On this episode of Financial Behavior Thought Leaders, host Dr. Mary Bell Carlson welcomes Jonathan Ainsley, a renowned keynote speaker with over 40 years of experience in the financial services industry. Jonathan is known for his transformative approach to financial planning, inviting both advisors and their clients to reimagine what it means to age, connect with technology, and deepen our relationships with ourselves and others. This episode goes behind the scenes of Jonathan’s unique perspective, unpacking his signature framework—the “three revolutions”: flourishing longevity, technology’s disruptive power, and the shifting landscape of relationships.

Mary and Jonathan begin with his personal journey, tracing his fascinating career path from bond broking and day trading featured in the Wall Street Journal to deep expertise in practice management at top firms like SunTrust, Schwab, and Merrill Lynch. Jonathan shares how his own discomfort with public speaking transformed into a passion for inspiring audiences, particularly around the profound societal shift from traditional retirement models to longevity planning. Mary and Jonathan delve deeply into how longevity, in both mindset and practical terms, is changing financial services—and why financial advisors must evolve to meaningfully guide clients across decades, not just dollars.

They discuss the growing need for financial professionals to go beyond numbers and embrace a holistic, human-centered approach. By weaving together stories from his workshops and keynotes, Jonathan illustrates how both advisors and clients have been profoundly changed when encouraged to think expansively about their futures. The conversation also explores the challenges—and opportunities—presented by AI and rapidly advancing technology, as well as the essential inner work advisors must undertake to serve clients fully.

Five Key Takeaways:

1. Longevity Planning is the New Frontier - Jonathan urges advisors to transcend the outdated retirement model and embrace “longevity planning.” With people living longer, more vibrant lives, he believes the industry must shift from simply ensuring clients don’t outlive their money to helping them thrive for up to four additional decades. This means encouraging clients to envision what living well across a 40-year “bonus round” could truly look like—and aligning financial, health, and personal goals accordingly.
2. The Power and Disruption of Technology - AI and technology are not just tools—they’re revolutionizing the advisor role. Jonathan emphasizes that while AI can take over knowledge and analytical tasks, the irreplaceable value advisors bring is wisdom, empathy, and the human touch. Advisors must focus on building trust, facilitating change, and supporting clients through emotional and psychological transitions, not just monetary ones.
3. Flourishing Longevity is Holistic - True flourishing in later life is about much more than financial metrics. Jonathan’s work recognizes the critical importance of metabolic health, mindset, purpose, community, and financial fitness—what he calls the six pillars of flourishing longevity. Programs and tools like his Flourishing Longevity Scorecard and the “InvestinU” platform help clients and advisors holistically assess where they are and create actionable strategies for growth in all areas of life.
4. Relationships and Inner Work Drive Fulfillment - One of Jonathan’s most powerful insights is that the third “revolution” is relational—both our connections with others and with ourselves. As the nature of career and life stages evolves, fulfillment becomes a central goal. Advisors must address not just client portfolios, but also purpose, resilience, community, and helping clients navigate personal transitions. Importantly, this requires advisors to do inner work themselves: addressing their own fears, beliefs, and aspirations so they can authentically support others.
5. Real Transformation Requires Action and Sustained Engagement - Jonathan goes far beyond inspiring keynotes—he’s committed to creating ongoing, measurable change for both advisors and clients. He offers training programs, workshops, and experiential journeys (such as the NASA-approved 12-module CE program), along with practical self-assessment tools. The feedback is resounding: advisors report newfound purpose, engage clients in deeper ways, and see business impact through increased referrals and client satisfaction.

This episode is a must-listen for financial professionals, event planners, and anyone seeking to understand—and leverage—the profound shifts shaping the future of aging, technology, and financial advice. Jonathan Ainsley’s story, expertise, and generously shared frameworks offer inspiration and tangible next steps for creating a truly human—and impactful—financial services experience.

If you’re seeking a speaker who brings not just expertise, but genuine transformation to your organization or clients, Jonathan Ainsley is helping folks unlock new possibilities—at work and in life.

