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Today’s episode features an insightful conversation with 
Derek Coburn, wealth advisor, author of “Let’s Retire Retirement,” and founder of the Cadre community. Derek brings decades of experience helping entrepreneurs and high achievers rethink conventional views on wealth, freedom, and the age-old concept of retirement.
Derek’s journey started in traditional financial advising, where he noticed how many people fell into outdated patterns—saving for a distant finish line while sacrificing health, relationships, and personal purpose. He eventually took a different path, focusing on building deep relationships and meaningful communities instead of sticking to the typical accumulation mindset. His book and philosophy challenge listeners to move away from the 18th-century idea of retirement and instead focus on creating freedom and fulfillment right now, not just someday in the future.
In this thought-provoking discussion, Derek and host Dave Wolcott dive into why the old model of working hard today for a delayed payoff tomorrow no longer fits our lives. They explore the mindset shifts needed to prioritize well-being, relationships, and purpose, while still making smart financial choices. Derek’s practical tips and real-world examples will help you reconsider what it means to live and invest wisely.
In This Episode
- Why the traditional retirement model is outdated and may not serve your real goals
- The difference between accumulation theory and passive income—building freedom today, not just for the future
- Mindset shifts to prioritize relationships, health, and meaning over postponing happiness
- Actionable strategies to align your wealth plan with your true priorities and avoid future regrets
I have no desire to ever stop working. I know that regardless of what I’m doing, I’m always going to be interested in providing value, sharing wisdom, doing some type of work. I’m pretty sure we’ll be able to get a return on that in a monetary form, and that just frees me up to really make sure I’m leaning into these relationships that are really important to me right now.
Welcome to The Wealth Strategy Secrets of the Ultra Wealthy podcast, where we help entrepreneurs like you exponentially build wealth through passive income to live a life of freedom and prosperity.
Are you tired of paying too much in taxes, gambling your future on the stock market, and want to learn about hidden strategies for making your money work for you?
And now, your host, Dave Wolcott, serial entrepreneur and author of the bestselling book The Holistic Wealth Strategy.
How’s it going, everyone? And welcome back to another episode on Wealth Strategy Secrets of the Ultra Wealthy.
Today, we’re challenging one of the most stubborn myths in finance — traditional retirement. My guest, Derek Coburn, wealth advisor and author of Let’s Retire Retirement, and founder of the Cadre community, has spent decades watching people optimize for a far-off finish line, only to sacrifice health, relationships, and purpose along the way.
In this conversation, Derek and I unpack why the 18th-century retirement model doesn’t fit a 21st-century life — how to think in terms of freedom now, not someday, and practical ways to realign your wealth plan with your real priorities.
We’ll dig into passive income versus accumulation, mini-retirements, and Derek’s Alignment Audit — questions that help you invest better in assets, relationships, and yourself.
If you want a playbook for living well today while compounding wisely for tomorrow, this episode is for you. Derek, welcome to the show.
What’s up, Dave? Great to be here.
Yeah, grateful to have you on the show. And I know the audience is going to enjoy this discussion. It’s really one of my favorite concepts to talk about too — these old constructs that societal norms have kind of put us under.
And one of them being retirement — which is really so outdated.
Right.
If you think about it, it literally comes from the 18th century. And yet we still live under this guise today, with certain things that just haven’t changed. People really try to take advantage—
Right.
—of some of these frameworks to kind of slot you into it. But it’s really their agenda, not necessarily your agenda.
So I’m really excited to unpack your book, talk about your ideas, and also some of the other great things you’re doing with Cadre — building an amazing community of entrepreneurs, investors, and really high-level thinkers.
So why don’t we begin with you telling us a bit about your story — how you got into the financial services industry, and how you ended up where you are today.
Yeah, that sounds great. So I began my career as a financial advisor in 1998. I got hired by MassMutual right out of Cox College and was growing that practice. I had a lot of early success, qualifying for all the trips back when those were a thing, and found myself 10–15 years younger than most of the people there.
I started having conversations with them and found a common thread — most financial advisors had 1,500–2,000+ clients and only really enjoyed working with about 20% of them. At that time, and even still to this day, there’s a lot of compliance and red tape that prevents financial advisors from marketing the way other industries can.
