I’ve already covered how to buy a business — the due diligence, the process, what to look for. Today we’re digging into something different. This is the one-year report on what actually happened after we closed.

The Basics

The business was an automated blinds and window treatment dealership in Georgia. Hunter Douglas brand. Strip mall location. Five employees. One owner who had been running the place for 20 years and was ready to be done.

His revenue was just under $2 million a year. What he actually took home after all expenses — his free cash flow — was between $225,000 and $250,000. He wanted a million-plus. Deals kept falling through, and once I dug in, it was obvious why.

The business only worked because of him. He capped himself at three sales calls a day. No CRM. No marketing. No systems that could survive without him in the building. When I ran the real math — what it would cost me to hire someone to replace him — that $250K in earnings became $75K to $100K in actual cash flow for me as the new owner. You can’t pay a 3-5x multiple on $250K when the honest number is $75K. That’s how people overpay for businesses and regret it.

So we offered $400,000. But here’s where it gets interesting.

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The Basics

Before anything else, you have to define what generational wealth means to you. That sounds simple, but most people skip it entirely. For me, there are two distinct phases.

Phase one is retirement wealth: building a vehicle large enough that when Emily and I stop working, we’re still earning more than we’re spending. Not depleting. Growing. Most retirement plans are designed to run out right around the time you die. Mine is designed to keep compounding so there’s actually something left to pass down.

Phase two is what comes after that: the stuff you leave behind. Here’s the thing nobody talks about. You can set up a trust, name an executor, hire attorneys, and do everything “right” on paper. My dad did exactly that. He died at 54 with $2,800 in his checking account, a car he owed more on than it was worth, and a pile of credit card debt. I spent months as his executor paying off creditors. All that preparation, and there was nothing to protect.

The vehicle only matters if you build something to put in it.

A trust is essentially a tax-advantaged bucket that holds your assets, including real estate, investments, life insurance, and other holdings, and governs how they’re transferred when you’re gone. Without one, the government taxes inherited assets at an aggressive rate. With one, you control the rules: who gets what, when they get it, and under what conditions.

Potentially the most important piece people underestimate is educating your kids. What’s the point of building something if the next generation burns through it? Spending problems, bad decisions, a divorce without a prenup. It happens constantly. The financial education you give your kids now is part of the wealth-building strategy, not a separate conversation.

The Action Steps

• Define your number. Know what it costs for you and your household to live well. Then figure out what you need to earn in retirement so that you’re still growing, not shrinking. That number tells you everything.

• Set your kids up now. We use 529 plans for education and whole life insurance policies started early. The better financial footing they have going in, the less likely they are to blow whatever you leave behind.

• Talk to a trust attorney. Not a financial advisor. An attorney who specializes in estate planning. They set the rules. A fiduciary, a financial professional with a legal obligation to protect your assets, then governs the decisions and distributions.

• Don’t lock things up too soon. Trusts become illiquid. Once assets go in, flexibility goes down. If you’re still actively building and earning off your assets, you may not be at the point where everything should be tied up yet. That’s okay. Timing matters.

• Keep building the snowball. None of this works if you haven’t built enough to sustain your own retirement first. A trust with nothing in it is just paperwork.

The Bottom Line

Generational wealth isn’t a product you buy. It’s a result of the right mindset, compounded over time, combined with smart legal and financial structure. Most people never get there because they skip the fundamentals: defining the goal, building past their own needs, educating the children who’ll inherit what they’ve built, and putting the right legal vehicles in place before it’s too late.

Start with the snowball. Protect it as it grows. And bring your kids along for the entire conversation.

Stock Tip

Sofi Technologies Inc (SOFI)…as I type this it is beaten up off of a decent earning report. It is trading at $15.55 as I type this. This was a $30+ stock 6 months ago. I think it is safe to buy at these levels with some stop loss triggers in place. I could see a bounce to the $22-$24 range over the next 3-6 months. That’s a 50% gain from here.

Most parents want their daughters to be happy, successful, and loved. But if you’re not also raising her to be financially indepe

ndent, you’re leaving her exposed in ways you might not realize until it’s too late.

