In short
The business owner’s dilemma—why selling or reaching financial freedom doesn’t guarantee fulfillment—and a framework (WISE) to plan intentionally. Ali argues entrepreneurs need courage (not constant confidence), and wealth is a means, not an end. He outlines three dilemmas: reinvestment (what to do with capital), legacy (what wealth is for—kids/charity/ego), and exit (scale vs sell and whether it supports purpose). He also challenges “retirement” for entrepreneurs, proposing “return on life experience” (ROL E) and a “2535” work-life target (e.g., 25 hours/week, 35 weeks/year). Notable example: a business owner who could buy back his sold company for 20 cents on the dollar but chose lifestyle/family time over conferences and “putting out fires.”
Guests
Ali Nasser—number one Amazon bestselling author and entrepreneur who helps business owners find their path and create desired lives; JLD (host) is John Lee Dumas of Entrepreneurs on Fire.
Written by AI. May contain mistakes. Listen to the episode to check what was said.
Chapters
Tap a time to open that second in VOCourage Over Confidence in Entrepreneurship
1:04 to 2:25
Understand the importance of courage for entrepreneurs in facing challenges.
“We'll book you eight to 20 qualified calls each month, then train you to run the system yourself.”
Ali's Purpose and Mission Behind His Book
2:25 to 4:48
Explore Ali Nasser's journey and motivation for writing 'The Business Owner's Dilemma'.
“Just like you had to take your medicine as a child, that castor oil, we swallow it down and we have the courage to do that every day.”
Three Dilemmas Every Business Owner Faces
4:48 to 6:40
Learn about the reinvestment, legacy, and exit dilemmas that business owners encounter.
“owners that might be earlier in the journey or those that are going through that transition, help them have more clarity as to what's coming and how to better prepare themselves for the journey.”
Unique Challenges Entrepreneurs Face in Planning
6:40 to 10:59
Discover how entrepreneurs' unique situations affect their planning strategies.
“Successful owners are going to face the first dilemma they face is called the reinvestment dilemma.”
Unique Challenges Entrepreneurs Face in Planning
11:07 to 12:54
Discover how entrepreneurs' unique situations affect their planning strategies.
“This is a custom LinkedIn client acquisition system built to help you connect with the right prospects, start real conversations, and turn those conversations into booked calls.”
Why Entrepreneurs Don't Truly Retire
13:00 to 14:00
Understand the reasons why many entrepreneurs continue working past traditional retirement age.
“And as I mentioned before the break, so many people have this golden vision for retirement.”
Creating Your Ideal Life Experience
14:00 to 16:20
Learn how to map out your ideal life and pursue your entrepreneurial vision.
“You're always going to be looking for opportunities that you can capture.”
The WISE Framework for Entrepreneurs
16:20 to 19:24
Discover the WISE framework to integrate wealth and enhance business success.
“Now I want to talk a little bit about the WISE framework, W-I-S-E.”
Return on Life Experience: A Paradigm Shift
19:24 to 21:36
Understand the importance of prioritizing life experiences over traditional returns.
“You have another amazing acronym, ROLL, Return on Life Experience, which you've already talked about a little bit.”
Taking the WISE Assessment
21:36 to 22:32
Learn about the WISE assessment and how it can help clarify your goals.
“The Business Owner's Dilemma is helping give business owners a lens so they can see their position more clearly so they can make those better decisions.”
Transcript
Automatic transcript. May contain errors.0:02John Lee Dumas:Who's ready to rock today, Fire Nation? JLD here, and welcome to Entrepreneurs on Fire, brought to you by High Level, the all-in-one sales and marketing platform. On today's classic episode, we'll be breaking down the business owner's dilemma. And to drop these value bombs, I brought Ali Nasser into EO Fire Studios. Ali is a number one Amazon bestselling author and entrepreneur who helps business owners find their path and create the life they truly desire. And today we talk about how entrepreneurs need a framework to see their position clearly and act more intentionally towards their goals and how wealth is a means, not an end.
