Tobi initially felt a sense of safety and security, but he quickly faced an identity crisis as he no longer had a defined role or purpose after stepping away from the company he built.
Tobi started with multiple jobs making $30,000 to $40,000 a year after high school, then grew his income to $150,000 in his first year as a personal trainer, and eventually reached $10 million in revenue within three years.
Tobi's identity was deeply tied to his role as the founder and CEO of Sweat. When the company was sold and he stepped away, he no longer had a clear sense of self, leading to a significant identity crisis.
After selling Sweat, Tobi woke up on an inflatable mattress, went to his favorite cafe for breakfast, and felt lonely and uncertain about his next steps. This period was challenging and lasted for about three to six months.
Tobi spent months meditating, journaling, and reflecting on what mattered to him. He also began consulting and advising other founders, which he found fulfilling and helped him redefine his purpose.
Tobi suggests that founders should understand that their business will survive even if they're not constantly micromanaging it. He compares it to parenting, where the first child is treated with extreme care, but subsequent children are handled more casually.
Tobi realized that having more money didn't necessarily lead to greater happiness. He found that his level of normalcy just adjusted, and the importance of happiness didn't come from material possessions but from personal fulfillment.
Tobi doesn't place much value on material possessions. He bought a new house but didn't spend any of the deal money on extravagant items. He still uses practical items like a $300 Samsonite suitcase over more expensive alternatives.
Thank you guys for joining me for another powerful moment from one of my favorite episodes. This is a highlight clip to enhance your week. I hope you enjoy. So obviously you had a very successful exit with Sweat, a $400 million exit at age 29. I think it was two weeks before my 29th birthday. No way. Okay, so you were still in your 20s, which is considerably young. What was it like to have that level of financial success increase?
at that age? Yeah. So going back to my very early 20s, so even before that, so I left home and I was working two or three jobs after high school, making $30,000 a year, $40,000 a year. And that was a lot at that point. For me, it was a lot. To starting PT, did about 150K in my first year. And then three years after that, did about 10 million. So
The curve of like financial or like wealth generation or income generation was like quite aggressive early on. So I think like by the time I got to like actually selling the organization and you obviously got some money as a part of that, I think...
There was two things happened at the same time. Like one was, okay, well now kind of hit a point where that's never ever going to be a problem in my life unless I've made a whole bunch of really bad decisions. Right. So presumably there's a different decent degree of safety there.
But then outside of the money, what ended up happening, which I probably naively didn't really consider enough, was that I had a massive identity crisis almost immediately after doing the deal. Because I'd worked very diligently in the background to set the organization up so that it would effectively run itself.
So by the time we sold the company, with a grain of salt, I would really do about five significant meetings per month and that would pretty much run the company. Yes, I did other stuff in between, of course, but it was really five primary meetings per month that ran the company.
So when we sold the company a few months later, my COO took my position and I was kind of out. And so like this, after that, it's like, okay, well, you're no longer the founder guy. You're no longer the CEO guy. You don't really have a job or a place to go. You don't really like see all of the people that you love working with, you know, this, that and the other. It's like, well, who the hell are you?
So like it all goes, you know, kind of just like, you know, disappears overnight. And I think for me, that was actually, it was a really valuable experience because it, it definitely helped me realize that although I loved the game, I had my own, you know, kind of like blinders on in some regards. So those remarks before about like people take a lot of status in the CEO title, this, that, the other, that wasn't, I didn't necessarily have that. That wasn't it for me, but I definitely kind of,
took status and being like, but I have a business. This is me. I'm hustling. The business is me. So there was no, in my mind...
there was no fundamental differentiation between the company and me. The identity was like quite shared. And it wasn't until after having gone through that process, I was like, oh, okay, that was a very risky position to be in. Yeah. And that was probably a very unwise, you know, like approach on my part. And obviously, you know, this is part of the development journey, you know, as we get older and hopefully wiser. So like that was like the money part was actually a much smaller component of it for me than necessarily like the identity piece. Yeah. That was actually something I was going to ask you about, you know,
Because I've had a lot of entrepreneurs tell me and Greg that is the hardest thing to experience. Very hard. Because your business becomes who you are, especially when it's bootstrapped. You were involved from the beginning. It's your child. It's everything that you know. I mean, Bloom is like the only real job I've had other than working the front desk at a gym making minimum wage. So I don't really know anything else.
How do you even begin to rebuild your identity after that? Because it's not like you necessarily needed to go work more. Yeah, well, it's like, who the hell are you? Right, this is a question I ask myself. And I remember it was quite an interesting thing. Shortly after I had moved house and I didn't have any furniture in the house. I had literally an inflatable mattress.