Emily and I have three kids: a 15-year-old son and 11-year-old boy-girl twins. And when it comes to our daughter Caroline, this topic hits differently. The world has changed, but the underlying assumption that a woman can always lean on someone else financially hasn’t fully gone away. We want to make sure she never has to.

The Basics

There are three things we’re focused on right now.

First: pay yourself first, and start early. Saving isn’t exciting. It’s not something you brag about on social media. But if you build the habit early, the snowball starts. And your whole job is to keep the snowball growing. When it stops growing, that’s retirement. The bigger you’ve built it, the longer it lasts.

Tied to that is delayed gratification. Our kids are growing up in a world of 15-second videos and instant everything. Teaching them to leave $100 alone and not touch it is genuinely hard. But the research backs it up and so does real life. The kids who can wait for the second marshmallow tend to build better outcomes.

Second: understand debt. Not fear it, understand it. Dave Ramsey was a great starting point for Emily and me, but if you stay in that mindset forever, you leave a lot of opportunity on the table. Debt is a tool. Used correctly, with a plan and a short-term path to results, it can be a vehicle to assets that outperform. We’re teaching our kids the difference between debt that traps you and debt that builds you.

Third: know where the money is. I’ve seen marriages where the husband handled everything financially and the wife was completely in the dark. Then things went sideways and she was stuck. Not because she was unintelligent, but because she never had a seat at the table. We want Caroline to always have a seat at the table, regardless of who she marries or doesn’t marry.

The Action Steps

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We’ve been getting a lot of questions in our DMs…good ones…and instead of answering them privately and forgetting about it, we decided to bring them all here. This is our first Ask Me Anything, and I’m going in cold. Emily collected about 15 questions and I hadn’t seen a single one before we hit record. Here’s what came up.

In no particular order:

Is it better to close unused credit cards or leave them open?

Close them. Call and actually close them, don’t just cut up the card. An open, unused line of credit tells the algorithm you could go into a large amount of unsecured debt overnight. That’s a risk flag. Consolidate down to what you actually use, then use those cards and pay them off immediately.

What’s the fastest way to repair credit in under three months?

Two moves: First, clean up your balances and close unused cards (see above). Second, look into credit repair firms that send dispute letters to old creditors on your behalf. If the creditor doesn’t respond in time, that negative mark can be removed from your report…even if it was legitimate. These services run a few hundred dollars and they know exactly what they’re doing. Worth it.

I have $5,000–$10,000 to invest. Where do I start?

First, make sure that money is actually available to invest. High-interest credit card debt paid off? Retirement accounts set up? Properly insured? If yes to all three, now we’re talking. Then pick two or three stocks: one stable company that pays a dividend, one product you use and believe in, and one longer-shot play with bigger upside. Don’t put it all on one. Even small amounts should be spread across different risk levels.

How do you budget when your income changes every month?

Build your budget around your worst month, not your best one. When I was 100% commission, my base was around $2,000–$3,000 a month. I lived there. Everything above that was extra. People get into trouble when they build their life around their ceiling and then have a bad month. Know your floor. Live there. Let the good months feel like a bonus.

What is a HELOC and should I use one as an emergency fund?

A HELOC (home equity line of credit) is a revolving line of credit secured against the equity in your home. You don’t get a lump sum…you draw from it as needed, like a credit card. It’s a smart debt tool for consolidating high-interest debt or funding home improvements. As an emergency fund substitute? I’d rather you have actual cash. If using cash doesn’t drain your reserves completely, use the cash. HELOCs can become a slippery slope and erode your home equity fast if you’re not disciplined.

How much should I keep in my emergency fund?

It depends on how predictable your income and expenses are. If both are steady, two to three months is fine. If your income is variable or your job feels uncertain, you want more — six months minimum. For us, with multiple businesses and variable income, I like over a year in reserves. Put it in a money market account, not a regular savings account. You’ll earn 3–4% and still have instant access.

Should I do my own taxes or hire a CPA?

If you have a W-2, a mortgage, and standard deductions — just use TurboTax. It’s easy, it prompts you through everything, and it works. You don’t need a CPA until your situation gets complicated: LLCs, real estate, active trading, multiple income streams. Once you’re there, get one. It becomes a year-long project, not a once-a-year filing.

What financial accounts do you recommend for kids?