0:32John Lee Dumas:Financial freedom alone doesn't guarantee fulfillment and oh, so much more. And a big thank you for sponsoring today's episode goes to Ali and our sponsors. Stop duct taping your business together. High Level runs your website, your funnels, email, automation, scheduling, payments, and memberships all in one place. And when you sign up at highlevelfire.com, you get a 30-day free trial, plus my exclusive bonus stack that includes weekly office hours with me and much more. Visit highlevelfire.com, highlevelfire.com. Fire Nation, if you have a high ticket offer and need more quality leads, Nexus Install is designed for you.
1:09John Lee Dumas:We'll book you eight to 20 qualified calls each month, then train you to run the system yourself. Email my team at john at eofire.com to learn more and see if Nexus is the right fit for you. Ali, say what's up to Fire Nation and share something that you believe about becoming a successful that most people disagree with. What's up, Fire Nation? JLD, great to be with you. That's a great question. And I think that the biggest thing that comes to mind is people assume entrepreneurs or business owners, they have confidence, confidence, confidence, and that there's always a sense of confidence in what they do.
1:50when in reality, I think it's a function of courage. It's not that entrepreneurs are always confident. I think we make a lot of mistakes and we fail often, but we have the courage to take risk. We have the courage to get back on our feet. And I think that oftentimes people think it's confidence when in reality, courage is the underlying trait that I think makes us do what we do.
2:16John Lee Dumas:Oh man, doubts, fear, stress, anxiety. we force that down for breakfast every single day, Fire Nation, because that's part of being an entrepreneur. But guess what? We swallow it. Just like you had to take your medicine as a child, that castor oil, we swallow it down and we have the courage to do that every day. So I do love that phrasing. That was cool, Ali. And as we're talking about the business owner's dilemma, I want to start by talking about your why, Ali, your purpose and mission for writing the business owner's dilemma. Thanks, Sean. I've spent almost 20 years guiding, helping entrepreneurs while also being an entrepreneur myself.
2:56And about seven to 10 years ago, I had a few experiences that completely changed the trajectory of my life. And I had some business owners I was working with that had all sold their companies. Exit, really substantial exits, 20 million, 100 million. The largest was 500 million. just sums of money that were just enormous. And while they had complete financial freedom and complete financial independence, the majority of them were struggling. They were struggling with the life after, they were struggling with big dilemmas they were facing, they were struggling with their identity. And watching them go through such a challenging period when you assume you just made it.
3:39You just hit the jackpot. You reached the summit. And watching them struggle, it crushed me. And it made me hyper aware that wealth is a means and not an end. And that if you're not really clear about what your end goal is, you can have all the wealth in the world. You can have all the financial freedom in the world, but you're not mentally free. And when I saw this happen, it made me lean in. It made me take greater care and greater attention to what they were going through what was going on. And what I learned in those few years working with those business owners, what the approach, the system, the paradigm shifts, the psychology, the planning, all the work that I was doing with these owners, it made a massive impact on their life.
4:24And not just from a standpoint of return on investment, but return on life experience and what they truly wanted to get as a result of their wealth. And once I kind of discovered the impact this made, I said, I really want to expand this message. I want to share this with every business owner. And how can I democratize this framework and share it with the world? And that was my motivation for writing the book, The Business Owner's Dilemma, is to make that impact and to help other business owners that might be earlier in the journey or those that are going through that transition, help them have more clarity as to what's coming and how to better prepare themselves for the journey.
5:06John Lee Dumas:It is mind blowing to me that as entrepreneurs, we set off on this journey of like, I'm going to create the best solution to a real problem. I'm going to create a company. I'm going to create a business products and services that are going to help so many people. And you do that. And it's so much work and so much stress and so much failure. And then you finally reach the pinnacle and you do what you've been dreaming of all these years is you sell, you are acquired and you have that huge financial windfall that's, you know, frankly, a reason why so many people do this so they can provide for their families and build generational wealth and all this jazz too.
