How to Feel Satisfied, When You Always Want More

0:00When someone comes to my door, I know, because I'm using SimpliSafe. I get an alert straight to my phone and I can see, is this someone I should unlock the door for because I know them? Or is it someone I need to tell to get lost? But here's the thing I love most about SimpliSafe. It works when I am not looking at my phone too, because when I'm not keeping an eye out, SimpliSafe is. SimpliSafe is proactive with a double layer of defense that stops crimes before they start. First, AI-powered cameras spot potential threats outside, and then live agents step in, talking to the person through the camera and letting them know they're on video and police will be dispatched if they don't leave.

0:44They can even trigger a loud siren or spotlight. That's how you help stop a crime before it starts. And SimpliSafe makes it easy to use. There are no long-term contracts, no hidden fees. You can cancel at any time. It was named Best Home Security Systems by U.S. News and World Report for five years running. It offers a 60-day money-back guarantee, so you can try it and see the difference for yourself. This month only, take 50 % off any new system. This is one of the best prices you will ever see for SimpliSafe, so don't miss it. Just go to simplisafe.com slash problem solvers. Again, that is SimpliSafe, S-I-M-P-L-I, S-A-F-E, simplisafe.com slash problem solvers and lock in your discount.

1:33There's no safe like SimpliSafe. From Entrepreneur Media, this is Problem Solvers, a show in which entrepreneurs do what entrepreneurs do best, solve unexpected problems in their business. We were completely wrong. And I'm just like, it's not selling. It was like, we have to start from scratch. I'm Jason Pfeiffer, the editor-in-chief of Entrepreneur Magazine.

1:59Andrew Wilkinson has a catchy way of describing himself. He says that he's gone from barista to billionaire. 20 years ago, I was a barista, and today I own 40 companies. So it's been a very strange ride. And what does it mean to own 40 companies? What it means is that he is the co-founder of a company called Tiny. It is a Canadian holding company that buys and holds what it calls wonderful businesses for the long term. And as you can probably tell from the barista to billionaire thing, this was not on Andrew's bingo card. This was not the thing that he was angling to do. He interestingly just kept following opportunity all the way up.

2:41The way it started was I was a barista and these two guys kept coming into the coffee shop where I worked and sitting on their laptops all day. And I asked them one day, what do you guys do for a living? And they said web designer. And I went, OK, being a web designer seems a lot better than being barista. Maybe I should try that. And that's where it all started. I started designing websites, taught myself web design, started designing websites, started freelancing. and then I just over and over again kept compounding and growing my knowledge and figuring things out as I went. And a lot of people have a story that's like this.

3:18They spotted some interesting opportunity, they made a change, they pursued it, and suddenly their life is different. The thing about Andrew, of course, is that he did this and then just kept leveling up over and over again to the point where he has enormous wealth and is controlling enormous value. And what is it that drives someone to do that? Even if you don't achieve what he has achieved. I think that if you're listening to this show, you can relate to this sense of wanting to constantly grow and pursue this idea that there is just never enough. And that phrase, by the way, used very intentionally because Andrew just wrote a book called Never Enough.

4:00And look, the book explores his own journey, lessons learned and mistakes made on the journey to building a fortune. But the reason I wanted to talk to him was because in Andrew, I figured here is someone who has been very thoughtful about what it means to pursue and to grow and when and where to stop or if stopping is even an option. I think a lot of people get to a certain point and then are satisfied and they coast along at that level. And frankly, I think they're probably much happier than I am. Because I feel this quite a lot. Again, I'm sure you do too, is we just keep growing. And every time that we achieve something more, we just want something more.

4:48It's never enough. And how do you find a balance? And has he? Anyway, these were the big questions that I wanted Andrew to answer with me. And I have to say, I am incredibly delighted by where he went. The conversation that we had was so deep and thoughtful and personal. And if you have ever grappled with your own question of what does enough look like, this is the conversation that you need to hear. And it's all coming up after the break. Grow your business with one of the world's most trusted brands in retail. With Walmart Marketplace, you can scale with built-in solutions for fulfillment, advertising, and pricing, all while reaching a customer base of millions.