Fast forward to about 2008–2009 — social media was popping up. I was developing a lot of relationships and connections with people I wanted to engage with and take advantage of word-of-mouth marketing. So I started to rethink: is this really the thing I want to be all in on?
I had about 350 clients at the time and was getting ready to have a kid. I basically kept about 20% of them — the good old 80/20 rule — and used the additional time and space I created to start Cadre, a community for CEOs and entrepreneurs that we still run today.
That came from my transition as a financial advisor from cold calling to attending networking events, which seemed to be a natural progression for most people. But the networking events were starting to become less and less useful. I realized that the majority of people I wanted to meet weren’t going to networking events because they were too busy building their business, spending time with their family, or doing other things.
So I started hosting smaller events that reflected my own approach to networking. I wrote a book about networking called Networking Is Not Working in 2014. Page one, chapter one — “Don’t go to large networking events.”
It was really a book about client acquisition disguised as client appreciation. I was hosting smaller events — wine tastings, business seminars, golf outings — and would invite clients to bring their friends and colleagues. For me, it was a great way to add value to our relationship, and, oh by the way, I got to meet people I probably wouldn’t have met otherwise.
So I took what I learned from that and started Cadre as a way to allow professionals, mostly in the D.C., Virginia, and Maryland area at the time, to connect and meet the kinds of people they wanted to meet.
Yeah, that’s quite a background. So tell us a little bit more about your book and this notion of retirement — because again, I find that it’s so outdated.
My perspective has been that when I originally worked with financial advisors 25 years ago, they were really trying to engineer this blueprint of how much capital you’d need based on accumulation theory — to get to a number at 65. Then you’d run the Monte Carlo simulation, take home 4% of your net worth, and hope you don’t outlive your money.
But you also have taxes, fees, and inflation to consider once you get there. There’s a whole component I want to break down with you — especially as a financial advisor — because maybe that model works for some people. There are the tactics and economics around it.
But does that really make sense for you? There’s also this whole other piece around psychology and mindset. Society has been forced into this role — globally, not just U.S.-centric — of thinking about the future at 65.
For 35–40 years, you’re told that then you’ll travel the world, spend time with family, live fully. But when you look at passive income theory, it’s about creating income today — not at 65 — to create the freedom to do the things you want to do now.
So there’s that mindset piece, and even on the passive income side — you could basically retire today, if you want to use that word. But why would you ever stop doing what you love? Work should be about purpose.
Right.
It’s about purpose and fulfillment. So, all right, I don’t want to steal any of your thunder — let’s go.
Where’s a good place to start, man? We can cover all that.
Yeah, just go for it — wherever makes sense.
Look, I really question the idea of retirement. I especially question how everyone just so easily and naturally accepted this as the default mode they needed to lean into — that the money game was the only game in town.
I was seeing people getting close to retirement not really finding it to be what they thought it would be. I remember reading The 4-Hour Workweek by Tim Ferriss back in 2006 or 2007, where he introduced the idea of mini-retirements — spreading out all the pleasures you’re putting off over the course of your life.
And you know, I never had anyone come into my office early on saying they didn’t want to retire. I would introduce the idea to them. Most financial advisors don’t ask if you want to retire — they ask what age you want to retire. So you don’t even get an option to opt out. You have to pick a number and a lot of other assumptions.
You have to guess what inflation will be every year for the next 30 years. You have to project your pre-tax return on retirement accounts, your post-retirement returns, whether Social Security will exist, and even the age you’ll die.
Most people give 10–15 minutes of thought to all this, get a number at the end, and feel proud — as if they should rework their entire lives to save that amount. It’s like an eight-game parlay on FanDuel — everyone’s going to be wrong about most of these assumptions, but they put so much faith in them that it just doesn’t work.
I’d have people say, “I want to retire at 65.” And I’d ask, “Great, what do you want to do?” Couples would say, “We want to travel the world together.” I’d ask, “When was the last time you two went on a date?” Usually, I didn’t get a great reply.
Or they’d say, “I want to spend more time with my kids and grandkids.” I’d ask, “How often are you home for dinner now? How many great trips are you taking each year with them?”
And maybe my favorite — usually men would say, “I want to play golf five days a week.” I’d say, “But you haven’t played golf in four years and you just had your hip replaced.” So when is all this going to happen?
People subconsciously opt into this idea and sacrifice their health, happiness, and relationships — all in the name of doing it someday. Then when they finally get there, those things aren’t available to them the way they hoped, and they wish they could go back in time and make different choices.