5:37John Lee Dumas:And then it's the worst day of their life. And I've interviewed people over and over again who are on their second, third, fourth venture who look back and say, man, I thought I was done after one when I was building it, but it ended up being the worst day of my life. And it was so hard for me to understand back early in my journey. I couldn't get it, but hearing it now thousands of times, 3 ,700 plus interviews I've done. So many of those people have faced scenarios like this. And I was like, man, there, there just has to be a better plan in place. It has, it has to be talked about more often.
6:08John Lee Dumas:So people are prepared and ready for this. Cause that was the thing. They just weren't prepared for it. They weren't ready for it. You know, just like somebody that works till they're 65 years old thinking they're going to retire, get a gold watch and have the best, you know, you know, 30 years of their life or 20 years of their life into retirement ends up, you know, within a year or two, you know, some people like to say the biggest cause of death for a retiree is retirement because they lost that focus. They lost that relevancy. They lost that meaning to be alive. So there are three dilemmas that every business owner will face, Ali.
6:41John Lee Dumas:What are they? Successful owners are going to face the first dilemma they face is called the reinvestment dilemma. And this is, I've been successful in my main company. I'm making great profits. What do I do with the capital? Do I reinvest it back in my company? Do I invest it in another company and private equity and real estate and the stock market and cash and crypto? What's my best reinvestment strategy for my balance sheet? That's kind of the first critical dilemma a successful owner will face. The second dilemma is the legacy dilemma, which is what is it all for? All the wealth that I've built, all the wealth I'm accumulating, perhaps more wealth than I'll ever need.
7:20Is it for fun? Is it for my children? Is it for charity? Is it for ego? will my wealth be a source of empowerment for my children or a source of entitlement for my children, right? What's kind of the purpose behind everything that I'm building? That's the second dilemma or referred to as the legacy dilemma. And then the third dilemma is the exit dilemma. I've built a successful company. I could scale this business or I could sell this business. Does it make sense to sell it to my executive management team, to private equity, or should I leave it to my son or daughter? If I did sell my company, would I now have the freedom to pursue my life's purpose?
8:02Or will I have just sold? Will I have just sold my life's purpose? These are all different functions of the exit dilemma. And what I've found in working with successful entrepreneurs for nearly two decades is that when it comes to planning their life's work, 90 % of the mental real estate surrounds one of these three dilemmas in some form or fashion. and the reason the dilemmas are so challenging to address is they're both a wealth decision and a life decision and when you're when you're hitting the intersection of both wealth and life things can become a lot more emotional a lot tougher to handle but these are these are the
8:39John Lee Dumas:three dilemmas and how they manifest so fire nation there's only so much we can talk about during this interview but of course the business owner's dilemma goes in depth into these three dilemmas. So if you're like, yes, one, two, or all three of those, I need to know more about, you know where to go. Because I want to talk next about why. Why planning is so different for entrepreneurs. Entrepreneurs, we're wired entirely different from a pure DNA standpoint, that usually we're very different in our approach than most individuals. And for many entrepreneurs, you started your first business when you were 10 years old or 14 years old, you had to cut the grass or you had a lemonade stand and you kind of evolved from there.
9:22And then today, chances are you've got 90 % of your net worth in one micro cap stock, which is your company, and 200 % of your emotion also invested in that business. And your balance sheet, your goals, your desire for control are very different than anyone else. And when you consider the way that professional guidance this is created, it's created for the masses, whether it's financial, tax, legal, different solutions in the marketplace are created for the masses because they're the masses. That's the big market share. When entrepreneurs, because of their unique balance sheets and being so concentrated in their own company, the entire landscape for planning changes.
10:05And it all surrounds around that company. And then from an education standpoint, entrepreneurs love control, They love to simplify the equation versus make it complicated. So a planning approach needs to adhere to those unique nuances that the entrepreneur has versus what the masses have, where they might just be saving money in a 401k or retirement plan, hoping that one day it'll be enough capital to give them income. Entrepreneurs are constantly moving, constantly changing, and their risk profile is entirely different because of this concentrated risk in their own company.