Greenlight. Start it early…there’s no too young. Our youngest kids were six. They have debit cards with their own photo on them, savings accounts, and small investment portfolios they actually watch. The lesson it teaches — this card is attached to your money, not mine…is worth more than almost any financial concept you can explain to a kid. One of our viewers also mentioned an app called Step, which is similar but without the fees. Worth looking into.

When should you sell a stock?

Three situations: when you’re up and want to lock in a gain (taking profits is never wrong), when the story around the company fundamentally changes, and when growth stalls or misses big. Also, set stop losses so the decision is automatic if things drop below a certain point. And don’t panic sell over market noise. If the company is still growing and nothing has actually changed, hold. Selling Shopify too early is one of my genuine regrets. Emily told me not to.

Stock Picks:

MicroStrategy (MSTR): 146.31/share

I’ve been buying MicroStrategy and I’m still buying it. My thesis is simple: I think Bitcoin has bottomed out. I’ve been saying it for a few weeks and I’m putting money behind it. MicroStrategy is essentially a leveraged bet on Bitcoin — the company holds massive amounts of it on their balance sheet, so when Bitcoin moves, MSTR moves harder in both directions. It’s been ripping. If you believe in the Bitcoin rebound story the way I do, this is one way to play it.

Grail (GRAL) 54.28/share

This one’s been a ride.

I’ve been recommending Grail since it was around $30. It’s a pharmaceutical company working on early cancer detection — genuinely important technology. It ran all the way up to $120. Then it missed a clinical study benchmark and dropped to $42 in about two days.

I didn’t sell.

Here’s why: the underlying FDA approval story hasn’t changed. One missed study result is painful, but it doesn’t kill the thesis for me. This has always been my speculative position — the one I’m swinging for outsized returns on, not the one I’m keeping safe dollars in. I actually added more at $42. It’s trading around $55 now, so that entry looks okay so far.

If FDA approval comes through, this could rebound significantly. If it doesn’t, I knew the risk going in. That’s the nature of pharmaceutical plays — they can move violently on a single headline.

The broader market

I think we’re close to or at the bottom of this recent selloff. The market has been getting beat up, and in my experience, that’s when you want to be buying the companies you’ve been watching — not sitting on the sidelines. The geopolitical noise is real, but it’s noise. The fundamentals on the companies I believe in haven’t changed.

Now is the time to be methodical, not emotional.

Disclaimer: I’m not a financial advisor. All opinions are my own based on personal experience. Always consult a qualified professional before making significant financial decisions.

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Then you realize we’re living through one of the strangest housing market environments in modern history. Millions of homeowners are discovering they literally cannot afford to move, even when they want to. Not because houses are expensive. Because cheap debt has become more valuable than square footage.

Here’s the math problem most people haven’t calculated: Your interest rate matters more than your home price when it comes to monthly payments.

Let’s break this down with real numbers:

Scenario A: $600,000 mortgage at 3% interest = $2,530/month (principal + interest)

Scenario B: $400,000 mortgage at 7% interest = $2,661/month (principal + interest)

You just “downsized” by $200,000 and your payment went up $131 per month. Over 30 years, you’ll pay $47,000 more in monthly payments for a house worth $200,000 less. And that’s before we factor in the total interest paid over the life of the loan.

Total interest paid in Scenario A: $310,000

Total interest paid in Scenario B: $558,000

By downsizing, you’d pay an extra $248,000 in interest over the life of the loan. That’s not a financial strategy. That’s a quarter-million-dollar mistake.

This is why the housing market has essentially frozen. It’s not a demand problem or an affordability crisis in the traditional sense. It’s an interest rate trap. People with mortgages locked in at 2.5-4% are sitting on an asset more valuable than their house itself: artificially cheap debt.

The compounding problem: Most people who locked in low rates did so between 2020-2021. Those mortgages are now 3-4 years old. You’ve barely made a dent in the principal. If you sell now, you’re giving up your best financial asset (the low rate) at exactly the moment you’ve built the least equity.

Why this matters beyond housing: This interest rate environment is affecting labor mobility, family decisions, retirement planning, and economic growth. Companies can’t relocate employees. Families can’t move closer to aging parents. People can’t downsize for retirement without taking a massive financial hit.

