Tailored Wealth

Strategic Financial Planning

Why the Financial System is Failing Young Families | Dan Pascone with Rebecca Irey | Ep. 41

Posted on November 3, 2025 by Dan Pascone

Answer Box (TL;DR)

This episode explores why the traditional financial system – and the “do everything your parents did” playbook – may no longer work for young families facing higher costs, flat wages, and record debt. Dan and guest advisor Rebecca Irey unpack how to rethink debt, protection, and saving so you can build your own system instead of relying on a broken one. You’ll hear how tools like insurance, leverage, and intentional diversification can help younger families design a life they enjoy now while still building long-term wealth.

Whether you’re a young family yourself or a high-earning professional trying to set your kids up for success, this conversation will help you see why money isn’t just about cutting lattes – it’s about building a structure that actually works for this generation’s reality.

Key Takeaways

  • The math changed for young families. Home prices, cars, and basic costs have grown far faster than wages, so the “just save, buy a house, and max the 401(k)” playbook may not get today’s 20–40-somethings where it got their parents.
  • Debt payoff alone isn’t a plan. Aggressively paying off debt without building assets or flexibility often leaves the bank with your money and you with no cushion; younger families may benefit from strategies that let them reduce debt and keep control of their capital.
  • Leverage and protection matter. Rebecca walks through using structures like permanent insurance and other protected assets to create a base that can be leveraged for goals (education, housing, business) instead of relying only on traditional loans.
  • Diversification is more than owning a few mutual funds. Real diversification includes both “protected” assets and investments at risk, not just spreading everything across different funds inside the same market bucket.
  • Education and intentionality beat rules of thumb. Classes on taxes, Social Security, estate planning, and women’s wealth can help families design their own repeatable money system instead of blindly following generic advice.

Key Moments

  • [00:00] Dan introduces the episode and frames why the old financial playbook may not work for young families.
  • [01:11] Rebecca shares her background: seven kids, six grandkids, and why she focuses on families 40 and under.
  • [06:08] The hard numbers: housing and cost of living vs. wage growth, and why younger generations feel stuck.
  • [08:33] Why delayed gratification isn’t landing with millennials and Gen Z – and why they still deserve a good life now.
  • [09:22] Reverse-engineering retirement for a young couple who wants work to be optional by age 40.
  • [10:58] How infinite banking and leverage can be used to pay off debt while keeping your money compounding for you.
  • [15:39] Timeframes and tradeoffs: what it takes to build a personal banking system you can actually borrow against.
  • [19:13] Rethinking diversification: protected capital vs. at-risk investments and why both have a role.
  • [21:37] The education gap: estate planning, taxes in retirement, and women & wealth classes for real families.
  • [23:40] Why financial education still “sucks” for most Americans and how content and classes can fill the gap.

Episode Summary

In this episode, Dan Pascone sits down with advisor and entrepreneur Rebecca Irey, founder of Blue Sky Financial, to talk about why the financial system feels like it’s failing young families – and what they can do about it. Rebecca has seven children and six grandchildren, so she’s seen firsthand how different the math is for today’s 20–40-somethings: housing costs, cars, and daily life have exploded in price while incomes have only nudged higher. The result? Traditional advice like “never use debt, skip Starbucks, and just max the 401(k)” often leaves younger families exhausted, behind, and still feeling broke.

Instead of just blaming discipline, Rebecca argues the system itself has changed, and the money strategy needs to change with it. She explains how wealthy families tend to use leverage and protected capital – not just brute-force debt payoff – to build generational wealth. Using examples like infinite banking concepts and cash-value life insurance, she shows how younger families can protect themselves, then borrow against their own assets to pay down high-interest balances, fund education, or make down payments, keeping their money working while they use it.

The conversation also dives into real diversification (protected vs. at-risk assets), why we may be overdue for a market correction, and how taxes and Social Security decisions can quietly destroy wealth if they’re ignored. Rebecca shares the classes her firm runs on estate planning, taxes in retirement, Social Security, women and wealth, and financial independence for young families – all with the goal of helping people create their own system instead of relying on one that wasn’t built for them.

Transcript

Dan: I’m Dan Pascone, CEO of Tailored Wealth and host of the Making Sense of Your Money podcast. Real conversations to help high earners make sharper decisions so their money works as hard as they do. This is episode number 41, and today I’m joined by Rebecca Irey, founder of Blue Sky Financial, to unpack why your parents’ money playbook no longer works and how young families can still build real wealth by leveraging their own system instead of the broken one.

