In this episode, host Travis Chappell answers a big-picture question from producer Eric: What is your current investment philosophy—and how has it changed since your first deal? He walks through hard-won lessons from real estate flips, angel bets, crypto, and his own failed startup to explain why most people should stop trying to “beat the market” and focus on boring, compounding plays instead.​

On this episode we talk about:

Travis’ early “invest in yourself and real estate” mindset—and what he actually got right from the start

How chasing deals he did not fully understand (random startups, friend projects, private loans) mostly went to zero

Why even elite angel investors like Jason Calacanis expect the vast majority of deals to fail

Dan Fleyshman’s rough allocation model: most into low-risk, compounding assets (index funds/blue-chip stocks), a slice into medium-risk plays (like real estate), and a small “home run” bucket for angel/venture-type bets

Why Travis now sees the S&P 500 and broad market exposure as a better default than stock-picking or timing trades

Regrets about selling real estate too soon and why his rule now is “never sell if humanly possible”

How he currently thinks about crypto (Bitcoin/Ethereum-heavy, minimal alt-coins) and why he treats big swings as speculation, not core investing

The crucial distinction between investing (long-term, compounding, boring) and speculating (fun, risky, totally optional)

Top 3 Takeaways

You are probably not going to beat the market. Unless investing is your full-time job, broad, diversified, long-term holdings will almost always outperform your attempts to time or outsmart the market.

Real estate rewards patience, not flipping for quick cash. Selling properties early to free up a bit of short-term liquidity often means walking away from six-figure equity decades later.

Speculation should be play money only. Crypto punts, angel rounds, and friend-startup checks belong in a small “casino bucket,” not in the same pile as your retirement and financial freedom money.

Notable Quotes

“If I had just put what I put into random companies into the S&P, it would be about double today instead of almost zero.”

“Most people use 100% of their investing for play money—and then get mad when the ‘big swing’ goes to zero.”

“Time in the market beats timing the market. Put it in, let it ride, and stop trying to be a wizard trader.”​

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