Welcome to Financial Behavior Thought Leaders. I'm Mary, and this podcast takes you behind the scenes with the top speakers in financial services. So whether you're a financial advisor, an event planner, or a financial professional eager to learn from industry thought leaders, you're in the right place. Be sure to subscribe so you don't miss a single conversation. Today we're featuring Jonathan Ainslie, a transformative speaker who is inviting us to reimagine how we age, how we relate to technology, and how we relate to ourselves. He calls these the three revolutions. Flourishing, longevity, technology, shifting role and relationships, especially the inner relationship with ourselves. So let's dive into his journey, his vision, and a story that always resonates.

Welcome, Jonathan.

Thanks, Mary. Very excited to be here with you today.

Me too. Jonathan, before we get started on the three revolutions, I want to hear about your speaking journey. What brought you to the stage?

What brought me to the stage? So financial services, 40 years. This is my 40th year of being involved. The first 20 was more at the other end. So bond broking. I even got featured in the Wall Street Journal for day trading in 1999, and then spent three years day trading when I arrived here in Central Florida. But then the pivot began to occur. So initially working at SunTrust as a licensed banker, and then 19 years ago, I joined Schwab on the independent side, working with the RIAs. I really enjoyed being on the sort of the practice management side, and that led to joining Merrill lynch for seven years.

And, you know, along the way, that pivot, I think one of the first Schwab events where we had to do our little pitch at some event, and standing there all wobbly kneed, thinking, oh, gosh, this is too much to do. 10 seconds. But somewhere along the line, the sort of the evolution has occurred. So getting more comfortable with doing it and then being excited, you know, the reaction from the audience. And then also this journey that I'm on around the whole sort of longevity realm expands way beyond financial services, and it just feeds off itself. So it motivates me in, you know, wanting to do more and having fun doing it well.

And that's what I really want to dive into is what you call the longevity realm. So I think let's back up a minute. Let's talk about longevity, how you define it and how it really shapes our lives. Start there.

Well, in a nutshell, I think we have it all around. So my grandmother, for instance, spent 30 years pretty much promising me each year would be her last because she was too Old and frail to go on and made it to just shy of 101. And if you think about it, the retirement model centered on 65, which most of us programmed on, I have amazing conversations with 20 year olds and they're still talking about retirement and things like that. But this model of retirement is nearly 100 years old. And yet the reality and the realm of these longer lifespans, many are living far longer than they expected. And yet we haven't really made this pivot or upgrade from retirement planning to longevity planning. And so at the end of the second workshop that I did still at Merrill in the Villages, one of the top places to age in the country, I had a 65 year old write, this workshop is all about the next 40 years, not just about the dollars. Well, how many 65 year old men or women are considering the possibility of the next 40 years? Whether you achieve that or not, once you open up that space, you've created a whole new landscape that most people don't operate on.

So it's really diving into what that looks like for the next 40 years. It's kind of envisioning or a vision board of the future and not just looking at the dollars and cents of it all.

Yeah, very much so. You know, and again, this is so fascinating. I was watching a YouTube recently of 103 year old man who doesn't use a walking stick, takes no medication. And you know, the question I asked myself was, what have I got to do to arrive at that point? Similarly, so run this dependence on, you know, the conveyor belt of aging. And you know, I've had advisors say to me that their clients measure which day of the week it is by which doctor they're visiting. So, you know, you have this sort of mindset of resignation of what's ahead versus again, once you open up to what I call this room of longevity and you turn the lights on and see how magnificent it might be. As one financial planner said, it's like a whole new world in our industry that no one's talking about.

So help me understand why now. Why is this such an important topic for financial advisors now?

Well, I think we're sort of creeping into the duality of both longevity. So there is the reality that if you are sitting with a, you know, for instance, 65 year old and you are helping them, you know, you may be doing a Monte Carlo simulation to age 95. And again, my experience at Merrill, going desk to desk, office to office, that is reality. But what's the real level of engagement around that and you know, the world has changed. In the 60s, you had Paul McCartney singing about fear and frailty. Will you still need me? Will you still feed me when I'm 64? Go look online at his world tour, aged 82. It's incredible. You can see the whole concert.

