The B2B Podcast Index
Index
All categories
MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
MethodologySubmit
Best of:MarketingSalesSaaSFinanceHROpsLeadershipCustomer SuccessAI & DataProductStartups & FoundersRevOpsEngineering & DevTools
An independent project byFame
SearchBest episodesGuestsInsightsMethodologySubmit a podcast
Index/Startups & Founders/Jim A. James & The UnNoticed Entrepreneur
Jim A. James & The UnNoticed Entrepreneur artwork

Sustainable Success Looks Nothing Like You Think.

Jim A. James & The UnNoticed Entrepreneur · 2026-06-20 · 37 min

0:00--:--

Key moments - from our scoring

Substance score

56 / 100

Five dimensions, 20 points each

Insight Density11 / 20
Originality10 / 20
Guest Caliber13 / 20
Specificity & Evidence12 / 20
Conversational Craft10 / 20

Chris Ducker, serial entrepreneur and author of The Long-Haul Leader, walks through his journey from near-total burnout in 2021 - despite loving his work - to building a sustainable framework for long-term success. After scaling Youpreneur to 380 members and growing his business 5x during the pandemic pivot, Ducker hit a wall: phase three adrenal failure, acute anxiety, and depression forced him to step back for three weeks and eventually seek therapy and medication. He discusses how burnout isn't about hating your work but doing too much of it for too long, even when you're passionate. The conversation covers AI's role in scaling without burning out (his team uses it for ideation while he maintains personal brand authenticity), the myth that you need massive employee headcount to be a 'real' entrepreneur, and his redefined legacy framework: family first, then spouse, then external impact. Ducker emphasizes that sustainable success comes from showing up authentically and consistently over years - Youpreneur just hit eleven years - not overnight tactics. This episode benefits personal brand entrepreneurs, business owners wrestling with identity after exits, and anyone confusing hustle culture with longevity.

Key takeaways

  • →Burnout can occur even when you love your work - it's about doing too much of something good for too long, not about hating what you do.
  • →Personal brand content must come directly from the creator to maintain authenticity; AI should ideate and support, not generate the final output.
  • →Community building requires showing up authentically, consistently, and with a serve-first philosophy over months and years, not weeks.
  • →True legacy starts with family and personal relationships first, then extends to business and external impact - not the reverse.
  • →Entrepreneurs should approach AI as a tool their team can use to gain productivity superpowers while the leader maintains creative control and human differentiation.

In this episode

  1. 1AI and Entrepreneurial Burnout Risk
  2. 2Authenticity and Personal Brand in the AI Era
  3. 3Building Communities Through Consistency and Generosity
  4. 4Chris's Burnout Experience and Adrenal Failure
  5. 5Identity and the Entrepreneur Post-Exit
  6. 6Redefining Legacy Beyond Business Success
  7. 7Prioritizing Family and Health Over External Achievement

Mentioned

Chris DuckerJim JamesYoupreneurSally HogsheadAmy PorterfieldChatGPTClaudeExpert to AuthorityLong Haul LeaderHalf TimeBob BufordJohn Lee Dumas

Guests

Chris Ducker

Topics in this episode

Sally HogsheadThe Long Haul LeaderYoupreneurPhase three adrenal failureExpert to Authority newsletterPersonal brand entrepreneurshipAI tools (ChatGPT, Claude)Half Time by Bob BufordBurnout recovery frameworkLongevity and biohackingburn outChris Ducker

Questions this episode answers

What is phase three adrenal failure and how does it relate to burnout?

Phase three adrenal failure is a clinical term for burnout where your adrenals stop producing cortisol (stress hormone), leaving you unable to handle stress, which causes further burnout. Chris Ducker was diagnosed with this condition after his 2021 collapse despite loving his work.

Can you burn out from work you actually enjoy doing?

Yes, according to Ducker. He was showing up for the right reasons and loving the work at Youpreneur, but he was doing too much of it for too long. Burnout isn't inevitable only when you hate your work - it happens when volume and duration become unsustainable, regardless of passion.

How does Chris Ducker use AI in his business without outsourcing personal brand authenticity?

He gives his small team (four full-time employees) free reign to use AI tools like ChatGPT and Claude for ideation, productivity, and brainstorming content series. However, all final output - newsletters, social media, scripts - must come directly from him, because his personal brand cannot be AI-generated.

What is the framework for redefining legacy after exiting a business?

Ducker's hierarchy is: family and children first (enabling them to be more successful, happier, and healthier), then being a great spouse, and third is external leadership impact. He references Bob Buford's 'Half Time' concept of moving from success to significance, starting internally rather than chasing external fame.

How long does it really take to build an authentic community as an entrepreneur?

