Debt as a Tool: How Leverage Actually Builds Wealth

Monthly Money Man on September 4, 2026

Over the last few weeks, we’ve climbed through this debt series together. You learned to spot when debt crosses from tool to trouble. You learned the difference between good debt and bad debt. Today we finish the climb by looking at something most people never get taught: how debt, used on purpose, actually builds wealth. There’s a word for that. It’s called leverage.

I sat across from a lot of families in my advisor years who flinched at the word “debt” — or “leverage,” once they learned it meant the same thing. That’s not an accident. A lot of us were taught, sometimes loudly, that all debt is dangerous. But debt used to grow your own wealth has a name, and it isn’t a bad word. It’s leverage.

Once you understand it, you’ll never look at a mortgage statement the same way again.

What Leverage Actually Means

Leverage is borrowing money to acquire something that grows in value or produces income, using a relatively small amount of your own cash to control something bigger.

Here’s the plain-English version: you put down $40,000 on a $400,000 house. The bank puts up the other $360,000. If that house appreciates 3% next year, you don’t just gain 3% on your $40,000 — you gain 3% on the full $400,000. That’s leverage working for you.

The same idea shows up in a business loan that lets someone buy equipment that pays for itself in revenue, or a student loan that unlocks a career earning far more than the debt cost. In every case, the debt is a tool that lets you control something bigger than your cash alone could buy.

Where You’ve Probably Already Used It

You don’t need to be an investor to have used leverage. Most Ascenders already have.

  • Your mortgage. If your home has appreciated since you bought it, leverage already worked in your favor — even if you never thought of it that way.
  • A business loan for equipment or inventory that generates more revenue than it costs. The debt pays for itself and then some.
  • Student loans tied to a real career outcome. If the degree led to income that outpaces the loan, that’s leverage doing its job.

Notice the pattern. In every good example, the debt is attached to something that either grows in value or grows your income. That’s the test.

Debt Isn’t Bad Every Time — Here’s the Proof

I recently came across a number that surprised even me: roughly 1 in 4 homeowners with a mortgage rate around 3% are paying extra toward that mortgage every month.

I get the instinct. Money isn’t just math — it’s emotional. Debt especially carries weight that a spreadsheet can’t capture. Paying it off feels like relief, like control, like proof you’re doing the right thing. That feeling is real, and it matters. But mathematically, paying extra on a 3% mortgage is often the wrong move.

If your mortgage is costing you 3% and the stock market has historically returned 10% or more over time, every extra dollar you send to the mortgage is a dollar that could have earned the spread — the difference between what you’re paying and what you could be earning.

That’s not a guarantee, and the market doesn’t move in a straight line. But it’s the clearest example of why debt isn’t automatically the enemy. A cheap mortgage sitting quietly in the background while your money grows elsewhere is leverage doing exactly what it’s supposed to do.

So Where’s the Line?

A few weeks ago, we talked about a 10% threshold as a rough way to flag debt that’s becoming a problem. I want to be careful with that number today, because it’s a guide, not a rulebook. A 9% loan isn’t automatically fine, and an 11% loan isn’t automatically a disaster. The real question is bigger than any single percentage:

Is this debt helping you climb toward your summit — or is it just weighing down your pack?

A mortgage on a home you can afford, at a rate lower than what your money could earn elsewhere, is leverage. A loan for something that doesn’t grow, doesn’t produce income, and stretches your monthly budget thin is a liability wearing a leverage costume. The rate matters. But what the debt is doing for you matters more.

Now What?

You don’t need to take out new debt this week. You just need to see the debt you already have with clearer eyes.

  1. Pull out your list from the last two weeks — the one where you labeled each debt good, bad, or straining.
  2. For every “good” debt, ask: is this attached to something growing? A home, an education, an income-producing asset.
  3. If yes, you’re not carrying debt. You’re using leverage. Let it keep working quietly in the background.
  4. If a “good” debt isn’t actually attached to growth, relabel it honestly. That’s useful information, not a failure.

That’s the whole series in one sentence: debt without the purpose of helping you grow toward your summit is just weight. Debt with a purpose is a tool.

This article is for educational purposes only and does not constitute personalized financial advice. Please consult a licensed financial professional regarding your specific situation.

Good Debt vs. Bad Debt: Not All Borrowing Is Equal

Monthly Money Man on August 28, 2026

A few weeks ago we talked about the 10% line, and last week about picking your payoff method and actually sticking to it. If you’ve been doing that work, good — you’re climbing. But I want to slow down for a second, because there’s a piece of debt talk that gets oversimplified almost everywhere else you’ll read about it.

You’ll hear a lot of finance voices tell you all debt is bad. Pay it all off, avoid it forever, never touch it again. I understand the appeal of that message — it’s simple, and simple sells. But it’s not true, and treating it as true can actually cost you money and opportunity. In fact, a lot of the wealth-building you see around you — the rental property down the street, the small business that grew into something real — was built using debt as a tool, not avoided because of it.

The real question isn’t “debt: yes or no.” It’s good debt vs. bad debt — understanding what each dollar you owe is actually doing for you.

What Makes Debt “Bad”

Bad debt has three things in common: it’s used to buy something that loses value, it usually carries a high interest rate, and it doesn’t build anything that pays you back over time.

