Train Your Ambition Like A Muscle To Transform Your Life

Steven Krein: Hi, this is Steven Krein from StartUp Health. I'm here with my good friend Dan Sullivan from Strategic Coach for another episode of the Free Zone Frontier Podcast. Hi, Dan.
 
Dan Sullivan: How are you doing, Steve?
 
Steven Krein: I am doing great. It's fall ‘25. I don't like to date these too much, but I'm great. You know, there's a lot of chaos in the world, but not in my head. I was really excited an hour ago or two hours ago when I got your email with your latest book. And I thought that would be a terrific topic for this episode, because if you could elaborate a little bit on not only what the book is titled and what it's about, but why you wrote it.
 
Dan Sullivan: Yeah, well, the book is called Always More Ambitious. It's just a thought that has really struck me over the last year. I was asked a particular question at a big event that we had in Nashville, Tennessee last year. A long-time Strategic Coach client, but not with me. So this is a person who has been coached by other coaches in The Strategic Coach Program. And he just asked me about the fact that I was ambitious at 80. The event coincided with my 80th birthday, so that was a topic of discussion. And, you know, I feel very ambitious at 80, and he said, you're ambitious at 80, so what are you going to be ambitious about when you're 90? And without too much thought, I said, well, my goal is that I'm going to be more ambitious at 90 than I am at 80.
 
And, you know, I wasn't just being glib about that. It was a serious question and I tried to give a serious answer. But afterwards, after we had talked for a few minutes, I wandered away and I said, you know, that's a really interesting topic. That's a really interesting idea that I just answered with. And it really struck me that a lot of people think about ambition like it's a gas tank you get when you're born, you know, and people get different sized ambition tanks. So there's great inequality. It seems to people that there's great inequality with ambition.
 
But even the people who get a big tank, they have a fear when they get to 40, 50 years old that they're going to run out of ambition because ambition is like electricity and their power is going to get cut off. And then they start thinking about retirement so they can bow out gracefully and hopefully they've got a solid foundation, financial foundation when they quit. It really struck me because I've got a lot of entrepreneurs now that are 20, 30-year entrepreneurs, and they're doing top-notch stuff, the top stuff that they've ever been doing, and they're in their fifties, sixties. You're in your late fifties.
 
Steven Krein: Mid-fifties.
 
Dan Sullivan: Mid-fifties.
 
Steven Krein: 55.
 
Dan Sullivan: Yeah. It's all young to me. So anyway, what if it's not a gas tank? It's actually a muscle. And like any other muscle, if you really challenge it with resistance, you know, with new challenges, with new things, that the ambition actually grows like a muscle does. We know that geriatrics, who can not get out of bed, if you give them weight training, they can grow a lot of muscle in a very short period of time. And I think ambition kind of works along the same principles. So that's the idea that I've been playing with for about a year.
 
And then at a certain point, I said, why don't we just write a book about it? Which allowed me to go deeper into the subject, and then I started creating some exercises around it, and it just got better and better as I went along. I did an introduction to new people coming into the Program yesterday, and I said, Strategic Coach is where already ambitious entrepreneurs become more ambitious. And it just seemed like a really good positioning statement. And are surrounded by other ambitious entrepreneurs. And that's the reason why they become more ambitious is because they're surrounded by other ambitious entrepreneurs.
 
Steven Krein: Yeah, well, I think there's another thing that I don't want to walk past here, which is you wrote this at 81 years old.
 
Dan Sullivan: Yes.
 
Steven Krein: And as we were talking about your impetus for this book being written was the conversation you mentioned another entrepreneur in your program who was 65 when he came in and what his plans were at 65 when he entered the Program and what ended up happening over the subsequent 8 or 10 years. So I would love to kind of pick at a little bit. Could you have written this book when you were 50 or 60? And maybe how might it have changed writing it at 81?
 
Dan Sullivan: No, I don't think I could have because the one, I hadn't zeroed on this as a particular topic, you know, one is that, you know, I've always pushed longevity in the Program, that you can live a lot longer than you can. And if you knew that you could live an extra 20 years beyond what's normally considered you know, length time and you had that. And of course, we have the exercise, The Lifetime Extender in the Program. But I never put the two thoughts together. It's only been within the last 12 months that this has become front and center. So I have five things that I came up with. The first one was that ambition is a capability and you can grow it as you get older.
 