Ducker emphasizes it happens slowly - Youpreneur is celebrating eleven years. Success comes from showing up authentically, consistently, serving first and selling later, and being around for a long time so people can trust your mission and stick around.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

11 / 20

The episode delivers moderate substance with some useful frameworks (hustle as a season, P2P philosophy, legacy redefinition) but relies heavily on anecdote and personal storytelling rather than dense, novel insights. Much of the content reiterates familiar entrepreneurial wisdom (consistency, authenticity, community building) without introducing counterintuitive or data-backed claims. The burnout discussion is valuable but relatively surface-level given the clinical detail available.

hustle is a season. It's not a lifestyle. You can hustle up. There's nothing wrong with hustle, but it's not sustainable. It's not a longevity plan.
people will rather do business with people than a logo or a brand

Originality

10 / 20

The core thesis - that sustainable success requires balance, authenticity, and redefining legacy around family - is familiar in contemporary entrepreneur discourse. While Ducker's personal burnout recovery and the specific framework of phase-three adrenal failure provide some grounding, the broader ideas (consistency, serving first, being yourself) are well-trodden. The P2P philosophy and legacy-inward-first approach are sensible but not contrarian or first-principles.

being different is better than being better
show me your calendar and I'll show you your priorities

Guest Caliber

13 / 20

Ducker is a credible practitioner with 22 years of entrepreneurial experience, successful exits, and genuine operational scale (480+ employees scaled down to 4 core staff). However, he is primarily positioned as a coach, author, and personal brand entrepreneur rather than a founder/operator currently building at scale. His value is retrospective wisdom and positioning rather than current, active operator insights. He's a legitimate voice but not peak caliber for B2B substance.

I've been doing it 22 years. I've earned the right to do it.
we went from almost five hundred employees to at that point probably about thirty or so

Specificity & Evidence

12 / 20

The episode includes concrete details (phase-three adrenal failure diagnosis, 480 employees reduced to 4, Youpreneur Incubator growth from 90 to 380 members in one year, four named family members in business roles, six-hour workdays Monday-Thursday). However, many claims lack supporting data or examples: community-building success is illustrated through longevity rather than metrics; the AI framework is described philosophically without implementation specifics; and the 'framework' promised is never explicitly laid out with steps or measurables.

we went from about 90 members at the beginning of 2020 to about 380 members at the beginning of 2021
phase three adrenal failure, which is a clinical term. For burnout fundamentally

Conversational Craft

10 / 20

The host asks reasonable opening questions and allows Ducker to elaborate, but rarely pushes back, challenges claims, or digs deeper into contradictions. When Ducker pivots to ask Jim questions, Jim obliges rather than maintaining journalistic pressure. The conversation feels collegial and supportive - appropriate for a friendly interview - but lacks the sharp follow-ups, disagreement, or skepticism that would extract more nuance or accountability. Most softball moments go unchallenged (e.g., the claim that AI won't cause burnout, or that 'everyone' should live like Ducker eventually).

Jim James (15:49) you know, that you're not going to make the money, you're not going to look after the team, you don't look after the clients. And but you don't really know where to look, right.
I'm curious to know your thoughts on this as well. I'm gonna turn the mic back on you here, Jim.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Most-used words

chrisducker39james38chris23back21book19entrepreneur16long15brand12first12entrepreneurs11leader10personal10different10feel10show9appreciate8

Episode notes

Get Noticed! Send a text. Chris Ducker - serial entrepreneur, founder of Youpreneur, and author of The Long Haul Leader - joins Jim to talk about what happens when a business built on genuine passion still burns you out. Chris scaled to almost 500 employees, grew 5x in the first year of the pandemic, then hit a wall so hard he couldn't turn on his computer. The diagnosis: acute anxiety, depression, and phase three adrenal failure. He shares why AI has a place in his business (ideation, team productivity) but never in the content that carries his personal brand, why "different beats better" as a competitive strategy, and why his recovery framework starts with family before it goes anywhere near the business. He's candid about the cost of his earlier pace, and equally candid that scaling down to a four-day week and a four-person team is something he earned after 22 years, not a shortcut available on day one. A practical, honest conversation for any entrepreneur who's enjoying the work and still running themselves into the ground. The Long Haul Leader by Chris Ducker Chris Ducker's Website Rise of the Youpreneur by Chris Ducker

Full transcript

37 min

Transcribed and scored by The B2B Podcast Index.

@ChrisDucker hustle is a season. It's not a lifestyle. You can hustle up. There's nothing wrong with hustle, but it's not sustainable.

It's not a longevity plan. Jim James my guest today burned out the old fashioned way before we all boarded the AI roller coaster. But having successfully rebuilt his world, he's created a practical framework for recovery and growth that I've read, I've enjoyed. And so I've asked him to come and talk us through it today because I know that this will be helpful to you.

Welcome to Chris Ducker, serial entrepreneur and author of The Long Haul Leader. Chris, welcome. @ChrisDucker Thanks for having me. Appreciate it.