And again, this is a world tour. So when you look at the energy and how he still sounds, the world has changed. But all too often our mindset is still stuck in this, what we've been fed with and programmed with. But why now A that reality in terms of most clients are longevity illiterate. So whether you're coming at it from a fiduciary stance or even suitability, unless you're looking at these sort of bigger elements of what does redefining and reframing what it means to successfully age look like? How can you really provide meaningful financial advice if you're not helping the clients and then yourself in the way you're putting these financial decisions together? That also flows into this sort of tidal wave. The idea of technology. I've been asking the question, are you consuming or being consumed? Probably getting on for a decade now. But the reality of that I'm seeing more and more in terms of the disruption coming with AI is going to be as significant as the shift from the agrarian to feudal system over 300 years ago to the industrial production system today.

And of course, you know, and for the last 300 years, and of course the system today is still the production, the industrial model. So this idea of where is the value of the human advisor? If AI is going to take over the knowledge part of the equation, then ultimately the wisdom side coming from the advisor. There's lots of sort of coaching focus I'm seeing out there on coaching AI and how to leverage it. But where's the human element of helping the advisor fill that space better? Much more who they're being rather than what they're doing. So they just had future proof last week and I know that creates a lot of great energy, but show me where they're talking about longevity. Show me, show me where they're talking about the human side beyond the traditional behavioral of holding a client's hand in a down market.

So let's jump into the keynote because I want to hear more about these three revolutions and I think you've started to get there, but I really want to go deep. What's the core message and what's the key takeaway for the audience here?

Well, I think think big. So again, the disruption of AI and technology, if technology is going to be as disruptive. And it's probably best to start by assuming that, you know, you can come out on two sides. You can either take the fear and the frailty or the fear side and the fear it's going to take your job over and, you know, you surrender and abdicate to it. Or conversely, how do you embrace it, how do you leverage it? And so building out through the keynotes, the longevity dynamic. And again, I'm having a lot of fun talking to 20 year olds about what does living successfully to 120 look like for you? And it isn't about living forever. It's making much more of these longer lifespans that we're being given that humanity's never been given before. But again, longevity plus the technology and the evolution of technology and recognizing how disruptive it is so helping, you know, in this case the advisor, but ultimately their end clients, you know, a client.

If you think 20 to 60 and 60 to 100 are the same time frame, what happens if we start looking at 20 to 60 as being the warm up and the real performance of our lifetime is actually the 60 to 190 no matter how much time we actually have in that place? I'm 64 now. How much better off was I at 60 with all my life's experience compared to when I was 20? And I may not go out and run a three hour marathon again, but how am I using all that experience? And again, most of us are looking at going out to pasture by then. And again, the traditional retirement model was if you wanted a longer term in retirement, look to retire early. Yeah. So again, it's really fascinating, Mary, you know, when you get in front of audiences and again, I'm not just sort of advisor focused, I get in front of their clients as well. And so it's really, you know, so much fun bringing this sort of inspiration, looking beyond the fear and the frailty. And most people don't really know how to lean into that conversation of what is really possible for you and what have you got to do to do it successfully. And so again, as I'm sort of finding myself building this out based on the experience I'm having, you know, this thing just keeps growing and growing well.

And what I love is this experience is just what you said, it's advisor facing. And I want to hear. So to that end, I want to hear what are advisors walking away with after this experience. But secondly, I want to really acknowledge that second audience and that is the everyday person, the individual. And since you can do this for Both audiences, I want to hear, what are you seeing the takeaways become the transformations I really want to say for individuals and advisors.

