Ep 88: What 100 Years of Market Data Tells Us
Money On My Mind
Is it too late to invest when the market hits all-time highs? That’s the question everybody is asking, and the truth will surprise you. This episode breaks down exactly why trying to “time the market” is one of the most expensive mistakes you can make, and why long-term, consistent investing still outperforms every prediction, headline, and emotion you have. I walk you through the data, not opinions: • Fidelity’s study showing the best investors were people who did nothing • How missing just a handful of the best market days destroys your returns • Why staying invested, even at...
info_outline
Ep 87: $0 to $5M Blueprint (see Google Drive Link to right)
Money On My Mind
From negative $8,000 to $5 million net worth, what's the real blueprint? 💰 It's not what most people think. The path to wealth isn't paved with higher income or perfect spreadsheets. It's built on requirements most people ignore completely. In this episode, I share the exact framework I used to build generational wealth from scratch. We dive into the non-negotiables: the mindset shifts, the environment changes, and the automated systems that separate the wealthy from everyone else. This isn't motivational fluff—it's the practical roadmap I've personally executed and taught to thousands of...
info_outline
Ep 86: Leading at Home and at Work: How I Balance Being a CEO, Father, and Husband
Money On My Mind
Episode Description What does leadership really mean when you're running both a household and a business? The truth is, I'm not just the CEO and founder of a growing brand I'm also the CEO of my household. I'm leading my team at work and my daughters at home, and while the stakes look different at the office versus the dinner table, the responsibility is equally high on both sides. In this episode, I dive deep into the traits, values, and daily behaviors that help me lead effectively in both spaces without sacrificing who I am as a person. I share the weight of dual leadership,...
info_outline
Ep 85: The New Financial System Is Already Here (And Most People Will Miss It)
Money On My Mind
If you think you’re using money the same way your parents did, you’re already behind. If your entire view of Bitcoin is based on headlines, you’re missing the point. And if you think this “crypto stuff” is just a fad, then today’s episode will shake your perspective. Because what we’re living through isn’t just a tech revolution; it’s the early stage of a complete financial reset. The system you were taught to trust is showing its cracks, and a new one is quietly being built in real time. In this episode, I’ll walk you through what’s really happening beneath the surface...
info_outline
Ep 84: Why Being in Debt Might Be the Best Time to Invest in Yourself
Money On My Mind
Episode Description "I'd love to join the Academy, but I'm already in debt. I can't justify spending more money right now." This is one of the biggest objections I hear, and I get it, I've been there too. But if you're in a tough financial position, this episode is going to completely flip your mindset and show you why being in a hole isn't a reason to freeze, it's the exact reason to move. Most people wait until they feel financially safe to invest in themselves, but that feeling may never come if you're drowning financially. You're not lazy, you're scared. And that fear keeps you stuck in...
info_outline
Ep 83: How We’re Unlocking Exclusive Real Estate Deals for Our Students
Money On My Mind
Episode Description I've been quietly working on something behind the scenes that I'm finally ready to share with Budget Dog Academy students, exclusive access to private real estate deals that were previously only available to wealthy, accredited investors. This isn't just another investment opportunity; it's a game-changer that removes the traditional barriers that keep everyday people locked out of these high-return deals. In this episode, I break down exactly what this new real estate business is, why I built it, and how it benefits Academy students. I'll explain what "accredited...
info_outline
Ep 82: I Spent $72,000 on One Decision—Here’s Why It Wasn’t Crazy
Money On My Mind
Episode Description Investing $72,000 in yourself might sound crazy, but it was one of the best business decisions I've ever made. In this episode, I break down why I joined an exclusive mastermind of 225 highly successful entrepreneurs and how it's already paying dividends in ways I never imagined. This wasn't an impulsive purchase or ego play. This was about proximity, getting access to the right people in the right rooms who could collapse my timeline to success. Within just five days of joining, I've already received deal flow worth more than my investment, access to 32 SOPs from $100...