Steven Krein: Instead of what, though? How might it have been misunderstood or viewed before you framed it that way?
 
Dan Sullivan: Yeah, I think that I was putting it more in the category of collaboration, you know, that as you go along, a lot of our ambition earlier in our career, and I can go back to 30 because I actually became an entrepreneur at 30. And I would say that the big jump you make is where you realize you have to make a jump from individual effort as an entrepreneur to teamwork inside your company, and then you have to jump to collaboration outside your company.
 
If you look at yourself as an example, you had your dot-com company, and then you did well with that, and your timing was very good, and you were a success. You were a success at 30, such that it gave you a lot of thinking time. You brought back a lot of thinking time, and then you started to zero in on creating a knowledge network and then you move that into StartUp Health. But it wasn't so much about individual effort; you were creating a network where there was a lot of talent in it. And we've seen that over and over again in Strategic Coach in different industries, in different fields.
 
But we are always saying, as the years go by, you have to make it less and less about yourself, and you have to make it more about Who Not How. But I hadn't really zeroed in on this central thing of ambition. And I think it's probably my own experience that I was noticing when I hit 70, I was more ambitious than 60. And when I was 80, I was more ambitious than at 70. So I was living in a particular experience that was proving for myself personally, just how the world in front of me was not getting smaller. It was getting bigger.
 
Steven Krein: Yeah, so I know you're likely older than most of your clients. I don't know if you have anybody older than you.
 
Dan Sullivan: I've got two or three.
 
Steven Krein: Two or three older than you?
 
Dan Sullivan: Yeah, yeah.
 
Steven Krein: And so what does it mean to you to be a role model for ambition? Forgetting about a role model for so many other aspects of your entrepreneur, but how do you think about it from the perspective of your impact on your clients and your collaborators?
 
Dan Sullivan: Yeah, I'm really conscious of it, I would say, since about 70. I made it through the 60 to 70 decade and that's where there's a lot of pressure that is supplied because a lot of people your age are actually bowing out at that time. And you're probably seeing it too.
 
Steven Krein: Yeah, starting to.
 
Dan Sullivan: There's a lot of headwinds between 60 and 70 just in terms of social feedback. And you go to social events and you talk about your plans and they say, why are you still doing this? When's enough enough? And maybe you're starting to get some of that already. I don't know. For me, there's been three tough decades. The teen years are really tough. Nobody has an easy, comfortable teenage decade. You know, I think 30 to 40 is the next one, at least for men. I don't know if it is for women, because I think that society invests enormous amounts in people up till about 30.
 
It's kind of like muscle, you know, we grow muscle until 30, but after 30, we don't grow any muscle. And then you have to do weightlifting to keep your muscle. And I think that if you have a sense of originality about yourself and you have a sense of uniqueness about yourself, when I see a hotshot 28-year-old, I'm never too sure if it's actually them or it's just the massive amount of support that they got from parents, from teachers, from other people. But by 40, you know it was either uniquely them or else they're just a Xerox copy of where they came from.
 
Steven Krein: And then your third decade?
 
Dan Sullivan: The third one is 60 to 70 because you're supposed to be quitting then. They want you out of the workforce so someone can replace you.
 
Steven Krein: So what are the other four?
 
Dan Sullivan: Yeah, second one, I think ambition is a capability that enables all other capabilities. Do you think it's a central capability or core capability?
 
Steven Krein: I think it's the central capability. Do you think it is natural at a younger age and more difficult as you get older? That's why I was asking you about the age in terms of consciousness of it, because if you go back probably to your marketing even in the ‘90s or the early 2000s. You have always talked about ambitious entrepreneurs, but it means something different to you today.
 
Dan Sullivan: Yeah. Yeah. I mean, I think one thing that's only become clear to me recently, why people stay in the Program for such a long time.
 
Steven Krein: Why is that?
 