Dan: If you find value in this episode, make sure to like and subscribe for more conversations every week.

Narrator: Brought to you by Tailored Wealth, helping business leaders live their version of a rich life.

Dan: Welcome to another edition of the Making Sense of Your Money podcast, where we cut through the financial noise and help business leaders to make smart, confident money decisions.

Dan: Rebecca, thanks for joining us. This is going to be a fun conversation. Excited to have you today.

Rebecca: Thanks for having me, Dan. I appreciate it.

Dan: You bet. You bet. So, bunch of stuff I want to get into with you, but as we always do, give our audience a quick high-level overview of who you are, what you do, who you serve, etc.

Rebecca: I am the founder of Blue Sky Financial. We’ve been independent since 2017. We’ve got about 150 advisers in all 50 states. Our focus, one of our main focuses, is families – kids under… kids, listen to me – families 40 and under. I have seven children, six grandchildren. So, that’s a big focus for us, is showing young families how to make the financial system work for them.

Dan: Really, really cool. That’s very interesting. You and I chatted offline, but most folks in our business are looking to serve the older niche, frankly, because that’s where most of the assets are, right?

Dan: But I think a really underserved population – and folks that maybe don’t get the financial education that they needed – is the younger population. And so I’m excited to unpack this with you. First off, what did you say, seven kids and six grandkids, or the other way around?

Rebecca: Seven kids. Six grandkids.

Dan: Seven kids. All right. So we could probably spend a whole different podcast on that alone, but tell me the age ranges and then I want to hear: has your family dynamic shaped what you do from a business perspective and who you serve and what you do to help them?

Rebecca: Sure. So my kids are – oldest is 34. Youngest is 14. So all my kids are summer birthdays, right? Because we’re entrepreneurs. So I’ve been an entrepreneur since I was 14. Happy Thanksgiving, Merry Christmas, Rebecca’s pregnant, here we go. Like this is what happens. I would tell you I am a slow learner. My husband, who is from Minnesota, would say, “We lived in Minnesota for 20 years. It’s cold. What are you going to do?”

Rebecca: So homeschooled all the kids, had a great time, always been entrepreneurial. So that piece of it was important. I actually – part of my kids’ high school curriculum, because I, you know, my theory was always if somebody’s going to indoctrinate my kids, it’s going to be me. Like, nobody else is going to do that. So part of their high school curriculum was Dave Ramsey’s Financial Peace University, prior to coming back to financial services.

Rebecca: So I got into financial services right out of college, 1991. We don’t need to talk about how old that makes me – too old – and then came back to it in 2017 when my husband got ill, dramatically ill, very suddenly. We can have a conver… that’s a whole another conversation. But it was important to me to set my kids up, you know, to have them be… I didn’t come from money. I came from “let’s make it through college on ramen and Mountain Dew and a little bit of Old Milwaukee,” right? Like that’s how we did it, right?

Rebecca: You bounce checks for Domino’s pizza because what else are you going to do? You make…

Dan: Been there. Yep. Been there.

Rebecca: …gather all the condiments from McDonald’s because you can make really good potatoes with them. Like that’s what we did. But I didn’t want that for my kids. So now, for me now, they don’t know this. What they know is that I have seven kids, so that means my retirement plan is two months with you and two months with you and two months with you. That’s what they think.

Rebecca: But for me as an adviser, as a mother, to know that all of my kids and grandkids will be financially stable – guaranteed, contractually, for sure – right? That means a lot to me, because now we’re talking generational wealth and we don’t have to go backwards anymore. It means a big deal. So, as a mother, as a Gen X mother, right, that means a lot to me. But working with younger families is a whole different conversation, saying, acknowledging – and do you have kids, Dan?

Dan: I do. I have a 10-year-old. Yep.

Rebecca: Okay. So 10 is young. So you have a Gen Alpha. Aren’t they fun? I love them.

Dan: My…

Rebecca: My youngest is 14. She’s a girl. Confidence is not her issue. She is going to take over the world and she will tell you so.

Dan: Thank you.

Rebecca: Last year, she said to me, “Mom, you need to have a team meeting, and I will teach all of your advisers how to take initiative.”

Dan: Did you do it? Did you take her up on that?

Rebecca: I did. I did. I’m like, “Hey girl, knock yourself out because couldn’t we all use that lesson?”

Rebecca: Yes. Yes. Absolutely. They’re sick of hearing me say stuff. So here you go. From out of the mouths of babes, right?