Yeah, that’s so spot on. And you know, really through my journey, I’ve discovered that it’s really all about freedom and—
Right?
And when we talk about, you know, a lot of people will kind of throw around “financial freedom,” right? But you know, I like to keep asking why, right? What does that really mean?
Right?
And when you really look at the essence, especially of entrepreneurs or high achievers, we’re looking to really create freedom in our lives. The reason why we want money is because we want to create an ever-expanding, bigger future, right? It’s all about that — or creating a bigger impact in the world. The money is actually going to amplify who you are and what you’re doing.
We also want to have this freedom of purpose, which is waking up every day and being excited about what you’re doing. We also want to have freedom of relationships — like, I get to have great conversations with people like you, like-minded people that I enjoy. We connect, we learn, we grow, we create value. And I get to do that all day versus spending time with toxic relationships where people are dragging you backward.
And then you also have freedom of time — to think about, you know, you get to spend, if you want to go take your kids to school or watch their game or spend some extra time working out or whatever it might be, you get to actually choose that.
So I believe it really comes down to freedom, and there are multiple dimensions of freedom. It’s what people are really looking for. So I think if people can figure out how to define what that vision is for them and figure out what that freedom really looks like for them, then they can define it today.
Yeah. And I think that the biggest thing that people don’t really understand is they don’t understand how much less pressure they will feel to have to save right now once they realize and recognize that they’re probably going to be working longer than what they’ve been told or what they thought.
The math is pretty crazy. I have a story in my book called A Tale of Two Tonys. Tony’s 45 years old, he makes $150,000 a year, and he has $150,000 saved up in his investments. Now, for people that are listening to this show, those numbers might be a little bit higher. And the numbers can be higher, we can change them around, but the basic math is not going to change.
Tony meets with a financial advisor and says he wants to retire at 65 because that’s the age everyone else is saying they’re retiring. And Tony’s advisor ends up telling him he has to save $2,400 a month every single month, adjusted for inflation, for the next 20 years in order to stop working.
So regardless of what you’re making, that’s 20%. $2,400 a month times 12 — 30 grand. He’s making 150. Saving 20% is a non-starter for most people. It means they’re probably saving almost as much as they’re spending.
Doesn’t have to be, but it can be. So I introduced this alternate reality. Have you ever seen the movie Sliding Doors with Gwyneth Paltrow?
Haven’t seen that one.
It’s a movie that basically has her own two timelines and how different her life will be if she catches a train or not. And so I create this alternate reality where Tony goes back home after that first meeting and he’s talking with his wife, and his wife says, “Why do you want to retire at 65? You like what you do, you like the people that you do it with. And even if you’re not doing this, I can’t imagine that you’re going to sit around and do nothing for 30 years.”
And he’s like, “You know what, you’re right.” So he reaches back out to the financial advisor and he says, “I want to retire at 75 instead of 65.” What do you think the amount that he needs to save goes down to — from $2,400 to what?
By working 10 extra years, it’s probably 50%. It goes down to $110.
It goes down by 96%. And if Tony were to say, “I’ll work five extra years, I’ll go until I’m 70,” then the amount goes down by 75%. Now he only needs to save $600 instead of $2,400.
And the reason for this is in the first example, I have him dying at 95 in both scenarios. In the first example, it’s 10 fewer years of working, 10 fewer years of saving, 10 fewer years of having that money grow. And he needs an amount of money that will last for 30 years.
In the second scenario, he has 10 extra years of working, 10 extra years of letting that money grow, and he’s not touching it. And then he only needs an amount of money that will last for 20 years.
And so I think everybody knows they should be spending more time with their spouse and their kids, going to the gym, being with friends, having more fun, and contributing to the world in a better way. But no one’s really addressed the elephant in the room, which most people feel — “I don’t know how I can afford to take the time away from my work in order to do these things.”
What I want people to realize is that by planning and recognizing that you’re going to work longer, you have a lot more money and a lot more time that you can spend differently right now.
Yeah, no, that’s definitely an interesting point. And one thing I think that’s really fascinating here — and hopefully our audience is ahead of the curve on this — but I think 80% of all of this is really mindset.