Jim James Well, it's wonderful to have you on the show because I've followed your work with Youpreneur of course, and see you reincarnating now with your book and authoring support and loved the "Long Haul Leader" But let's start with the elephant in the room, Is AI creating a solution or giving us all a greater risk of burnout because it's always on and it's setting the pace. That's the danger. We're all on the roller coaster. What's your view on AI?

the risk gets crazy for entrepreneurs. @ChrisDucker I think I think overall we should be looking at it from a positive perspective. I think a lot of people are probably still quite confused about how to utilize it in their business, in the best way. I know that I was a little late to the party in terms of wanting to understand AI better and wanting to I guess appreciate how it can help us run, support, grow, scale what we're doing.

once I was on board, you know, I was on board. But we were talking just before we hit record here, you know, I don't use AI tools like ChatGPT or Claude, you know, on a daily basis. Of course I use them. They're installed on my computer and, you know, I can see the little Claude logo on my task bar here or or my nav bar on my Mac.

I'm not like a lot of people that are using it every single day. I'm I'm not doing that. However, I've given my team, or albeit a sport team, only four full time employees now. since selling a couple of businesses, I've been able to size down that payroll quite quite substantially.

god, so good. I you know, I I enjoyed being an employer. I enjoyed being a quote unquote boss. but that era has gone now.

Jim James Yeah, that must be nice to not have to worry about that every month. Yeah. @ChrisDucker And you know, when you've got up to almost 500 employees, I think we had about 480 odd people at one point, you know, and to go from that to just a handful of employees is fantastic. And so I have I, you know, ultimately given them free reign to be able to utilize AI for any purpose in terms of being proactive, productive, et cetera, et cetera.

but I have made it very clear that the output Of the content very specifically that we produce. So we're talking about our weekly newsletter, expert to authority. we're talking about, you know, anything that you might see on social media. We're talking about any kind of scripts that I might write in regards to solo podcast sessions and things like that, which I don't do very often.

But if I've got a point that I really want to, you know, slam home, I'll I will script it in some capacity. All that stuff has to come from me. It has to. Because it's my personal brand.

That doesn't mean that we're not utilizing AI to be able to ideate certain ideas and particularly series of of posts and things like that. We did a six part podcast series on how to write, launch, market, sell, and make money from a business book, which we published all at once for people to binge listen on the Youpreneur podcast feed. And it went Off like gangbusters. People absolutely loved it.

So that was ideated using no idea what platform the team used to do it, but it came to me in terms of sort of different sections, different bullet points, and different ideas. I went then ahead and decided to, you know, elaborate on certain things and dive deeper on certain things, or even completely omit certain subjects and topics as well. So I think overall. Is it here to help us?

Yes. Is it here for us to become more productive? Absolutely. Is it something that the average small business ownerslash entrepreneur should be over concerning themselves with?

No, I don't think so. will it contribute to burnout? I think it's like any other system tool or process. it has the ability to get out of control, but We're the ones that are still in control.

That's a beautiful that's why it's our business. Jim James You know, I think that's a really refreshing perspective, but it'd be interesting to hear your view because, you know, we used to have this issue about printing presses and about tractors and all, all mechanization and the internet and so on was all, I wouldn't use it myself, but it sounds as though Chris, you're in a position where you can delegate to people who then gain superpowers by using AI, but you're, retaining the authenticity and the guidance of your own personal brand.

@ChrisDucker Yeah, exactly. And that that's, you know, it's called personal brand. It's not called AI generated brand. I just feel that particularly as a as a personal brand entrepreneur, that if you are creating content and publishing that to be able to build that brand to attract that that avatar that you're wanting to serve, it's gotta be you.

It's gotta come from you. It can't it can't come from a computer or or a program. It's it's the very core of it. has to come from you.

Like I said, you can utilize it to I ideate and get things out of your head a lot faster. That's fine. But ultimately you've got to get it out there and and doing it on your own back. Jim James Yeah, and in some school of thought, really, that the last defense against AI will be being human, know, ironically enough, right, that actually it will be your human element that that differentiates you from from the competition and the big companies.

@ChrisDucker Yeah. Well yeah. And you know, like my good friend Sally Hogshead, who's an incredible New York Times bestselling author and speaker, she said many, many years ago, you know, being being different is better than being better. I do feel that that is still one hundred percent legitimately true.

You know, being being different is much better than being better when you wanna stand out and find the right people to work with, to sell your products, services, experiences, whatever it is. I think it's incredibly important that we don't lose track of that, you know? Jim James Chris, one of the things that struck me listening to your podcast, reading the book and looking at the reviews, you've got Amy Porterfield you've got Sally Hogshead, who I've just also heard the other day too about, better to be different.

And that's a differentiator and a source of competitive advantage long term to be yourself. You've managed over the years to build an amazing community of thought leaders who are both supporting you and that you support What's been the secret to that success? How have you built that? @ChrisDucker Built it slowly.

And I think that's the key. the issue nowadays is that everybody wants things just like that. I think a lot of people, you know, particularly the younger generation of entrepreneurs, they expect things to happen immediately. I've been posting on Instagram for three weeks now, three times a week, and you know, I've only got twelve new followers.

