Mentor Debates
Watch great minds clash on life's biggest questions. Cast your vote for who makes the better mentor.
All Topics77♔Leadership & Management9⚖Ethics & Philosophy13♡Relationships & Family8↗Career & Professional Growth9▲Resilience & Mental Health6◎Wisdom & Life Skills7✦Spirituality & Purpose2✎Creativity & Innovation7✚Health & Wellness2◈Money & Personal Finance2⚙Technology & AI1⌂Home & Lifestyle1◇Style & Self-Presentation3➤Travel & Culture1
2 debates found
Wealth & Investment
I just inherited $5 million from my grandfather. I'm 35, make a good salary, and don't need this money to live. It's pure opportunity capital. My financial advisor wants me to put it in a diversified portfolio—index funds, bonds, some real estate. "Slow and steady," he says. "In 30 years, this could be $30 million. Don't gamble with your grandfather's legacy." But I've been studying markets for years. I see opportunities he doesn't. Tech is transforming entire industries. There are companies I believe in deeply. I could concentrate my bets and potentially 10x this money in a decade—or lose a significant portion. My grandfather built his wealth by taking calculated risks on specific businesses he understood. He didn't diversify; he concentrated. My advisor says that's survivorship bias—for every grandfather who succeeded, ten lost everything. I don't need to preserve this money. I could afford to lose half of it and still be fine. But is that permission to speculate, or is it precisely the thinking that destroys wealth? — The Windfall Inheritance in Greenwich
J.P. Morgan
"The first thing is character, the second thing is character, the third thing is character—and then comes judgment"
29 votes
Jesse Livermore
"It was never my thinking that made the big money—it was my sitting and my willingness to be wrong"
32 votes
61 votes total
Wealth & Society
I sold my tech company last year for $800 million. After taxes, I have about $500 million. I'm 45, my kids are set up, and I want to do something meaningful with this money. Some advisors say I should focus on "effective" giving—malaria nets, direct cash transfers to the extreme poor, causes where I can measure lives saved per dollar. "Don't let your personal interests distort your impact," they say. "The arts and culture don't need you—people dying of preventable diseases do." But I love music. I grew up poor, and the public library's CD collection changed my life. I could fund a world-class music education program in underserved schools, or endow a concert hall, or support emerging composers. It wouldn't save as many lives as malaria nets, but it might create beauty that lasts for centuries. My wife says I'm overthinking it: "The money is yours. You earned it through the market, and the market is where it should go back—invest in companies solving problems, create jobs, let the invisible hand work." She thinks philanthropy itself is the wrong approach. What's the best use of wealth that exceeds any person's needs? — The Billionaire's Philanthropy Question in Palo Alto
Otto H. Kahn
"The financier who merely knows how to make money is a poor financier indeed—culture elevates civilization"
30 votes
Adam Smith
"The market, guided by self-interest, allocates resources better than any individual judgment—even well-intentioned"
27 votes
57 votes total