So if you think about it, if you’re working toward accumulation theory, you are actually manifesting yourself into this whole scarcity mindset around, “Hey, I’ve got to have enough for this retirement number,” when in reality, you could be one relationship away from the biggest opportunity of your life and 10x your income for sure.
But here you’re playing a small game by just trying to save 10–20% a month and trying to get to some kind of number.
Now, Derek, let me ask you this question. Okay, this is great. I know my audience has probably heard this example a couple of times, but I think it’s a great example, and I would love to see you really validate this or see if I’m incorrect because I’m always open to learning. I love to learn new things.
But let’s just make a comparison for people. You had a great example of the two Tonys, so let’s pick another name and we can come up with another example. But let’s just track Investor A, who is tracking toward accumulation theory.
And let’s say they build up a nest egg of $4 million. So high level — if you then break that $4 million down and 4%, I know planning has even come down off of that 4%, but let’s just conservatively say you got 4% of that $4 million. So that’s $160,000 in income for that year at 65, guessing that that income is coming from qualified funds.
So you’re probably at the highest taxable rate. So therefore, what do you think that net is? Ballpark — if you take out taxes, fees, and inflation off that $160,000? Like $90,000, I guess? Or okay, yeah, $90,000. I don’t know the exact number, but let’s just call it $100,000 — let’s be conservative.
So if you worked your whole life to scrounge $4 million, you think you’re doing well, and now you’re netting $100,000.
Now let’s compare that to Client B here in another scenario who’s been investing into passive investments and private investments like commercial real estate and other things. You could take that same $4 million, and it’s very realistic to have an 8% yield off of those assets, which would give you double that — $320,000.
And if you’ve been doing them in the right real estate assets, you should be paying nominal tax or maybe even no tax on that.
So now you’ve actually doubled your income right there, and at the same time, that asset value of that real estate or those other investments is still growing about 10% a year, in addition to the cash flow that they’re kicking off.
You could be one relationship away from the biggest opportunity of your life and 10x your income.
Yep, I love it.
So, okay, so it’s like, which scenario would you rather be on? It’s even the same amount of capital, but just a different strategy. And so therefore you’re actually creating more income for yourself, and that’s how you can actually create generational wealth.
No, I agree, man. You know, and I think that the game that I’m playing right now is like, I’m in the business of minimizing future regrets. And I think that regardless of what we’re saving, I want to try to significantly reduce the number of people 15–20 years from now who have distant relationships with their kids, who have uninspired relationships with their spouse, people that are sitting around their house not really engaging with other people very often, people who are taking a lot of medications because they didn’t take care of themselves.
I think that, for me, I’m a huge proponent of the passive income approach, and I work that into a lot of my conversations. I subscribe to it myself, but I also feel like the best asset that any of us have is our ability and desire to continue to show up in the world and produce an earned income in exchange for the value, wisdom, and gifts that we share with the world.
And so for me, we can talk about what types of investments to use.
And maybe even using better investments will free up some of the time and money that will allow us to do that. If my macro thesis is, look, I think that banking on having money coming in in your 70s is going to create more time for you to do different things, right now I’m living that on a micro level at the moment because I’ve got two boys who are 15 and 13, and they’re going to be off to college in three and five years respectively.
Tim Urban, on his Wait But Why blog, shared a few years ago that—when do you have kids?
Yeah, I have four.
He said that when they go off to college, you have already spent 93% of the time that you’re going to spend with them over the course of your life. And then you can also look at that in reverse to see how often you see your parents, where they live, and how many more times you’re going to get to spend with them.
For me right now, what I’m solving for on a daily basis is maximum time with my kids—spending as much time with them as possible—in part because I feel like the five- or six-year-from-now version of me is sponsoring my current decisions. It’s almost like it’s writing me a sponsorship check to say, you can lean into this now because once your youngest is gone, you’ll say yes to a lot more speaking gigs, more work, 50–60 hour weeks again.
That just liberates me to have the freedom to lean into being a dad, a husband, and a friend right now.
Yeah, I’m right there with you. Let’s help the audience really understand one dynamic here, which is where I think it can get a little tricky sometimes.
Right.
I think what we’re really talking about, if you kind of look at it high level, is really a balance between the present and the future.
Right.
And so, you know, we’re investing, we’re doing things for the future because you want to have a rich and wealthy future, but at the same time, you need to be investing today and doing things today, because all we really have is today.
