Roxanne Duckels, comedian and money educator who makes finance funny and practical, and Jesse Cramer, long-term investing podcaster focused on retirement and order of operations, debate which rich-person investing ideas to steal, scale, or skip. They tackle long-term thinking, tax priorities, alternative investments and leverage, and why some flashy strategies are best avoided.
56:52
forum Ask episode
web_stories AI Snips
view_agenda Chapters
auto_awesome Transcript
info_circle Episode notes
insights INSIGHT
Think Long Term But Act In 90 Day Chunks
Long-term thinking is the highest-value habit to copy from the 1% because it prevents impulsive trading and short-term mistakes.
Roxanne and OG recommend pairing a 25-year horizon with 90-day execution checkpoints so short-term actions feed long-term goals.
question_answer ANECDOTE
Filling The Tank Was Roxanne's First Investment
Roxanne illustrates long-term thinking with a personal habit: she refilled her gas tank fully when broke in college to avoid running out.
She also started buying bulk items (toilet paper) as a simple form of forward planning.
volunteer_activism ADVICE
Optimize Taxes After Core Priorities
Do prioritize basic tax strategies but avoid obsessing over tax tricks before core steps like saving and proper account use.
Jesse ranks tax optimization around 7 of 10 priorities and warns future tax assumptions are uncertain.
Get the Snipd Podcast app to discover more snips from this episode
You've seen the ads. Invest like the ultra-wealthy. Get access to what the 1% does. But what does the 1% actually do -- and how much of it should a normal person try to copy? Joe, OG, comedian and finance educator Roxanne Duckels, and Jesse Cramer run every popular "rich people investing" idea through a simple filter: steal it, scale it, or skip it. The answers will surprise you -- especially the one where OG wants to delete an entire asset class from existence.
What You'll Walk Away With
Why long-term thinking is the one habit the 1% has that every Stacker should steal immediately -- and the short-term execution piece most people miss when they try
The tax strategy obsession that the wealthy genuinely use -- and why Jesse ranks it seventh on his list of financial priorities, not first
What paying for advice actually means when you're smart enough to do it yourself -- and why the wealthiest people surround themselves with even smarter people anyway
The alternative investment marketing trap hiding inside every "invest like the rich" pitch -- and OG's case for why most people have no business touching any of it
Why the accredited investor designation protects almost no one -- and what the real risk is when you lock up money in illiquid investments chasing slightly better returns
The leverage conversation that exposes a contradiction hiding in plain sight for every real estate investor
Why Roxanne's path to financial independence started with filling her gas tank all the way up -- and what that tells you about long-term thinking at any income level
The one question that should precede any alternative investment conversation: does the expected return actually beat what publicly traded equities already offer?
What the trivia competition scoreboard looks like heading into the back half of the year -- and whether OG's historic lead is as safe as it looks
Why rich habits and "what the 1% does" are two completely different things -- and which one is actually worth chasing
Why This Matters Now
In a noisy market environment, the "invest like the wealthy" pitch gets louder every time volatility spikes. Private credit, non-traded REITs, leveraged real estate, alternative assets -- the marketing machine never stops. For Stackers in their 40s who've built something real and don't want to blow it chasing a category that mostly benefits the people selling it, this episode is a useful reset. The habits worth stealing from the 1% turn out to be remarkably unglamorous.
From the Basement
Joe, OG, Roxanne Duckels from Finance Rox, and Jesse Cramer run the "invest like the rich" playbook through a steal-it-scale-it-skip-it framework -- and nobody agrees on everything, which is exactly what makes it useful. Doug arrives with Mayday trivia about the origin of the distress call and the year it was coined, which turns into one of the cleaner trivia finishes of the season. Whether the basement scoreboard moved in OG's favor or Jesse closed the gap is a question best answered with your earbuds in.
Resources Mentioned
Finance Rox -- Roxanne Duckels on YouTube and Instagram @FinanceROX
The Stacking Benjamins Show 