We’re finally doing it: the drive from Pennsylvania to New Mexico—the move that launches our downsized, nomadic lifestyle we’ve been building toward for years.

But this trip isn’t happening the way we originally planned. Winter weather, slow progress on a condo rehab and van build, and Tim’s last-minute training push for a 3-day bike race have changed everything. And that’s the point of this episode: life is always in flux—so your plans have to be built to flex.

We Hate Highways… Guess Where We’re Driving

In this episode, we compare:

• A conventional road trip plan (typical route, hotels, eating out, standard timing) vs.
• Our real-world plan (highways for time, possible night driving, slower pace for two older vehicles, frequent stops for cats, cooking + sleeping in the van at rest stops)

We also talk through the constraints that force smarter decisions that deviate from our normal preferences:

• Why we’re avoiding forest overnights (snow, mud, getting stuck = losing time)
• How time pressure changes the “ideal” route
• How preferences (like avoiding highways) shift when the stakes change
• What we think this trip will cost—before we track the real number

And in a future episode, we’ll report back with the actual totals: what stayed on-plan, what surprised us, and what we had to pivot on.

This isn’t just travel planning. It’s the same framework we use for investing: Start with the conventional path → tweak it to fit your life → plan intelligently → pivot for reality.

If you’re planning a big move, a road trip, or a major lifestyle change (financial or otherwise), this episode will give you a practical way to think through costs, tradeoffs, and the hidden variables people forget.

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2026 is the year of financial realism. Americans are still dealing with high prices and inflation fatigue… but the shift is this: people aren’t just panicking anymore—they’re getting strategic.

In this episode, we break down what the data says about the average American’s relationship with money in 2026:

• persistent money stress + cost-of-living pressure
• “paycheck-to-paycheck” life becoming normal (not fun, just normal)
• record debt levels + why credit is being used as a bridge
• and the biggest change: a widespread determination to improve finances—cut debt, build savings, and manage money more intentionally.

Then we move from “yep, that’s the problem” to how people actually implement the changes they want, including:

• Loud Budgeting: saying “that doesn’t fit my goals” without embarrassment
• Sinking funds: turning predictable “surprises” into planned expenses
• Convenience tax audit: finding money without a raise
• Loyalty tax check: retention pricing, renegotiating recurring bills
• Value-based spending: stop budgeting like a punishment
• automation + micro-saving to build momentum without relying on willpower
• and simple accountability systems that don’t feel like financial prison

If you’ve been feeling the pinch and feeling ready to get your money together—this is your episode.

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Questions? Email Tim at debrine9@gmail.com

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DISCLAIMER Ticker metrics change as markets and companies change, so always do your own research. The content in this podcast is based on personal experience and is for educational purposes, not financial advice. See full disclaimer here.

Episode music was created using Loudly.

This episode breaks down what we consider the core pillar of our entire investing framework: the income-first retirement portfolio.

An income-first strategy prioritizes interest and dividends as the primary source of retirement cash flow, with price appreciation treated as a secondary benefit. This is fundamentally different from the traditional total-return approach, which relies on selling shares to generate income.

In this episode, we cover:

• What an income-first retirement portfolio actually is
• How it differs philosophically and practically from total-return / 4% rule strategies
• Why selling assets in down markets creates sequence-of-returns risk
• The benefits of predictable, internally generated cash flow
• The biggest mistake income investors make: stretching for yield
• Asset types commonly used in income-first portfolios:
  • Dividend-paying stocks and dividend growers
  • Bonds and bond ladders
  • REITs and preferred stocks
  • Closed-end funds (CEFs)
  • Annuities (with important caveats)
• Real examples from our own portfolios, including dividend growers, income ETFs/CEFs, and higher-yield income producers
• How we use income from higher-yield assets to pay bills and reinvest into more stable dividend growth assets

We also walk through the first steps to building your own income-first portfolio:

• Defining your income goal and time horizon
• Calculating the gap between expenses and guaranteed income
• Treating your portfolio like a business that produces surplus cash flow
• Assessing emotional and financial risk tolerance for 2026
• Building emergency buffers so income assets are never forced to be sold

This episode isn’t about chasing returns or predicting markets.
It’s about building a retirement strategy designed for stability, predictability, and peace of mind—one where your portfolio works for you instead of being slowly dismantled.

Questions? Email Tim at debrine9@gmail.com

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**DISCLAIMER**
Ticker metrics change as markets and companies change, so always do your own research. The content in this podcast is based on personal experience and is for educational purposes, not financial advice. See full disclaimer here.

Episode music was created using Loudly.

If you feel like your money disappears before the month is over, you’re not imagining it — the numbers confirm it.

In this episode, we walk through updated 2025 data showing that the average single American earns about $4,300 per month after taxes, while average monthly living costs now approach $5,000. That structural deficit explains why consumer debt has exploded, why record numbers of people are working multiple jobs, and why shared housing is no longer optional for many.

We break down:

• Where the average American’s money actually goes each month
• Why debt has become a survival tool instead of a strategy
• How multiple jobs and doubling up on housing became the norm
• Why “unplanned” expenses aren’t really surprises — they’re statistically inevitable
• The true cost of car repairs, medical bills, and home maintenance
• Why most households can’t handle a $1,000 emergency
• How emergency funds can be built even while running a deficit, using automation, tax refunds, and small behavioral shifts

This isn’t about blame or budgeting harder.
It’s about understanding the math, recognizing the warning signs, and preparing for the expenses that will happen — before they derail everything.

Questions? Email Tim at debrine9@gmail.com

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**DISCLAIMER**
Ticker metrics change as markets and companies change, so always do your own research. The content in this podcast is based on personal experience and is for educational purposes, not financial advice. See full disclaimer here.