Right.
Tomorrow is not guaranteed. So things like your health or those relationships that you talk about—that could mean maybe you’re not working a 40–60 hour work week. Maybe you’re putting in two hours a day working out.
Right.
Because that’s your priority. Or maybe you’re spending extra time with your kids. Or if your parents are aging and you’re taking time away from your workout plan or your other family to go see them, how can people really think through some of those nuances about balancing investing in the present—being mindful in the present—for what we have with those future goals we have?
Yeah. You know, one of my favorite sayings or mantras, I would say, is I live my life like I’m going to live to 100, and I live my life like I’m going to die tomorrow. I try to hold both those beliefs and give them the same weight.
There are some days where I need to hear one versus the other. There are some hours where I go back and forth. And so I think it’s going to be different on a case-by-case basis.
As it applies to my kids, I’ve spent time thinking about this. When my kids were 10 and 7, we had a nighttime routine where my wife and I would take turns putting them to bed. We would read a story, say a prayer, and snuggle with them.
I found myself a lot of nights wishing he would hurry up and fall asleep so I could get out of there and go watch a show or respond to an email. And I’m thinking, gosh, he’s not going to really want me doing this for that much longer. He’s getting older, and I tried to lean into it more.
I eventually landed on this crazy hypothetical—what if 25 years from now, there’s a company that invented a time machine and they’re offering me the opportunity to go back in time for one night, if I’m 60 or 70 at the time—one night with the 10-year-old version of my kid? That one nighttime routine where I get to read him a story, snuggle with him—what would I pay for that?
I just blurted out I would write a check for $50,000 without even thinking twice about it. And I think there are just a lot of $50,000 moments that we’re all taking for granted on a regular basis.
Even though I’m not snuggling with my kids to put them to bed anymore, I have a gym in my house and I work out three days a week with my 15-year-old. Granted, he’s not talking to me for 45 of those 60 minutes, but I’m in the game and I’m present, and we are talking for some of that time.
My youngest is doing travel soccer now, so we’ve got a lot of time in the car together, and I just think we’re really going to miss this when it’s gone.
This is time that we’re not going to be able to reinvent. I don’t think there is going to be a company with a time machine in the future. And so for me, just to double down on everything you were saying, I have no desire to ever stop working. I know that regardless of what I’m doing, I’m always going to be interested in providing value, sharing wisdom, doing some type of work.
I’m pretty sure we’ll be able to get a return on that in a monetary form, and that just frees me up to really make sure I’m leaning into these relationships that are really important to me right now.
Yeah, you know, it’s so interesting because we’ve talked to thousands of investors also, and at the end of the day, we’re talking about tactics sometimes of investments and different strategies and all these things, but the real goal is all these things that we’re talking about actually have nothing to do with money. One question I love to ask people to think about is, if I gave you $100 million today, how does that change your life?
Right. Yeah.
Some people haven’t even really thought through it. They don’t know. I mean, outside of maybe buying a car or getting a bigger house or whatever, they haven’t really thought about what that could be.
Right.
And maybe a good way to think through that is the Top 100 Be-Do-Have List — it’s a great one.
Right.
Because what I find is that so many of the things you’re actually really longing for and aspiring for are totally within your reach today and don’t even require capital to get there.
Yes. And again, to your point, just buying into the concept of retirement — you’re buying into the idea that life’s going to be better in the future than it is right now. And even that mindset can weigh on you so much.
It’s funny that you have that $100 million question, because that’s question number one in a set of three questions that I’ve always asked my clients. I call it the Alignment Audit.
I ask them:
If you ended up winning the lottery and getting $100 million, how would your life change?
If you meet a doctor and the doctor tells you that you have a year left to live, what are you going to do?
If the same doctor said you’re going to die tomorrow, what would be your biggest regret?
Answering those questions can really inform you as to whether or not you’re really living your life in alignment with the way you want to be living your life.
Yeah, no, that’s totally spot on. And if we just go back to this retirement notion — the definition of retirement is really putting something out to pasture.
Right.
And this came from a different generation, where we were working in factories.
Right.
That’s why they did that. People couldn’t really work past eight hours; you would wear people out. But today we live in the information age with so much technology and resources at our disposal.
So how can we live a more fulfilled life and work? I think if you can really start to create work as your purpose — it’s not work.