Rebecca: I think it’s refreshing for millennials and Gen Z, right – those folks – it’s refreshing for them to hear someone say, “The financial system is broken. If you feel like it is, it’s because it’s true. It’s true. You will not – utilizing the tools that I got to use and my parents got to use – ever become financially independent. It will never work for you. So if you feel that way, there’s a reason.”

Dan: Unpack that a little more, Rebecca. Tell us – because I hear this a lot and I think our audience probably hears a lot – “The financial system is broken. What worked for our parents won’t work for you.” Dive a little bit deeper into that. Give us some thoughts on the specifics around why that is, and then we’ll get into a separate discussion around what do we do.

Rebecca: Sure. So let’s just talk about that for a second. Average cost of a house in 2000 – any guesses?

Dan: Average cost of a house in America in 2000. Median price…

Rebecca: Median.

Dan: Let’s go with $120,000.

Rebecca: Okay.

Dan: Right?

Rebecca: Right in the ballpark.

Dan: Yeah.

Rebecca: A home today, average median across the country?

Dan: 325.

Rebecca: 513.

Dan: Wow.

Rebecca: Average salary in the year 2000?

Dan: Average salary in the year 2000… 45,000.

Rebecca: 32.

Dan: Okay.

Rebecca: Average salary today?

Dan: 68.

Rebecca: 47.

Dan: Wow. Okay.

Rebecca: What’s the problem?

Dan: I got it. I got it. One thing is growing faster than the other.

Rebecca: Right. We have tripled the cost of things. We add a trillion dollars to our national debt approximately every five months. The cost of things has tripled, and our income – our kids’ income, right – has gone up by 25%.

Rebecca: Okay, they’re screwed. And don’t believe me. Go to US Debt Clock. You want to be really frightened – like a horror movie, Happy Halloween frightened – go to usdebtclock.org and watch the numbers spin, and it will tell you average cost of a home, average cost of a car.

Rebecca: Can you believe people spend $80,000 to $100,000 on a vehicle? On a car? To me, when I bought my first car, it was like $14,000. It was brand new off the lot, right? Again, I’m old. I get it. But still, if you’re making $47,000, what are the gurus saying? Like, let’s just acknowledge the elephant in the room – Dave Ramsey, right?

Rebecca: Never get into debt. Never go to Starbucks. White-knuckle your whole adult life. Get used to being broke so that someday maybe you could have a new car or go on vacation. What do you think?

Dan: Our kids are like, “Pass.”

Rebecca: No. The delayed gratification for our children – that’s not a thing. Like I tell this story about my son, and he will tell you these words were probably never said, but he will tell you that the feeling is the same. My oldest son has three children. They’re wonderful children. He’s 27 – 27. He’s 27.

Rebecca: He came to me the other day and he said, “I’ve been doing this full-time work thing for like seven years, Ma. I’m tired.”

Dan: 20…

Rebecca: And what? You just spin? You’re not going to be a YouTube star, baby. So turn yourself around. Go back to work. That’s adulting, right?

Rebecca: This delayed gratification that we did – “Hey, I’ll wait. I’ll wait forever just so I can someday have it.” No, no, no, no, no. They want a nice life now. And what’s wrong with that? Shouldn’t they have it? Shouldn’t they? I think they should have it.

Rebecca: So that’s what we help families create. There is a way to do that, but it is not what worked for you and I or our parents.

Dan: Yeah, I got it. All right. So now let’s fast-forward. What do we do about it? What do you and your team help the younger generation to prepare for and to ultimately live a life that is a little bit more fulfilling than just delay, delay, delay, and then get a chance to maybe spend it one day?

Rebecca: Well, I mean, first of all, there is a path, but I will say that the first conversation that I have with a young family is: “When do you want to retire?” So I just met with a family last week, and they’re lovely. Oh, I love working with young families so much because they’re excited and they want a path forward. And so, she’s 25, he’s 28. And I said, “Okay, so when do you want to retire?”

Rebecca: And they’re like, “I mean, we really can’t imagine working past 40.”

Dan: Okay.

Rebecca: Which I think is…

Dan: I love that.

Rebecca: So, you know, we looked at their income and I said, “Okay, let’s talk about your debt.” And we talked about maxed-out credit cards and car loans and debt consolidation loans already, at 25 and 28, right? And then I said, “Look, we can get there. Wherever you are, we can get to where you need to go, but you’re going to have 12 years of sacrifice. Know that you don’t have to have 40 years of sacrifice.

Rebecca: But if you tell me you want to retire at age 40 with $100,000 inflation-adjusted, I can help you reverse engineer that.” Right? So the first thing that we need to do is look at how do wealthy families deal with their money. Well, I’ll tell you something for sure: they don’t spend it. They leverage it.

