Ever wish you could time your investments perfectly? Spoiler: you can’t. On this Think Like an Investor Thursday, Britt and Whit unpack a classic Charles Schwab case study that pits five fictional investors—like Peter Perfect and Rosie Rotten—against each other over a 20-year market stretch. The surprise? Even the worst-timed investor outperformed the one who stayed in cash. Whether you invest monthly like Matthew or jump in with your bonus, the lesson’s the same: time in the market beats timing the market. Tune in for practical tips on budgeting with an investor mindset, automating your strategy, and why the real magic is starting early—not perfectly.

How do you build a budget when your paycheck barely covers rent? Whit and Britt break down their real-life early 20s budgets—from $2K/month in SoCal to shoebox apartments in NYC. They walk through essential expenses, the trade-offs they made (RIP, savings), and what they’d do differently now with an investor mindset. Whether you’re early in your career or just curious how two future finance pros started out, this one’s honest, practical, and proof that every investor starts somewhere.

Would you survive on a 1900s budget? In this Way Back Wednesday, Britt walks us through over a century of spending habits, while Whit plays along with a surprisingly accurate impromptu quiz. From when food took up half your income and running water was a luxury, to today’s car payments and tech subscriptions, this episode breaks down what’s changed, what hasn’t, and how understanding budget history can sharpen your modern money mindset.

Can you have fun and financial discipline? This Topic Tuesday is a deep dive into conscious budgeting—especially when your salary doesn’t stretch and your friends seem to have bottomless brunch budgets. From side hustles to set-it-and-forget-it savings hacks, Whitney and Brittany break down how to build a system that actually supports your goals (without eating oatmeal forever).

Everyone’s heard the latte line, but what about the sneaky costs baked into your default lifestyle? This week, Whitney and Brittany explore how unconscious decisions—from where you live to how you lunch—can quietly dictate your financial future. They share mistakes made, lessons learned, and how rethinking your monthly budget can fast-track your investing goals. Bonus: tips for spending less without feeling like you’re missing out.

Can two companies in the same industry have completely different investment risks? In this deep-dive episode, the co-hosts compare large-cap Costco with micro-cap Maison Solutions to explore how scale affects everything from cash position to credibility. From competitive advantages to red-flag accounting, this is a masterclass in asking the right questions—whether you’re buying blue chips or betting on underdogs.

Can a budget airline turn into a budget-friendly stock play? In this Think Like an Investor Thursday, the co-hosts do a full diagnostic on Spirit Airlines—from financial filings to Reddit threads. Whitney unpacks the investor relations strategy (or lack thereof), employee sentiment, and customer reviews, while Brittany zooms out to evaluate macro trends, market volatility, and competitive dynamics. Along the way, they ask whether low-cost carriers can be high-value investments—or whether regulation, razor-thin margins, and reputation risk make airlines too turbulent to touch. It’s a masterclass in going beyond vibes and balancing instinct with analysis.

How did people invest before Google, phones, or newspapers? Before ChatGPT and online databases, due diligence was a painfully slow—and surprisingly creative—process. This Way Back Wednesday, Whit and Brit explore the early days of public markets, why coffee shops were the original stock exchanges, and how laws like the 1933 Securities Act helped protect investors.The duo also debates whether modern research is better—or just faster—and shares hot takes on AI-powered sourcing (spoiler: verify everything).

Do you really need a finance degree to analyze a company? Absolutely not.What started as a “boring” topic turns into one of the most practical episodes yet. Brittany breaks down the key elements of an analyst report—like growth projections, industry trends, and market concentration—while Whitney shares how to trust your instincts and look for signals in the noise. This episode sets up the rest of the week, where they’ll apply this process to real-world companies.

Can a boring skill be your biggest investing advantage? The Finance Files crew starts the week with a deep dive into how political uncertainty fuels volatility—and why that matters to investors. Greg breaks down options, futures, and implied volatility, while Britt and Whit play translator for the rest of us. This episode is a crash course in how pros think about market movement and why doing your due diligence is especially important when the headlines get loud.

