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?

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?

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.