How Lucky Are You As An Entrepreneur?
February 18, 2025
Hosted By
Do you believe in luck, or do you make your own success? In this episode, Dan Sullivan explores the concept of luck in entrepreneurship. Drawing from 50 years of coaching experience, he reveals how successful entrepreneurs create their own paths, often starting young by seeking opportunities to grow their wealth. Discover how self-made success intertwines with luck in the entrepreneurial journey.
Here’s some of what you’ll learn in this episode:
- The top ways Dan has been lucky.
- Why it’s more difficult for someone born into wealth to become an entrepreneur.
- The new Strategic Coach® thinking tool that will help you recognize and increase your luck.
- Why being an entrepreneur requires a lot of courage.
- How Strategic Coach is run like a live theater company.
Show Notes:
50% of your success comes from luck, and 50% of it comes from the ability to take advantage of the luck you've had.
An entrepreneur’s success is an act of self-creation.
Entrepreneurs create their own income streams and their own capabilities.
Entrepreneurs understand intuitively that freedom requires money.
It’s difficult to separate luck from skill.
The U.S. is an entrepreneurial country created by entrepreneurs.
Even the challenges you’ve faced have shaped who you are today.
Recognizing the luck you’ve had keeps you centered and grounded.
Whether your capability drives your luck or vice versa depends on your perspective.
Resources:
Your Business Is A Theater Production: Your Back Stage Shouldn’t Show On The Front Stage
Episode Transcript
Shannon Waller: Hi, Shannon Waller here, and welcome to Inside Strategic Coach with Dan Sullivan. Dan, one of the things that you've been coaching on lately has to do with the idea of luck, which actually has a large role to play in terms of a lot of entrepreneurial success. But you brought a really interesting dimension to it. So let's talk about luck, its role in entrepreneurism, its role in people's success. What's your take on luck? What is it exactly?
Dan Sullivan: Well, this is an observation I've made over 50 years about entrepreneurs. So I started coaching entrepreneurs in 1974. And to a person, they're mostly self-made. From where they started, their success, since they decided to be an entrepreneur, has been an act of self-creation. For two things, it's not a usual choice for most people when they become adults that they would take a chance working directly with the marketplace and employing themselves. Essentially, they're employing themselves. And they're creating their own income streams. They're creating their own capabilities. And let's say you started doing that, it's surprisingly early. I discovered when I do surveys of the clients that I'm working with who now may be 40 or 50 years old, but they can remember even in school, even before high school, of always looking for jobs that they could do so they could get paid.
Shannon Waller: Right.
Dan Sullivan: You know, the other kids were out socializing and they were playing and they were getting involved with shopping. They were getting involved in this. And the entrepreneurs are distinctly different. They take a different path and they know intuitively that freedom requires money. They have to get more money. And oftentimes they're not from wealthy circumstances. As a matter of fact, it's a bit harder for somebody from wealthy circumstances to do this because to a certain extent, you have a safety net. You have a guarantee. That's just the setup for this. But what I've noticed is that when they've been successful over several decades, okay, so let's say they did it in teens or they certainly did it in their twenties. I didn't do it until 30. So you put in a couple of decades. And it's hard. It requires a lot of courage. There's a lot of risk involved. There's a lot of frustration. There's a lot of setbacks. In my case, I had two bankruptcies. I went through a divorce, but then, you know, by the time I was 50, you know, so when I started 1974, I'm 30. And then 20 years later, things are rolling with Strategic Coach.
Okay. And what I noticed, not too much in myself, but what I noticed in some of the really successful entrepreneurs, they had sort of an attitude of contempt towards people who weren't entrepreneurial. Or people who were entrepreneurs and quit and went back and got a job, they had sort of a dismissive attitude. It wasn't a major theme, but it was like a low-grade fever. You know, and they had this. And just to guarantee that I didn't get that myself, that I didn't develop this. It's a bad mindset. I said, why don't we just make a list of everything that your success has resulted from where you were just lucky. You know, I would say it's a little bit hard right at the beginning because it's hard to separate luck from skill. You know, it's a bit hard. But right off the bat, one of the first things that I came to was just how I was born.
Shannon Waller: Right.