What if doing less could make you a better investor? News isn’t always knowledge. The trio dives into how over consuming news—especially sensational or biased sources—can actually harm your mindset and decisions. Britt and Whit share personal routines and research habits, Greg explains entertainment vs. information, and together they discuss how to evaluate sources, recognize misinformation, and know when to step back. Perfect for investors craving clarity over chaos.

What separates a true investor from a casual speculator? Successful investing requires more than vibes. On this Think Like an Investor Thursday, The Finance Files trio discusses how to form a solid investment thesis, avoid hype-driven buying, and tailor your due diligence to a company’s stage and sector. Greg shares valuation methods, Britt explains industry analysis, and Whit adds color on staying curious and informed. Whether you’re team index fund or team early-stage equity, this episode will level up your approach.

How far back does fake news go—and who really benefits from it? From the Knights Templar to Theranos, Whit, Britt, and Greg trace the long history of fake news and financial fraud. They unpack how misinformation—whether for power or profit—has shaped markets and manipulated minds. Learn how to spot red flags, question sources, and do your own research before making investment decisions. Because when the story sounds too good, it often is.

Can you trust the source—or are they selling you a story? Whit, Britt, and Greg dig into how headlines and stats can mislead more than inform. From biotech trials to political polls, they break down how small sample sizes, weak study design, and margin of error distort outcomes. Even accurate data can be spun into false narratives. Whether you’re investing, voting, or just staying informed, this episode helps you think critically, verify sources, and spot red flags before they skew your judgment.

Do you know the difference between hype and a healthy investment? Fake news, campaign spin, and volatile headlines—this Market Monday dives into how misinformation and narrative manipulation impact politics, markets, and investor behavior. Whit, Britt, and Greg unpack the hype around Trump Media, the speculative nature of SPACs, and the inflation risks tied to tariffs. Plus, a new legal ruling could allow employees to redirect 401(k) matches to healthcare or student loans—if employers opt in.

What’s the real difference between stocks, bonds, and “safe” investments? Not all diversification is created equal. In this episode, Whit, Britt, and Greg break down how to build a resilient portfolio—covering stocks, bonds, derivatives, and index funds, plus what it means to truly diversify across asset classes and strategies. They also explore how real investors think, the risks of blindly following advice, and how reading, research, and mindset can shape smarter decisions.

Are you investing with strategy—or just hoping for the best? This episode dives into how investors like Ray Dalio and Warren Buffett build portfolios that stand the test of time—and how you can, too. Whit, Britt, and Greg explore diversification through asset types, sectors, and macroeconomic context, while digging into legendary investor strategies—from Buffett’s index fund simplicity to Dalio’s precise asset allocation. They also share hard-earned lessons from years of investing in mining, biotech, and AI, showing how reading, research, and even asking “dumb” questions can make you a smarter, more strategic investor.

Could following the herd be your biggest financial mistake? On this Way Back Wednesday, Whit, Britt, and Greg trace diversification back to 6,000 BC, when farmers rotated crops to protect their livelihood. From Keynes and Markowitz to cattle-buying billionaires and the crash of ’87, they explore how diversification has evolved into a critical strategy for building resilient portfolios. It’s a historical deep dive with real lessons for today’s investors—With Greg’s behind-the-scenes stories from billionaires and Wall Street, you’ll learn how to protect and strengthen your investments through wise diversification.

Are you putting all your financial eggs in one basket? Whit, Britt, and Greg explore the full spectrum of diversification—beyond just owning a handful of stocks. From real estate and bonds to microcaps and global markets, they explain how smart investors reduce risk and optimize returns by thinking across sectors, asset types, and even currencies. This Topic Tuesday, the team helps you think more broadly—and wisely—about how you’re building long-term wealth.

In this Market Monday episode, Whit, Britt, and Greg dig into how politics and policy ripple through markets—and why even long-term investors should care. From tax plans and government spending to party control and Federal Reserve reactions, they explore how elections influence inflation, industry trends, and investor behavior. With real-world examples (hello, cannabis stocks) and practical strategy talk, this episode is your guide to staying prepared—not panicked—when election season hits.