I’m watching this play out in real time. We’re hiring a CEO for one of our companies and need someone local. Multiple qualified candidates have declined to relocate, with one citing the cost of relocating as one factor. These are executives who could afford the move from a pure cash perspective. But the math still doesn’t work.

If you’re considering a move, here’s the framework for making the decision:

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Fair question. Especially when you’re seeing all over the news, your teenagers are talking about meme coins, and Venmo asking if you want to send crypto instead of dollars. This isn’t some fringe internet thing anymore. It’s everywhere, and if you don’t understand it, you’re going to get left behind. Let’s break this down.

First, you need to understand what gives anything value. Why is gold worth something? Why is a Picasso worth millions? Because someone is willing to pay for it. That’s it. Value is just a collective agreement.

Our U.S. dollar is backed by gold stored in Fort Knox. That’s why people refer to something secure as “Fort Knox” …it’s where the government keeps massive amounts of gold to back our currency. This physical backing is why the dollar is one of the preferred currencies worldwide.

Bitcoin is sort of a digital gold. That’s the simplest explanation, but it goes deeper.

Cryptocurrency is the umbrella term for digital currency. Bitcoin is the kingpin cryptocurrency – the biggest, most established, most valuable. There are thousands of other cryptocurrencies (Ethereum, XRP, and yes, meme coins like the Mr. Beast coin Brady’s invested in), but Bitcoin is the gold standard.

Here’s what makes Bitcoin revolutionary: It was created as a digital asset completely outside the banking system. You can transfer it instantly to anyone in the world, anonymously, without any bank or government intermediary. It’s tracked on a digital ledger, but you can move it freely as long as you have a crypto wallet.

There’s a fixed supply. Only 21 million Bitcoin will ever exist. This scarcity is built into the system, which is part of what gives it value. You can’t just print more Bitcoin like the government can print more dollars. This is part of the concept that I just can’t overlook. This could play a major role in its ability to work as a hedge against inflation in the future.

The creator goes by the pseudonym Satoshi Nakamoto. Nobody knows his real identity. He owns more Bitcoin than anyone, and he’s never revealed himself. There are even theories …some involving Jeffrey Epstein funding the startup – but the truth is we don’t know. That mystery is part of what makes Bitcoin fascinating and slightly terrifying.

Why Bitcoin has a sketchy reputation: The anonymous transfer capability made it popular for black market dealings. Ransomware attacks demand payment in Bitcoin. Criminal enterprises use it because it’s hard to trace. That’s the dark side.

But that same efficiency is exactly why it’s valuable. Think about how archaic our monetary system is…physical dollar bills, coins, checks that take days to clear. Cryptocurrency is simply a more efficient way for currency to move.

Right now, Bitcoin is crashing. It peaked at $126,000 per coin and dropped to around $62,000 as I’m writing this. Part of that is the Epstein connection surfacing in recently released files. Part of it is large institutions deleveraging their positions. These are real market forces affecting real money.

If you’re just learning about crypto and want to get involved without getting destroyed, here’s the practical approach:

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I had an HBO subscription from when Game of Thrones was still airing. The show ended years ago. Still paying. I had a McAfee antivirus subscription for $100 a year attached to an old email address, billing through an old credit card that had somehow been updated. A notes app. A scanner app I could have gotten for free. Tyler had a Duolingo subscription from when he was learning Spanish in elementary school. The twins had Canva accounts at $112 each when students get it free.

In five minutes, sitting in our living room, we found over $300 a month in subscriptions we’d completely forgotten about. And that was just the beginning.

Money Matters

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This year, the numbers told a story I didn’t love. But that’s exactly why this exercise matters.

Money Matters

There are only two ways to improve your family’s financial position: earn more or spend less. Most people focus entirely on the first one and completely ignore the second. That’s a mistake.

Here’s the reality: your expenses are probably creeping up without you noticing. It happens slowly. A new subscription here, a lifestyle upgrade there, a few months of “we deserve this” spending. Before you know it, you’re hemorrhaging cash and can’t figure out why you feel broke despite making good money.

The fix is simple but uncomfortable: you have to look at the actual numbers.

