This episode features host Travis Chappell and producer Eric having a rapid-fire, hilarious, and surprisingly deep “Would You Rather” session built entirely around money, investing, and lifestyle tradeoffs. Using a list of AI-generated prompts, they unpack how real people should think about risk, retirement, lifestyle creep, and building wealth with their actual constraints in mind.​

On this episode we talk about:

Whether to take $10 million today or $1 million a year for life

Swinging for a 10x moonshot vs. locking in an 8% return forever

Being “early to the next Apple” versus compounding slower, safer returns

Choosing between keeping your investments or keeping your business

Building one $100M company that burns you out vs. multiple smaller businesses you love

Working 80-hour weeks for a few years to make work optional vs. coasting forever

Unlimited VC money with no control vs. slow, bootstrapped freedom

Fame with no privacy vs. quiet wealth no one sees

Driving a paid-off Toyota with rentals vs. renting a house with a Lambo

Taking a $250K job you hate vs. $75K doing work you love

Top 3 Takeaways

Safe, consistent returns beat reckless moonshots—especially early on. Travis leans toward guaranteed growth and stacking cash first, then taking bigger swings once a solid base is built.

Your best wealth-building lever at first is income, not investments. Until your portfolio can support you, your business and skills are the engine that funds long-term wealth.

Money decisions are really lifestyle decisions. Tradeoffs like privacy vs. fame, burnout vs. freedom, and hating a high-paying job vs. loving a lower-paying one matter more than raw dollar amounts.

Notable Quotes

“Get to a hundred grand, then put as much money as you can into the safe thing before you go start playing around.”

“The goal isn’t retirement; the goal is to make work optional.”

“There’s a massive difference between having to work to eat and choosing to work because you love what you do.”​

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