Dan Sullivan: Their ambition is they don't have to work to be ambitious when they're in the workshop setting. Everybody's reinforcing them. In other words, that it's a lot of hard work to maintain their ambition on their own. But when they're in a setting where everybody else is positively ambitious, in other words, they have a positive attitude toward ambition, that it becomes easier to think big thoughts. It becomes easier, you know, to go through the work it requires to develop new capabilities when you get that social reinforcement. Yeah.
 
Steven Krein: So what's the third and fourth and fifth?
 
Dan Sullivan: Well, Strategic Coach, that's what we do is we enable entrepreneurs to continually grow their ambition. So that's the setting. And that at 50, you can be more ambitious than at 30. And at 80, you can be more ambitious than you were at 50. Those are the five. So ambition is a capability. It enables all other capabilities. At Strategic Coach, our goal is to enable already ambitious entrepreneurs to become more ambitious, such that they could be more ambitious at 50 than at 30, and more ambitious at 80 than at 50.
 
Steven Krein: You know, when you think about how to contextualize that, you know, there's always a thinking tool that you create for your concepts. And I'm wondering how you thought about or thinking about what kind of framework is used to both assess going backwards your ambition and then your look forward.
 
Dan Sullivan: Yeah, I should mention this. This is another thing that in addition to the conversation I had in Nashville, I did a diagram one day on the whiteboard and I said, you know, I've been coaching now—so this was about two years ago. I said, you know, I've been coaching now for almost 50 years. And I said, there's a diagram that I think describes every entrepreneur that I've met. And it was, if you think of a whiteboard in the lower left-hand corner, you draw a little circle and in the upper right-hand corner, so you're going corner to corner, lower left to upper right, and you've created a big circle, and I write in the little circle here, and in the bigger circle, I write there.
 
And then I draw a straight line with an arrow tip on it, and I say, and this is every entrepreneur I've ever met, you're here and you're striving to get to there. How many of you would agree? And everybody's hand goes up. And I said, and you're striving. You're striving to get from here to there. When you were 10 years old, you were striving to get from here to there. At 25, you were striving. You're at 40, striving. At 60, you're striving to get from there. And I said, that's a really powerful habit for 50 years, striving to get from here to there. So what I'm saying is, do you ever think you'll get to there since you got a 50-year habit of never being there?
 
So I said, what if we could actually take the here and put it in the middle of the there? The middle of the there, you're here, but you're actually there, too. And that you're actually there, and now you're just going to expand your there. I remember we got this great guy, he's from Sacramento, Chris Johnson. He's in Free Zone, but I think he comes to a different workshop than you do. He's really great. He's an amazing guy. He had two companies when he started. One of them was Instant Raymond. He won on Shark Tank and he created instant ramen, you know, the sort of noodles?
 
Steven Krein: Yeah.
 
Dan Sullivan: And it was ready in 60 seconds and then he had an instant ramen maker and everything else and he was making money but he hated the business, you know, his retail product business, and he was trying to get it into Walmart he was trying to get it into Costco and he could under the conditions that he makes no money. So in other words, he would get a big check, but the check that required to get it there just drove him crazy. That was one business. His other business was that he was a talent hunter for engineering and architectural companies. And he loved it. He loved it.
 
And the way he did it is that part of the deal was you paid an annual fee, not all of it up front, but you paid an annual fee. And one of his people was in your company. And he would always be asking, well, who's next you get? So his company was always directly in contact with your company. You know, they would constantly say now, six months from now, the way you're going, you're going to need somebody. So that he would generally be addressing the need about six months before a normal head-hunter organization would do. And then he's really bright.
 
He created an AI telephone program. It's just an amazing telephone program. You listen to the voice and it's a woman. She has, you can't quite tell, it's sort of like a Southern voice, but not quite Southern. And it seems like she's from someplace else, but she's American. And it's totally cold call. They fire out cold call after cold call. And she says, I'm just wondering if you're right now looking for a different position. The person says, yeah. And she says, well, I just wondered if I can set up just a 10-minute phone call with you where we can just explore what you're looking for.
 
