True Wealth - Financial and Investing Podcast

“Almost bought it. Almost sold it. Almost started it.” Funny how one little word can change your financial future. Today we’re talking about why “almost” may be the most expensive word you’ll ever say.

Feeling behind financially? You might be doing better than you realize. In this episode, we look at the overlooked signs that you are quietly building wealth. Are you paying down debt, owning appreciating assets, improving cash flow, gaining stability, and making choices that compound over time? Sometimes wealth does not feel like luxury, so what are the signs things might be going better than you thought?

“This time is different.” It’s one of the most common, and potentially dangerous phrases in investing. Every generation believes the rules have changed as new technology emerges and yesterday’s impossible becomes today’s normal. In this episode, we explore why history keeps rhyming, how our definition of “normal” quietly shifts over time, and why recognizing those changes may be far more valuable than trying to predict the future.

History is full of confident predictions that never happened. From market crashes to economic booms, the future has a way of surprising everyone. In this episode, we explore why uncertainty isn’t something to fear, how investors can think differently about the unknown, and what lessons history teaches us about preparing for whatever comes next.

Tempted by the latest IPO hype? It’s easy to get caught up in the excitement, but history shows that excitement often leads to significant risks for the unprepared. In this video, we break down the mechanics of IPOs to help you see past the marketing, analyze how institutions approach these debuts, and identify the patterns that drive volatility for retail investors.

From buying on hype to selling during market declines, investors often face challenges that have little to do with stock selection and everything to do with behavior. Join us as we discuss ten common investing mistakes and the habits that may help investors stay focused on their long term goals.

The world has changed dramatically in just five years. We have moved from cheap money and low zero interest rates to inflation, higher borrowing costs, AI disruption, and growing geopolitical uncertainty. Today, we explore what these changes mean for families and businesses, while exploring potential investment impacts.

AI was supposed to replace human labor, cut costs, and supercharge productivity… But what happens if the math stops making sense? This week Dave and Matt dive into the exploding cost of AI infrastructure, massive energy demand, billion dollar data centers, and growing questions about whether companies are actually seeing returns on all this spending. From expensive AI queries to rising chip costs and signs that some companies may be slowing or re-evaluating parts of their AI spending. Is artificial intelligence becoming too expensive to scale the way investors imagined? Or are we still in the early innings of a technological revolution bigger than the internet itself? This is not investment advice, just a conversation about technology, markets, and the rapidly changing world around us. 

Bond yield’s hot. Are portfolios droppin’? Treasury rates up, But inflation keeps rockin’. Stocks are up, Bond prices floppin’. Some want safety, But purchasing power’s stoppin’.

The AI revolution is underway… but will you even recognize this world in 5 years? Will you even recognize the stock market? Today we explore the massive changes quietly unfolding beneath the surface, why speculation and investing walk a dangerously thin line, and the opportunities and risks most people still are not paying attention to.

This week we dive into the GameStop & eBay style market chaos, & how a major acquisition like this could reshape the future of retail & online marketplaces. We also explore the race toward quantum computing & why some believe it could completely transform cybersecurity, AI, banking, & the global economy faster than most people realize.

An off the cuff look at the forces shaping markets and the global landscape. We connect economic trends, policy shifts, and investor behavior to explore what could lie ahead.

Death is not the only risk: poor planning is. We walk through what happens to your money, your spouse, and your legacy when you pass and how a proper plan can help put everything on autopilot.