I keep a spreadsheet tracking our monthly spending going back five years. I know our average monthly spend, our year-over-year trend, and our three-year trailing average. This kind of data tells you things your gut never will. It told us we were on pace for a great year until Q4, when holiday spending blew through everything we’d saved in the first nine months.

The numbers also revealed something two years ago that changed how we operate: we were spending an insane amount on groceries. Instacart convenience fees, Publix prices, food rotting in the fridge because we weren’t meal planning. Once we saw the actual dollar amount, switching to weekly Aldi runs became an obvious decision. We’ve saved thousands since then.

Your finances have leaks. The only question is whether you’re willing to find them.

Action Steps

Here’s the exact process I use for a January audit:

Step 1: Consolidate everything into one view. Pull every credit card statement and bank statement from the past 12 months. If you use one card for most purchases like we do, this is easier. The number you’re looking for on credit card statements is “new charges this month.” Add up all cards to get your true monthly spend. Put these numbers in a simple spreadsheet, month by month.

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Here’s how I think about it: Imagine you’re playing a football team that historically crushes opponents in the fourth quarter. You’ve got two options. You can obsess over building a better defense for those final fifteen minutes, or you can focus on dominating quarters one through three so hard that their fourth-quarter run doesn’t matter. I’ll take option two every time.

We’re currently in the first half. The game isn’t over. There’s still time to invest, to build, to grow. But the clock is ticking, and smart players are already thinking about how they’ll be positioned when the momentum shifts.

Money Matters

I was 28 years old during the 2008 financial crisis. My mortgage career had just evaporated, and I was scrambling to reinvent myself in insurance sales. Every morning I’d go for a run through Tampa, passing waterfront properties with For Sale signs everywhere. Prices had collapsed to levels that seemed almost fake.

I remember the thought loop that played in my head constantly: If I could just buy a few of these properties, I’d never have to worry about money again. I knew Tampa was a growth city in a growth state. I knew these prices would never come back. I knew I could rent these places out immediately because the rental market was actually heating up while the buying market collapsed.

But I couldn’t do anything about it. I had no capital. No reserves. No plan. I didn’t even realize at the time that I could have raised money from others to make it happen. That window opened and closed, and I watched from the sidelines.

I’ve since met people who were buying ten, twelve houses a week during that period. They weren’t smarter than me. They weren’t luckier. They were simply prepared. They had cash when everyone else was scrambling. And they built fortunes while the rest of the world was in survival mode.

That experience taught me something I’ll never forget: Recessions don’t just destroy wealth. They transfer it. The question is which side of that transfer you’ll be on.

Action Steps

Here’s my preparation playbook. These aren’t things I’m thinking about doing someday. These are specific moves I’m planning to execute between now and early 2029.

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The signs are already here if you know where look. Interest rate policies, government spending patterns, and market behavior are all pointing in the same direction. The question isn’t if this downturn is coming. It’s whether you’ll be ready when it arrives.

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Financial Terms You Need to Know

Before we dive in, let’s define a few key terms so everyone’s on the same page:

• Recession: A period when the economy shrinks instead of grows, typically marked by job losses, reduced spending, and falling stock prices. Think of it as the economy going backward for several months.

• Interest Rates: The cost of borrowing money, set by the Federal Reserve. When rates are high, loans are expensive and people spend less. When rates are low, borrowing is cheap and people spend more.

• Bull Market: A period when stock prices are rising consistently. It’s called “bull” because bulls attack by thrusting their horns upward.

• Liquidity: How easily you can access your money. Cash in a bank account has high liquidity. Money tied up in real estate or retirement accounts has low liquidity.

• Overleveraged: When you have too much debt compared to your income or assets. It’s like maxing out all your credit cards while barely making minimum payments.

Money Matters: Why 2029 Changes Everything

Economic downturns follow patterns. We saw it in 2000 with the dot-com crash. We lived through 2008 with the housing collapse. Now we’re watching the setup for the next major correction, and this time the ingredients are different but equally dangerous.

Here’s what makes 2029-2030 particularly concerning. We’re coming off a period of unprecedented monetary policy. The Federal Reserve has been walking a tightrope between controlling inflation and avoiding recession. They’ve raised interest rates dramatically over the past few years, and while that’s been necessary to cool inflation, it creates downstream consequences that take years to fully materialize.

