It’s Gotta Be the Investor — Not the Investment

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Do you remember those old Spike Lee Nike commercials where he kept saying, “It’s gotta be the shoes”? Everybody wanted to believe Michael Jordan’s greatness came from Air Jordans. 

But we all know the truth: it wasn’t the shoes, it was the player. And in money, it’s not the investment that makes you wealthy… it’s the investor.

In this episode, I’m breaking down a trap I see all the time: people chasing the “hot” investment like it’s a magic bullet. Real estate. The stock market. The perfect policy. The newest strategy. 

Everyone’s looking for the shortcut, and I get why. I’ve been on countless podcasts where people ask me, “Chris, what’s the best investment right now?” But the real question should be: “How do I become the kind of investor who wins in any market?”

I share why your results aren’t determined by the vehicle, but by the person behind the wheel. That’s exactly why some people gamble in the stock market and lose their shirt while a small group consistently wins. It’s why some people buy rental properties that never appreciate, or end up with “cheap” houses that come with headaches, vacancies, and regret. And it’s why people can invest in multifamily syndications and still lose money when they don’t know what questions to ask, what risks to identify, or how to verify what’s actually happening behind the curtain.

I’m also adding context to the popular line from Rich Dad Poor Dad: “There are no risky investments, only risky investors.” I agree with the principle, but I’m also going to be blunt: there are investments that are just plain stupid. I’ve watched investors chase hype, speculation, and “get rich quick” plays… and the market eventually exposes all of it.

I walk through the key perspectives that separate investors from gamblers, including why the belief that “high risk creates high returns” is backwards. Risk is the chance of loss. A higher chance of loss does not magically increase your odds of winning. That idea often benefits the people collecting fees while you take the volatility.

Then I shift into one of the biggest lessons I learned from downturns: liquidity matters. Markets can change fast, and long time horizons can magnify risk if you’re not protected. We saw it in the last recession, and we saw it again when interest rates spiked and valuations dropped in commercial real estate, retail, self-storage, and multifamily. I explain why short-term strategies can reduce market-timing exposure, and what you should be looking for when evaluating operators, audits, financial transparency, and cash reserves.

Finally, I pull back the curtain on infinite banking and why people misunderstand it. I explain why it’s not enough to pick a “good” carrier like Penn Mutual, MassMutual, or Guardian. Not all agents are created equal. I walk through a real example from a neurosurgeon who was put into a poorly designed whole life policy where her first-year cash value was zero after paying $60,000. Then I contrast it with how we design it, where the first-year cash value is about $50,000 same company, same health rating, totally different outcome because the levers matter.

This is what I teach my VIP clients and inside the Work Optional Blueprint and Wealth Accelerator Academy: become an investor first, and the investments take care of themselves. Stop chasing the shoes. 

Start becoming the player.