We have openings tomorrow morning at 10 o'clock. We have one at three o'clock, or the day after we have it at 10 o'clock. Would that be possible for you to do that? The guy says, yeah, and she says, okay, which one would you like tomorrow? 10 tomorrow or 3 or the day after? I said last one. And she says, okay, that's great. Now I'm just going to tell you what's going to happen. We have a person who's going to just ask you some questions and we're not going to waste your time. If it's not working for you, we're not going to call you back, but we just want to have a thing. And they line up and she's cheerful and she's up and down and she's talking. She says, oh, that's great. We can do that. And you can't tell which one's the human. It is so good.
 
Steven Krein: Right. It's getting that good.
 
Dan Sullivan: Yeah. So he had 32 people phoning and they did about 2000 calls a day. This one does a thousand calls a minute.
 
Steven Krein: Is his conversion the same?
 
Dan Sullivan: Yeah, it was exactly the same. And he just has two people who work on the quality control. Now, when they have the 10-minute call, the person who actually interviews is actually a program. It's an AI, too.
 
Steven Krein: Yeah. Well, let me ask you a question, because, you know, you talk about ambition as a capability.
 
Dan Sullivan: And the reason I told you that story is that I showed him the diagram of the little circle in the big circle. He says, whoa, whoa. Oh, he said, oh, that's me. That's me. You're telling me that I'm just never going to get to there. No, I said, I'm just drawing a diagram and you're responding to the diagram.
 
Steven Krein: But when you align them from being apart. Was that for him the big breakthrough?
 
Dan Sullivan: Yeah. And he says, that means I can be both ambitious and contented. And I said, yeah, yeah. It's a great vision. I said, would that be a big breakthrough if you could be both contended and ambitious? Yeah. Because the reason entrepreneurs don't like being contented, because it's at the price of their ambition.
 
Steven Krein: We had this conversation with a group of friends last night who I think when I had, prior to framing it from ambition, I thought about it as purpose or mission. And I'm wondering why that's such a challenging place for an entrepreneur to be, which is when you feel like you have lost your ambition, and it feels so out of character for you when you've been doing it your whole life. How do you think about that from the perspective? What's the difference between ambition and purpose? And how do you contextualize them against or alongside each other?
 
Dan Sullivan: Well, one of them is a socially acceptable word and the other one isn't. Ambition is like having dirty pictures.
 
Steven Krein: How so?
 
Dan Sullivan: Well, it's not an acceptable topic in social discussions about ambition. My feeling is purpose is a way to cleanse ambition. I want to solve world hunger and everything else. No, it isn't. You just want to be excited with a future that's bigger than your past. That's all you want to do. But there's just enormous headwinds. The document I sent you where it has the 10 points of the headwinds that people face with ambition and how Strategic Coach solves each of the 10 headwinds. I went home for a family reunion in June, where I have a sister who is 90 years old. I was there, and I have four brothers who are retired, four of them. And the question is, why are you still doing it? And I'm clearly the most successful sibling in the entire family.
 
Steven Krein: Six of you?
 
Dan Sullivan: Yeah, there's six of us now. One is dead. And I have sister 90, brother 88, brother 86, and then a brother 72, and a brother 70, you know, and I'm in the middle there. But they're all, they're out of the game. But I'm surrounded day in, day out by ambitious people. They're not.
 
Steven Krein: So talk a little bit about the headwinds. You think people don't like to talk about their ambition or they're ambivalent about talking about ambition. What have you found in the community that is true?
 
Dan Sullivan: Well, I think, first of all, it's seen as very, very unequal. It's very, very unequal that some people have ambition and other people don't have ambition. You know, we're into a very egalitarian age that people should be equal. The problem, you know, you see the whole thing, you know, if you go back to the American Declaration of Independence or anything, you talk about all people are created equal. But it's very, very clearly that the results are not equal. Basically, we're all for equal on our side of the line. We're all very much for equality of opportunity, but we're not for equality of outcomes.
 
I mean, the political spectrum is really divided on that principle. Your potential new mayor in New York really is looking for equality of outcomes. You could do a whole episode on that. We're not talking about him. I mean, a graduate of Baudoin talking about equality of outcomes, you know. But my sense is that it's one of those words that people don't really engage with it. You're expected to ambition.
 