The Boring Path to a Million Dollars A lot of people spend their whole lives looking for the clever way to build wealth — the hot stock, the timing play, the business idea that finally works. Meanwhile, the couple next door just put fifty bucks a month into a retirement account when they were twenty-two and quietly became millionaires. On last week’s True Wealth Show, Matt Dickson and I worked our way down a list of ways to actually build wealth in America — ranking each one from easiest to hardest. The top of the list wasn’t glamorous. The top of the list was almost embarrassing in how simple it was. The easy paths These all scored high on “this actually works” and low on “this is hard”: Start early. Keep going. A small, regular contribution to a broad market investment over fifty or sixty years becomes a genuinely large number. Matt set up an account for his son Micah when he was born — a thousand dollars, then fifty a month. Not because it was a lot, but because time was the thing doing the heavy lifting. Compound interest doesn’t care about your feelings, your timing, or your cleverness. It just wants years. Get a job that matches your retirement contributions. If you put in a dollar and your employer puts in a dollar, you just made a 100% return the moment the money hit the account. This is free money, and people skip it all the time. A lot of them skip it because they “can’t afford to contribute.” But think about the math for a second: if you contributed enough to get the match and then withdrew all of it tomorrow and paid every possible early-withdrawal penalty, you’d still have more money than you started with. The free money is worth more than the penalty. Take the match. Spend less than you make, and invest the difference. The number-one rule of financial success, and the one people most often fight. Not because they don’t know it — everyone knows it. But because lifestyle creep is a quiet, relentless force, and most raises turn into more spending instead of more savings. Stay out of high-interest consumer debt. This one is the flip side of the compound-interest story. The same math that works for you over decades in an index fund works against you every month on a credit card. If you’re paying 24% on a balance while your investments earn 10%, you’re running up the down escalator. Why “easy” doesn’t mean “common” Here’s the thing about the easy paths: the reason they work is that they compound over decades. And the reason people don’t take them is that they compound over decades. Most people want the result in a timeframe that matches their attention span. Compound interest works on a timeframe that matches a career. Matt’s wife started saving at eighteen, putting 10–15% of her paycheck into a retirement account from her very first job. No clever moves. No timing. Just consistent contributions from age eighteen through the rest of her life. She’s doing great. There is no magic to this — the magic is that she started early and never quit. The harder paths exist too We did make it through a long list of harder paths — side hustles, real estate, small business ownership, rental properties, franchising, commercial development. They can all work. They’re just harder, and they require different combinations of capital, skill, risk tolerance, and discretionary time. The pattern we kept seeing: as you move up the difficulty scale, the paths become more dependent on you — your skills, your timing, your ability to manage risk and stay disciplined. The easy paths, by contrast, mostly require you to get out of your own way and let time do its work. That’s not a small insight. Most people aren’t going to become venture-backed founders, professional athletes, or franchise magnates. But almost anyone who earns a paycheck can start early, capture a match, spend less than they make, and avoid predatory debt. What we actually do with this When someone walks into Littlejohn Financial Services and says “I want to build wealth,” we’re not looking for the clever play. We’re looking at where they are, where they want to go, and whether the simple math can get them there. Usually it can. Sometimes it takes longer than they’d hoped. Rarely does it take more cleverness than they have. Want to hear the full ranking — including the lightning round where we argued about real estate, sales careers, and whether “pick rich parents” should count? Listen to the full episode on littlejohnfs.com. If you’re wondering how the simple math applies to your situation specifically — that’s what we help people with. No pressure. Reach out when you’re ready.

David and Matt rank different ways people try to become millionaires, discussing the tradeoffs of risk, effort, and difficulties along the way.

Justin and Emma discuss retirement timelines, planning considerations, and where people often go wrong.

David, Justin, and Emma discuss how various taxes work and how different tax treatments can shape financial outcomes.

David and Derek cover a fun new holiday, sports betting, and how platforms like prediction markets are changing the way people view outcomes.

David and Emma discuss investing strategy, market patience, and why successful investing often looks more like farming than hunting.

How do markets actually react to war? We dive into history to uncover surprising trends and economic truths that challenge everything you think about investing.

Starting from scratch? Worried you’ve waited too long? We answer common financial planning questions to help you pivot from uncertainty to a solid long-term plan.

Stop overpaying for hidden fees. We expose advisory costs and the “order of operation” for wealth to help you break the cycle of reactive spending. Tune in!

Retirement used to follow a simple script. Work, save, retire, relax. So why does it feel more complicated now, even for people who did everything right? In this episode, we break down what changed, from disappearing pensions to rising healthcare costs and shifting tax rules, and why understanding the new rules matters more than ever.

Markets don’t always send clear messages. Sometimes prices rise while warning signs flash elsewhere, leaving investors unsure what actually matters. In this episode, we talk through why different parts of the market can move in opposite directions, how competing signals develop, and what it usually means when traditional relationships stop lining up. We explore how to think clearly when headlines conflict, emotions run high, and the market itself seems undecided.

You don’t need to be reckless to end up behind financially. Small habits can compound just as fast as bad decisions. We break down how to assess where you are right now and the micro changes that can quietly transform your financial future.

Are you overly cautious and delay enjoyment, or do you take on more risk than you can handle? We talk about how hard it is to find balance, why money decisions often feel emotional instead of logical, and why so many people feel stressed no matter which side they fall on. The goal of the conversation was not to give advice, but to acknowledge the reality people are living in and why money often feels heavier than it should.

Geopolitical change abroad and growing support for stimulus style policies at home are converging. This episode explores what is happening in Iran why tariffs and redistribution are back in the conversation and how markets typically respond when monetary and fiscal lines begin to blur.