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Pre note…Emily and I are 1000% going to do a Substack live on this topic…its very applicable to us!

I was reorganizing my office last week and came across a box of baseball cards from my childhood. My first thought wasn’t nostalgia—it was dollar signs. That’s what our culture has done to hobbies. Everything’s becomes a potential side hustle, an investment vehicle, a way to “make passive income.”

My wife Emily collects designer bags. I’ve got sports cards, comics, bourbon and watches. And yeah, I’m guilty of justifying most of these purchases by telling myself they’re “investments.” But here’s what most people pushing the collectibles-as-assets narrative won’t tell you: for every Mickey Mantle rookie card that sells for millions, there are ten thousand cards sitting in someone’s attic worth exactly what they paid for them…or less.

The collectibles market has exploded over the past five years. What started as hobbies have morphed into alternative asset classes that some people treat like stocks or real estate. The problem? Most collectors are making terrible financial decisions because they’re mixing emotion with investment strategy.

Money Matters: The Collectibles Gold Rush

The numbers are real. A 1952 Topps Mickey Mantle card sold for $12.6 million in 2022. Hermès Birkin bags have outperformed the S&P 500 in some years. A Rolex Daytona “Paul Newman” went for $17.8 million (such a beautiful watch!!!). These headline-grabbing sales have convinced an entire generation that their hobbies should be part of their wealth-building strategy.

The collectibles boom really took off during COVID. People were stuck at home, nostalgic, and had stimulus money burning holes in their pockets. The sports card market went absolutely insane. Suddenly everyone was an “investor” in rookie cards, sneakers, Pokémon cards, vintage video games, bourbon bottles, and whatever else could be flipped on eBay or StockX.

Here’s what actually drives collectibles values: scarcity, condition, authentication, and cultural relevance. That Hermès bag appreciates because Hermès intentionally limits production and maintains exclusivity lists. That vintage gold Rolex holds value because certain models were discontinued and the brand has maintained its luxury positioning…or simply because the price of gold is at a record high. That comic book is worth money because it’s graded, authenticated, and represents a culturally significant moment (like Superman’s first appearance).

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This week is more of a discussion and less about having all the answers…

When I sold disability insurance years ago, we’d tell clients something that stopped them cold: “If you had a money printer in your garage that spit out $100 bills, you’d do everything possible to keep it running. You’d maintain it, never let it run out of ink or paper, make sure the electricity stayed on…or at the very least insure it. This isn’t about insurance…it’s about the printer…that printer is you and your ability to work and earn a paycheck.”

Your earning capacity is your most valuable financial asset. Not your 401k. Not your house equity. Not your investment portfolio. Those things only exist because you can earn money to fund them. Everything flows from your ability to generate income.

And right now, that asset is under direct threat from artificial intelligence and its ability to make everyone more efficient with fewer people in a particular work force.

I’m not talking about some distant science fiction scenario. This is happening right now, accelerating faster than most people realize. A year ago we were just learning about ChatGPT. Today, companies are quietly shrinking workforces through hiring freezes because AI allows remaining employees to do the work of multiple people.

Just recently, I part of a small business acquisition in Georgia. In the past, we would have needed attorneys reviewing lease agreements and operating agreements, accountants auditing financials, investment bankers providing analysis. This time, I fed everything into ChatGPT—lease documents, financial data, competitor analysis, dealer agreements. The scope of work I needed from professionals shrank dramatically. I still used an attorney, but for a fraction of what I would have paid two years ago.

That’s one transaction. Now multiply that across every industry. If you’re an underwriter at a bank, your firm probably needs one person doing what five people did before. If you’re a junior CPA at an accounting firm, your firm might need four people instead of seven. If you’re reviewing real estate contracts as a paralegal, AI is already doing most of that work.

This isn’t about AI taking every job. It’s about AI being a force multiplier—allowing one person to do the work of many. Which means some will lose their ability to print money.