Rebecca: They spend other people’s – OPM, right? Hello, Gen X. OPM is what we want: other people’s money. So first things first, for a young family, we’re going to set up a debt plan to get them out of debt while we protect them. So typically, we’re going to use an infinite banking program, right? We’re going to use a whole life policy with flexible paid-up additions. We’re going to use an IUL.

Rebecca: Why are we going to do that? Now, I will acknowledge to you I get a little bit of grief from financial advisors for taking a young family like that and saying, “We’re not going to put your money first in the stock market. We’re not going to… even though you have 40 years technically, we’re not going to do that. No, we’re going to protect you first and we’re going to protect you in a way where you can put money away and then you can leverage that money to get out of debt.

Rebecca: Because here’s the thing about – not to pick on old bald guys too much, names shall be removed – here’s the thing about getting out of debt. When I pay off AmEx, AmEx has my money. I don’t have my money anymore. AmEx has my money. So if I can build an account where I can leverage my savings to pay off my AmEx card, so now I have my money and I’m out of debt… I mean, ask the fat girl, can I have the cake and eat it too, please?

Rebecca: Yes. Yes. Yes. I want that. I want the cake and eat it too. That’s what I want. And that’s what these plans allow you to do. So, we protect them as a couple and their tiny humans, right? And we show them how to start leveraging their money. So now we don’t pay for college anymore. We leverage our savings to do that. We don’t pay for our down payment on our house anymore. We leverage our savings to do that.

Rebecca: We don’t white-knuckle ourselves to death. We leverage our wealth to do that because that’s what wealthy families do. And we need those habits. We need those tools. So, we start there. Once you have a foundation, Dan – and you know this – once you have a foundation and you know you’re good, no matter who’s in office, love them, hate them, whatever, whether they’re alive or dead, it doesn’t matter, right? We’re good. I’m safe no matter what.

Rebecca: Like my kids right now, they’re safe. So now we can look at investments. We can look at mutual funds. We can look at… we could even look at a little crypto if we wanted, right? We can take advantage of that because all of that is the frosting. It’s not our cupcake. Our cupcake is safe. It’s our frosting.

Dan: Tell us a little bit about the idea – so the infinite banking concept is an interesting one. We’ve talked about this on the podcast on a couple of different episodes. Explain to the audience what leveraging your money means and how that concept really works.

Rebecca: Sure. Now I will – and again, infinite banking is very trendy right now. IULs are very trendy. So I always say that IULs, annuities, insurance products – they’re just tools. They’re tools like a hammer, right? And with a hammer, you can kill somebody with a hammer or you can build a mansion with a hammer. So the tool itself is not the be-all end-all. It doesn’t actually matter, right? The tool is what we utilize.

Rebecca: So the key is to develop a program, and there are some strategies, right? You want to have low expenses. You want to be able to lock in your interest rate. So the best IULs out there are going to be able to say, “We’re going to allow you to lock in your interest rates.” They’re going to notify you every month, “This is what your allocations are doing,” and when it hits a certain point, you’re going to be able to say, “Never let it go below 10%.” And right now, with the market doing what it’s doing, we’re locking in at 15–18%.

Rebecca: In insurance products, that’s crazy to me.

Rebecca: But what that allows you to do is think about those products as like an insurance policy – so you’re protected if the worst happens – married to kind of a Roth IRA. If I were to have a young couple and they were, let’s just say for the sake of argument, they had $50,000 built up and she wants to go to college, so she needs 25 grand out, well the great thing about that particular scenario and how we leverage that is I can say, “Hey, no problem. I’m going to have that directly deposited into your account, but we’re going to use her equity as collateral.”

Rebecca: So she’s never actually going to spend that money. It’s going to continue to stay in her account, earning that interest. We’re going to use it as collateral, give her a loan against it for less than what she’s making, so she’s always net to the positive, and now she gets to spend the money and use the money too. We have it in both hands. And these are kind of the out-of-the-box, not-your-traditional financial plans that are going to make it work for our kids, because they’re going to know now, “I’m not paying interest. I’m not bowing to ‘the man,’ so to speak, right?”

Rebecca: “I’m not doing that. I got my own, and you can take your wheel and kick it on down the road because I’m fine without your system. I make my own system. In Texas, that’s how we do it.”