5:37Sellers who join today can save up to 50 % on referral and fulfillment fees. Launch your store on Walmart Marketplace before July 31st to lock in your discount. Head to marketplace.walmart.com slash solvers. That's marketplace.walmart.com slash solvers to get started today. Conditions apply. All right, we're back. I'm talking with Andrew Wilkinson, co-founder of the holding company Tiny and author of the new book, Never Enough. And Andrew's origin story, as you heard a moment ago, is he was a barista, and then he got interested in web design, and then he got interested in bigger and bigger and bigger and bigger and bigger things.

6:27And he describes this as stumbling his way through success. And I wondered, I've heard stories of many people doing versions of that. They didn't know where they were going exactly, but they just got there. I guess that's everybody, isn't it? That's me. I didn't plan on being editor-in-chief of Entrepreneur Magazine. I just kind of kept doing stuff and it grew. And my question to Andrew to start in this ultimately very deep conversation about what it means to be in a position of never enough and to figure out how to find happiness when nothing ever seems to be enough is to ask him, how do you get into this situation in the first place?

7:05What drives someone to just keep growing? Yeah, I think it's a general dissatisfaction. There's a great James Dyson quote. He says, I'm perpetually 20 % dissatisfied with everything. And if James Dyson's story, so he's the inventor of the Dyson vacuum, and he's gone into great success, and he's now one of the wealthiest people in Britain. But he has a very traumatic childhood. And I think that he had a, there was something missing for him. He didn't have a father. And his strange way of channeling that pain was to become a great designer and engineer. And I think that still drives him. And I think what I've seen in most successful people is that they have some sort of, there was once a football coach who told them they weren't good enough for the team or a dad who didn't hug them or someone who didn't tell them that they were adequate in some way.

8:03And I see that in myself as well. Not, you know, I don't have capital T trauma. I have lowercase t trauma. But growing up, I was always surrounded by people that I perceived to have more than me, and I felt inadequate. And it stoked me for whatever reason. And so for me, I think that it's just been a general feeling of being dissatisfied constantly and always feeling I need more money to solve that pain. For me in particular, my parents would always fight about money. And so I think at a very young age, I went, OK, how do I make them stop fighting? I get money. And that is just inborn. That's like a genetic thing now inside of me.

8:45And so I think a lot of people get to a certain point and don't have that and then are satisfied and they coast along at that level. And frankly, I think they're probably much happier than I am and many other successful people. Yeah, I don't know. That's what I've observed as I've met more and more successful people. I've heard a version of that answer before. In particular, I remember Barbara Corcoran from Shark Tank telling it to me. She carries with her sister something, some teacher at a Catholic school that she went to, telling her that she wouldn't amount to anything. And she seems to still feel like she's talking to that teacher or proving something to that teacher.

9:28And she said that the entrepreneurs that she wants to invest in are the ones that also carry that, because it means that they will not stop when things get hard because there is something deeper inside of them that's driving them and it's a hole that they're trying to fill. Here's the thing about that hole. At some point, does it inhibit you from appreciating or enjoying enough of the thing that you have done? I wonder if you feel that as someone who now gets to call themselves a billionaire that you're also carrying around at least 20 % dissatisfaction. Is it a 20 %? I'm curious. Is it a 20 % for you?

10:11Is it larger? What's the percentage dissatisfaction? I think it's, yeah, it's about maybe call it 20%. Okay. Is it still useful to you? Totally. And I think that's partly why I wrote the book is I reached this point where it was at first when I was running my business, call it 10 years ago, I had enough on paper. I could have retired and had a nice life. And I had a very adequate amount of money for whatever I needed. And then I was like, you know what? I really just need to make sure that's bulletproof. Let's get double that. And that process continued over and over again until finally I had taken a business public and I looked at a net worth statement and I saw hundreds and hundreds of millions of dollars staring me back in the face.

11:03And I still felt that feeling, that pit inside of, is this all there is? Have I arrived? The anxiety isn't gone. It's still there. And I asked myself that, is this really functional? Is this helping me in any way? And what I've found is that it has reached a point where it's actually a burden. I write about this in the book. If you spend the money, your life gets more complicated. People think you're a jerk because you're driving a fancy car. You now have to have a staff of people because you have three houses and they're constantly asking you questions and that's stressful. Your family members think you're being flashy or whatever it is.