Right.
It’s fun. And these are some of the lessons we talk about in our mastermind community and also with my kids, because my kids are in their 20s now too. I want them to experience all these different things in life — go take whatever job you’re going to do and learn from it. It’s all about the learning, so you can find out where you’re congruent with your own values and your own path, and feel fulfilled.
The money comes later. Don’t chase the money — chase where you’re going to be fulfilled. And then things just really line up for you.
I hope I look like you when I’ve got kids in my 20s, man. You look great.
Well, I appreciate that, but that goes back to everything we’ve been talking about — it’s making investments. I’ve been investing in my health since my early days, and I continue to. Now with all kinds of new technologies, regenerative technologies, and biohacks, I love all of that because you are your greatest asset.
You said it earlier, and people should actually write on their balance sheet you as the biggest and most foundational asset.
Right.
Because as you said, that’s where I see 10x–100x type of return. But the minute you turn that off or you stop working, you kind of stop contributing. And that’s also a real psychological upgrade.
Right.
When you see yourself like that, you can really transition from that scarcity type of mindset — “Hey, I need to just get money and hold onto it and not lose it” — to really living your fullest life.
Yeah. You know, I’m glad you brought up purpose. I have a whole chapter in my book about purpose versus happiness, and I’ll share the basic premise and a little research around that with you in a second.
When I started writing the book, I was using language like find a job you love and have it be your purpose. Before I turned in my final manuscript, I changed that language to have a job that you don’t hate — a job that doesn’t suck your soul.
I think for some people, feeling the pressure or the need to find work that fulfills their life purpose can feel like a lot.
There are also a lot of people out there where their purpose might be that they’re the ones who organize the two trips all the friends take together every year, or they plan the big family excursions or outings.
I mention a guy in my book — a friend of my brother-in-law’s — who works at a tech firm. He likes his job and the people he does it with. He doesn’t love it; he doesn’t think it’s his calling. What he loves is live music — he loves the live music community and seeing Phish.
He found a job that he thinks is good — not great, not his reason for being on Earth — but it gives him the flexibility and freedom to live out his purpose and do what he wants to do.
I think that can work for some people. For you and me, I think it’s more that we aligned our purpose with our work, and I feel great about that.
For others, maybe there are a couple of in-between steps. They don’t have to think, Gosh, I hate this job, I have to find my purpose for being here. Just get out of the thing that’s really ruining your life right now, find something more palatable, regain your footing, and maybe go from there.
Yeah, that’s spot on, Derek. One of the best interviews we’ve had on the show was a gentleman named Charlie Garcia, who runs a community called R360 — it’s a centimillionaire community.
Right.
And I had asked him the question, you know, what is one of the most important attributes, you know, of your members and what do you think people hold true the most? And he said his answer was self-awareness.
Right.
So you don’t need to be the next Steve Jobs or Tony Robbins, right, to have some kind of purpose and really conquer the world.
Right.
To be fulfilled. However, I think that when you can really understand yourself and understand where there is friction and where there is flow…
Right.
Where can I be in flow? Maybe I’m a people person, maybe I’m not a people person.
Right.
What are the things that I really excel at and that come easy to me, and then they’re difficult for other people? Well, that’s my unique ability. So, you know, we often talk in our mastermind community about your superpower, right? What’s your superpower? Because it’s easy for you. I think it’s really about that self-awareness.
Right.
And figuring out what that is for you. And of course, it’s different for everyone. And yeah, whether that’s, you know, seeing fish or, you know, being a marine biologist or anything, you know, that’s amazing, right, to be able to kind of get there. But I encourage people to, first of all, be courageous.
Right.
And trying to find that and be committed to really trying to find where you can be in flow, where you have, you know, the most success and freedom. Because money and some of these other things, they all come. They all come with that.
Right.
You don’t want to chase it in the wrong order.
Yeah. You know, I feel like the best person for any of us to get advice from is the best and highest version of ourselves. And I think that most people are not really close to that. Most people are dealing with the stresses of a business, of things going on in their family, with their health — fill in the blank. And so using some of the time that you may now have, recognizing that you can work longer because you’ve got some good passive income plans set up in place, to get yourself right, get yourself a little bit closer to making better choices, to being a more reliable source of advice.