Dan: That’s right. You sure do. Getting started with this type of financial plan, talk a little bit about the time frame that people need to commit to, to sort of build up that banking system so that you can be leveraging your own assets versus just paying interest to the banks and whatnot. Help our audience understand what’s the commitment, what’s the time frame, and how long does it take so that I can actually leverage the assets to go make some of those purchases, whether they be for lifestyle stuff or business investments.

Rebecca: You know, a couple of different things to look at, right? So are we looking at you already have debt and we want to get out of it? So if that’s the scenario, then we have programs that we can put you in where you can leverage that money within 30 days, right? We just divert, reallocate, redirect – no problem. We can do that. So 30 days.

Rebecca: If we’re saying, like my clients from last week, “Hey, we want to retire at 40,” then we’re going to say, “Let’s reverse engineer that back down to say this is the investment that you need to make.” And make no mistake, it is an investment. You and I both know we have people come to us every day and they say, “Well, I want to retire.” I had a guy – no kidding, and I’m going to pick on him because he is 48 years old, so he’s not my kids. He’s older. He’s closer to our age, right?

Rebecca: And he’s making $42,000 a year. He wants to retire at 65 with $250,000 a year in income. Not impossible – struggle. It’s going to be a lot, right? Sacrifice – 12 years of sacrifice. And I said, “Okay, so I’ll reverse engineer that, but what are you thinking as far as what you could put away?” And he’s like, “Well, how close can you get me for a hundred bucks a month?”

Dan: Okay.

Rebecca: I can’t. Like, you’re 48 years old. That’s $24,000 in 20 years. That’s not going to get you there, darling. It’s not going to. And we owe it to people to be that frank, to just say, “Sorry, kitten. You’re 48 years old. You should know that this is not going to work. That is not going to get you there. I’m not a magic genie. Would that I were, but I’m not.

Rebecca: “How much you have is a function of how much you put in.” So if we’re dealing with a situation where a family has debt, well great. Let’s do a debt census. Let’s figure out where all your money is going and where we can redirect to start that leverage process. And not everything that the gurus say is bad, right? So let’s look at where the money is going. We can still use the debt avalanche concept or the debt snowball concept. We all know what that is. We can still use that.

Rebecca: The key is, are we going to have the money at the end, or is the bank going to have the money at the end? Well, to my way of thinking, you’re the one that your blood, sweat, and tears go into that money. You should have the money at the end, not the bank. That’s the difference, right? And then you add on to it, right – alternative investments, traditional mutual funds and stocks and bonds. All of that can come, but don’t bet your life on it, because…

Rebecca: Well, here’s a question: when’s the last time we had a major market correction? Major.

Dan: Major would probably be defined as 2007–08.

Rebecca: Yeah, absolutely. And before that, it was 2002. Before that, it was the ‘90s. Before that, it was the ‘80s. Every decade, economics tells us every decade we should have one. It’s been 16 years.

Dan: Yeah, we haven’t had one. We’re overbaked at this point, right? It’s going to happen.

Rebecca: Do I want to bet the farm? And I’m a rancher’s daughter. I know what it means to bet the farm because we bet and lost, right? I was raised in the ‘80s. We bet a four-generation farm and we lost. I know what that means.

Rebecca: So, 16 years since the last major market correction. Am I going to bet the farm for myself or my clients? No, I’m not. Do I want to take advantage of what it’s doing right now? You bet I do. Absolutely. So how can we have both?

Dan: So let’s talk about that. How can you actually have both? Because a lot of people talk about this concept that we’re way overdue for a correction, and when that comes, you and I have no idea, but it’s going to come at some point in time. What can we do to not bet the farm, but still take advantage of what has been a very, very profitable, growth-focused economy and capital market system?

Rebecca: Sure. I mean, I think the answer is diversification, right? So you diversify macro all the way down to micro. So you diversify protected and at risk, right? So your protected asset is going to be your IUL. It’s going to be your… Please don’t do a CD because CDs are – I always call them certificates of depreciation. Like, come on. By the time you take taxes and inflation off that deal, you’re just losing money. Don’t do that.

Rebecca: But, you know, your guarantee – you have a contractual guarantee you’re not going to lose your money. You have that on one side, and then you have your at-risk part of your portfolio, your mutual funds and your stocks. So make sure that you’re protected is enough to keep you, and then absolutely take advantage of that. But then inside the at-risk portfolio, we diversify again, right, across asset classes.

Rebecca: Now in my classes sometimes – this is my favorite example – I had a client say… I always say, “Who thinks they’re completely diversified?” And I had a lady raise her hand and she’s like, “I am diversified.” I’m like, “Great, tell me what you got.” She’s like, “Well, I have a CD at Wells Fargo. I have a CD at Bank of America. And I have a CD at Chase. I am diversified.”