Dan Sullivan: Okay. And I was born 1944, farm family. And I have four older siblings and I have two younger siblings and there's a big age gap between me and the next oldest and an even bigger gap between me and the next youngest. And I'm a fifth child, but not only that, but both my parents were fifth children in their families. My mom was fifth of seven. My father was fifth of nine. I was fifth of seven. And there seemed to be a special understanding of these three fifth children, such that I just had very light supervision. I had some rules and I more or less stuck to them. I just had this freedom to explore. But not only that, I didn't have to do farm work because the first four, girl and three sons, they were out and doing all the field work. And I was in the house and I was helping my mother. And I learned to be really useful to my mother. Anything my mother want, you go and do it or you anticipate it and you do it before she asks you. And that gets you all sorts of special treats. You know, she tried to be fair, but she was more fair to the person who was always being useful.
Shannon Waller: More fair. That is an awesome term. I love that.
Dan Sullivan: She was more fair. And I know from her saying it and from other things that there was a bit of resentment on the part of my other siblings. Okay. But it was an easy trick. I mean, there's a rule here. If you want things to go smoothly, just be useful to mom more so than dad, because mom's the one who holds everything together. So I had this list. I've had this list for quite a long time. And then I said, you know, I think it's a good time to turn this into a thinking tool for a Strategic Coach, which I have done just within the last couple of weeks. And boy, it's a knockout. It's a knockout tool. So you just have two sides to it. You brainstorm everything where you've been lucky.
Shannon Waller: Right.
Dan Sullivan: So I mentioned the one about my birth order. Another one is that all my life I've been fit and healthy. You know, I've had bone breaks and Achilles tendon breaks and everything else, but those are carpentry type injuries. These are not plumbing. These are not diseases. You know, you just put it back together again, put some nails and screws in and you're all set. But basically I've always had a lot of energy and I get a lot of exams and I'm good. You know, I'm good. But I have a lot of energy and I've always had a lot of energy. Well, I consider that luck. I think that's genetic.
Shannon Waller: Mm-hmm.
Dan Sullivan: A brain good enough.
Shannon Waller: There you go. Brain good enough.
Dan Sullivan: I've always had a brain good enough for what I was taking on. But another one, and I'll get to the number one luck, but I'll say another one. I was born American, okay, with entrepreneurial instincts, and it's a sweet thing to have entrepreneurial instincts and be born in America. You know, America is an entrepreneurial country that was created by entrepreneurs. All the founding fathers were one way or another, legal or illegal, they were entrepreneurs. That's been really good. And then I was born in one age where it was everybody strove to have a job in a big corporation where you had lifetime security. But technologically, things were changing so that individuals using technology could really prosper as entrepreneurs. I was old enough to really understand the significance of those things. And I've really utilized them over the last 50 years. I've really taken advantage of technology that were not available for other people.
But the biggest thing is meeting Babs Smith. And Babs and I met 42 years ago. And it was a real click. And I had been a lone, rugged individualist until I met Babs. And Babs has great instincts towards creating teams. I think she's a great team creator. So we're married happily, more than happily, and we're great partners in the business, which isn't always the case with married couples. But we have a strict division of labor. Strategic Coach is like a live theater. And Babs runs the entire theater. She runs everything about the business of the theater. And I put the material on stage. I create the new presentations on stage. Biggest stroke of luck in my entire life. And Babs will say the same thing when she does this exercise, that meeting me was the big stroke of luck. And it was luck. If I had made a different decision on a particular day, I would never have met her, but I just made a decision and ended up meeting her.
And there was sort of a click right from the beginning. Not a kind of real romantic click or that, but there was a real friendship click. There was a real, I like hanging out with you, you know, sort of thing. And so I list that and I do the top three. And that's what's true up until now. And I say, given the luck you already have, how can you be luckier in the future? And this is where a previous podcast we did where we talked about ambition, knowing that I've had this luck and I've developed this skill, now I can go much bigger and I'm going to have even more luck in the future. Based on my recognition of the luck I've had, I've opened myself up to much greater luck moving forward.
Shannon Waller: Agreed. You're on my list, Dan.
Dan Sullivan: You're on mine.
Shannon Waller: Yay. Well, and it's powerful.
Dan Sullivan: And I don't want to screw it up.
Shannon Waller: Ditto, I'm with you. It's interesting, Dan, because going around the room and hearing about it, and this was just a couple of days ago, people were so grateful for their beginnings, and some of them were not fabulous circumstances, like very challenging, poverty, escaping persecution in other countries, but they appreciated how—escaping poverty. Escaping poverty, surviving their early rambunctious youth would be another one.