info_outline
Ep 81: How Ryan and I left our Deloitte Job
Money On My Mind
Ryan made $3 million, lived in a Chicago penthouse, and had only been to three of his daughter's soccer games in 16 years. That moment on his rooftop changed everything for me. In this raw conversation with Rayn Bakke, I share why we both walked away from Big Four careers to build something that actually matters. From getting mocked by Deloitte leadership for pursuing my dream to proving I could replace my salary in just 10 months, this is the real story of leaving corporate America's golden handcuffs. I'll take you inside the moment HR gave me an ultimatum, why I paid off my house the same...
info_outline
Ep 80: Why I Started Hating the “Grind” Culture (And What I Do Now)
Money On My Mind
Hustle culture nearly destroyed my health, my marriage, and my ability to be present for my daughters. In this deeply personal episode, I share why I stopped glorifying the grind and learned that working smarter not harder is the real path to sustainable success. From leaving Deloitte to build BudgetDog while caring for my daughter with Dravet syndrome, to discovering toxic mold that threatened our entire family's health, this is the raw truth about what endless hustle really costs. I'll walk you through the moments that forced me to choose between proving my worth through output...
info_outline
Ep 79: Eight Investing Rules of Thumb
Money On My Mind
Investing can feel overwhelming with all the strategies, opinions, and noise out there. That’s why in this episode, I break down eight simple, time-tested rules of thumb that will help you cut through the confusion and make smarter decisions with your money. These aren’t rigid formulas—they’re practical guidelines to keep you on track whether you’re just getting started or fine-tuning your portfolio. From understanding how long it takes your money to double, to calculating your “freedom number,” to knowing whether to prioritize retirement or college savings, these rules will help...
info_outlineIs it too late to invest when the market hits all-time highs?
That’s the question everybody is asking, and the truth will surprise you.
This episode breaks down exactly why trying to “time the market” is one of the most expensive mistakes you can make, and why long-term, consistent investing still outperforms every prediction, headline, and emotion you have.
I walk you through the data, not opinions:
• Fidelity’s study showing the best investors were people who did nothing
• How missing just a handful of the best market days destroys your returns
• Why staying invested, even at all-time highs, creates far more wealth than waiting for crashes
• How students are growing $90K… $140K… even $240K in net worth using a simple, repeatable system
• And the psychological trap that keeps most people broke, even when they earn good money
This isn’t theory. This isn’t hype.
This is the real, proven, boring-but-powerful strategy that builds wealth every single time.
Episode Timeline & Highlights
[0:00] – Why “all-time highs” scare people
[2:15] – Emotion vs. data (and why one always loses)
[4:40] – The student results you can’t ignore
[7:30] – Market timing: the most expensive mistake you can make
[10:55] – The Fidelity study that shocked everyone
[13:10] – Missing the best days: how it kills your returns
[16:20] – The $300,000 growth example (data only)
[19:45] – Why simple investing beats complicated strategies
[22:10] – Final truth: wealth is built by staying in the game
Key Takeaways 💡
• Market timing destroys more wealth than market crashes
• The best returns go to people who stay invested consistently
• Simple, automated investing beats emotional decision-making
• Data > predictions, always
• You don’t need complexity to build real wealth
• All-time highs are not a reason to pause—they’re a reason to keep going
Quotables 🗣️
“Trying to time the market isn’t strategy—it’s gambling with your life savings.”
“Missing five of the best days can erase decades of smart decisions.”
“Consistency builds wealth. Emotion destroys it.”
Links & Resources
Learn more about Budgetdog Academy: https://budgetdog.com
My book, The Roadmap to Financial Freedom: https://budgetdogacademy.com/order-now
Follow me on Instagram: https://instagram.com/budgetdog
If this episode gave you clarity, share it with someone who’s stuck waiting for “the perfect moment” to invest. There is no perfect moment, only a perfect strategy. 🎯