I'm like, well. Be happy. That's 12 people. If you had all those people around for a barbecue, your back garden would probably be full.

You know. So I I think that we've we've got to we've got to understand that when it comes to community building specifically, you know, this is not going to be something that happens overnight. People's attention spans are the lowest they've ever been. and also, regardless of what niche you're serving, you are in a competitive niche now.

The competitiveness of business has never been as high. Jim James Yeah. Yeah. @ChrisDucker as it has today, because the barrier to entry is as low as it's ever been as well.

I truly believe that the reason why I've been somewhat successful in building communities over the years, and there's much bigger communities out there than ours at that at Youpreneur at my personal brand, is that, you know, we've shown up in an authentic way. We've shown up consistently. We've shown up with serving first and selling later, as a philosophy. And we've, you know, we've been around for a pretty long time, Jim.

I think that's the thing is like we've we're about to celebrate eleven years at Youpreneur in September this year. So you can look back on that. You can look back at when we used to run large events at the Queen Elizabeth Center in London. You know, you can look back at the you know the tropical think tank events that we ran in the Philippines, you know, in Jim James Yeah.

@ChrisDucker two thousand seventeen, eighteen, et cetera, et cetera, et cetera. You can look back on all those things, and understand that, you know, we've been around for a while and and if the community is still hanging around, there's gotta be good reasons for that, right? Jim James Yeah. Yeah, and I think that you've touched on a few things I've noticed about what you're doing is one is the generosity, what you share, but also the consistency of quality, Chris, you which is also impressive, you know, having run my own businesses for 25 years, to maintain consistency and focus for that length of time is really impressive.

And as a testament to your endurance, and maybe this is also bringing us a little bit onto the book topic, @ChrisDucker Appreciate Jim James entrepreneurs suffer some form of burnout, especially those of us that start early. You went to the Philippines when you were quite young, think. You went out there for work. I went to Singapore in 1995 as a 27-year-old and started a business.

@ChrisDucker So I was twenty seven when I went to the Philippines, Jim James Chris, in his book, Long-Hall Leader, has got an amazing sort of recipe and framework, part of which is self-care, let's move on to this book and the Long-Haul Leader because, you've managed to do, which is really impressive, is to maintain this quality and this generosity, but also then to reinvent yourself. With this book, The Long-Hall Leader, do you want to just tell us what's been the genesis of that book and tell us why you've written this book?

@ChrisDucker Yeah, so twenty twenty-one, you know, flashback to that we were all in the middle of the pandemic. the first year of the pandemic pandemic 2020, obviously we pretty much like every business on the planet, maybe bar a few, had to pivot quite substantially. at Upina, we are at first a I guess an educational business, right? We help entrepreneurs and particularly personal brand entrepreneurs.

To build their business in a sustainable, profit-driven manner, right? That's what we've always been about. And so we used to do, I would say probably about 80% of that would be done in person at live events, both here in the UK as well as in the US, and even as far as Australia, where I'd run smaller mastermind events and things like that, when I was traveling for speaking engagements, add on an extra two or three days to do these smaller events for our community around the world.

And so I think the big thing here is understanding that if you show up in the right manner for long enough, people will appreciate where that heart centered focus comes from. and that's what I did. In 2020, we pivoted, we went all in on going online. we grew our business 5x in that year, 2020, because we could open up.

everything we were doing to an international, serving people internationally online. And so, you know, at the program at the time was the Youpreneur Incubator, which was a one year program. And we went from about 90 members at the beginning of 2020. Jim James Yeah.

@ChrisDucker To about 380 members at the beginning of 2021. So it just it ballooned, it went mad. and then middle of twenty twenty one, we have our sabbatical every August as a family. And we went away.

And I realized going into that sabbatical, thinking to myself, man, I really need this one. Like I'm exhausted. Like I feel really tired, mentally, physically knackered, you know? And and we we We came back from that at the end of August and I remember walking into this very office at the beginning of September, sitting down, turning on the computer for the first time in a month, and staring at the screen for about, I don't know, ten, fifteen minutes or something, turning it off, walking back out through the doors behind me, and I didn't come back in for another three weeks.

There was something wrong, there was something up because I always have a pep in my step when it comes to work. I loved this is the really ironic thing. Jim James Yeah. @ChrisDucker I was loving the work we were doing.

So I wasn't not enjoying my work. And I think that's a key thing to point out here. Because a lot of people think, burnout, probably hate the work you do. You're showing up for the wrong reasons.

Yada, yada, yada. No. I was showing up for the right reasons. I was loving everything I was doing from a work perspective.

but I was just doing it way, way, way too much, plain and simple. And so, Jim James Hmm. @ChrisDucker I went to the doctor, I had some blood work done. I actually went in and spoke with a mental health expert as well because I was feeling kind of anxiety-driven quite a bit.

and it ended up with me being diagnosed with acute anxiety, depression, and put on antidepression medication initially. and then the big one was phase three adrenal failure, which is a clinical term. For burnout fundamentally. So your adrenals create cortisol, which is your stress hormone.