Dan: Diversified across the major banks.

Rebecca: And that’s funny, right? And I say it – it’s true – but I say it as a joke. However, most of us will say, “I am diversified,” and dang near 100% of our assets are in mutual funds, bond funds, mutual funds, stocks. Are we diversified? No, we are not. We are not diversified because 100% of our assets are at risk. We’re no more diversified than my little old lady there with her three CDs, right? We’re not either.

Rebecca: What’s the average rate – and most of us invest in bond funds, right, and that’s our “safe” part of our portfolio – average bond funds over the last 12 years, what’s our interest rate?

Dan: Six, seven percent.

Rebecca: 1.13.

Dan: Okay.

Rebecca: In bond funds in 2022, averaged -3%.

Dan: Yeah. If you take those…

Rebecca: That’s our safe. That’s “safe.” That doesn’t feel safe to me. That’s not a happy-wife, happy-life moment right there. No. No. We’re not diversified either. And if you start looking – and I don’t know how much politics you talk about, Dan – but if you start looking at, listen to what politicians are saying, there was a senator that was asked not so long ago, “Are you concerned about the national debt?” And she looked right in the camera and she said, “I am not, because we haven’t even started taxing 401(k)s.”

Rebecca: We have a $37 trillion debt and we have $40 trillion in IRAs and 401(k)s. Funny how that works, isn’t it?

Dan: Problem solved.

Rebecca: Yeah.

Dan: You mentioned your classes. Tell us a little bit about the classes and who participates in them and what are the goals.

Rebecca: So we do a series of classes. We do estate planning, because that’s a big deal. Everybody’s retirement – you’re in partnership with your favorite uncle, Sam, when you retire because of taxation, because of estate cost. So estate planning is a big thing.

Rebecca: We do Social Security maximization. So there’s over 500 different ways to file for Social Security, and most of us get to Social Security and say, “When can I take it? How much do I get?” Like, these are our questions. And yet, there’s hundreds of thousands of dollars of difference depending on how you choose to do that.

Rebecca: We do taxes in retirement because I always say to people, if your financial adviser is not talking to you about Roth conversions, fire them. No kidding. No bones about it. Fire them. And if you’re a DIYer and you are not looking into that, fire yourself and find a reasonable adviser. Like, no kidding. Whether it’s me or someone else, I don’t care. Please do something.

Dan: In retirement, I always say, is where the most wealth gets lost. There’s not even a question about it.

Rebecca: Huge. Huge. Huge. Not to quote our president, but huge.

Dan: Yeah. Huge.

Rebecca: Yeah. So we do that one, and then we do Women and Wealth because statistically, we’re going to last longer. My husband will say because men want to die first. And he’s still been married 30 years – how that works. Anyway, we last longer. And here’s the thing: we live longer. We start saving later, and statistically, we make 30 cents on the dollar compared to our comparably educated peers.

Rebecca: Now, that’s not a political statement. There are reasons for that. Not saying there’s not. But it’s true. We have to plan more. So Women and Wealth is a big deal. And then working with young families and financial independence – that would be the last one that we do. But I have a great time educating people because financial education in America, despite the gurus, it sucks.

Dan: It does suck. I agree. That’s why I’m passionate about what you do, what I do, and our ability to not only help people on an individual or family basis, but help a broader audience through the content that we put out, the education that we put out. And that’s one of the things I’m most passionate about.

Dan: Awesome, Rebecca. We’re going to shift gears a little bit. That was great learning about you and who you help and what your business and your team does. Now we’re going to get to know Rebecca a little bit more. I’m excited about this. I think this is going to be a fun one.

Dan: All right. So you’re entering the lightning round. All right. So first thought that comes to your mind. Could be a one-word answer, could be a long drawn-out thought, or anywhere in between. You ready?

Rebecca: We’ll start easy.

Dan: Coffee or tea?

Rebecca: Tea.

Dan: One meal for the rest of your life. What is it?

Rebecca: Crème brûlée.

Dan: We haven’t had crème brûlée yet. That’s a good one. I like that. I like that.

Dan: All right. What’s one… question: what’s one tool or piece of technology – could be hardware, could be software – not your computer, not your phone, that you can’t live without?

Rebecca: Not my computer, not my phone. What can I have that’s not on my computer and not my phone? That’s a hard one.

Dan: It could be on your computer and it could be on your phone, but it can’t be those specific devices. Could be…

Rebecca: Okay. Okay. So I have a new one. I have a new one.