10:40John Lee Dumas:Fire Nation, I really hope you're understanding this planning process and why it's so different for entrepreneurs than it is for just your, let's just call them civilians, you know, people that don't go down this entrepreneurship path. And we're going to be talking about a golden vision for retirement. We're going to talk about the WISE framework and also the return on life experience when we get back from thanking our sponsors. Fire Nation, if you have a high ticket offer, but you are not getting enough quality sales calls on the calendar, Nexus Install is exactly what you need. This is a custom LinkedIn client acquisition system built to help you connect with the right prospects, start real conversations, and turn those conversations into booked calls.
11:24John Lee Dumas:Here is what makes it different. We do not just hand you a bunch of theory and tell you, good luck. We build the system with you, dial in your audience, sharpen the messaging, run the outreach, and aim to book you 8 to 20 qualified calls each month. Then once the system is proven and installed, we train you on how to run it yourself so you are not dependent on another agency forever. If you have a strong offer, a clear result, and are ready for more quality conversations with real prospects, email my team at john at eofire.com, and then we'll set up a call to see if Nexus install is the right fit for you.
11:59John Lee Dumas:Simple, focused, and built for predictable, long-term, quality lead flow. Fire Nation, ideas are exciting, but systems will allow you to create freedom. That is where High Level comes in. High Level allows you to build and run your entire business from one platform. Website builder and hosting, funnel and landing pages, email marketing, automation and workflows, calendar booking, payments and subscriptions, even course and membership hosting. Everything works together. seamlessly plus award-winning 24 seven support. So you are never stuck. And when you go through my link at high level fire.com, you unlock my full bonus stack, a 30 day free trial of high level with full access, a private 15 minute coaching call with me, weekly live office hours with me, a digital copy of my book, the common path to uncommon success, my 50 days to something execution roadmap and more.
12:50John Lee Dumas:Stop piecing tools together. Start building momentum. them. Visit highlevelfire.com and start building your something today. Ollie, we're back. And as I mentioned before the break, so many people have this golden vision for retirement. What the last 20, 30 years is going to look like after they've worked 40 plus years in a certain industry or company. And we all know how that pans out for most people. Hey, some people have fantastic retirements. I'm happy for them, but some people don't. but I want to talk about why entrepreneurs actually don't retire. JLD, one of the chapters in my book is on entrepreneurs don't retire.
13:29And there are certainly exceptions to the rule, but the norm is, and as you mentioned earlier in our conversation, is that they might sell their company, but then they get back on the saddle and they do something else. Or they might have enough wealth that they don't have to work, but they want to work. The best analogy I can give you is if you're an artist and you sell enough artwork, that you now have financial independence, does that mean you're going to stop painting the next day? Of course not. You're going to continue to paint. It's your passion. It's your purpose. In a similar way, if you've got that entrepreneurial spirit, you're always going to be looking for ways that you can create value.
14:06You're always going to be looking for opportunities that you can capture. So the concept that I try to promote in the entrepreneurial community is, what's the return on life experience or the role, R-O-L-E, what role do you want to play in life? And what does that look like? And paint that picture, paint that vision. For me, I have an Excel spreadsheet and I categorize all the different things that I love to do in life. And I lay it out into a 365 day time map where I can say, this is how many days a year I want to be traveling and exploring. This is how many days a year I want to be working. This is how many days a year I want to be teaching or podcasting or sharing the message.
14:46And by creating that time map for like my ideal life, it's like, that's the return on life experience I want. And a little example of that is in my ideal world. And I'm getting there. I'm not there yet. We're all working on it. It's I'd love to, I'd love to work 25 hours a week, 35 weeks a year. It's a 2535 five kind of formula. And that's all that I want to have committed to having to work. I might work more, I might choose to do different things, but I've got an end goal that I want to get to that 25, 35 plan. And I want to be in a place where I can embrace nature, be with family, pursue the entrepreneurial vision, take care of my health, build a family, and bring these different things together.