And when you stop creating that, when your adrenals go into phase one, phase two, and then eventually phase three failure, you don't have any stress hormone. Therefore, you can't handle stress, therefore you burn out even further. And that was basically what had happened. I was on the antidepressants for about a year, slowly took myself off those.

Jim James Well. @ChrisDucker started therapy for anxiety and just talk therapy, nothing sort of intense or anything, just talking through feelings and all that kind of stuff, which I never thought I would, you know, have a therapist in any way, shape, or form. No, a lot of my American friends do. and, you know, fair play to them.

They it's a big thing in America. I'm gonna talk to my therapist about this. but I think it really taught me that even if you're really enjoying what you're doing, if you're doing too much of it. for too long, which I certainly had been, burnout's inevitable.

It's not a matter of if, it's just when. and I think a lot of entrepreneurs are in that spot, you know, they're in that position. Jim James You know, Chris, I think it's really, really important there a couple of things that you said. No, one is that you can be enjoying what you're doing and still burn out.

As you say, the assumption that you burn out because you're forcing yourself to do something that you don't really want to do. But actually I found with my PR firm after a decade and I'd grown it like you and so on. But actually I just also one day just couldn't get out of bed, you know, and you feel this huge sense of anxiety that you're not leading anymore. @ChrisDucker Yeah.

Jim James you feel, you know, that you're not going to make the money, you're not going to look after your team, you don't look after the clients. And but you don't really know where to look, right. @ChrisDucker Yeah. Yeah.

I I'm curious to know your thoughts on this as well. I'm gonna turn the mic back on you here, Jim. when we exited from our larger business in early or early to mid 2023, and we went from almost five hundred employees to at that point probably about thirty or so, I kinda had for the first time really in my career, I think I Of had a little bit of imposter syndrome. I was like, well, am I really like, am I this serial entrepreneur anymore?

Like, I don't I don't have all these people working for me anymore. I no longer have a you know a medium to large sized business that I'm running. Am I still really the that that serial entrepreneur? And I kind of like had this thing that I need to needed to battle with for a little while.

and I spoke with a good friend and mentor of mine over in the United States about it. And she said to me, of course you are. Like, you know, you've exited successfully from this business that you spent 15 years building. You've still got another two businesses.

Like you are a true blue serial entrepreneur. And with her tough love, you know, she kind of slapped me out of it. looking back on that, and I've spoken about this a few times now, like I didn't see that coming at all. Not at all.

when you had your PR agency up and running and and you went through this, how did you feel about this? I'm curious. Jim James Yeah, it's interesting this idea of how we associate ourselves with the company and our identity being in interlinked, right? What one realizes is that we really attach our activity to our identity.

I do things, therefore I'm an entrepreneur. And when I'm no longer doing those things, because I sold off those various businesses like you, not as successfully as you have. But then you find yourself saying, well, am I really an entrepreneur? So Chris, thanks for turning the mic back on me, but coming back to you again, you know.

@ChrisDucker No, it's but it's interesting. You know, I was curious, you gave me a good answer because I just I don't think we're the only ones that think like that. I think a lot of entrepreneurs think like that when they're presented with an opportunity to either and the word exit, there's so many different versions of that. Like you either sell it or you slowly but surely have yourself bought out, or you shut the business down because you don't want to run it anymore.

Like there's so many different ways to look at exiting, right? But I I'm sure there's there's gotta be factors. Jim James That's right. @ChrisDucker Thousands of entrepreneurs right now thinking about this exact same thing of when I'm no longer connected to this thing that I've built, what am I?

Who am I seen as? Sort of thing, particularly in this very social media heavy environment where, you know, everything's a bloody highlight reel right now. On so that's why I don't like social media, really. I'd prefer not to have to include it in my business.

But as a personal brand entrepreneur, it's kind of goes hand in hand, really, you know. Jim James Yeah. Well, and Chris, it's very interesting to say that because one of the conversations I've been having as we move into this next stage of life is, you know, am I an entrepreneur or am I a coach? Am I a business consultant?

Which I think brings us nicely onto a topic in your book, Chris, which is about legacy. Because I thought what you've done really neatly there is to transition from, I'm an entrepreneur to I'm a a citizen. I'm a father. I'm a contributor.

Can we just talk about some of what you've built in the framework there in terms of how entrepreneurs and let's face it, men and women in their 50s and 60s exited or not. how they can redefine who they are, because let's face it, most of us will hopefully live till the 70s, 80s, 90s, maybe have quite a long time to redefine and play an important role in society. Take us through that Chris @ChrisDucker longevity overall is is a is a great thing. And I think that a lot of us are going to live longer than we would have done if we weren't yeah, if if we weren't in this period of time right now, I believe we will probably live on average about ten years or so longer, hopefully, with a little bit of luck, you know, right now.

because of things like and you mentioned sort of some of the biohacking stuff, you know, the Jim James Fingers crossed, yep, yep. @ChrisDucker Red light glasses to promote better and deeper sleep. you know, cold plunges and saunas and, you know, all these other things that I kind of I wouldn't have seen myself doing three, four years ago, but now I'm all over them because if there's anything I can do as a father first and foremost, a husband secondly, and then a leader third, if there's anything I can do to be around longer for all of those reasons, I'm all in on it.

