jay Shetty 1:26:47 Totally

Alli Webb 1:26:48 ... what kind of world it would be? So much better.

Jay Shetty 1:26:50 Well said. Everyone, the book is called The Messy Truth: How I Sold My Business For Millions But Almost Lost Myself by New York Times Bestselling author Alli Webb. Uh, you can grab the book right now. It's out right now. Share it. Make it your next book club pick.

Alli Webb 1:27:06 [laughs]

Jay Shetty 1:27:06 Discuss it. Dissect it. I mean, if you want to have a real entrepreneurial story and journey in your hand, this is the one to have. Uh, Alli, thank you so much-

Alli Webb 1:27:14 Thank you

Jay Shetty 1:27:14 ... for coming on the show today and-

Alli Webb 1:27:16 This was amazing

Jay Shetty 1:27:17 ... genuinely being so open and honest and courageous in your own life and here. And, uh, I look forward to continuing our, our new relationship.

Alli Webb 1:27:25 Me too.

Jay Shetty 1:27:25 And, uh, very grateful for it. Thank you so much.

Alli Webb 1:27:27 Thank you so much for having me.

Jay Shetty 1:27:28 Thank you. If you loved this episode, you will also love my interview with Charles Duhigg on how to hack your brain, change any habit effortlessly, and the secret to making better decisions.

1:27:40 Look, am I hesitating on this because I'm scared of making the choice, 'cause I'm scared of doing the work? Or am I sitting with this because it just doesn't feel right yet?