Episode music was created using Loudly.

Weekly-paying ETFs are exploding in popularity — but most investors don’t understand what they’re actually buying.

In this episode, we analyze 19 high-yield weekly dividend ETFs across YieldMax Roundhill, Defiance, Tuttle, Granite Shares, and Nicolas Global products to answer one question:

👉 Which weekly ETFs are worth your money — and which function more like Ponzi schemes?

We break each ETF down using:

• Total return (price + dividends)
• NAV erosion and price decay
• Return of Capital (ROC) percentages
• ETF structure (synthetic vs covered call vs 0DTE)
• Performance vs the underlying benchmark

This isn’t theoretical. We’re managing $50,000+ in a weekly income ETF portfolio, and this episode reflects what we've learned after owning these assets over 2+ years.

You’ll learn:

• Why 90–100% ROC is a massive red flag
• Which weekly ETFs are structurally broken
• The “sweet spot” for sustainable high yield (25–40% with 30–60% ROC)
• Why synthetic ETFs decay faster than covered call ETFs with real holdings
• How to use weekly ETFs for bridge income, not long-term retirement
• When to turn DRIP on — and when it makes things worse

We also explain how we personally use weekly ETFs:

• DRIP off until capital is recouped
• Diversification across structures (not tickers)
• Expecting some ETFs to decay — and planning for it
• Using macrotrends for better odds

This episode is for income investors who want cash flow without self-inflicted losses.

Questions? Email Tim at debrine9@gmail.com

Want FREE weekly market updates, Tim's top 10 dividend picks, and our portfolio updates delivered right to your inbox? Subscribe to our email list.

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**DISCLAIMER**
Ticker metrics change as markets and companies change, so always do your own research. The content in this podcast is based on personal experience and is for educational purposes, not financial advice. See full disclaimer here.

Episode music was created using Loudly.

Most investors obsess over what to buy.
In 2026, the real edge is when and where you buy it.

In this episode, we break down the valuation-driven framework we actually use to decide whether something is a buy — across:

• Individual stocks
• REITs
• BDCs
• Closed-end funds
• ETFs (including the S&P 500)

We walk through real examples like UPS, Realty Income (O), Main Street Capital, USA CEF, and VOO to show:

• How entry price impacts total return more than exit timing
• Why yield and dividends act as downside protection
• Which valuation metrics matter for each asset type
• How to spot overvalued “favorites” before they correct
• Where income investors can still find margin of safety

This episode isn’t about predictions or hype — it’s about having your own valuation framework, so you’re not relying on analysts, headlines, or hope.

If you’re preparing for a volatile 2026 and want to protect capital while still getting paid, this is our playbook.

Questions? Email Tim at debrine9@gmail.com

Want FREE weekly market updates, Tim's top 10 dividend picks, and our portfolio updates delivered right to your inbox? Subscribe to our email list.

Stay connected. Follow us on social!

**DISCLAIMER**
Ticker metrics change as markets and companies change, so always do your own research. The content in this podcast is based on personal experience and is for educational purposes, not financial advice. See full disclaimer here.

Episode music was created using Loudly.

2025 looked like a great year on paper — but most investors didn’t experience those returns.

In this episode, we break down what really happened beneath the indexes, why passive investing masked widespread underperformance, and how a dividend-first, total-return strategy quietly outperformed the market.

We walk through:

• Why the S&P 500’s gains were driven by ~7 stocks
• Which unexpected sectors crushed it (utilities, REITs, commodities)
• Why many “obvious” AI and tech plays underperformed
• The biggest winners, losers, and surprises across 46 real holdings
• How dividends changed the math in flat and down positions
• Why total return matters more than price return
• How we rebalance without chasing winners or panic selling
• What these results mean for positioning in 2026

We also explain how we track everything manually using spreadsheets, why DRIP isn’t always your friend, and how income investing reduces emotional mistakes when markets get choppy.

If you care about real performance, not marketing returns, this episode will change how you look at your portfolio.

Questions? Email Tim at debrine9@gmail.com

Want FREE weekly market updates, Tim's top 10 dividend picks, and our portfolio updates delivered right to your inbox? Subscribe to our email list.

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**DISCLAIMER**
Ticker metrics change as markets and companies change, so always do your own research. The content in this podcast is based on personal experience and is for educational purposes, not financial advice. See full disclaimer here.

Episode music was created using Loudly.

How We Invested $150,000 for Monthly Income | Dividend Portfolio Breakdown

In this episode, we break down exactly how we invested a $150,000 lump sum across 2 portfolios with one primary goal: reliable monthly income without reckless risk.

We walk through how we structured the portfolios, why certain stocks and ETFs made the cut, and how we’re building a dividend stream that functions like a paycheck — with flexibility, downside protection, and upside optionality.

What we cover:

• How we split $150K across income and our conservative fallback portfolio
• Why undervalued dividend growers matter more than yield chasing
• Using covered call ETFs responsibly for income
• Preferred shares, utilities, packaging, semiconductors, banks, and data centers
• Turning DRIP on and off strategically based on valuation
• How we’re targeting $2,500+ per month in dividends in our income portfolio
• Backup cash flow plans if our income portfolio underperforms
• Where excess cash goes when there’s nothing to buy

If you’re trying to understand how dividend income actually works in practice, this episode lays it out step by step.

Questions? Email Tim at debrine9@gmail.com

Want FREE weekly market updates, Tim's top 10 dividend picks, and our portfolio updates delivered right to your inbox? Subscribe to our email list.

Stay connected. Follow us on social!

**DISCLAIMER**
Ticker metrics change as markets and companies change, so always do your own research. The content in this podcast is based on personal experience and is for educational purposes, not financial advice. See full disclaimer here.

Episode music was created using Loudly.