Podlipodcast player Webplayer

The Stacking Benjamins Show

The Stacking Benjamins Show

Invest Like the 1%? What to Steal, What to Scale, and What to Skip (SB1836)

The Stacking Benjamins Show · May 1, 2026 · 56:52

0:0056:52

Listen in the Podli app 🎧

Follow your favourite podcasts, listen offline and in the car with CarPlay and Android Auto, and always pick up where you left off. Free to try.

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 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



See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Episodes: The Stacking Benjamins Show

PodliGet the free Podli app
↓ App