11:46There's just so many odd downsides. And I think wealth, frankly is really not something that continues to add value to your life past a certain point past being able to have a really great house and a great car and go on vacation and pay your bills i don't think it delivers any happiness and in fact i think it's quite negative so for me the book was working out okay what do i do with the byproduct of my anxiety right like I've gotten very good at using my anxiety for productivity. And I've been very productive. And the byproduct of that is money. And I don't have a good use for that money, yet I'm still working really hard.

12:27And so I was really trying to figure out, okay, what's the ethical thing to do with that money? In my case, it's I want to give it all away for the most part, which is an unsatisfying answer as well, because it becomes a burden in and of itself. Great, now I've got to make a foundation and figure out how to give it away. and people criticize how I give it away or whatever. But that was the conclusion that I came to personally. But yeah, it's not the book. Ultimately, what I wanted to do was show my experience to other young entrepreneurs like myself who think that adding zeros is going to make them happy and really show that it doesn't and that I wouldn't recommend it.

13:04And I read a couple of books that were similar when I was younger. And unfortunately, I didn't listen to the advice. It was very poignant. it. Dave Eggers wrote a novel many years ago that I really loved called You Shall Know Our Velocity. And do you know it? The story is about a guy who inherits a lot of money. I can't remember exactly where the money comes from. And he finds it to be a tremendous burden and wants to give it away and ends up just traveling the world trying to hand it to people physically. And the burden that is that, possibly worth reading. But what you're saying there really resonates to me, not as someone who has earned that much money, because I have not, but in, I'll share this, in that, let's take this job.

13:48So I'm the editor-in-chief of Entrepreneur Magazine. People think that's cool. And it is, it's cool. I spent a lot of time working in magazines, and then I got to have the best title at one that people know. And the thing that I did almost immediately as soon as I got the job was that I started to think, what else can I get because of this? Where else can this get me? And then I have spent the vast majority of the time that I am editor-in-chief of Entrepreneur Magazine, which I got in 2016. Here we stand at 2024, so it's about eight years, trying to answer that question. I still do the work of entrepreneur, but I keep, in my mind, I keep trying to remind myself that it is an accomplishment all its own, that it is an honor that I carry, that I should be able to look back on this time and say, I held that role and it mattered to people and I enjoyed that.

14:41But instead, I think all I'm gonna think is I held that role and I was trying to figure out where else can I get. And for me, what I do is that I get involved in other projects, I create other things, I start, whatever, I travel around and I talk, I'm just doing whatever is afforded to me because of this role. And I do grapple with this question of whether or not that is the right way to handle the thing that I have at this moment. And so I want to double click on the thing that you said a moment ago about helping founders understand that the money isn't all that there is, the money won't satisfy them.

15:18And I want to get there. But before I do, I just want to ask you if what I just said about appreciating or trying to appreciate or remembering to appreciate or not appreciating the position that I'm in is a thing that resonates with you. And if you have figured anything out for yourself about how to appreciate the position that you are in. Yeah, it's really, first of all, it totally resonates. And I was going to say, I think accomplishment is like ice cream. You can eat a lot of ice cream and you're always going to want more. You never take your last bite of ice cream and then say, I can never eat.

15:53I don't need to eat ice cream for the rest of my life. I've eaten a lot of ice cream. You notice that the craving very quickly sets in a few days later, and that it takes more and more ice cream to satisfy the craving. It's like a drug. And I think that accomplishment and achievement is this wonderful thing when you're doing it for intrinsic reasons. So if you enjoy writing, let's say you love writing fiction, and you write it because you love it, and it just so happens that other people love your writing. I think that's wonderful. But if you're writing because your dad always told you you're a bad writer, and so you're writing to impress your dad, I think that's a really negative thing.

16:35And so what I've found is that if I'm in line with my values, with my intrinsic desires, and I'm achieving for those reasons, I'm doing things that actually bring me joy, and I would do regardless of any extrinsic validation, then I think it's wonderful. Work can be so wonderful. But I think that as soon as you get caught up into status, that's just a pool of misery. And I think one of the hardest things about getting successful is that people start to put you in boxes. They say, and you had a great post about this on your newsletter, actually, about how people will assign all their value to a title or a box.