Dan: Let’s go. There you go.

Rebecca: It’s called a vibe tracker, right there.

Rebecca: So I am a hippie, full disclosure. Totally a hippie. But here’s the thing: in any business, I can go from “I will fork-stab you in your eyes” to kumbaya in the span of like 13 seconds, right? So this little gadget will vibe-check me – like, “Hey, where you at?” It’s really cool. Okay.

Rebecca: So I love this. I use it all the time. Literally all the time.

Dan: Very cool. And like, what does it actually tell you? Like, is it giving you a state of your overall vibes at any given moment, or what is it saying to you?

Rebecca: So how hippie do you want me to go? So it measures your chakra energy, supposedly. So I get a little spiral that says you are in your root chakra, which means you’re probably going to fork-stab somebody in the eyes, or you’re in your third eye and you’re good. Okay. Okay.

Rebecca: But for me, it’s a “Where am I? Am I irritated?” And honestly, the older we get – and I am a grandma, shocking, but I am, right – this is important. Monitoring mental health is a big deal. And the fact is, in our business, money impacts everything. Where you live, how you live, what you eat, what you get to do, what your hobbies are, your mental health, your physical health – it’s all… you’ve got to manage your vibes.

Dan: I love it. I’m glad I dug a little deeper on that, because that’s a new one for me. I’m glad I learned about the vibe tracker. Very cool.

Dan: All right. Do you have a favorite quote or phrase about money or success?

Rebecca: Judge Learned Hand was a Supreme Court justice, and he said, “It is not your patriotic duty to pay more in taxes. In fact, it is your responsibility to avoid as many taxes as possible.”

Dan: Oo, I love that one. I’m going to use that. That one might go on my YouTube channel. That’s a good one, because we do a lot of tax content.

Rebecca: He’s got a lot. Look him up. He was very learned.

Dan: I like it. I like it. Very good.

Dan: How about a favorite book on finance or business?

Rebecca: There are a lot. If I were a young family, I would start out with What Would the Rockefellers Do? I think that’s fantastic. I think that’s fantastic. It’s a primer on legacy wealth.

Dan: Yeah. Very cool. Very cool.

Rebecca: It’s about time legacy wealth looked like our neighborhoods. And not to put too fine a point on it, but if you look at wealth in America, it’s all old white men. Like, sorry y’all – down with the patriarchy, man. Let’s go. It should look like our neighborhoods. Wealth in America should look like our neighborhoods. And it doesn’t. It’s time. Time has passed.

Dan: Yeah, I agree with that. Do you have a personal routine or a hack that you can share with our audience?

Rebecca: Money?

Dan: No, doesn’t have to be money. In fact, let’s stay away from money for this one.

Rebecca: So I am a biohacking nerd.

Dan: Okay.

Rebecca: I absolutely am. So big believer in meditation, which won’t shock you now. Big believer in cold showers. Hate them, but I still do them. I do 75 Hard. If you don’t know 75 Hard, it’s fantastic.

Dan: Okay.

Rebecca: So love all of those things. Like my morning routine – and I’m not one that will say, “I can’t have a good day if I don’t do my morning routine,” but I literally block out four hours in the morning.

Dan: Wow.

Rebecca: I do. I’m up at four, and I do all the things.

Dan: 4 a.m. is Rebecca time.

Rebecca: It actually is. It actually is.

Dan: All right. I like it.

Rebecca: I’m a nerd. A hippie nerd, which is, you know, let’s just paste on more labels. Let’s do that.

Dan: What’s one bucket list item you’ve already accomplished? Seven kids – was that on your list?

Rebecca: That was not on my bucket list. Believe it or not, I didn’t want children at all.

Dan: Wow.

Rebecca: None. I know. Crazy how the universe works. Trickster. Bucket list that I have – so, okay, here’s a bucket list thing. And I put it on my bucket list like four years ago.

Rebecca: So I was raised as an only child. I am the child of my father’s misspent youth. But I have five sisters from my parents’ multiple marriages after me. And my bucket list was that I wanted to get to know all of them and take sister trips. And we do that. We do that.

Dan: I love that. I love that.

Rebecca: Yeah. I just came back from one in New Mexico with one of my sisters. We went to Santa Fe and we hiked and we went to the Chile and Wine Festival and it was fantastic, to be grown up and do grown-up things. It was awesome. And that is a bucket… relationships are so important.

Dan: Agreed.

Rebecca: You know, the distance between me and my next sibling is 12 years.

Dan: Okay.