I'm all in on it. Jim James I think again, come back to some of the Americas like John Lee Dumas, they're now talking about, you know, longevity and sustainability, which is kind of a luxury after you've attained wealth, isn't it Chris, to some degree? @ChrisDucker Well, yes, to a certain degree, you are right. this burnout really taught me that if I didn't look after myself properly and be quite selfish about it, that, you know, I wasn't going to be able to build that level of legacy that I really wanted.

And I think as entrepreneurs, we also get a little twisted in our idea of what legacy really is. Like, I want to, you know, build great companies or promote, you know, great charities or, you know, you know, create products that change people's lives, all these other kind of legacy things. At the very core of it, my legacy is going to be my children. And it's a very simple focus of me to enable my children to be able to be more successful than I have become, be happier than I have become, be healthier than I have become, and so on and so on and so on.

And so that's what I'm all about with with my level of legacy is to be able to leave a lasting impression first and foremost on my kids, right? And then secondary to that, to be a great partner, to be a great spouse to my wife and to love on her as much as I possibly can. and then lastly, as a leader, is to be able to help people affect their own level of change, their own idea of change and servitude in in what it is that they're doing from a business perspective as well. You know, there's a really, really good book called Half Time, written by a a gentleman of the name of Bob Buford.

And he talks about going from success to significance. And I think that's a really, really cool way of looking at what legacy really is, you know. Jim James Hmm. Yeah, that's what's interesting as well for me in reading your book and listening to you talk as well as that you've kind of flipped the script because for many people legacy starts with external influence, know, to be famous, to be the first trillion dollar person.

you look at Elon Musk, you know, he's got all the money in the world and he's got 12 children, half of whom are trying to estrange themselves from him, I really enjoyed your book because you've got your personal details, but you've got an intellectual structure. And as an entrepreneur, I also liked that it was practical. But I also really, as it really resonated with your sense that it actually starts, if you like, at home, right? It starts with your children.

I've been very blessed to take my girls to school every day on scooters, first of all, in prams and then scooters, and then on the back of the bike. and then teach them to drive. now they drive themselves to school. Right.

And I love that we've been able to play that role, but I thought it was really interesting that you start with your family and then you go external rather than external to internal. Where does that come from Chris? Because it's a little bit counterintuitive because many people think success is about fame, not necessarily about connection. So where does that come from for you?

@ChrisDucker Yeah. it's just something I've always done, Jim You know, we started my business, you know, with with my wife. She's she's a hundred percent, you know, by my side and supportive. And she runs still now.

I mean, even when we we have almost five hundred employees, not everybody got a handful, like she still runs the finances, she still runs the ops of the business. I'm the face and the marketing and the sales and you know kind of the delivery side of things. My daughter, Chloe, my eldest, you know, she is the COO at UPener now. So she runs things sort of day to day and works with our clients from a an admin and kind of operational sense.

If we put on a live event, it's all her. Like everyone's, Chris, your events are amazing. Like I literally show up, strut myself like a peacock on stage for the weekend and then leave. Like my daughter Chloe does.

Jim James Yeah @ChrisDucker everything. She does everything else. So so she's twenty seven. She's twenty seven.

Jim James Well, and how old is Chloe? Okay. Well, like the magic age, 27, mean, like takes after her dad, Gets in the business at that age. @ChrisDucker Yeah, yeah.

Yeah, yeah. my my eldest, CJ or Chris Jr., he's 30. You know, he he doesn't work for the company full time, but he will help out with videography.

He's an incredible videographer and content creator. He actually works with F1. and then my my second youngest, Charles, he's almost gonna be 18. He is a complete self-taught graphic design and video editing genius.

and then my little girl. Cassie, who's going to be nine in a couple of months from now, you know, she's she's sort of figuring out what she wants to do. One minute she wants to be a vet, the next minute she wants to be an actress. You know, so very, very varied, very varied.

Right, right. And she actually she's a very she's a horse girl. She does horse riding every weekend. She absolutely loves it as well.

to your point, like my kids are always around at our live events as well. Jim James Be a pantomime horse then she could be both, you know, she could do. Dice. @ChrisDucker And in fact, actually last November we ran the second long haul leader summit.

we're taking a break from it this year, but we probably will bring it back in 2027. And there was actually a comment, and I've never encountered this, and I've run events from 10 people around the boardroom table right the way up to 500 people in an arena before. there was a comment from somebody about halfway through the first day. and my little girl Cassie would run up on stage and she would give me cue cards that Chloe had written out to, you know, reminders before lunch and all that kind of stuff.