Action Steps

Assess Your Career’s AI Vulnerability

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Money Matters

Looking at my stock recommendations over the past four months, the results have been exceptional. My average return sits at 22% (in just the last 120 days!!) across 20 picks, with some individual positions up 42% (Palantir), 85% (Grail), and 45% (UnitedHealthcare on the second recommendation). If you invested only $1,000 in each recommendation, you’d be sitting on $24,480 right now from a $20,000 investment. How many other SubStacks are making you money :)

But here’s the uncomfortable truth: paper gains aren’t real until you lock them in. I learned this lesson the hard way with Grail earlier this year. I watched it run from $35 to $64, thought it could only go higher, and rode it all the way back down to the high $20s without selling a single share. Those weren’t losses…they were gains I never captured.

The challenge every investor faces is knowing when to take profits. Sell too early and you leave money on the table. Hold too long and you watch your gains evaporate. This is especially critical right now because the market is expensive, momentum is strong, and we’re heading into year-end tax loss selling season where big funds will start taking profits.

The solution isn’t trying to time the perfect exit. It’s using mechanical strategies that protect your downside while letting winners continue running. The most effective tool for this is the trailing stop loss.

Below is a chart showing each stock recommendation, the date recommended and the price at the time of recommendation…versus Current stock price and performance…… I did a similar recap on Aug 28 if you would like to revisit that post…same stocks.

***Since Aug 28 I have recommended mostly to stay away from any new names…minus Goldman Sachs. But I wanted to do a month over month update for comparison, so I omitted any new recommendations from this chart.

Action Steps

Understand How Trailing Stops Work

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The car lease versus buy debate usually comes down to this: dealers push leasing because of lower monthly payments, while financial advisors push buying because “you build equity.” But both sides often get the math wrong.

I decided to run the real numbers on a $50,000 car purchase, and the results surprised me. Unlike the dramatic differences you’ll see in most analyses, the true cost comparison is much closer than people think…at least over short time periods.

Here’s what the correct math shows:

The key insight most analyses miss: when you buy a car with financing and sell it after three years, you still owe a substantial amount on the loan. After 36 payments on a $45,000 loan at 6.5%, you still owe nearly $20,000. That remaining balance dramatically reduces your net equity compared to the gross resale value.

Over three years, buying saves you only $1,402…about 5.5% less than leasing. That’s significant, but not the massive difference most financial content claims. The real advantage of buying emerges over longer time periods, where the savings grow to $7,703 over five years.

IF a particular vehicle make/model depreciates faster than others…. or you don’t accomplish good trade-in value…. the 3-year lease option could come out ahead

The mistake most people make is focusing on monthly payments ($880 to buy versus $676 to lease) instead of understanding the total cost equation. But the bigger mistake is not accounting for loan payoff amounts when calculating equity.

Action Steps

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That advice is costing you money.

If you're sitting on a mortgage with a 3-4% interest rate…which describes most homeowners who bought or refinanced in recent years…paying it off early is one of the worst financial decisions you can make. Not because debt is inherently good, but because you're giving up liquidity and opportunity to save a small amount of interest.

Here's the reality: mortgage debt is the smartest debt you can carry. It's simple interest, not compound interest like credit cards. You get tax deductions on the interest payments. The payment is fixed for 30 years, meaning inflation actually reduces its real cost over time. And most importantly, the interest rates are historically low.

Money Matters

I learned this lesson the hard way. After a major investment win around 2019, my first instinct was to pay off our mortgage completely. Done. No more house payment. Great feeling, right?

Wrong. Within months, investment opportunities started appearing that I couldn't participate in because all my cash was tied up in house equity. I had to make a choice: miss out on deals that could generate 10-15% returns, or do something that felt crazy…take out a new mortgage on a house I'd just paid off.

We chose the mortgage. That decision has generated more wealth than any other financial move we've made.

Action Steps

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Money Matters

Your parents crushed it financially. Emily's mom retired after 38 years as a Florida teacher, her dad after 40+ years at the power company. They both have full pensions paying 85-90% of their working income for life. They bought a 2,700-square-foot house with a white picket fence in suburbia when housing was affordable relative to income.

That world doesn't exist anymore. God we wish it did.

The financial advice that worked perfectly for Boomers can actually hurt your wealth-building efforts today. When your parents tell you to "play it safe," "buy the small house you can afford," or "avoid debt at all costs," they're giving you strategies for a game that no longer exists.