Credit card debt on things you’ve already consumed — vacations, restaurants, clothes you’ve since donated — is the clearest example. So are most personal loans taken out to cover a shortfall rather than an investment. The car itself isn’t inherently bad debt, but a car loan on a vehicle that’s depreciating fast, at a rate that eats into your monthly cash flow, edges toward bad territory the more it strains your budget.

The test I’d give any client: is this debt working for you, or are you just working to pay for it?

What Makes Debt “Good”

Good debt has the opposite profile: it’s usually lower interest, and it’s attached to something that either grows in value or grows your income over time.

A mortgage on a home you can comfortably afford is the classic example — you’re borrowing at a fixed rate to hold an asset that’s historically appreciated, and every payment builds equity that’s yours. Certain education debt fits here too, when it leads to a real increase in earning power, though this one deserves a careful eye since not all degrees pay off equally. Business debt used to grow a company that’s already generating revenue is another example — you’re borrowing against future income you’re confident will materialize.

The common thread: good debt is a tool you picked up on purpose, not a hole you fell into.

The Line Isn’t Always Where You Think

Here’s where I’ll push back on the “good debt” label a little, because it’s not a free pass. A 3% mortgage payment that’s still eating 45% of your take-home pay is straining your climb even if the interest rate looks great on paper. Good debt can still be too much debt. The category tells you how the debt is structured — it doesn’t tell you whether you can afford it.

So the real framework is two questions, not one:

  1. Is this debt attached to something that grows in value or income? (Good debt vs. bad debt)
  2. Is the payment sized so it doesn’t choke my monthly cash flow? (Affordable vs. not, regardless of category)

A debt needs a yes on both to actually be helping you climb.

What This Means for Your Next Move

If you’re carrying a mix — which most people are — here’s the order I’d want you thinking in:

First, attack anything that fails both questions: high rate, depreciating purchase, straining your budget. That’s your credit card balance, most likely. This is exactly what the avalanche and snowball methods from a couple weeks back are built forif you haven’t run your numbers yet, the debt payoff calculator will lay out your fastest path.

Second, leave good debt alone if it’s affordable. Don’t rush to pay off a 4% mortgage early at the expense of your emergency fund or retirement contributions. That instinct feels responsible, but it’s often not the highest-value move you can make with that money.

Third, if a “good” debt is straining your cash flow anyway, treat it like a budget problem, not a debt problem. That might mean a smaller car next time, not panic-paying down the loan you already have.

This Week’s Climb

You don’t need to restructure anything today. You just need clarity on what you’re actually carrying.

  1. List your debts again — you may already have this from the payoff plan work.
  2. Label each one: good, bad, or “good but straining my budget.”
  3. Circle the bad debt. That’s still your priority for extra payments.
  4. For anything labeled “good but straining,” ask honestly if the real fix is the debt or the monthly budget around it.
  5. Leave the truly good, truly affordable debt alone. Let it keep doing its job quietly in the background.

Not all debt is a mountain you need to tear down. Some of it is part of the trail. Knowing the difference is what lets you climb with a clear head instead of blanket fear.

See you at the top.

This article is for educational purposes only and does not constitute personalized financial advice. Please consult a licensed financial professional regarding your specific situation.

The Debt Plan: How to Actually Stick to It

Monthly Money Man on August 21, 2026

You don’t have a debt problem. You have a finishing problem.

If you’re like most Ascenders, you’ve started a debt payoff plan before. Maybe more than once. You made the spreadsheet, you felt the rush of motivation, and then somewhere around week six — a car repair, a kid’s birthday party, a “we deserve this” dinner out — the plan quietly died. Not because you’re bad with money. Because the plan wasn’t built for real life.

This month, we’re building one that is. A real debt payoff plan you can actually stick to — not the one that looks best on paper, the one that survives contact with your actual, chaotic, wonderful life.

The Method That Actually Sticks

Here’s where most debt advice goes sideways: it leads with math. Pay off your highest-interest debt first, they say. Mathematically, that’s called the avalanche method, and it will save you the most money in interest over time.

The math nerds will tell you to pay off your highest-interest debt first — and they’re not wrong. But if you’ve started and stopped a debt plan before, the method that gets you to the finish line beats the method that’s 2% more efficient on paper.

That’s why, for most people just getting their footing, I point them toward the snowball method instead: list your debts smallest balance to largest, ignore the interest rates for a minute, and throw every extra dollar at the smallest one until it’s gone. Then roll that whole payment into the next smallest. And the next.

Researchers at Northwestern’s Kellogg School actually studied this, and it’s not just a feel-good idea — people who knock out small balances first are significantly more likely to finish paying off all their debt than people who chase the “optimal” interest-rate order. A quick, real win in month one does something a spreadsheet can’t: it proves to you that this time is different.

Is it the most mathematically efficient path? No. Is it the path most likely to still be running in month eight, when life throws its next curveball at you? Yes. And a plan you finish beats a plan you abandon, every time.

(If you’re the type who genuinely loves a spreadsheet and wants to see exactly what the interest-optimized order looks like for your specific debts, our free debt payoff calculator will run both methods side by side so you can see the trade-off in real numbers — link at the bottom.)