How long have we got? So what's fun about this is that, you know, I've captured a lot of data. So when clients fill out the forms, you know, unlocking a bigger view on life, what does that look like? The 65 year old, you know, this is about, you know, the next 40 years and not just about the dollars. Having a 24 year old say this is amazing. So a lot of this and, and even bubbling it down. Mary, one of the presentations I did earlier this year at the FSU College of Medicine, I had a 70 year old lady come up to me afterwards and she's in one of the independent living facilities up there and she said yeah, I know that our coffee and donuts morning mornings don't really do me a lot of good because of course the sugar.

Yeah.

So you know, I, I lay out some of the sort of the metrics like 12.4 years of chronic illness is the average in this country. So this gap between lifespan and health span, when I put that in front of people which most aren't aware of and say, and what is your mum going to be and, and what are you going to do to reduce it? There are, I won't say simple solutions but for instance, I'm not a doctor, but from what you read, 90% of chronic illness is down to metabolic dysfunction. So that's one of the six pillars that we focus on in the flourishing longevity. Then you flow into the. Well, I'm just sort of wrapping that bit up about the clients. I've been talking to both FINRA and the SEC around all of this and talking to one of the chief researchers at finra. There is an acknowledgement that clients at large are longevity illiterate. So simply asking a client what are your plans? Doesn't really pass muster.

I don't feel in really being able to evaluate again their suitability or a fiduciary focus. So the client education part becomes important and again I'm seeing this gain a lot of traction outside of financial services, but then pivoting into the financial world. It's brilliant because you know, I've had advisors say I've known these people a long time and they're being changed in front of me. I've had a portfolio manager say I've always hidden behind the numbers, now I don't have to, I can meet the clients who are as important to them and then from a business metric You've got so many different elements. Most of the tenured advisors haven't figured out their own flourishing longevity. So it's a brilliant way of helping them. Again, I've had a 65 year old advisor say, this has given me a new mission. I can see me doing longevity advising into my 90s.

I've mentioned the portfolio manager. I've had a CFP of 30 years bring a client of 22 years to a workshop. In 22 years, she'd never had a single referral. He gave her four referrals because of the workshop. I've had another Advisor get a $17 million client through a referral. So again, when you look at what's important in the industry at large in terms of running a business, this is delivering on all the key metrics. I've never had my clients so engaged. The referral door is wide open.

This is what is volunteered to me as a result of the experience that this is all creating. And I'll just wrap this up back to the clients. I've even heard a client say, this is the portfolio manager. We've always wanted to refer you, but we never knew how to differentiate you from what our friends get. Now we can.

Well, and what I like about this too is it's so holistic. You really can. I think sometimes as advisors we go into this with tunnel vision, right? Because at the end of the day, what are we paid for? We're paid for our financial advice. So we look at one part of the whole person. And what you're saying here is that can't be anymore. We have to rewrite that story. It needs to be more holistic, which we're really seeing a shift, as you mentioned, technology and the change that is taking place. If you're having to be more human and connect on a human level, which encompasses what their future looks like, how they feel now, how.

You know, I love that example of the donuts and the coffee because you feel like crap, you're not going to want to live to 102. That is not going to be a fun conversation. And so I really love how holistic and you really can't separate out one component of it and just analyze that without looking at the whole person.

Well, absolutely. And that's a sort of segue into the third revolution. Because when you take the longevity and you take the technology, that third revolution of relationships, ultimately, again, think bigger picture of the agrarian to the industrial. Ultimately, I think Elon Musk was asked, well, if robots and computers are taking over production, what are humans going to do. And his answer was seek fulfillment. So even there, there is a lot of focus. That first workshop I put together was, you know, very. I wanted to keep it as a safe space because again, the idea of, hey, let's talk about your aging is generally met with, yeah, let's not and say we did.

Yeah, yeah.

So in creating this environment, people came back and said, well, we want more. Well, okay, great, what do you want more on? And purpose? You hear a lot about it in today's world, but part of purpose can be finding things that become a checkbox exercise. You think you're doing something that's purposeful. Ultimately, to me, fulfillment. So this third revolution, not only the relationship we have with others, but ultimately the relationship we have with ourselves, which comes down to this big pivot of transition towards much more of who are we being rather than what are we doing?

