BIO: Blair LaCorte is a dynamic executive with experience across entertainment, aviation, AI, aerospace, consulting, and more.

STORY: Blair shares three catastrophic investment failures and the life-altering lessons that rewired his approach to wealth.

LEARNING: Chase knowledge, not hype, and don’t let greed hijack logic. Invest with friends only if you’re willing to lose both.

“The worst investment that you can make is to put your time into something that you don’t enjoy or that you know is not going to work out.”

Blair LaCorte

Guest profile

Blair LaCorte is a dynamic executive with experience across entertainment, aviation, AI, aerospace, consulting, and more. He has held CEO roles at companies such as PRG, XOJET, and Autodesk, and led startups to successful IPOs. Currently, he’s training as an astronaut for Virgin Galactic and is Vice Chairman at the Buck Institute.

Worst investment ever

Fresh out of college at 22, Blair met a smooth-talking investor who flaunted his “lifetime monthly checks” from an oil well. Blinded by dollar signs and zero industry knowledge, he poured his savings into a single well.

Blair ignored basic due diligence, diversification, and warnings about low-quality reserves. It was all about greed. He had seen someone make money where they got paid every month for the rest of their life, as long as the well lasted.

The greed kept him in and kept him investing in the well. At the end of the day, the oil was of below-average quality and was not as much as they thought it would be. Blair’s ignorance caused him a 100% loss. The well underperformed, and his greed trapped him in a sinking ship. Blair even commissioned a plaque to memorialize his shame—a daily reminder that “easy money” is a predator in disguise.

Burning $200k and a friendship

After Blair’s first IPO success in 1999, his roommate pitched him on Coffee.com—a visionary play on single-origin beans (decades before it became trendy). Blair invested early, then panicked as losses mounted. When the roommate begged for more capital, he refused because he did not think it would succeed, but guilt kept him from cutting ties.

After a while, the startup imploded. Worse? Blair’s friend never spoke to him again. He learned the hard truth from this unwise investment: mixing money with friendship is financial suicide.

The $59.50 ego tax

At the peak of the dot-com boom, Blair had just scored a top-tier IPO. His broker urgently called and advised him to sell immediately at $59.50 as he believed the boom would not last. But pride convinced him that the broker was just chasing commissions.

Blair held stubbornly as the stock bled out to $2. He lost $570,000 in vaporized gains. Blair’s ego had bet against reality, and reality won.

Lessons learned

Chase knowledge, not hype, and don’t let greed hijack logic. If you don’t understand how the money is made, you’re the exit strategy for someone else.
Friends + money = atomic risk. Invest with friends only if you’re willing to lose both on the same day.
Pride is the silent portfolio killer. The market doesn’t care about your ego, and exit signals don’t negotiate.
Your time is your ultimate currency. Grinding your years into a dying venture to ‘prove a point’ is the costliest investment of all.

Andrew’s takeaways

Macro trumps micro. Brilliant ideas fail if they’re too early or too late. Always ask: “Is the world ready for this?”
Preserve capital like your life depends on it. A young you can risk time; an older you must protect capital.
Passive high-risk bets (like an oil well) are gambling. Invest where you can influence outcomes.

Actionable advice

When temptation knocks:

Demand the “Why You?” clause. If a “sure thing” lands in your lap, ask: Why me? Why now? What do they know that I don’t?
Map the macro weather by using tools like Google Trends, industry reports, and Fed data to pressure-test timing.
Cap the bleeding by allocating a max of 5% of net worth to high-risk plays. Set automatic exit triggers (e.g., “Sell if -25%”).
Sign contracts, define failure clauses, and never mix personal loans with equity, especially if investing with pals.

Blair’s recommendations

Blair recommends checking out PPE Mastermind Talks (available for free at PPEmastermind.com) to learn business tactics from battle-tested CEOs. He also recommends reading biographies, examining companies’ histories, and watching documentaries or listening to speakers that prompt you to think differently about things, to accelerate your ability to learn.

No.1 goal for the next 12 months

Blair’s goal for the next 12 months is radical self-care. Blair wants to do things for himself without feeling guilty.

Parting words

“Go out there and have fun, it’s a privilege. Approximately 50% of the world’s population lives on a subsistence level. Another 25% don’t get to make the decisions. If you have the financial or mental capability to try new things, you’re blessed. So go out there and have some fun.”

Blair LaCorte

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My Worst Investment Ever Podcast

Blair LaCorte – How Greed, Pride, and Friendship Cost Me Everything

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