The One-Page Debt Plan

You don’t need software. You need one page. Here’s what goes on it:

1. List every debt, smallest to largest. Balance, minimum payment, interest rate. Yes, even the store card you’re embarrassed about. Especially that one.

2. Find your “extra” dollars. Look at last month’s spending and find $50, $100, whatever you can find without white-knuckling it. This isn’t about deprivation — it’s about direction. Every dollar just needs a job.

3. Attack the smallest balance. Minimum payments on everything else, extra dollars all go to debt #1.

4. Snowball it forward. When debt #1 hits zero, its entire payment — minimum plus extra — rolls into debt #2. Your payments don’t shrink as debts disappear. They grow. That’s the whole trick.

5. Put a date on the page. Not a guess — do the math on your current pace. A real date turns “someday” into a destination you’re actually walking toward.

That’s it. One page, five steps, and you can build it this weekend at your kitchen table.

When Life Blows Up Your Plan Anyway

Here’s the part most debt advice skips entirely, and it’s the part that actually matters.

If you’ve been reading along, you know this has been a hard stretch around here — a big family trip, the loss of my father, getting my oldest ready for college, all stacked in the same few weeks. In our last article, “When It Rains, It Pours“, I wrote about what happens when several financial pressures hit at once. The truth is, life doesn’t pause your debt plan to let you catch up. It just keeps happening.

So build this into the plan from day one: some months, you won’t hit your extra-payment number. That’s not failure — that’s the plan meeting real life, which is exactly what it’s supposed to do.

When a rough month hits, don’t scrap the plan. Just pay the minimums, protect your emergency fund, and pick the extra payments back up the next month you’re able to. A debt plan that bends without breaking is a plan you’ll actually still be using a year from now. That’s the whole goal.

What Sticking to It Looks Like This Month

You don’t need to overhaul your finances this week. You need one page and one decision.

This month:

  • Write out your one-page debt plan using the five steps above.
  • Pick your smallest balance and decide exactly how much extra you can send it.
  • Set a recurring reminder for the same day each month to check your progress — not to judge yourself, just to look.

That’s the climb. Not a sprint, not a 30-day transformation. One page, one payment, one month at a time.

Ready to see the numbers for yourself? Head over to our free debt payoff calculator to plug in your own balances and watch both the snowball and avalanche paths play out side by side — so whichever way you go, you’re going in with your eyes open.

When It Rains, It Pours: How to Tell If Your Debt Is a Problem

Monthly Money Man on August 15, 2026

There’s an old saying: when it rains, it pours. Anyone who’s lived long enough knows exactly what that means. It’s never just one thing.

This summer, it wasn’t just one thing for me. We had a family trip already on the calendar. Then, in the middle of it all, I lost my father. Two months later, I’m in the thick of getting my oldest ready to leave for college. Travel, loss, and a launch into the next chapter of his life — all stacked on top of each other, all needing attention at the same time. If you’ve noticed Monthly Money went quiet for two Fridays, now you know why. I’m back, and glad to be.

I’m not telling you this looking for sympathy. I’m telling you because I think most people know exactly this feeling, even if the specifics look different. Life doesn’t ask permission before it piles things on. A trip you’d already planned. A death in the family. A kid heading off to school. And it’s not just the big, obvious things — it’s the water heater that picks the worst possible week to go out, the car that needs new brakes the same month the roof starts leaking. None of it waits for a convenient time. It shows up all at once, like it’s coordinating against you.

Here’s what I’ve noticed, both in my own life and in years of sitting across kitchen tables with people going through exactly this kind of stretch: this is often precisely when debt creeps in. Not because anyone was careless. Not because anyone overspent on purpose. Just because when everything is happening at once, the credit card gets the overflow. A flight gets booked without much thought. A repair goes on plastic because there’s no time or bandwidth to think it through. A few extra expenses land on a card “just this once,” and then life moves on to the next urgent thing before you circle back.

That’s not a character flaw. That’s just what happens when the season is heavy. But it’s worth knowing, because if you don’t catch it, that overflow debt can sit there quietly long after the season has passed.

So this month, I want to help you do two things: recognize when you’re in one of those “it’s pouring” seasons, and know what to do about the debt that tends to show up during them.

The 10% Line: Is Your Debt a Tool or a Problem?

Not all debt is the same, and not all debt deserves the same reaction. A mortgage at 4% and a credit card at 24% aren’t cousins. They’re not even in the same family. One is a tool. The other, past a certain point, becomes weight you’re carrying for no good reason.

Here’s the line I use, and it’s simple on purpose: if the interest rate on a debt is above roughly 10%, it’s no longer working for you — it’s working against you.

That’s not an arbitrary number. It’s close to the long-term average return of the stock market. So if you’re paying more than that on a debt, there’s no reasonable investment strategy that out-earns what that debt is costing you. The math just doesn’t work in your favor.

Below that 10% line, debt can genuinely be a tool. A mortgage helps you build equity instead of paying rent forever. A reasonable auto loan gets you to work — though it’s worth watching the payment, not just the rate. A low interest rate on a car you can’t comfortably afford can hurt your cash flow almost as much as a bad rate would, just in a different way. Used carefully, even some low-rate personal loans make sense. These aren’t weights — they’re mostly load-bearing.