"Former Venezuelan leader Nicolás Maduro was captured in a dramatic military operation that has raised more questions than answers. Was it about oil? Drug trafficking? Political power? Or something even deeper? Let’s break down the theories and what just happened."

A big picture conversation about money, purpose, and planning and how the perspective we have at Christmas can impact financial decisions year round.

Learn how to spot and stop today’s most common phishing and scam tactics—from fake emails and texts to phone calls and deepfakes—so you can protect your money with confidence, not fear.

The stock market has lived through many bubbles, but knowing when one will actually burst is nearly impossible. In this episode we explain what defines a bubble, why staying invested usually wins over fear, and how small portfolio adjustments can help while big emotional moves can hurt.

Believe it or not, interesting discussions about interest rates do exist! When rates move, they can shake up everything from homebuying to saving for the future, making them far more exciting and impactful than most people think.

Last-minute financial planning simplified! Your hosts, two expert advisors, tackle year-end tax tips, retirement contribution deadlines, and smart spending moves you can still make.

From misunderstanding risk, to stock overconcentration and crippling cash balances… your financial plan could have hidden dangers. We’ll show you some places to look.

Unemployment is rising, wage growth has stalled, and consumer debt is exploding. At the same time AI is reshaping the job market. This episode breaks down what is happening, why so many Americans feel financially squeezed, and what you can do to stay ahead in a rapidly changing world.

It’s not about how much money you have: it’s about how well you understand it. Here are the five questions that separate people who retire confidently from those who just retire hopefully.

Are you chasing financial extremes? We break down the difference between high-stakes gambling and hyper-frugal penny-pinching, and show you the strategic middle path to a disciplined, long-term financial plan.

Between talk of insurance, trusts, and risk management, we somehow ended up debating espresso machines and tacos versus burritos. Tune in for a fun and fast paced conversation about protecting what matters and keeping the caffeine flowing while you do it.

We break down the truth about investing for everyday people. Some get ahead by being smart, some by being lucky, and some are just still figuring it out. From lottery-ticket logic to quiet wealth builders, this episode shows where you land on the Pyramid of Investing Greatness and how to move up without needing a finance degree.

On this episode of True Wealth, we’re tackling the powerful connection between faith and finance. We’ll dive into what biblical stewardship truly means and how you can apply these principles to your everyday financial decisions—from tithing and giving to saving and spending.

Everyone talks about the dream of running your own business but few mention the challenges that come with it. In this episode we dig into the highs, lows, and lessons from entrepreneurship, what it takes, what to expect, and how to navigate the journey.

Markets move in strange ways that often spark whispers of conspiracy. Are these just coincidences or signs of something deeper? We explore the stories, the patterns, and the possibilities that keep investors guessing.

Getting good financial advice can make or break your future. But how do you know if you’re working with the right person? In this episode, we’ll expose the red flags you need to look out for in a financial advisor. Whether you’re considering a new partnership or want to double-check your current one, we’ll help you spot the signs that it’s time to find a better fit.

In this episode of True Wealth, David and Justin make investing less intimidating. They break down core concepts you need to know, including dividends, how the S&P 500 works, and the simple truth behind valuing your assets. Get ready to build your financial confidence and enjoy the process.

The best offense in investing is often a strong defense. Short term slumps and seasons of underperformance may feel discouraging, but they are rarely the whole story. Maybe what matters is not who’s ahead today, but who’s still standing decades from now. When you anchor your strategy in discipline and patience, the short run becomes noise and the long run becomes your greatest advantage.

Fantasy football meets finance—Justin & Matt share strategies, avoid one-hit wonders, build depth, and reveal Boom or Bust picks for the season.

5% yields had some of us feeling like kings, but that yield has trickled lower and the party might be ending soon. This episode unpacks what’s coming, how it’ll impact your savings, and why people who always seem to win are already making moves.

Retirees often fear the stock market, but the real danger might be the IRS. This episode breaks down how RMDs can trigger surprise taxes, hike Medicare premiums, and hit your Social Security—and what you can do to stay ahead of it.

This week we unpack robo-advisors, DIY investing pitfalls, and why human insight can still be your best financial asset. Sometimes cheap comes with hidden costs—know what you’re really paying for.

New tax reform is here—and it’s introducing some powerful deductions. From “Senior Bonus” write-offs to new breaks for tip and overtime income, the 2025 rules could mean big savings… if you plan ahead. We’ll break down what’s changing, who it impacts, and why timing is everything.