And this was, I was like working out my last couple of months of, you know, kind of handover. And so I, you know, kind of finished up on a Friday. Yeah. I went to like give this speech to the company saying, thank you for your support and all this stuff over, you know, the many previous years.
Anyway, I like, like, I'm not typically a very emotional guy, like in this regard, but I was like, like sobbing, like I couldn't even get words out. Like, you know, it was, I felt very embarrassed at the time almost because like I'd spent seven years or whatever working with all these people and like never once having given like any emotion at all, you know, to being like completely just like, yeah, could not control, you know, the emotion.
Anyway, finish that call, hang up and that's it. My job there is done. So I go away for the weekend, I get home and then I wake up on my inflatable mattress on a Monday morning and I'm like... So you just made $400 million and you woke up on an inflatable mattress? Yeah, yeah. I don't attach much to things. You probably come to know that over time, but like... This is so funny. So I wake up and I'm like, oh...
I'll go to my favorite cafe. So I got a breakfast and I was like, but I would normally, my routine would be like, I'd go to the cafe and get coffee, go to work. And I was like, well, I'm not going to go to work. And I was like,
So I go home, I read for a bit and I'm like, this is actually, this is, this is quite hard. This is a very good thing to do. You know, I'm like, fuck, I'm pretty lonely actually. You know, like I was sitting here and I'm like, what do I do? You know? And so like you go through this massive, and for me it was probably like a three to six month process. It was quite hard actually. Like, and my coach, you know, my psychologist I've worked with for sort of six or seven years, he said to me, he's like, Toby,
this presents you an incredible opportunity to get really good at being bored. And like I didn't properly understand, you know, like what that meant, you know, like at the time, but it was excruciatingly painful for me.
But yeah, like literally it was months of like, you know, kind of like meditating and, you know, journaling and talking to people and trying to figure out like what actually, you know, mattered to me. Like, cause when you're in a journey like that, and I mean, you're in yours right now, like it is, it is in many regards kind of a bubble, right? Like you're in that bubble for a little while and it's hard to get out of the bubble to like kind of zoom out and get like perspective. Yeah.
and figure out like who are you kind of agnostic of the bubble that you're in. And so for me, like I sat there for many months being like, well, what do I actually even like doing? Yeah, because I would just work because I like the game. I was like, well, I definitely love business and I want to be in business, but I don't want to rush into something because I want it to be good to do. But I was like...
Well, what I do in the interim, and I was like, oh, well, yeah, so this was one of the things that led me to the position that I'm in now, which is sort of doing consulting and advisory with, you know, with founders is because I was like, well, I love the game, you know, and I love learning, which, you know, game is learning to me. But then I'm like, I really like the idea of helping other people achieve similar success that I had, but without them having to go through all the pain that I went through. Yeah.
Yeah. And so for me, like that, I personally don't like this word, but, you know, the idea of like teaching, it feels kind of weird using that word. But like for me, that like is and has been some of the most fulfilling stuff I've done in my career that I would have never, ever imagined. Yeah.
you know, in my time at SWEAT, I would have never ever thought for one minute, oh, like I'd love to actually help other people do that. It would have never occurred to me. That's kind of beautiful though. And I do feel like a lot of the time we find purpose in the pain. Oh, absolutely. And I love that you've turned it into that. Rachel mentioned to me actually that we were talking about
what do we like outside of our jobs? Like that is such a common issue, I think, for entrepreneurs. Yeah, huge. And she said you've actually helped her a ton focus on her personal life as well as her career. How do you approach balancing the two? Yeah. So for me and for a lot of people who are first-time founders that I've engaged in, you have this fear that if you kind of don't like touch and control and be across everything that the whole thing will blow up, right? Yeah.
And this is an elaborated story, but an example, a friend of mine, he's in his mid-40s, he's got three children and three daughters. And I was talking to him once about kids and he's like, oh, you have the first one and you wrap them in cotton wool and you gently place them in the cot and then...
five or ten times a night, you come in just to listen to them or poke them to see if they're still alive because you're not sure if they're dead, right? Because you have massive paranoia that something's going to go wrong, right? You've left the hospital and you're like, what the hell is this little nugget, right? You know?
Anyway, obviously that all works out. And then you have the second kid and you're like, "Oh, you're just kind of a bit sloppy. Throw him in there, chuck a blanket over it. That'll be all right. All right. Whatever." And he's like, "Tell you what, the third kid, kick him down the hallway. That'll be fine." And the same principle is kind of apply in business, but it's really hard to get that perspective early on. And so to your initial point, it's like, how do you kind of disassociate the business and personal life and whatever? Part of this is understanding. So one, there is no disassociation. Your identity is in some regard tied up with the business.