Dan Sullivan: Or in bad circumstances, bad family, you know, bad parents and everything like that.
Shannon Waller: Yeah, exactly. War for some of them surviving being in the military. And it's interesting because they were appreciative of those circumstances, even though it was they were not always, you know, happy, rosy pictures, which was powerful. People just appreciated that those circumstances that they had survived had helped create who they are now.
Dan Sullivan: Yeah.
Shannon Waller: So it was really quite moving to hear those.
Dan Sullivan: There was a real noticeable transformation in the room as they fill out their own form and then they go into breakout groups and then they talk about it. And then we shared it generally. It was very moving. It was very moving. I mean, a couple of them teared up, but they were just talking about such fundamental things that they're now able to do in their life, what they're doing because they recognize I've been really lucky. And I think what it does, it keeps your mindsets correct that you can see that other people don't have luck. And I don't go too deep into this, but people have said, yeah, but it's because of my capabilities that I'm lucky. And he says, it's because you're lucky you have these capabilities. It all depends on how you wanna look at it.
Shannon Waller: That's one of the things that came out is the difference between the circumstances, right, luck, and what you did with them. The capabilities and skills that you leveraged off of those.
Dan Sullivan: Exactly.
Shannon Waller: So Dan, talk a little bit more about how you're getting luckier. What patterns do you see or where do people go with the information? It's like, okay, so that was up until now. What's next? What kind of things do you observe as people talked about that?
Dan Sullivan: Well, and I think this is unique to being in Strategic Coach. And the first thing is that the fundamental concept of Strategic Coach is Unique Ability. That everybody has a Unique Ability, which means it's not comparable to anybody else's ability. And so what I realized that the more I just stay in my Unique Ability, which is doing kind of what we're doing right now, you know, I like talking off the cuff. You know, I like being in podcast conversations. I like coaching workshops. I like creating new thinking tools for the entrepreneurs. I like writing books and podcasts, lots of podcasts. So I'm a front stage person. And the more that I just keep myself in the front stage, doing front stage things, and finding teamwork to the parts of it that I'm not, and bringing in people who are in their Unique Ability. It's only with entrepreneurs, the quality of our entrepreneurs is getting greater, you know, over 35 years of the Program. The more we just stay right in the center, the luckier you get.
Shannon Waller: Right, yeah, now before you were born into or happenstance to meet somebody, but now you can actually create the circumstances for being luckier.
Dan Sullivan: Yeah.
Shannon Waller: That's exciting.
Dan Sullivan: Yeah, they're unpredictable.
Shannon Waller: Hmm, say more about that.
Dan Sullivan: Well, what I mean is they're not actually a goal, they just happen because you're moving forward. There's people you meet, there's resources that become available, like patents. We've gone full bore over the last two years of taking our thinking tools and moving them into patents. In 18 months, we have 47 new ones. We had four before. But this time next year, we'll have over 100 patents. And these are assets, and they just come from taking advantage of creativity that we've done for the last 40 years in one case, 42 years in one case. But now I'm just creating new thinking tools that'll become patents.
But it was because I met a person by happenstance, who came to one of our Free Zone events in Chicago, and I just started talking to him. He didn't join the Program, and then he did join the Program about a year later, but not in my workshops. And then we were going to Boston for a conference, and his headquarters is right at Copley Square in Boston. And he says, do you mind when you come in if we could have lunch together? And he started telling me what he does and what his story is, Babs was with me. And we went up to his office, and he's on the 54th floor looking out over Boston in four directions. And he said, we're just getting the news today that we're the fastest growing law firm in the United States. He's an IP lawyer, intellectual property lawyer.
And then I got interested and then I have another podcast series where we invited him on to do a podcast of how he does what he does. And it's just totally unique how he approaches intellectual property. Both Steve Krein, who is my podcast partner, we were sitting there with our mouths open and we said, how do you do this? Then he joined the Free Zone Program. And I came in one morning and I structured everything he had told me. I'm good at diagrams. And I created a diagram. And I said, at 11 o'clock today, you're going to get up and give a complete explanation of how you do what you do. And here's your method. I want you to talk through your method. That was a two day.workshop and at the end of the second day he had 35 new clients. Because everybody just totally got what he was doing.
Shannon Waller: Yeah, that's awesome. Yeah, you're taking advantage of that chance-ish meeting.