Above that line — most credit cards, a lot of personal loans, buy-now-pay-later balances that crept up during a hard season — that’s different. That’s the stuff worth setting down before it sits there quietly for another year.

A quick way to check where you stand:

  1. Pull up every debt you’re carrying — cards, loans, anything with a balance and an interest rate.
  2. Write the interest rate next to each one. Not the payment. The rate.
  3. Draw a literal line under 10%. Anything above it goes on your “deal with this” list. Anything below it can wait.
  4. That’s it. You now know which debts are tools and which ones are problems.

You don’t have to fix all of it this week. You just have to know which pile is which.

Setting Down What Piled On

If you’ve had a season like mine — or any season where too much landed at once — the goal isn’t to beat yourself up over what accumulated. It’s to notice it, name it, and start setting it back down now that things have settled.

And there’s a longer-term fix here too. The reason a pile-on season turns into credit card debt is usually the same reason every time: there’s no cushion sitting between “life happens” and “the credit card absorbs it.” A solid cash reserve doesn’t stop the storms from coming — nothing does — but it gives you somewhere else to pull from besides a 24% interest rate. If you haven’t built yours yet, that’s worth doing before the next season catches you off guard. For now, just notice if you had one this time, and if you didn’t, file that away.

This week, I’m not asking you to build a whole payoff plan — we’ll get there over the next few weeks, with specific steps for tackling the above-10% debt once you’ve identified it. Right now, I just want you to know what you’re carrying. That’s the whole assignment.

This month’s climb: Sit down for fifteen minutes. List every debt, its balance, and its interest rate. Draw the 10% line. No spreadsheet skills required, no big decisions yet — just clarity.

Life will pile on again at some point. It always does. But you don’t have to keep carrying what piled on last time.

See you at the top.

This article is for educational purposes only and does not constitute personalized financial advice. Please consult a licensed financial professional regarding your specific situation.

I Built a Financial Literacy Course for My Kids. Now It’s for Yours.

Monthly Money Man on July 31, 2026

During COVID-19, it nearly broke my heart watching my boys get handed a laptop by their teachers. All they had to do was click a button and say they were there. No learning. No experience. No effort. That was the new reality.

As a dad, this was not acceptable.

So I did what any slightly crazy but loving father would do. I withdrew them from public school — knowing that with my passion for teaching and even minimal effort, I could do far better than what the schools were doing. It turned out to be one of the best parenting decisions I ever made.

What followed was a two year journey I will never forget.

The RV That Became a Classroom

Two children walking toward a family RV at a forested campsite, representing the homeschool road trip journey that inspired Monthly Money: Base Camp
Our living room, classroom, and adventure vehicle — all in one

We had a junky RV that I used to complain about constantly — until the world shut down and we couldn’t fly anywhere. Suddenly that RV became a portal.

We studied history and science at home, then hit the road to live it. Our curriculum followed a simple but powerful idea — learn it first, then go experience it. We took a course called the History of Science, and it took us through the stories of the world’s greatest inventors, then challenged us to repeat their discoveries ourselves.

We spent a week camping at the Outer Banks of North Carolina studying flight — reading about Wilbur and Orville Wright, building our own understanding of aerodynamics, and then flying large kites on the same airstrip where the Wright Brothers first left the ground during their annual kite festival.

Those two years also took us across the country on countless family field trips — and contributed significantly to what is now a family total of 36 National Parks hiked and explored. Windows down, maps out, learning things that no classroom could have taught us.

I could write a book about those two years. It was a magical period of my life and theirs.

The Course I Built for My Boys

But during that same time, I noticed something that bothered me. Schools weren’t teaching financial literacy — not in any meaningful, comprehensive way. Some covered the basics. A checking account here, a savings account there. But most kids were leaving school with enormous gaps in their financial knowledge. Those gaps don’t stay hidden. They show up in adulthood, causing a whole variety of problems that follow people for decades.

So I decided to do something about it.

I created my own financial literacy course for my kids — and made them take it.

I built it to be fun and interactive, because personal finance doesn’t have to be dry or intimidating. It can be a journey. Much like this website, I wanted it to feel like an adventure worth taking, not a lecture worth dreading.

My boys took it. It worked. And I’ve been thinking ever since about how to make it available to other families who want the same thing for their kids.

Now I’m finally doing it.

Introducing Monthly Money: Base Camp

Where the financial climb begins.

Monthly Money: Base Camp is a youth financial literacy course built for parents and kids to take together. It covers the foundation — earning, saving, budgeting, first accounts, and basic investing — in a way that’s engaging, age-appropriate, and designed to actually stick.

We plan to launch in late summer or early fall 2026. The timing is a little bittersweet for me personally — my oldest is heading off to college right around launch. This course was built for him and his brothers first. Now I’m passing it on to your family.

There is a massive gap in our kids’ financial education and most schools aren’t going to fill it. That’s on us as parents. It’s our job to make sure our kids are prepared for adulthood — even when the system falls short.

Join the Waitlist

If you want to be among the first to know when Monthly Money: Base Camp launches — including early access and any launch pricing — join the waitlist below.

No spam. Just one email when the doors open.

See you and your kids at the top.