Like, I think human connection is a big thing. There was a study done a few years ago that showed the amount of time that Americans spend with various people ranging from themselves — how much time you spend alone, how much time you spend with a significant other, coworkers, friends, children.
And one of the big takeaways from a lot of the online influencers was: you’re going to spend 400 minutes a day by yourself beginning in your 60s, so you better learn to get comfortable being by yourself. And I think that’s important. The one that stood out to me was the friend category.
So, with friends between the ages of 10 and 25, we’re spending over 100 minutes a day hanging out with friends. When my kids wake up, they’re like, “What are my friends doing today? What am I going to do to have a good time with them?” And it goes down to about 30 minutes in your 30s and then goes even lower than that and just flattens out.
And I don’t know when we decided to devalue the importance of friendship. We spend so much time thinking about how much money we need to retire, and not really any time thinking about who we want to retire with and who we want to be around now — because being around people that light you up, that are like-minded, that make you feel good, that give you good advice and good feedback, going to the gym more, and having a strong connection with your wife…
I mean, look, I’ve spent $250,000 on couples therapy over the past 20 years. I’ve resisted putting that number into a calculator to see what it would be worth if I had invested it. But my game’s not over right now. I’m creating and I’m producing. I’m 48, and I’ve got an incredible relationship with my wife because of how much time and money we’ve invested in that relationship.
And the way that I’m showing up — my output, my writing, my influence — is much better than it would be if I had more of a stagnant relationship with her. And so these are opportunities. The last chapter in my book is called Investing in You — opportunities to put the money that maybe we thought we had to throw into a retirement plan so that we could stop at a certain age.
We can now put that back into us and make that “you” on the balance sheet a little bit more valuable, and then see what comes from this rejuvenated version of you compared to maybe the one that’s out there right now.
The best person to take advice from is the highest version of yourself.
Yeah, love that. So, you know, you run a high-end community. How do you talk to clients about that type of investment?
Right.
Because people are always thinking, you know, again, right, it’s a big ticket item, I’m sure, to invest in your community — but it is an investment.
Right.
And, you know, what is really the thought process you talk to with people about trying to make that type of commitment?
You know, I drew a line between my businesses for better or for worse. I just said as soon as I committed to charging for Cadre — we charge $1,000 a month, and we host a variety of events, both virtual and some in-person for our local members — I said, you know, I’m not going to, because I’m charging them, use it as a way to pitch my wealth management services.
And I’m not doing that really anymore anyway. But when I first started, I was very much still running the wealth management practice. And what I told my wealth management clients was, look, I’m going to be doing this other thing. I don’t want you to think I’m not paying attention to you.
I got rid of a lot of my other clients to free up the space for me to grow my network, to have a lot more connections, and to be more resourceful for you. A lot of my clients were partners in big law firms, and I had some business owners, and the business owners typically came over and became members, but I never really mixed the two up.
But I think now, in 2025, with everything going on in the world, it’s just a really important piece that people need to lean back into again. Find people that you like being around, find people that lift you up, find people that are not a drain on you — because energetically and chemically in your body, what it’s going to do for you can’t really be replicated with a pill or anything else.
Yeah. I got to tell you, it’s been one of the most rewarding things watching people inside of our mastermind community grow and learn and connect. From the beginning, people are always a little, you know, “Yeah, this is a big commitment, right. It’s expensive, it’s a big check.”
These guys, what do you guys charge?
Our mastermind community is $15,000 for the year.
And we basically, you know, will try to find the right-fit clients who want to come in and make that commitment to themselves. And our goal is to actually 10x your investment in that.
And you can 10x that through things that you’ve learned — through tax savings, through optimizing your different investments, through creating new connections, through creating accountability, through leveling up, through increasing your health, through increasing your relationship — all these kinds of things.
And sometimes it’s interesting because the biggest thing holding people back is themselves.
Right.
It’s the mindset. But then once you make that commitment, right? And then you have the courage and you invest — the minute you sign that check, you are invested. And then to watch the trajectory of these people, because now they’re… When you pay, you pay attention.
Right.
And now these people are committed to grow, and the levels of their life that they’ve grown in is just, it’s really spectacular. It’s like just watching a complete transformation.
Yeah. You know, the reason why the quality, the curation has been, has always been so good with our community — and people will ask, and I don’t expect anybody to believe me when I say that — but one day, you know, I just blurted it out there. Somebody said, “Why do you have such great people in your community?”