For example, there's a big difference between female entrepreneurs and male entrepreneurs. Okay. We're up to about 25% now of the total client base is female, but at the Free Zone level, we have five women out of 120 right now. I have conversations with the female entrepreneurs and I said, you've got a problem because you as a woman and an entrepreneur, you have to justify why you're ambitious. The males have to justify why they're not ambitious. And I think in life, females at a certain point, once you get beyond taking care of your needs, you have to justify why you're still at it.
 
Steven Krein: Yeah. So is your belief that the book, obviously it's written for and to entrepreneurs, but is it anything that anyone should care about outside of the universe of entrepreneurs they surround themselves with or their teammates that they collaborate with?
 
Dan Sullivan: Yeah, I don't know. I guess in a certain graduate school, I'm sure, you know, the very prestigious business schools and that, everybody's ambitious. But it's competitive ambition, it's not collaborative ambition. And I think that's the other thing is that people don't want to talk about it because they're in extremely competitive environments.
 
Steven Krein: Yeah. So let's bridge that to the Free Zone community, because the Free Zone community is all about collaboration, not competition. And it's also about staying in your own Unique Ability or unique capability. So what do you think is true about ambition in collaborations?
 
Dan Sullivan: Yeah, well, it's really where you're putting two ambitions together to create a new third thing. And my sense is that after people, you know, they're in their Unique Ability, because that's the basic cornerstone of Strategic Coach is Unique Ability. You might as well not be comparing yourself to other people because you have everything you need to grow so you don't have to beat somebody else to do it. You know, if you just focus in on your Unique Ability and surround yourself with a network, you're just going to grow, okay? There's nothing outside of your company that's going to stop you from growing if you focus on Unique Ability and Unique Ability Teamwork.
 
But you're going to get to the point where your company is so good, and it's constantly growing, that you're looking to put it together with some other completely different kind of capability of another company to create a third thing. You know John Bowen. You've met John. Yeah. Well, we're bringing out a book. It's ready to go to Hay House right now. We wrote a book over the last six months, and it's called The Greater Game. Okay. And it's what's possible now, especially since AI has come on the scene of how big a game can entrepreneurs actually play.
 
Well, John is a coach. He coaches entrepreneurs. His are all high-level financial advisors who generally have clients like family offices. So we put it together and John just has enormously greater reach than we do because he just knows hundreds of thousands of financial advisors and all the big financial companies that have these people as agents or they have them as independent operators. And we put this together, and it was just so easy to put it together. And I'm really good at framing the topics, so I frame most of the book. John's a good writer, so he did a lot of the writing of the book.
 
But I created a lot of the framework for the book, what the topics are for the chapter and that, because I'm used to doing that. Every week of my life, I'm creating a chapter for a book, so I'm really good about it. And it's just going to be an amazing big success next year. You know, and I'm doing the one with Jeff Madoff, you know, the Casting Not Hiring, because, you know, he really knows the theater world. So that's a capability that I have that he has that we can put together.
 
And so I think when you get to the point, and you're at the point now, you've created this massive capability called StartUp Health. I mean, there's nothing like it on the planet. You've created this and you've created a whole structure of how you bring them on, how you get them to work with each other. You have them collaborating with each other. And it's just that when you're so confidently successful, with a capability that you do, it's very, very easy to take that capability called your company and join it with a capability of another network out there to expand the reach and the impact of what you're doing.
 
Steven Krein: The filter that I think is interesting to integrate into this conversation as it relates to ambition is it's probably a muscle that you want to see in whoever you collaborate with as well. I think it could be relevant for choosing spouses. I think it could be relevant around choosing other kinds of business relationships or personal relationships where you want to match up with somebody who is either equally ambitious or feeds your ambition or you're inspired by their ambition. Is that how you would think about it?
 
Dan Sullivan: Yeah, you don't want friction. You know, I only have my relationship with Babs to go on as far as personal life. But right from the beginning, you could just see that we were mutually supportive of growing. You know, we both wanted to grow very different skills, very different impact. But I've never sensed any slowdown in her notion of how big things can be or any slowdown in my notion of how big things can be. And it's always bigger. Steve, I think we've reached a good breaking point here for the first part of this podcast and there's a second. So I really, really appreciate your questions and we'll now continue the discussion with a lot more interesting dimensions of it when we come back for number two.
 
Steven Krein: Fantastic.