A devastating financial mistake became the beginning of a much bigger lesson about failure, self-worth, success, and the questions that can change the direction of a life.

Jerremy: I Lost $39 Million, but it's ok

June 23, 20261 min read

In this episode of Unexpected Happiness, Ariel talks with Jerremy Newsome, whose life has been shaped by entrepreneurship, risk-taking, and a willingness to learn from even his biggest mistakes.

Jerremy shares how a bad investment wiped out not only his own money, but the life savings of his father and three of his father's closest friends. Convinced he had destroyed their trust forever, he braced for anger, disappointment, and rejection.

Instead, his father responded with something Jerremy never expected.

That moment became the beginning of a journey that would reshape how he thought about failure, responsibility, success, and what it means to believe in yourself.

Throughout the conversation, Jerremy reflects on the questions that changed his life, the difference between working harder and thinking differently, and why many of us are chasing goals we never stopped to examine.

Listen to this episode if you want to:

  • Hear a remarkable story about failure, forgiveness, and second chances.

  • Learn how the questions you ask shape the answers you find.

  • Explore the difference between success that looks impressive and success that actually feels fulfilling.

  • Understand why clarity about what you want can be more powerful than ambition alone.

  • Be reminded that one mistake, even a very big one, does not have to define the rest of your life.

Ariel Steele

Ariel Steele

Ariel Steele is a lawyer, business owner, and the owner of Tax Credit Connection, where she has spent more than twenty years leading complex conservation transactions. From the outside, her life looked successful and stable. Inside, she was exhausted, anxious, and constantly bracing for something to go wrong. Today, through Unexpected Happiness, she helps high-achieving women who have good lives on paper learn how to feel calm, present, and genuinely happy now.

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