But like to understanding from an emotional standpoint, like if you're not on top of everything and you don't know everything and it's not all working and it's perfect, this, that and the other, the baby will still live. It'll still survive. You know, like, and that's a very important mentality, I think, for founders early in their journey to have. It's like not everything has to be perfect. And it's part of that like emotional tension that makes it really hard for people to switch off. Yeah.
So they might work a 40, 50, 60-hour week, but mentally they're working 120 hours because they're freaking out about it all the time. And this is like what Rachel and I would talk about all the time. She's like, you just are never worried.
worried she's like you were just never stressed about anything you should have seen me five years ago yeah that's crazy yeah you're in a position where you don't need to be worried no I have a very very different perspective on it now and again like that's I'm very grateful and fortunate of course like to have that perspective yes part of that is having some money but a huge part of that is actually learning you know it's actually having the knowledge and the perspective to be like okay well oh if your business dies cool you did it once you do it again
Did that financial success change your view on success and happiness at all? Yeah, yeah, it did. And this is a fun aside, right? So if you're a first-time founder who didn't come from wealth or you have a reason that money is very important to you and you want to build it, you spend your first half of many years trying to get it. You're like, got to get money, got to get money, got to get it, got to get it. And then you get it. Maybe you sell a company or you have a really big year of profit or whatever. And you go, cool. And you go,
well, fuck, I don't want to lose it now. Yeah. And then that becomes a really big problem. Right. And the fear of not losing it is in some regards, almost worse than the fear of trying to get it because you didn't have it. So you had nothing to lose, but when you have it, then you're like, oh shit, I don't want to lose it. So it's a very different, you know, kind of mindset, right. Like to, to go through and like that in itself is a really interesting journey to try and have a go. Part of the learning that even having money doesn't change your, but won't necessarily change your perspective or the fear with it. That's a
journey like you have to go through that journey you know to try to disassociate from the safety that it provides you but I think even some of the earlier remarks people will see success as money yes they'll see success as a CEO job title or an entrepreneur job title or a big office or lots of employees or winning a business award or whatever right you know it's like
But like, and this is so cliche, but like if all that shit makes you really miserable, like, are you really winning? Yeah. Cause I have lots of friends. You have a few friends who are, you know, billionaires and they've got planes and yachts and this and that and the other and whatever. It's like, we've spoken about this many times. I'm like, are you any happier since having those things? And they're like, no, they're like, sure. I have like, it's more convenient.
yeah, like maybe my holidays are slightly, they were here and now they're here, but it's like, but the importance of happiness doesn't come from those things. And I know some people would certainly argue that and we're all entitled to our beliefs, but like,
Having more money doesn't really make you any happier. And I guess your level of normal is just different. Yeah, absolutely. You just adjust to the new normal. Yeah, absolutely. In my position, I bought a new house shortly after doing the deal. And a few friends of mine were like, oh man, you have a new house, you've massively upgraded. I'm like, I didn't buy that with the deal money.
You bought it before? Yeah. And they're like, well, what do you mean? I was like, well, I haven't spent any of the dual money. And they're like, what do you mean? And I was like, well, what would be the point in that? Have you bought anything crazy? No. Oh my gosh. Not a single thing. Well, literally the most crazy thing is a nice holiday. Which I think is amazing because it's such a good experience and memory. Yeah. Yeah. But like...
And this is like part of the point too, right? You're like, yeah, I bought a slightly nicer, larger house. At the moment in that house, at least 50% of the rooms have no furniture still. Are you just a minimalist? That stuff's just not that important to me. Yeah. Like, and it's really strange. So, you know, going the other way around, right? Like, you know, when I was...
very early in the journey. It's like I had made about $300,000 or $400,000 a year as a personal trainer and I bought myself a watch, right? I didn't know anything about watches. I literally straight up bought that watch because I thought that that's what you did when you made money. It was a $15,000 Breitling, right? I still have it. I never wear it, like literally ever. It's cool to keep that though. Yeah. And of course, I was like, oh yeah, I'm going to buy a set of Louis Vuitton suitcases. Yeah.
Right. Because that's what you do. Because this is what you do, right? Anyway, when I got them, and shortly after that discount, I'm like, yeah, they're nice looking and they're nice leather, but they're really bloody hard to use. I have like a $300 Samsonite one, and I use that, and I've got a July suitcase as well. They're great.
I don't have to worry about damaging them. And like, you can probably see I'm quite practical more than I am. Style is not my thing. I'm not like cool. You look great. Yeah, this is Rachel. I was going to say, does Rachel help? Do you like, do you, these are like cargo pants, right? Yeah, yeah, yeah. I didn't even really know what they were until we met. Thanks for listening to this powerful moment. If you want to hear the full episode, click the link in the show notes. Love you guys. Bye.