Rebecca: So that’s a big deal. My people are my favorite people. My kids and their spouses and my grandkids and my sisters are freaking fantastic. They’re amazing people.

Dan: I love it. Very cool.

Dan: All right. Last one. One piece of advice to your younger self – what would it be?

Rebecca: Don’t buy anything right away.

Dan: Okay.

Rebecca: Like, wait. And if you still want it in 90 days, then… Because if I look at all of… And occasionally, you look back and go, just the utter waste sometimes of, you know… and I will say I have one of my business partners is from Chicago and he is forever – he’s an African-American guy from Chicago – so he’s forever talking about “the young people in my community, they spend so much money on shoes,” and I’m like, “I don’t get that at all.”

Rebecca: Like, I’m still wearing the same shoes I was wearing 15 years ago. But if it comes to gadgets…

Dan: Yeah. Right.

Rebecca: She spends a lot. She spends… Right. And some of them are cool and some of them are like, “Well, that’s going to Goodwill,” right? And so we have these things. If you just take a breath, find your pace, and you don’t have to have it right now. It’s not going to change your life. I promise it’s not. Probably. Maybe it will. But yeah.

Dan: Very cool, Rebecca. And if our listeners want to connect with you, collaborate, learn more about you and what you do, what’s the best way to follow you, reach you, learn about you?

Rebecca: I’m on all the socials – Instagram, Facebook. I don’t TikTok. Sorry.

Dan: The one… only one I don’t.

Rebecca: Right? I don’t TikTok. Blue Sky Financial is the website – blue like the color, skyfinancial.com. You’ll know all about all the things that we do. But yeah, look us up.

Dan: Very cool. Well, thanks for sharing your insights. I enjoyed the conversation. Great having you on.

Rebecca: Absolutely. Thanks for the opportunity.

Dan: Very cool. That’s it for the episode. You can find our podcast along with our newsletter, our YouTube channel, all for free at makingsenseofyourmoney.com. And as always, prioritize your version of a rich life.

Resources & Citations

FAQs

Why do you say the financial system is “failing” young families?

Because the math has changed. Housing, vehicles, and basic living costs have grown much faster than average wages, so younger families may not reach the same milestones using the same playbook their parents used. When you combine that with higher student debt and tighter credit standards, simply “working hard and maxing the 401(k)” may not be enough to create financial independence without a more intentional strategy.

Is the solution just to avoid debt altogether?

Not necessarily. High-interest consumer debt can be very destructive, but a blanket “no debt ever” rule may keep families from investing in education, housing, or businesses that could improve their long-term trajectory. This episode highlights using structured strategies – including building protected assets first and then borrowing against them prudently – so you can reduce harmful debt while still moving important life goals forward.

What does it mean to “leverage” your own savings instead of the bank’s?

Leveraging your own savings means using assets you control as collateral, rather than draining them or relying entirely on outside loans. For example, some families use permanent life insurance or other protected accounts to build a pool of capital that can be borrowed against for education, down payments, or business investments. The key is understanding costs, risks, and tax treatment, and making sure any strategy fits within a broader financial plan and complies with product rules and eligibility requirements.

How can younger families balance enjoying life now with saving for the future?

It starts with clarity. When you know roughly what it takes to reach your version of “work optional,” you can decide how much needs to be directed to long-term goals versus near-term experiences. Many families find that automating savings, building a safe foundation first, then adding growth-oriented investments allows them to spend more confidently today while still making steady progress toward future independence.

Where do traditional investments like 401(k)s and mutual funds fit into this kind of approach?

They still matter. Retirement accounts, taxable portfolios, and other market-based investments can be powerful tools, especially over long time horizons. The difference is that in this framework they’re part of a bigger system that also considers protection, leverage, taxes, and timing. Rather than “betting the farm” on the market, you may want to combine protected assets and growth assets so your plan can weather downturns without forcing you to sell at the worst possible time.

Should I use strategies like infinite banking or IULs for my own family?

These tools can be helpful in specific situations, but they are not a fit for everyone. They come with costs, complexity, and product-specific rules, and results can vary widely depending on design, funding, and how you actually use them. Before implementing any strategy like this, it’s important to review your full financial picture, understand tradeoffs, and consult with a qualified adviser and, where appropriate, tax and legal professionals to ensure it aligns with your goals and risk tolerance.

Disclaimer

The information in this episode and on this page is for educational purposes only and is not intended as individualized investment, tax, or legal advice. Strategies discussed may not be appropriate for every investor and are subject to product terms, eligibility, and changing laws. Always consult with your own financial, tax, and legal professionals before making decisions.

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