So she'd run up and she'd give me a kiss and then run off backstage and stuff. And this comment came that somebody in the audience had said that they had they they didn't appreciate the fact that there was children running around at a business event. They thought it was unprofessional. And I just couldn't help myself, Jim.

I had to talk about it. I had to talk about it on stage. if that's your thing, like, it's okay. Like, I'm not looking at you from a negative perspective, but you have to understand that this isn't your event.

This is my event. I'm the one that's running it and putting it on. and one of my favorite things to do is to show my children. what I do for a living and to get them involved in a way that they feel like they're part of the team because they are part of the team, you know.

funnily enough, this lady was not there on day two. She did not turn up on the second day. And so, you know, you're not for everyone is what I'm getting at here, I think. You know, you can't please all the people all the time.

Now I could have avoided talking about that on stage and she probably would have come back on the second day. Jim James Right. @ChrisDucker But that's not me. That's not my personal brand.

And when you feel strongly about something, you know, I think it's something that you should stand behind, you know, and get on your soapbox a little bit about it. and I'm glad that I did it. You know, will she ever sp you know spend money or invest money with us in the future? Probably not, but that's okay because there was another ninety-nine people in the room that day that probably will in some capacity, right?

So I'm fine with it. Jim James Yeah. And I think that brings us in a way full circle back to what you were saying at the very beginning when we took about AI, that it's still you, right? And one of the messages for people to take away, know, for us to take away from this conversation is, know, AI is not going to, is not going to remove the human, not going to remove us from being mission critical to the company.

And I think there's so much sort of anxiety at the moment in the market about AI. It's really nice to hear you talk with such great confidence about the need to be you and to be different. And that's okay. And it won't appeal to everybody, but that's also okay.

And we don't have to try and be, I feel like, homogenous and vanilla flavor. We can be cherry with ice cream and a little bit of something on top. Yeah. @ChrisDucker Absolutely.

Yeah. Absolutely you can. I talk about it in my second book, Rise of the Upreneur. I talk about this P2P philosophy or people to people philosophy that I've had for, you know, well over 20 years now in business.

And that and that is that people will rather do business with people than a logo or a brand. And, you know, I realized this a very long time ago in my career, before I became an entrepreneur, that You know, I was in the infomercial business for a few years in sales and distribution. And I remember we used to go to Vegas every year for a big, big, big conference. It was a three-day conference, massive, massive conference.

And I would be at dinner with some clients. I was the sales guy who would show up looking back on it now, it's just so good. But I would show up with the purchase order pad to dinner. Jim James You would, right?

@ChrisDucker Not to close the deal, not to close the deal, but to be ready if I did close the deal, you know? and and it always got quite interesting reactions. I'd be like, Well, I'm glad that you say that we're gonna go ahead and do this because I've got this piece of paper here and you can, you know, sign up. And they would be like, Wow, like you really thought you were gonna get this business, didn't you?

And I'm like, Well, honestly, I thought that you and I got on with each other, and knowing what I do about my business. Jim James Yeah. @ChrisDucker my business and and the industry. If you get on with someone, then you're more likely to do business with them.

And I'm also the kind of guys, you know, when I when I get the business, I want to make sure I can action it for you, the client, as quickly as possible. So, you know, signing this off now means I can fax it to my team this evening I talk about that a lot. You know, that that instance of Jim James Yeah. it's.

@ChrisDucker being being ready for the conversion that comes from the conversation. When that happens, you should be ready to act on it. But equally understand that people will only really truly do business, particularly today, with people that they really know, love and trust. and it used to be no like and trust.

Jim James Yeah. @ChrisDucker But now it's love. Someone has to love you to do business with you, particularly to do it over and over and over again. So that P to P philosophy is something I still stand by very solidly, you Jim James I do want to ask you, Chris, you know, about demand.

You've got now in your book, you say, you know, you only work Monday to Thursdays, right? And you've got your family working for you. What would you say to the person who says, no, Chris, that's all great for you. You've exited at 50 something.

I can't do that. What would you say to that entrepreneur who's listening to our conversation saying, Chris, I'm happy for you. You say you don't need to use AI. You say you can do this.

You can do blood work. But that's not my life. What would you say to that person? @ChrisDucker Okay, do you.

You know, it wasn't my life for a long time. Simple as that. You know, I I didn't do blood work every quarter until four years ago. I didn't have my ducks in a row, you know, since day one.

You know, I wasn't working f you know, six-hour days, four days a week, when I first started. I was doing 16-hour days, seven days a week. You know, you earn your stripes, Jim, I think is what I'm getting at here. I know that I'm at the point now where I can take my foot off the gas a little bit and I can run things day to day differently to other people.

But guess what? I've been doing it 22 years. I've earned the right to do it. You know, I've done the sleepless nights.

I've I've you know, I've worried about the bank balances. I've, you know, had people try and screw me over, you know, like I've earned the stripes is what I'm getting at. And everybody has to take their own path. So if you see somebody else doing all these things and you think, Well, I I can't do all those things, yes, sure.