The Grocery Store Classroom: Teaching Kids to Shop Smart

Monthly Money Man on July 24, 2026

Some of the best lessons about teaching kids to shop smart don’t happen at a desk. They happened in a souvenir shop. In a grocery store aisle. At a cruise ship port in Mexico with a belt buckle and a phone.

The moment you leave your home, the world is trying to take your money.

The classroom is everywhere. You just have to be willing to let the lesson happen — even when it’s uncomfortable.

The Dinosaur Souvenir Shop That Changed Everything

Isaiah was three years old when he received $25 in birthday money from his grandfather. A week later we found ourselves at a local dinosaur adventure attraction — the kind where you walk through and narrowly escape getting eaten. Great fun. And like every great tourist attraction, it ended the only way it could.

In a souvenir shop.

I watched his eyes light up the moment he saw the dinosaurs. He had his birthday money. He was ready. And then I looked at the price tags.

A single small plastic dinosaur. Thirty-five dollars.

I was disgusted. He was three. This was his money — money his grandfather gave him — and I wanted him to feel the full experience of spending it. But I also wasn’t going to let him get ripped off without at least showing him there was another way.

We walked out. He was disappointed. That part was hard. Watching your kid not get the instant gratification he was hoping for is genuinely uncomfortable as a parent. But I knew what was down the street.

Walmart.

We walked in and found the exact same dinosaurs — same size as the medium ones at the souvenir shop — for one dollar each. I told him to buy as many as he wanted.

He bought somewhere between fifteen and twenty dinosaurs. He still had money left over.

I will never forget the look on his face pushing that cart. It wasn’t just happiness — it was the beginning of understanding. He traded his birthday money for something that gave him far more value than one overpriced plastic dinosaur ever could.

Those dinosaurs were played with for years. Then passed down to a younger sibling. Then passed down again to a nephew. The lesson outlasted every one of them.

The Same Lesson — Ten Years Later in Mexico

Fast forward about a decade. Our family took a cruise — something we had never done. We found one leaving Texas headed to Mexico, kept it simple, kept it affordable. After our excursion we did what you always do at a tourist destination, something similar to our dinosaur experience.

We exited through the souvenir area.

Isaiah had been looking for a large belt buckle from Texas the entire trip and hadn’t found one. Then he spotted it — exactly what he wanted — at a vendor stand in Mexico. The lady wanted $85. He tried to negotiate. She wouldn’t budge.

He borrowed my phone, found a similar “but cooler” belt buckle on Amazon for $10, and placed the order right there on the spot.

It was waiting for him when we got home from the cruise.

Same kid. Same lesson. Ten years apart. Except this time I didn’t have to say a word. He did it himself.

That’s what happens when you let the lessons stick early.

The Grocery Store Is Your Best Classroom

You don’t have to wait for a dinosaur adventure or a cruise to Mexico. The grocery store is the most underused financial classroom in America and you’re probably already there every week.

Here’s how to turn every shopping trip into a lesson:

Unit pricing — show your kids the price per ounce or per unit on the shelf tag. The bigger package isn’t always the better deal. Let them figure out which one wins.

Generic vs name brand — pick one item and compare. Same ingredients, different packaging, different price. Let them decide which one to put in the cart.

The list vs the impulse — give older kids a budget and a list. Tell them they can keep whatever they don’t spend. Watch how quickly they become comparison shoppers.

The phone is a tool — teach teenagers to check Amazon, Walmart, or Google before buying anything over $20 in a store. Thirty seconds on a phone can save real money.

The Parent’s Job Is to Step Back

Here’s the hardest part of all of this — and the most important.

Your job is not to fix it. Your job is to let the lesson happen.

When Isaiah stood in that souvenir shop at three years old and couldn’t afford a single dinosaur with his birthday money — I could have just bought it for him. It would have been easier. He would have been happy in the moment.

But the discomfort of walking away is exactly what made the lesson stick. The joy of getting fifteen dinosaurs instead of one is exactly what made comparison shopping feel like winning instead of sacrifice.

You have to be willing to sit in the uncomfortable moment with your kid. Don’t rescue them from it. That moment is the classroom.

The families who raise financially smart kids aren’t the ones who shelter their children from financial reality. They’re the ones who let them experience it — safely, at a young age, with small stakes — so that when the stakes are high they already know what to do.

Start This Week

You don’t need a special occasion or a tourist trap souvenir shop. You just need a grocery list and a kid willing to learn.

Hand them the list. Give them a budget. Let them make the decisions.

And if you want to take it further, check out how we teach kids that work has value too.

And when they want to spend $35 on one thing when $15 could get them fifteen of the same thing— let the moment teach what no lecture ever could.

See you at the top.

The Lemonade Stand That Started It All — Raising Kids Who See Opportunities Everywhere

Monthly Money Man on July 17, 2026

One thing I’ve tried to repeat to my kids about kid entrepreneurship is this: opportunities are everywhere.

Every time I collect the mail, walk around the yard, or drive my kids to school — I see them. You can’t pursue them all. But they’re there, constantly, waiting for someone to notice.

And when you find one that lines up with your passion, your interests, and your talent — you have to stop and ask yourself three questions:

Should I take this opportunity? Can I solve this problem? Can I make money doing this?

When the answer is yes — especially at a younger age — it’s worth pursuing. Because a kid who learns to spot opportunities, make money, and put their money to work early has a massive head start on the rest of the world.