Yep.

And that to me, again, is another exciting part of this journey that I find myself on.

Well, and it goes back to what you were saying about the advisor earlier, is it requires the inner work, not just for the client, but for us, ourselves. What have we thought? How have we projected out? Because a lot of our own fears, own insecurities can be projected into our financial plans and we can project those fears with our clients. And so how are you as advisor, working through your own insecurities to be able to project more of that?

Positively, Mary, you've just again, I feel so fortunate. The last 20 years I have been privy to so many different, very in depth conversations with advisors. You know, when I joined Merrill, I had one of the sort of admin managers, the compliance side, shadow me. And they turned around to me and said, wow, I wish I could have the conversations you have. They open up to you in a way that they don't to me because of what I represent. They being the advisor and mapping into that again, all day long you look at the industry. To succeed, you had to be a type A in essence. So again, no matter whether you're on the RAA side or the broker dealer side, but I had one of the managers in one of the Merrill offices say to me, and this is over a decade ago, he said, well over 20 years ago, every day for two years, I live with a fear of rejection, the fear of failure, and the fear of being fired.

So if it takes six to eight weeks to create a behavioral pattern, what is embedded in the psyche, living in that climate of fear? And I've shared that with so many advisors over the years and they all come back and say, yeah, I have that fear and I still have it. So I love the way you picked up on that because it's very easy to sort of gloss over it. And that's part of the exciting thing we're talking about the sort of the keynote side. But building out a training program because advisors said to me, great, you're coming up along and you're presenting Jonathan, you're doing these workshops and keynotes but no one's training us and helping advisors navigate through. And the first step of that is helping the advisor lean into the flourishing longevity for themselves and exploring that with their significant others, their inner circle, because most of them have not lent into that. So how can you really deliver it to others unless you're living it for yourself or not just living it, experiencing it. That's the key thing here.

Well, and that's where I'd like to go to next is what tools do you have now that advisors or individuals could reach out and access today?

Well, we're building out. Thank you for that question. So we're building out longevityplanning me. So that's the sort of landing zone. We have just been approved by the NASA for the 12 hour IARCE, which is all a mouthful, but advisors have to take it. I've had advisors say to me it's a thorn in my side. I just have to sit there, you know, getting all these statues. In statutes.

We now have a 12 module training program approved by the NASA for the 12 hours CE and it's a three month, well, 12 week experiential program to take advisors through, becoming longevity advisors. So upping what they're delivering to their clients and experiencing it for themselves. So that's in the, you know, the, the B2B along with the keynotes as well, but then also on the other side for the client side. So the flourishing longevity program Powered by Invest in you. And we haven't mentioned Invest in you, but in the background, Invest in you is a program that we created nearly a decade ago. I've had a financial planner using it for a year who turned around at the end of it and said I could see all 8,000 Raymond James advisors using Invest in you with their clients. So you know, we can get people excited in rooms in the moment. But I've always been sort of more curious about well, what are 6 months, 12 months, how do we create sustained outcomes? So the Powered by Invest in you is the sort of the backstop, but then actually taking the clients through the essence of the workshop and getting them into A place where a.

Experiencing this sort of the introduction to the flourishing longevity. And then we've created this flourishing longevity scorecard, which is a very simple sort of 60 questions. And to me there are a lot of commonalities out there around longevity and then flourishing longevity. So mindset, physical health, metabolic health, purpose and fulfillment, community and the importance of having the right people around you and then financial education and financial fitness. So it's a very simple look and the advisors can take that and plug it into again. Once they've done the program, they can then set their clients up to be able to do and engage for themselves in the flourishing longevity program with invest in you to then help elevate the experience that the clients, the clients are having with the advisor.

