How Anthony Scaramucci Found Peace, Purpose, and Bitcoin

At 18, Anthony Scaramucci came home from school to find a $10,000 check waiting for him. His father, a crane operator, had cashed out his life insurance policy to help Anthony start college. That act of sacrifice marked a turning point : from chasing fast money to chasing a different kind of future.

On When Shift Happens, Scaramucci sits down with host Kevin Follonier to unpack his unlikely journey: from a blue-collar upbringing to hedge fund fame, Bitcoin maximalism, and ultimately, to a life built on gratitude and conviction.

From Financial Anxiety to Financial Freedom

Scaramucci’s early drive came from a desire to escape the money stress he witnessed growing up. Everyone in their generation had been farmers. His father, one of seven siblings raised in a poor coal-mining town, worked as a crane operator. “There's no wealth in the family, and with that comes a lot of anxiety,” Scaramucci recalls. He hustled from the age of 11 with a paper route, watching his father stretch every dollar to make ends meet.

One moment shaped everything: his father cashed out his union life insurance policy to give Anthony $10,000 toward college.  It made him realize he had to go all in, study, and earn a white-collar future.

Still, he admits his relationship with money was fraught: “I probably would've been richer if I put less emphasis on that.” Even now, some of his billionaire friends can’t shake the anxiety.

A Life-Changing Lesson on Partnerships

One of Scaramucci’s most important lessons came over a cup of tea with Hong Kong tycoon Li Ka-shing. The advice was simple but profound: "Leave money on the table for your partners." That mindset, Scaramucci says, not only makes you wealthier over time, but also happier, because more people will want to work with you. Still, he notes, generosity must be paired with discernment. If you pick the wrong partners, leaving too much on the table can cost you dearly.

From Skeptic to Believer: Bitcoin's Appeal

Initially dismissive of crypto, a 2017 encounter with Federal Reserve officials discussing a digital dollar sparked his curiosity. He went back to SkyBridge and launched SkyBridgeBitcoin.com. After careful research—including its legal classification as tangible property by the IRS, scalability to millions of wallets, and availability of secure custodial services—he and his team made a $100M investment.

He emphasizes that this is not speculation for him. It’s ownership. “Bitcoin is digital property. Just like land. And in the U.S., property rights are sacred.”

He now holds over 70% of his net worth in Bitcoin, not by design, but because it grew faster than everything else.

“Don’t Let the Press Manage Your Portfolio”

Scaramucci urges investors to tune out sensationalism and focus on fundamentals. “When the headlines say the world’s ending—that’s when you buy.” He recalls the extreme panic during the 2022 crash, where Bitcoin plummeted from $69,000 to as low as $12,000 in a flash. Despite the chaos, he held his position.

To him, this moment revealed a core lesson: don’t use leverage, don’t panic, and don’t let the media shape your investing decisions.

The Bitcoin Vision: Freedom Through Belief and Tech

For Scaramucci, Bitcoin represents more than just profit. It’s about taking the keys away from “central bankers who are drunk drivers.” He believes in the power of decentralized money that can’t be inflated or monetized by institutions.

His recommendation? Treat Bitcoin like property. Hold it like you’d hold a building. “You can be a short-term renter or a long-term owner. I’m a landlord.”

Books and Beliefs That Shaped Him

Scaramucci is drawn to books that reflect the complexity of human nature. One of his favorites is The 48 Laws of Power because of its honest portrayal of the light and dark sides we all carry. He often speaks about how modern technology evolves rapidly, yet our minds are still wired like they were 100,000 years ago. That gap, he believes, explains much of our inner conflict.

This awareness has helped him tame envy and ego. For him, maturity means learning to celebrate the success of others without feeling diminished by it. He encourages people to become the kind of friend others want to call when something great happens.

He also finds grounding in The Bitcoin Standard. When the volatility of crypto markets shakes his confidence, he returns to the book as a philosophical anchor and a reminder of why he bet big on Bitcoin in the first place.

On Gratitude, Mortality, and Living With Urgency

Scaramucci reflects often on death, not to be dark, but to stay focused. “You’re going to die anyway, so what are you scared of? Go for the thing you want to do.”

He’s lost close friends to cancer at just 44 and 58. “You're not in control. You can try, but you’re not.” For him, the answer is gratitude. “You get a great coffee? Be grateful. Coconut water on the table? Be grateful. That’s how you stay happy.”

Final Thought

Anthony Scaramucci’s story is one of evolution. From chasing wealth to questioning it, from doubting Bitcoin to betting on it fully, he’s proof that conviction can coexist with self-awareness. At his core is a message about embracing the present and letting go of fear. Life, after all, is temporary. The only rational response, he says, is to stay optimistic, stay curious, and yes, stay foolish.

“So when your kids want ice cream at 11 p.m., don’t say no. Get in the car. That’s what life’s about.”

👉If you enjoyed reading the summary, head over to When Shift Happens on YouTube or your favorite podcast platform to access the full convo.