The Day Lemonade Day Came to Town

My oldest son Isaiah was young when Lemonade Day — a national youth entrepreneurship program — showed up in our area. The moment I heard about it I recognized the opportunity immediately and signed him up without hesitation.

What happened next still gives me chills.

Isaiah didn’t just set up a stand on the corner. He met with Kroger and got an agreement to set up his lemonade stand outside one of their stores. He met the mayor. He was featured in a commercial shoot with Junior Achievement. He won awards from both IBM and Chase.

That one lemonade stand lit an entrepreneurial fire in him that has only grown brighter every year since. As a parent watching that unfold — it was one of the coolest things I’ve ever witnessed.

That was the beginning. And it all started because we were paying attention when the opportunity showed up.

A Note From Isaiah — My Son, and Now My Business Partner

Hi — I’m Isaiah, Tony’s oldest. When I saw my dad writing about young entrepreneurship I thought this was the perfect opportunity to jump in. And that’s exactly what entrepreneurship is about — jumping on opportunities.

At its core entrepreneurship has three parts:

Finding a problem. Solving it. Telling others and getting paid.

It really is that simple. And the best part? Anyone can do it — even kids. You don’t have to reinvent the wheel.

Think about Apple. They didn’t invent the computer or the phone. But they looked at what existed and asked — how do we make this simpler, more beautiful, and easier for people to use? That’s it. Find the problem, build the solution, make it accessible. Apple resonates with millions of people because they solved a real problem in a way anyone could understand.

Your version doesn’t have to be that big. It can start with something as simple as — people are thirsty. How do I solve that? Lemonade. Put up a sign so people know what you do. And put a dollar in your pocket.

That’s entrepreneurship. It starts younger than you think.

How to Create an Entrepreneurial Ecosystem at Home

Here’s the thing — you don’t have to wait for Lemonade Day to show up in your town. You can start building an entrepreneurial mindset in your kids right now, right inside your own home. This is kid entrepreneurship at its most basic level.

It doesn’t have to be outside the house. If finances allow you can also solve problems inside — like the trash is full or I’m hungry. The trick is creating what I call an entrepreneurial ecosystem right inside your own home.

Pay your kids to solve problems. Let them identify needs and fill them. Let them fail small and win small. Give them the experience of earning, solving, and delivering — before the stakes are high.

The earlier they learn to see the world as full of problems worth solving, the earlier they start building the mindset that creates wealth.

The Three Questions at the Heart of Kid Entrepreneurship

Post these somewhere. Say them out loud. Make them a habit.

Should I take this opportunity? Can I solve this problem? Can I make money doing this?

These are the questions at the heart of kid entrepreneurship. When all three answers are yes — encourage them to go. You’ll be amazed what happens when a kid believes the answer is always within reach.

See you at the top.

Chores, Allowance, and Teaching Kids That Work Has Value

Monthly Money Man on July 10, 2026

From the time we start toddling around the house, we contribute. Maybe not intentionally at first — but at some point every family figures out the same truth: survival means everyone works together.

Think about it. Someone has to cook. Someone has to clean. Someone has to earn money, pay bills, go to the store, take out the trash. Every single thing that keeps a household running takes work. And when kids grow up understanding that — really understanding it — they develop something most adults wish they had learned earlier.

The understanding that work has value.

Chores Are Not Optional — But They’re Also Not a Job

Here’s a distinction worth making early with your kids.

Chores are the baseline. Making your bed, cleaning your room, helping with dishes, taking out the trash — these aren’t things you get paid for. These are your contribution to the household just for being a member of it. We all eat. We all make messes. We all clean them up.

This isn’t punishment. It’s survival. And teaching kids that early sets the foundation for everything else.

But here’s where it gets interesting — and where the real money lesson begins.

Above and beyond chores is where kids learn that solving problems has monetary value. When your child does something that goes beyond what you normally expect of them — that’s worth paying for. Mulching the yard. Washing the car. Organizing the garage. Helping with a project. These are real jobs that solve real problems and they deserve real compensation.

That distinction matters. Chores are contribution. Extra work is entrepreneurship.

Give Them the Opportunity to Earn

Once your kids understand the difference, give them opportunities to go above and beyond.

Every week or so I look around the house and if I see projects that need doing, I offer them to my kids before I ever call a contractor. I don’t have enough time to do everything — and paying my kids is not only more affordable, it’s more fulfilling. Watching them build skills and create their own wealth is worth more than any invoice. I keep a running Google Reminders list nicknamed after each kid, add jobs as I think of them, and have them check things off and hand me a bill. It’s free, it syncs across phones, and it works for us.

There are a few ways to set this up. Apps like Greenlight automate chore tracking and connect earnings directly to a kids savings account — worth looking into if you want a more structured system. Or keep it simple with a shared Google Reminders list that both you and your child can access from your phones. And if you want something fun and educational, we’re building a free Chore Tracker and Bill Maker right here on Monthly Money — coming soon to the Backpack.

Pay them fairly. Not a token amount — a real amount that reflects the work. When a kid earns $20 for a hard afternoon of work they remember it differently than when they get $5 for doing something small. Fair pay teaches them that effort has proportional reward.