Their generation benefited from employer pensions, affordable housing, and a job market where you could work 35 years at one company with steady raises and comprehensive benefits. Most companies today don't offer pensions. Housing costs have skyrocketed relative to wages. The idea of a single-income family supporting a comfortable middle-class lifestyle is largely extinct unless you're a high earner.

Meanwhile, we're dealing with problems our parents never faced: the need to fund our own retirement entirely, housing markets that price out young families, and an economy that demands multiple income streams just to maintain purchasing power.

The most dangerous part? We're conditioned to accept parental financial advice without question. We assume they're the smartest people we know because they successfully navigated their financial lives. But when do you recognize that your parents' world was fundamentally different from yours?

Action Steps

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Not bad, but let's dig into what actually happened… the wins, the losses, and what we can learn from both. It’s worth noting that the overall market is performing, so it makes some of us “day traders” appear smarter than we actually are! With that said, we have had some very quick pops to the upside in a few of these names.

Below is the date recommended here on ILT, the company ticker, and the performance

The Home Runs

Shopify (SHOP) - Recommended May 29 at $107, currently at $142.47 This one paid off big with a 33.15% gain. I caught this during a broader tech selloff when the fundamentals were still solid. Sometimes the market overreacts to sector-wide pessimism, creating opportunities in quality companies. I wish I could say that I am still holding my SHOP, but I sold it a little early once my target return was accomplished.

UnitedHealthcare (UNH) - Two recommendations, both winners. My first call in May at $270 netted 12.20%. But the second recommendation in August at $244.67 during the DOJ investigation scare? That's up 23.82%. This perfectly illustrates why I keep hammering the point about buying quality companies during temporary panic selling. I am still long this position and probably own more of it than I should.

Palantir (PLTR) - Recommended July 3 at $130, now at $157.75 Up 21.35%. This AI play caught the broader artificial intelligence momentum, though as I've warned repeatedly, these high-growth tech names can be volatile. I actually sold my PLTR at $172 last week and moved those dollars into CRWV when it was trading in the mid $90’s.

The Strikeouts

IBM - Recommended June 13 when the stock was at $276, currently at $245.63 Down 11%. However, if you read that post again, you will see that I actually said this stock was too expensive and that you should buy it if it got back below $250. Here we are. You would only be down 1.75% if you were patient as suggested.

Grail (GRAL) - Recommended July 21 at $35, now at $34.20 Down 2.29%. This biotech pick shows why I constantly emphasize position sizing with speculative investments. Small positions in high-risk, high-reward names can work if you manage them properly. This price actually went up to $42 and represented a nice gain if I would have sold before this recent sell off. Still holding this very turbulent stock.

The Solid Singles and Doubles

The majority of my picks fall into this category—nothing spectacular, but consistent positive returns:

• Apple (AAPL): Up 16.38%. Easy buy when blue chips sell off.

• CoreWeave (CRWV): Up 14.18% (despite the volatility I warned about). New position for me here, but up big after just a week.

• USB and BAC: Up 10.21% and 12.40% respectively with most of the financial sector.

• Elevance Health (ELV): Up 9.28%

These represent the kind of steady, quality company investing that builds wealth over time.

What This Report Card Actually Teaches Us

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But something shifted for him this summer. His kids are 11 to 16 years old, right in what I call the "core memory zone." That narrow window where the experiences you create will shape how your children remember their childhood…and judge your effectiveness as a parent…for the rest of their lives.

So this incredibly frugal friend did something completely out of character. He bought a motorhome. Not a small one either, the kind with slide-outs, a fireplace, and all the bells and whistles. A significant financial purchase that goes against every savings principle he's followed for years.

His reasoning? "I've got maybe five years to make these memories with my kids. I can work an extra year or two and retire later, but I can't get this time back."

Money Matters

Here's what I've realized about my own childhood: when I think back to what shaped me as a person, it's not spread across 17 or 18 years of memories. It's concentrated into about a three to five year window…roughly ages 11 to 16.

Your kids don't care that you max out your 401k or have their 529 plans funded. When they're 45, they're going to remember the lake house, the family dinners, learning to drive the boat with dad, or whatever core experiences you created during those critical years.

Action Steps

Recognize Where Your Kids Are in the Timeline

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