And it was the revenue that I generated from my wealth management practice — this is like back in 2015, 2016 — that was paying my bills. Like, I don’t need anybody’s $500 a month, which is what we were charging at the time, to pay for my kids’ education. It’s always just been more like me having two things going side by side really freed me up to have the ability and the courage to stick to my guns about who’s a good fit — in a way I don’t think I would have done if I was relying on just one of them as a source of income.
And, you know, we were at 78 members, all but three were local to D.C. going into COVID, and we got really good at doing some virtual programming during COVID and providing a place where a lot of people could come together. We ended up getting as high as 130, and we lowered the price point a little bit. And I just noticed recently some languishing.
I’m noticing it just in general — like the world at large — where people are just kind of in this little groove, and the fire’s not burning inside them anymore. They’re not looking to do big things. And so we just ended up reducing our membership. We doubled what we were charging and cut our membership by about 50% as a way to reboot the energy.
Like everything that you’re talking about, I wanted extreme buy-in from the people that were really excited about leaning into doing big things in their life, in their business, what have you. And I wanted to be able to give those that maybe that’s not where they’re at right now the opportunity to step away.
And so it ended up being a really great exercise and everybody’s really excited. It’s like, “Yeah, I’m paying more, I’m going to lean into it even harder.”
And I think the good old “you’re the average of the five people you spend the most time with” — we’ve all heard that, we all know about it. And I think that a lot of us are a little slow sometimes to update the software. As we advance, as we improve our lives, as our vision gets bigger, we’re not looking around immediately to say, “Are these the people that I want to be? Are they the best people for me to be hanging around to help me achieve this next level that I’m trying to get to?”
Yeah. Derek, if you could give just one piece of advice about how the listeners could really accelerate their own wealth trajectory, what would it be?
You know, I think I would just piggyback on some of what we’ve been talking about already. And that is, I think that a lot of people — whether they think they’re waiting for retirement, or waiting for the sale of their company, or waiting to bring in the CEO, or waiting to have a little bit more money in their investment accounts — they’re not really focused on living their life and leaning in right now.
And I think a lot of the things that I mentioned — the time with friends, the time with kids, the time with the spouse, you know, taking care of yourself — a lot of people feel like they don’t have time to do those things. And there’s a lot of data to support what I’m about to share.
And that is, and it’s been true for me in my personal experience, that when I take a step back and I spend less time working and more time investing in those things, even though I am spending less time in the office, I am more productive, I’m making more money, I’m generating better ideas, and I’m adding more value than I was if I weren’t doing that.
And so sleep is another example, right? Like, I would say, I have an Oura ring which tracks and monitors your sleep. I’ve had it since 2017. I don’t think I ever got higher than an 80 out of 100 sleep score for the first five years I had it.
And I just said, you know, I am going to set a goal for myself — I want to wake up and feel amazing every single morning. And now I get like high 80s, low 90s almost every night when I’m at my house. And the way I wake up, the way I feel in the morning, I didn’t know that it was on the menu a couple years ago.
And when you wake up and feel great, you make better choices at 9 o’clock. And those better choices at 9 o’clock lead to you picking the salad for lunch instead of the cheeseburger. And you having the salad for lunch instead of the cheeseburger means you’re showing up better for your client at 3 o’clock than you would have if you had the cheeseburger.
And you showing up better for your client at 3 o’clock makes it more likely you’re not going to skip your workout at 5 o’clock. And so I really do think I want people to recognize and realize that pouring more into them and their life — filling their cup, filling their soul, filling their spirit — the ancillary benefit of all that is, I think you’re going to end up having a lot more money than you would if you just kept grinding it out at work.
Yeah, that’s great. Awareness is everything. And once you can really make that paradigm shift to investing in yourself and starting to see these things, you’ll see how things can really blossom for you.
So, Derek, really appreciate your time and insights today — full of wisdom and everything. We’re definitely aligned, I think, in terms of how we think. And, you know, appreciate you sharing those stories and wisdom with our audience.
Yeah, thanks a lot, Dave. It was great talking with you and excited to stay in touch.
All right, thanks. Thanks for listening to this episode of Wealth Strategy Secrets.
If you’d like to get a free copy of the book, go to holisticwealthstrategy.com — that’s holisticwealthstrategy.com.
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