Have the Conversation First

Before any of this works you need to sit down and have a real conversation with your kids. Here’s what that sounds like:

“In this house there are two kinds of work. There’s what we all do just because we’re a family — and there’s extra work that earns extra money. When you see something that needs doing and you step up to do it, I’ll pay you fairly for it. And when you earn that money we’re going to talk about what to do with it.”

That last part is important. Don’t let the money just disappear into a pocket. Have a plan for it.

A simple split works well for younger kids — some to spend, some to save, some to give. But as they get older the conversation needs to go deeper.

Where the Money Goes — and Why It Matters More Than You Think

Here’s where chores and allowance connect to something much bigger.

A teenager who earns money from consistent above-and-beyond work at home has something powerful in their hands — earned income. And earned income opens a door that most teenagers don’t even know exists.

A Roth IRA.

If your teenager has earned income they can contribute to a Roth IRA — up to the amount they earned that year. The money goes in after tax, grows completely tax free, and can be worth hundreds of thousands of dollars by the time they retire. All from money they earned mowing lawns or moving stones as a kid. For casual work like lawn mowing or odd jobs paid by a neighbor or family member, there are typically no payroll tax complications for either party — just keep a simple record of what your teen earned so you’re ready to make that Roth contribution at year end. As always consult a tax professional for your specific situation.

We covered exactly how to open one and what to put in it in a previous Financial Friday — if you missed it go back and read it. It might be the most valuable thing you do for your teenager this summer.

The habits start with chores. The earning starts with extra work. The wealth starts with what they do with that money next.

Start Simple. Start Now.

You don’t need a formal system or a chore chart app. You just need a conversation and a commitment.

Tell your kids what’s expected for free. Show them what’s available to earn. Pay them fairly when they deliver. And then help them put that money to work.

That’s the whole system. And it starts younger than you think.

See you at the top.

The Other Kind of Freedom

Monthly Money Man on July 3, 2026

Every July 4th, we celebrate freedom — but the freedom that changes your life doesn’t get a parade, fireworks, or flags. That’s financial freedom. We fire up the grill, watch the fireworks, and take a moment to appreciate what it means to live in a country built on the idea that people deserve to be free. It’s a big idea. A worthy one. But most people spend their entire lives chasing financial freedom without ever quite reaching it

And here’s the thing — it doesn’t look the way most people think it does.

What Financial Freedom Actually Looks Like

Let me tell you about my day.

My mechanic handled my car. A contractor worked on my AC. I picked up two fast casual meals so I didn’t have to cook. And I spent the day doing work I love.

No yacht. No beach in the Maldives. Just a regular Tuesday where my time was mine.

Last week looked different — I paid my kids and my nephew to handle the majority of my 12 yards of mulch and a load of stones. Saved about 20% off a professional rate, the work was just as good, I made sure of it, and instead of writing a check to a business I put that money in three kids’ pockets. That’s everybody winning.

Two different days. Same idea. I had the freedom to let others handle what I didn’t have to do myself — because I’d built enough financial breathing room to make that choice.

That’s financial freedom. Not a number in a bank account. Not early retirement on a tropical island. It’s optionality — the ability to decide how you spend your time because you’re not trapped by financial pressure.

Most people celebrate freedom every Fourth of July and then go back to living paycheck to paycheck the other 364 days. They’re not free — they’re just busy.

Living paycheck to paycheck means every unexpected bill is a crisis. Every job you hate, you keep. Every dream you have, you defer. That’s not freedom. That’s the opposite of it.

Financial freedom is buying back your time. Every dollar you save, every debt you eliminate, every investment you make — you’re purchasing more Tuesdays like mine.

And the earlier you start, the more Tuesdays you buy.

The Conversation Worth Having This Weekend

Here’s where you come in.

This Fourth of July weekend, while the kids are around and the mood is light, try this. Ask them one question:

“If you never had to worry about money, what would your perfect Tuesday look like?”

Let them answer. Don’t redirect. Don’t correct. Just listen and write it down together.

Then tell them — that’s the goal. That’s what we’re building toward. And here’s how we start.

The Freedom Day Challenge

This is an exercise you can do with your kids this summer and it will teach them more about financial freedom than any lecture ever could.

Here’s how it works:

Step 1: Give your child a task or small job to earn a set amount — $5, $10, whatever fits your family.

Step 2: Tell them they can use that money to hire a sibling or you to do their chores for one full day.

Step 3: They spend that day doing whatever low cost or free activity they choose — a bike ride, a board game, a trip to the park. Their call entirely. They own that day.

Step 4: That evening, sit down and ask them — how did that feel?

Then connect the dots. That feeling of having your time be yours? That’s what financial freedom feels like. And every dollar you save and invest is buying you more days like this one.

It works because they don’t just hear about financial freedom — they experience it. And once you feel it, you want it forever.

Starting the Journey Early

You don’t have to wait until your kids are teenagers to make investing real for them.

When my boys were young, if one of them said “Dad, I want to buy stock in that company” — we did it. I’d purchase a share or two inside my own brokerage account and keep a simple spreadsheet tracking their holdings. At the end of the year I’d pay out their dividends. Real investing. Real money. Real lessons.

No special account required. No paperwork. Just a parent making the concept tangible before it had to be.