17:15So they say, I am a really good stock market investor. when really they should be saying, I'm actually a really great thinker and analyzer because that allows them to move from stock market investing to running a nonprofit or whatever it is and applying that same skillset. And I think, yeah, a lot of people get caught up in those things and lose themselves and end up doing a lot of things that make them miserable. In terms of what's actually brought me real happiness and joy, usually it's presence. So being in the present moment, And so it's walking in a forest or reading a book or flow states like that.

17:55And then frankly, lasting satisfaction, really the only thing I can think of is my children. Having kids and seeing them grow has been really satisfying. And I look at all of my professional achievements and I think that kind of pales in comparison, which is such a lame answer. And it's for people, I remember not having kids and I'd always hear people talk about their kids and I'd just be like, oh, that's so lame. But I think there's like a biology to it. I think that you really unlock a certain chemical in your brain when you have kids. And for me, that chemical has been unlocked and I drive a lot of satisfaction from that.

18:32It's funny you say that at this moment because I don't know, maybe I don't have enough of that chemical that's been unlocked. But I keep running into these moments where I'll give you an example from literally five minutes before you and I started talking. Here on June 3rd, 2024 at 4.38 p.m., which is when I'm saying these words, just before you and I started talking, here's what happened. I sent an email to a speaking client. I've been, I did something with that speaking client last year and they paid me very nicely and it was wonderful. And then I spent the year staying in touch with them because I wanted more, never enough.

19:12I wanted more. and I line something up and it's good and I'm happy and I want it. And then we realized, I was just going through the schedule with my wife, we realized that it conflicts with a school thing for my kids. And my wife feels very strongly that I am at that school thing, which means that I got to email the speaking client and I got to tell them that I cannot make it work on their schedule, which probably means that this deal is going to blow up. And I do not know how to find it inside of my soul to say, to feel good that I am sacrificing the work thing for the school thing, even though it will be good for my kids, even though they will be happy that I am there.

19:48All I can think of is I would have made more money this year if that speaking gig came through. And now I will make less and I'll have one less thing. And I do not feel good about that. And I do not know how to reconcile that. And you are not a therapist. I'm not asking you to untangle it for me, but I'm sure that you've had these conflicts too. It's easy to say the things that I love in life are walking through the woods and taking care of my kids. And that's wonderful that you have that. But surely these things also come into conflict with that desire for more. How do you navigate that? I think it's a really hard question.

20:22And I don't know that I've figured it out. I think when I had a, I have a really good therapist, speaking of therapists, and I was talking to her about this exact problem. And she just said, look, I want you to reframe when you say no to something, you're saying yes to something else. And when you say yes to something, you're saying no to family, kids, time to yourself, all the things that make you happy. And so what I've tried to do is use a framework. You might have heard of it. I love the writer Derek Sivers. He talks about the idea of hell yeah or no. And something is either hell yeah or no.

20:58And I often find the things that make me miserable are the things where I go, I should. Whenever I use the word should, that's a big flag that there's something going wrong for me. And I try when I hear the should word. And for you, do you really authentically want to get on a plane and fly to Ohio or wherever you got to speak and do that speaking gig? I don't know. But the money is nice, right? You should make the money. It's a should. and I the way I would think about that is will that money actually make a real impact on your life or not or is it a should yes because I think I'm like you like I I've got a newsletter too and I charge ads on the newsletter now I don't need to right obviously like yeah I have a successful business but I have this thing about me where I go if I'm going to do something I want to it's I'm not just going to send out this newsletter without charging for it it costs me money to run it.

21:55And I've got a team of people that helped me put it together. So I should get my money's worth. But I very quickly find myself going, man, now that means I've got to do the occasional phone call with an advertiser. Now I have more email, etc. So I think that's an example of a should in my world. What you just said made me think this. To the question that you asked, do I really want to get on a plane and go to Ohio? It's actually Vegas, which is even worse. I think I'd rather go to Ohio. The answer is, like, not exactly. But what I really want is the momentum of that business. What I really love is that I built that speaking business.