Dan Sullivan: I said this is lucky. I'm going to take advantage of this luck. So I think one thing, there's a skill that develops that when something happens you have a filter. This is a new stroke of luck, so you're alert, you're curious, you're responsive, and you're resourceful in relationship to luck.
Shannon Waller: Which also means paying attention, as you said, taking action, not taking it for granted is huge, like recognizing it and taking action on it is absolutely vital. Very cool, Dan. I really like this. This is exciting. Just to share a little bit of my own experience. So my three top experiences were the family that I was born into. Very warm, loving, supportive, open-minded, abundance-minded group. And then I met my husband, Bruce. Another lucky stroke and we're together for 34 years so far. And this is our best year yet, which is pretty cool. And then very shortly thereafter meeting you and Babs. What's interesting, though, that I found is that the mindsets between all three are the same. So it's interesting, like that's the environment I thrive in. That's the one I worked hard to create. That's the one I'm attracted to with other people. So that's one of the insights from this exercise for me is like, oh, I can see the connection points between those things. And it's a bellwether for me that I'm going to go in this direction, which is really kind of fun.
Dan Sullivan: Yeah, you get more alert. Once you do a really good accounting for the luck you've had up until now, it creates a filter in your mind that you're looking for luck. And you know the difference when you see it.
Shannon Waller: Something very compelling about the phrase looking for luck. Yeah, but it does, it becomes, as you said, a filter through which you're assessing your experiences and you're like, oh, that's one, bam, I'm gonna move forward like that, like you did with meeting Keegan and pursuing IP. Yeah, that's very cool. Any other thoughts, Dan, about how people can put this into play for themselves in terms of both appreciating where they've come from and then how they can build on that to expand their luck?
Dan Sullivan: Well, I think it's a 50-50 proposition, and that is that if you're an entrepreneur, it's useful that you have this mindset that your success is 50-50. 50% of it comes from luck, and 50% of it comes from the ability to take advantage of the luck that you've had. And I think that keeps you very centered. I think it keeps you very grounded, and it keeps your head the right size. And it makes you very alert, it makes you very curious. And if you spot one, you respond to it instantly. And you use it as a tremendous resource the moment that you see the luck. And you don't second guess yourself.
Shannon Waller: Ooh, I like that. As you're talking, Dan, all I can think of is entrepreneurs are by far the best people in the world, or the people in the world best at doing this. Let me put it that way.
Dan Sullivan: Yeah, I think there's probably a spectrum of people who've actually had the luck to be much more successful than they are. And what was lacking is their recognition of it. And there are other people who are saying, I keep improving my skills to be luckier. That, I think, is a skill. But you don't get the skill until you appreciate the luck you've already had.
Shannon Waller: I was just gonna say that, Dan. It's the whole point about 50-50.
Dan Sullivan: And tell people, you know, and actually announce it. You know, I've been really lucky. I know there was just a little, it was just a little five-minute thing right around the election. And apparently, you know, Trump's 78 years old, you know. The way he eats, you know, his lifestyle and everything else suggests someone who would die at 60. You know, and the last 48 hours, this is the recent presidential election, he did not sleep. He was interacting, he was on the phone, he was talking to people for 48 hours. And there was this man who's sort of famous in his own right, was staying at Mar-a-Lago, the Trump home in Palm Springs.
Shannon Waller: In Florida, yeah.
Dan Sullivan: In Florida, Palm Beach, not Palm Springs, Palm Beach. Right, you know the difference.
Shannon Waller: Now I do.
Dan Sullivan: Yeah, and he said, how do you do it? You're eating Big Macs, you're eating fries, you're drinking Coke. And he says, genetics. He said, I can do it just because I inherited this capability. But he knows that he can depend upon this genetic luck.
Shannon Waller: Mm-hmm. Well, we all have certain things. You know, there's certain things that were the opposite of that too. But if we appreciate what we've landed in, what benefits us, and then work to take advantage of it, the whole thing again also, but when you're appreciative of something, you are much more grounded rather than arrogant or complacent or those other wrong mindsets that will not help people move ahead. So I really like this way of appreciating what got you here. Your own efforts for sure, but also … Oh no, but it's 50-50.
Dan Sullivan: Yeah, I love that. And I think whether it's 47 or 53 doesn't matter. Just give half the credit to luck and half the credit to your capability of taking advantage of luck and everything's cool.
Shannon Waller: Brilliantly summarized. Thank you, Dan.
Dan Sullivan: Thank you.
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