When they’re ready for the next step — typically around 14 or so — a custodial brokerage account lets them invest in their own name with a parent or guardian co-signing. That first account is a real act of financial independence. Their money, their decisions, their future. If they have earned W2 income, its not too early to start their ROTH IRA.

The earlier they start, the longer compounding has to work. And the sooner they feel what it means to own a piece of something, the sooner financial freedom stops being an abstract idea and starts being a destination they’re actually climbing toward.

This Fourth of July, Celebrate Financial Freedom Too

We are lucky to live in a country that was built on freedom. Take a moment this weekend to appreciate that — it’s real and it matters.

And then take one more moment to think about the other kind.

The freedom to wake up on a Tuesday and decide what happens next. The freedom to not panic when the car breaks down. The freedom to work because you love it, not because you have to.

That freedom is buildable. It’s teachable. And it starts with a conversation at the kitchen table this weekend.

Start the climb.

See you at the top.

Fill Your Summer Without Emptying Your Wallet

Monthly Money Man on June 26, 2026

Every summer has a moment that defines it before it even begins.

For me, it’s the last day of school. My boys come through the door and suddenly I’ve got two-plus months where they’re looking at me like — okay Dad, what’s the plan? The pressure is real. And my plan has always been the same: enjoy every single minute.

But enjoyment doesn’t happen by accident. Neither does staying on budget. The summers I remember most — the ones my kids still talk about — weren’t the expensive ones. They were the ones where we had just enough on the calendar to keep things moving, and just enough flexibility to do whatever we felt like on any given day.

That’s the system for turning local summer adventures on a budget into the summers your kids remember forever. And it’s simpler than you think.

Step One: Pull Out Your Calendar and Look for Empty Space

Before you spend a single dollar on summer entertainment, open your calendar. All of it — June, July, August. Look at what you already have and more importantly, look at what you don’t.

Those empty slots are opportunities.

Now open your local community calendar. Most cities, townships, and parks departments publish summer events online — festivals, parades, free concerts, 4th of July fireworks, outdoor movie nights. Go through the entire summer. When something looks interesting, put it on the calendar.

Here’s the key: you don’t have to go. Writing it down just means you have something there if you want it. It’s a menu, not a commitment.

Then expand outward. Check the neighboring town. Check the county. Check your state parks calendar. You’ll be surprised how much is out there that costs nothing or next to nothing. Some of our most fun nights were free events where we packed a cooler, and invited friends — and honestly, those nights were better than plenty of things we paid for. When something is free, it’s easy to say yes, easy to invite people, and easy to just show up without any pressure.

Step Two: Build Your Boredom Buster List

Even the best-planned summer has dead days. The weather turns, plans fall through, or everyone just wakes up restless with nowhere to be.

That’s where your boredom buster list comes in.

This is separate from your calendar — it’s not scheduled, it’s just waiting. A running list of ideas for home and for getting out. Think about the people you’re spending summer with. What are they into right now? Dinosaurs? Trains? A topic from school that sparked something? Sports, music, cooking, building things?

Build the list around their interests and your budget. It doesn’t have to be elaborate. Some of our best summer days were completely unplanned — we just grabbed the list, picked something, and went. Our family was big into board games, so at the start of every summer I’d pick up at least one new one. By August there was always a rainy day or a slow evening where breaking it out was perfect. Plus we had years of games already waiting on the shelf.

The list is your backup plan. And having a backup plan means boredom never wins.

Step Three: Build In at Least One Tradition

This is the part that costs the least and sticks the longest.

Every summer we spent a day at Lake Michigan with family. Picked a beach, built our annual sandcastle, packed a cooler full of food we were going to eat anyway. The kids got bigger, the sandcastles got more elaborate, and we photographed every single one. Some years we’d pick a different beach just to mix it up — but the day always happened and it was always happened on the coast of Lake Michigan somewhere.

Other than gas, that tradition cost us almost nothing. What it gave us was everything.

Another one that became a summer staple for us was flashlight tag — a nighttime game that costs nothing and gets better the more people you invite. Everyone grabs a flashlight, one person seeks, and the chaos begins. We’d plan it last minute, call a few neighbors, and end up outside until way too late. Some of our loudest, best nights of summer.

Think about your summer on a budget and what your version of that looks like. A yearly hike. A backyard movie night on the first Friday of summer. A road trip to a place you’ve never been. Traditions don’t need budgets — they need intention.

The Financial Angle Nobody Talks About

Here’s what most people miss: a planned summer is a cheaper summer.

When you have nothing on the calendar, boredom fills it — and boredom is expensive. You end up at the theme park on impulse, or buying things to fill the time, or saying yes to stuff you didn’t really want to do just because nothing else was happening.

A State Park annual pass, a cooler bag, and a community calendar will take you further than you think. We’d pack a lunch, grab the pass, and have a full day of hiking, canoeing, or fishing for practically nothing. That same money spent on a family trip to the movie theatre disappears before the previews end— a family of four can hit $100 between tickets and concessions without even trying.

The goal isn’t to have a cheap summer. The goal is to have a full one — full of memories, full of moments, full of the kind of days your kids will still talk about when they’re grown. Kids don’t care about summer on a budget, they just want to have fun.

That doesn’t cost as much as you think. It just takes a little planning before the last day of school.

See you at the top.