15:30That's the return on life experience that I want. So when it comes to retirement, for me, if there were entrepreneurs version of retirement, that would be it. It's pursuing your purpose. Because at the end of the day, what gives us joy as human beings is being able to use our gifts and pursue our purpose. So if we wake up every morning and like, gosh, you're using your gifts, you're helping people, you're making an impact in the world, you're creating value for yourself, you're going to feel fulfilled. And if you can create that life experience that combines the perfect balance of what it is that you want.
16:03Well, you don't even need retirement because your life, you're living the ideal life experience that you truly desire.
16:10John Lee Dumas:Fire Nation, this is powerful stuff. I love that 2535 framework and just the overall way of looking at what our future can hold. Now I want to talk a little bit about the WISE framework, W-I-S-E. Fire Nation knows I love acronyms. Focus is actually my favorite acronym, follow one course until success, focus. What is the WISE framework? JLD, I love that. The WISE framework, so WISE stands for the Wealth Integration System for Entrepreneurs. And essentially, wealth is everything that you have, not just money, but your values, your assets, your businesses, all the things you hold dear. And how do you integrate all those pieces together as an entrepreneur.
16:58Essentially, that's what WISE addresses. So one of the challenges is, as entrepreneurs, we don't have a framework to see our position more clearly. In many cases, we are building, building, building, and it's functional chaos in some ways. And having a lens or a framework that we can see all of our position is very helpful, both for us to be more intentional with planning our goals, as well as having the integration that it is that we desire from the people that support us, our family, our teams, our professional advisors. So there's six components within the wealth integration system for entrepreneurs.
17:34And similar, I know many entrepreneurs use a system called EOS. And actually, Gino Wickman, who the creator of EOS, was one of the early collaborators on my book. And what he referred to Wise as is, it's like EOS, but for a business owner's personal wealth. And the six components essentially uncover the first is a balance sheet strategy, which is how are all the different assets that you have working together to build the ideal outcome that you want from a wealth standpoint. Next is liquidity and cash flow, all the capital that's coming in, going out, how it's positioned. Third component is lifestyle and legacy.
18:13What's for you and what's for others that might be part of your legacy, children, charity, etc. The fourth is exit strategy, which is begin with the end in mind. What's your end goal for the company? Even if it's just cashflow, what's the plan? How are you getting there? The fifth component is asset protection strategy. How do you protect everything that you've built? And the last component is a lifetime tax strategy. How do you pull all the pieces together in a way that is going to minimize not just the annual tax that you pay, but the tax that you pay over your entire lifetime. And by bringing all these pieces together, you can then look at different aspects of your planning, look at different aspects of your wealth, look at different decisions, and see how they impact each other.
18:57Because the biggest mistake that many entrepreneurs make when it comes to planning any of this is they look at one component in isolation, and they don't have a holistic view. And when you don't have the holistic view, it usually leads to major planning gaps, or it's a less than optimal solution because you didn't know what other levers you had available. So the WISE framework allows a business owner to see all those pieces much more clearly and essentially enhance their success.
19:24John Lee Dumas:You have another amazing acronym, ROLL, Return on Life Experience, which you've already talked about a little bit. But is there anything else you want to add to that before we end with a bang? I'll share a little story with you. A business owner of mine, he had sold his company and he came to me and he said, hey, my company that I sold several years ago, we're able to buy it back for 20 cents on the dollar. And my management team and the old executives I used to work with, they came back to me and said, hey, we want you to lead this again. We can go back and we can buy the company and we could make a huge return over the next five years.
20:04And he said, I've got the deck and the Excel documents I wanted to show you and kind of review and get your opinion. But I just want to talk to you about it. And I said, well, what are your, before we look at the documents and spreadsheets, what are your thoughts or feelings about all of this? And he goes, you know, Ali, I just really love climbing mountains. And I really love the lifestyle I have right now. And I love the family time that I'm getting. And my hesitation with all of this, even though there's a lot of money involved, I know that if I get back on this saddle and do this again, I'm going to have to be on conference calls during the day.