22:30And to me, everything that I do either enhances it or it makes it go slower. And so even though the individual grind of it sometimes doesn't resonate with me, the having have built it, and having have profited from it and the deep satisfaction, personal satisfaction of creating it that I do like. But here's what was so interesting. And maybe this is a, this is, maybe this is a subject for your therapist as well, but like I, or maybe I should get a therapist, but is when you said, when you were talking about should, here's what happened in my brain. I thought, you know what I have done? I have attached the should to the thing that I should do for my kids.

23:06I should be there at that thing for my kids. And because that's the way that it's framed in my brain, like the thing is you're not taught, you don't need to be taught that should feels bad, should inherently feels bad. But the thing is that we don't recognize what we're doing when we think that we should do things and the way in which the should feels bad. So here I have said, oh, I should be there with my kids. That is what my wife basically told me. You need to not do this because you should be there with the kids. And that means that the should is attached to the kids. And that's why I'm not feeling enthusiastic about it.

23:36Maybe the thing that needs to happen is that you need to recognize where you have placed the should and then take it away and then and say, wait, I shouldn't be thinking about how this is something with my kids that I should be doing. Maybe I should be thinking about why this is so valuable to be doing. And that it's not just about recognizing where the should is, but it's also being intentional about where the should is being placed. What do you think? I think that I do that same thing. So for example, I've got a field trip that I'm going on with my son and it's four hours and we're canoeing to an island where we live in Victoria.

24:13His school is right on the beach. And every year they do this thing where they canoe to an island and they have a little field trip out there. And so I'm going. And it's one of those things that I naturally resist because I've got a lot going on at work and it's hard to take a whole day off. And I don't really want to go and put on boots and go stomp around on an island for four hours with a bunch of grade ones. But I know that But the risk is the downside is so significant because if my son thinks, if he even has the thought, I wish daddy was here and it's something that I could have done. I think that's just so tremendous in terms of downside.

24:56Like my father was wonderful. My dad's actually really a lovely, warm dad. I've been very lucky in that regard. but I remember when I was a teenager I was really obsessed with computers and I started this website writing about Mac News and he would never read it I'd always tell him about it and he'd always say I'm so proud of you but he would never read it I always wanted him to read the articles and I'd tell him about the articles but he wouldn't read it and I think that I'm okay that's fine I'm a relatively well-formed person. I don't know that's traumatic, but it definitely affected me. It gave me this feeling of I'm not being paid attention to and I'm not being seen.

25:38And so I just worry about anything like that where my kid is trying to show me something or has an event and is looking for me in the crowd or whatever it is. I'm really scared of those things because of that. And I guess I wonder also with this thing is, could you go and chat GPT and say, write me a very emotional response to the speaker people and explain the situation and say, I am so choked, but I need to do this for my son. Because I think it's such a universal thing. I think if I was hosting an event and you canceled on me, I'd be mad. But if you told me that it's because my son has this thing at school, I would immediately be like, oh my God, go, it's fine.

26:22We'll reschedule. So I don't know. I think one has total potential downside and one has very limited downside. I think that's a really good way of thinking about. To me, that resonates a lot is measuring the downside. I don't know. Maybe it's because I'm a logical thinker, but I know how to measure downsides of things. And yet I think sometimes you overlook the downsides of things. One downside is concrete. One downside is abstract. For this particular example, the downside that is concrete is loss of income. The downside that is abstract is I don't know how my kid's going to think. So you have to make that concrete or you have to engage with it directly and deeply in the same way that I'm going to engage directly deeply with the question of the lost speaking gig.

27:06And for what it's worth, that is exactly what I did when I emailed the CMO of this company. I explained that it was a family thing. And I know exactly what he's going to say because I've gotten to know the guy. He's going to say, I totally understand. I do the same exact thing. He's not going to be angry at me. I totally get it. I think that measuring things by downside, I don't know who needs to do that, but I think I need to do that. So that's a really useful, that's a really useful observation. One thing I would add to is there's a downside to this as well. But the problem is if you build your business around you, where you're going, you need to go to speak and you're the product versus you build a business that's a machine and you set it up and you hire the people, but ultimately it can operate without you.