You know, that's one of the things I love about you is it's not just here, let me talk to you for 60 minutes and walk away and feel good. Like I always call those the marshmallow speeches where they're really good to eat, but there is no substance inside. And what you have just described is the work, right, the work you mentioned a workshop, but it's the work that you can then put into place to make action oriented outcomes that you're actually seeing tangible results for yourself, for your clients, for their loved ones. And I think that's, that's the transformation, right? Not just hearing a great speech, but really getting the work done.

Well, thank you for that, Mary. I mean, again, I've got goosebumps just hearing those words come back at me. Because it is amazing. I mean, I don't really know what the heck I'm up to. But you know, when I get out of the way of the universe and let it channel through me, suddenly all this stuff sort of happening and the neat thing is is it all comes back from the advisors. It all comes back from the clients. You know, I've gotten to a place where I sort of pick up on things when I talk of initially the four pillars of flourishing longevity. And the clients start picking up on that, oh, this is important.

That was the catalyst for the scorecard, you know, and so again, just building this out, but to your point, and it reminds me, gosh, we're going back nearly 20 years ago. We did the Invesco Rainmaker event when I was at Schwab and one of the advisors at the end of it said, jonathan, that's the best event you guys have done. And I looked at him, I said, no, Tom, it's the best event we've done. When you show me in 6 months time what you've done with it. So you know, I've always had that. Well, certainly for the last 20 years or so I've had that lens. But then build in my coaching training. I'm a certified Gallup strengths coach.

So again, just because you're having a great coaching session or engagement, what does that look like for the coachee a year down the road? Well, invest in you takes care of that. If the client is willing to engage and participate, you create this Runway to help people again achieve something far more powerful. And, and as you can tell from my own enthusiasm, I mean half of this is about fixing Jonathan. So you know, it's a little bit like Steve Jobs, you know, putting the ipod and just because he wanted better way of play, I think maybe it was for his daughter. But nonetheless it sort of starts at home.

Yeah, yeah, it's fixing internal before being able to take it out. Okay, well Jonathan, this has been great. Now I want to my final question is really going to be around what do people not know about Jonathan? We know you love longevity, we love talking about this, but what do most audience members don't know about you?

So when I was at University College London a lot of moons ago, I was asked, it was actually my parents 25th wedding anniversary and one of my father's rowing friends said, what do you want to do when you graduate? And my answer to him was not wear a suit. He worked for Oceaneering International in Aberdeen and said why don't you become a North Sea oil diver? So I went and took on scuba diving at college in the remaining 18 months of my degree. And then phoned him up and said right, I'm ready. And he phoned my parents up and said, ooh, what do I do now? And they said, well, you better let him do what he needs to do. So I never actually became a North Sea oil diver, but I worked on diving boats for a couple of years which was very seasonal. That allowed me to travel extensively both in South America and then in, in China in the mid-80s. And then I became a roughneck on one of the platforms in the middle of the north sea. So by 86, that's when the pivot into the oil market.

They used to call me rigger for 13 years.

Oh wow.

Market. So it actually proved the North Sea work proved quite a good training ground for the rigors of working in, a pun intended, of working in a dealing room for 13 years. But how about the oil industry? How about the sharp end of the oil industry? How about that well.

And you're quite the scuba diver then. I had no idea.

Well, I was. But you know, I probably haven't scuba dived since the mid-80s. We had three kids in 33 months, so everything kind of stuck stopped when that happened. But sleeping at Sharm El Shack, which is a huge resort now, I was there just after the Israelis handed it the Sinai back to the Egyptians. And you know, a group of us from college, we slept on the beach for a week and the diving was incredible. So part of note to self is to get back to it. But yeah, that's again part of John Johnathan's flourishing longevity.

Well, and there's your longevity planning right there, right? I love it. Well, if you're looking for a speaker who can guide your organization or clients into the future by embracing the revolutions of longevity, technology and relationships, you want to learn more and book Jonathan Ainsley@financialbehaviorthoughtleaders.com thank you for listening to us. We bringing keynote stories come to life and if you liked what you heard, share this episode with a friend. Thanks so much and we'll see you next time.

Sam.