20:35I'm going to have to put out fires. I know I'm going to have to be involved. And that's my concern. So I looked at him, I said, sounds like you've already made your decision. Do we even need to look at the spreadsheets? And he had this big smile on his face. He said, no, we don't have to look at the spreadsheets. That's what I needed to hear. I just needed someone to validate that for me. And it was one of those moments where he had spent many, many years focusing on return on investment, return on investment. But he was at a point where at this point in life, what was more important to him was the return on life experience.
21:09And he still had investments and things that he was doing to grow and build. But he was at a place where something else is more important to him. And he was pursuing that. And the whole concept behind a role is there's not a right or wrong. There's just different phases in life where you may focus on different things. But having the intentionality and the clarity to be able to make that choice is really, really powerful. and everything that I've poured into the book, The Business Owner's Dilemma is helping give business owners a lens so they can see their position more clearly so they can make those better decisions.
21:47John Lee Dumas:Well, if we want a more in-depth look at that lens, what's your call to action for our listeners today to get this book and then we'll say goodbye. Definitely read the book. It's up there on Amazon, but the call to action I'll tell them is the most powerful thing you can do is to take the WISE assessment to get clarity over where you are today, your current position, how do you score and how is your current position versus where you ideally would like to be. And the URL to do that is WISE, just W-I-S-E, wiseglobalnetwork.com slash assessment. Or if you go to the WISE Global Network page, you'll see a button there for taking the assessment.
22:28But wiseglobalnetwork.com forward slash assessment. And that's the number one thing you can do to get total clarity as to where you are today, get perspective of where you would ideally like to be and start building the path towards getting there.
22:42John Lee Dumas:Fire Nation, you're the average of the five people you spend the most time with. You've been hanging out with Ali and JLD today, so keep up that heat. Head over to eofire.com. Just type Ali, A-L-I, in the search bar. The show notes page will pop up with everything that we've talked about here today. And of course, wiseglobalnetwork.com slash assessment. Get over there. Take that assessment today. Ali, thank you for sharing your truth, knowledge, value with Fire Nation. And for that, we salute you and we'll catch you on the flip side. Hey, Fire Nation, a huge thank you to Ali for dropping value bombs and sponsoring today's episode.
23:22John Lee Dumas:Fire Nation, are you ready to rock your very own podcast? Check out our free podcasting course where I will teach you how to create and launch your podcast for, you guessed it, free, freepodcastcourse.com, freepodcastcourse.com. I'll catch you there or on the flip side. stop duct taping your business together high level runs your website your funnels email automation scheduling payments and memberships all in one place and when you sign up at high level fire.com you get a 30-day free trial plus my exclusive bonus stack that includes weekly office hours with me and much more visit high level fire.com high level fire.com fire nation if you have a high ticket offer and need more quality leads nexus install is designed for you We'll book you 8 to 20 qualified calls each month, then train you to run the system yourself.
24:14John Lee Dumas:Email my team at john at eofire.com to learn more and see if Nexus is the right fit for you.
From the publisher
From the archive: This episode was originally recorded and published in 2022. Our interviews on Entrepreneurs On Fire are meant to be evergreen, and we do our best to confirm that all offers and URL's in these archive episodes are still relevant.
Ali Nasser is a number 1 Amazon bestselling author and entrepreneur who helps business owners find their path and create the life they truly desire.
Top 3 Value Bombs
1. Entrepreneurs need a framework to see their position clearly and act more intentionally toward their goals.
2. Wealth is a means, not an end, financial freedom alone doesn't guarantee fulfillment.
3. Dilemmas are hard because they sit at the intersection of wealth and life, making decisions more emotional.
Improve Your Return on Investment as well as Your Return on Life Experience - The WISE Assessment
Sponsors
HighLevel - The ultimate all-in-one platform for entrepreneurs, marketers, coaches, and agencies. Learn more at HighLevelFire.com.
Nexus Install - Have a high-ticket offer? Nexus Install builds you a custom LinkedIn prospect booking system designed to generate more quality sales calls. Email JLD at John@EOFire.com to learn more.