Do what you need to do right now. But when you are in a position to be able to hit the pause button a minute and step back and look at what it is that you've built and how you've built it, ask yourself the question, how am I going to be able to sustain this? Because as I talk about in the book, hustle is a season. It's not a lifestyle.

You can hustle up. There's nothing wrong with hustle, but it's not sustainable. It's not a longevity plan. And so, you know, if you want to be in business 20, 30, 40 years, that's not a sustainable situation.

You've got to be able to figure out what to do. And maybe it comes down to, you know, team building and delegation. Maybe it's coming, maybe it comes down to slowing things down across the board. maybe making a little less money.

but making it for a longer period of time. Like, you know, everybody has their own different goals, right? Jim James Yeah, and think Chris, what's wonderful is a couple of things. One is that you've shown what can be accomplished in spite of burnout to reposition and rebuild.

You've demonstrated the potential that it's never too late to come back and it's never too late to redefine and rebuild yourself. But also in your book, there is a genuine framework that people can follow, which I, you know, I personally have found use. @ChrisDucker Mm-hmm. Mm-hmm.

Jim James in your book just over the weekend and started to take notes for how I can do things differently. Chris, if people want to find out more about you, obviously, and want to find out about Long Haul Leader book, where can they do that? @ChrisDucker Well, I wouldn't be much of a personal brand entrepreneur if I didn't have Chris Ducker dot com, would I? So that Jim James That's my first piece of advice to my clients is buy your domain name.

Right? Yeah. @ChrisDucker Yeah. Yeah.

I I've got all my kids as well, by the way. My eldest my eldest actually bought the domain name off me. I probably registered it for about fifteen years or something. He eventually bought it off me a few years ago, for the measly sum of just fifty pounds, even though I probably spent ten times that amount looking after it for them.

Yeah. Jim James Yeah. Thanks for setting the price. I've bought them for my daughters as well, funnily enough.

So now you've given me a good pricing @ChrisDucker Yeah, yeah. I've got hers as well. I feel like I'm we're just incredibly blessed to be alive at this time as entrepreneurs. There's so much opportunity out there, but I'm also really, really aware now at this point.

I kind of look at where I'm at right now, Jim as like this is my second act. I'm just really aware of the fact that success that costs you your your health, your relationships, you know, that sort of thing, it isn't really success at all. It's sacrifice. And so I'm just very aware of that right now.

I'm also aware of the fact that, you know, being busy is a bit of a trap. You know, impact should be the real focus. And when You know, any any idiot can fill up a calendar, you shouldn't be looking at that that motion as a way of momentum. And I think it's important to to focus more on the momentum side of things rather than just saying, I'm so busy, I've got so many things in my calendar.

Well, look at those things. You know, a very wise man once said to me, you know, show me your calendar and I'll show you your priorities. and I always thank Michael Hyatt for asking me that question because he's still a close friend and a mentor he actually wrote the foreword for the long haul leader as well. So I was very, very blessed for him to be involved with a project too.

Jim James Yeah, I saw that as well. Well, I think we've been blessed, Chris, that you've come on the show. Thank you. And I think that, as you said, you've really earned your stripes.

I've watched your career and read your content, listened to your podcasts. so, I will appreciate you. And I think really appreciate your honesty and your courage and exposing your vulnerability, but also in creating a framework that helps others to move through their journey. So Chris Ducker, thank you so much for joining me today on the Unnoticed Entrepreneur.

@ChrisDucker Thank you. Thank you, mate. Appreciate it. Thank you.

It's a pleasure. Had lots of fun.

Related episodes across the Index

Other episodes covering the same guests and topics, from across The B2B Podcast Index.

  • Chris Ducker on Leading for the Long HaulLean Marketing · features Chris Ducker77 / 100
  • Ep 727 Becoming A Long-Haul LeaderHR Interviews Playlist · features Chris Ducker55 / 100
  • The Last Ever EpisodeConfident Live Marketing Show · features Chris Ducker38 / 100
  • From Fried to Focused: Burnout fixes for personal & business growthNot Nice. Clever. · on burn out66 / 100
  • How Jake Kelfer Leveraged The Power Of Networking | CEO StoryThe CEO Story · on Chris Ducker53 / 100
  • Why Reputation Is the Most Valuable Asset You Own with Amber Erickson-Hurdle of Brandage AcceleratorThe Vacation Rental Show, Hosted by Lynell Gordon · on Sally Hogshead49 / 100

More from Jim A. James & The UnNoticed Entrepreneur

All episodes →
  • Your Website Can't Compete With This New Rule71 / 100
  • The AI Voice Problem Nobody's Talking About in Podcasting.
  • How to Survive The Big AI Reset Happening Now, with Brad Sugars.
  • Vibe coding...the risks to your business and how to avoid them.
  • Don't pay Dumb tax - Learn These Rules Now Before It's Too Late!
Explore the best B2B Startups & Founders podcasts →
All Jim A. James & The UnNoticed Entrepreneur episodes →