The Strategy Skills Podcast: Strategy | Leadership | Critical Thinking | Problem-Solving

David Leiter learned one of investing's hardest lessons while sitting on a trading desk during the dot-com boom. After watching seemingly everyone around him get rich, he finally gave in to the crowd, bought into the hype, and took a painful loss. The experience shaped a principle that has guided his investing ever since: "avoid big losses."
In this conversation, David explains why most investment mistakes are not caused by fraud alone. Many begin with emotion, social proof, fear of missing out, and the assumption that if sophisticated investors or large institutions are participating, an opportunity must be safe. As he puts it, "Wall Street will sell you whatever is popular."
Drawing on lessons from his book, Stop Making Stupid Investments, David discusses why successful investors often think differently from the crowd. He shares how contrarian thinking helped him recognize opportunities others ignored, why market euphoria and panic repeatedly create mispriced assets, and how investors can avoid being swept up by speculation.
A central theme of the discussion is the distinction between innovation and investment. David believes artificial intelligence will transform the world, but cautions that "the technology is different than the investments." Investors can be right about a trend and still lose money if they pay too much for the underlying asset.
Key topics include:
• Why "avoid big losses" is the foundation of long-term wealth building.
• How investors become vulnerable when they follow popularity, momentum, or fear of missing out.
• What Jeff Bezos meant when he said, "the stock is not the company, and the company is not the stock."
• Why great businesses can become poor investments when purchased at excessive prices.
• How private investment opportunities can fail when decisions are driven by trust, charisma, or social proof instead of analysis and oversight.
• The warning signs of scams and bad investments, including urgency, pressure tactics, and emotional manipulation.
David also outlines his four-part framework for evaluating opportunities: understand how the business makes money, assess where it is likely to be in five to ten years, evaluate the quality of management, and determine whether the price is reasonable. Even a great business, he argues, can become a money-losing investment if purchased at the wrong valuation.
Beyond investing, the conversation explores how AI is reshaping work and why human capabilities may become more valuable as technology advances. David argues that communication, empathy, relationship-building, and the ability to create "win-win situations" will remain powerful differentiators in a world where intelligence becomes increasingly accessible.
The episode concludes with a deeply personal reflection on a recent medical misdiagnosis that forced him to confront the possibility that time might be limited. The experience led to a simple but profound realization: stop worrying about what other people think, stop waiting for permission, and focus on the work that matters now.
Throughout the discussion, David returns to the same idea: investing, business, and life all improve when decisions are grounded in fundamentals rather than emotion. The challenge is learning to see clearly when everyone else is being pulled by fear, excitement, or the crowd.
Get David's book, Stop Making Stupid Investments, here: https://tinyurl.com/nhaje6jt
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For this episode, let's revisit a strategy skills classic interview with an experienced founder, leader, and thinker across a variety of domains, Rick Walker.
In this episode, Rick walks us through his leadership journey, how he built his first company in his 20's, the lessons he learned across multiple domains, and how he was able to do multiple things successfully, simultaneously. He also shared his views about fear, pride, faith, religion, and ethics in relation to leadership and business.
Rick Walker scaled his first company to 400 employees when he was 26, and simultaneously, as Chairman, scaled a 53-country international nonprofit from 800 to 2,100 team members, simultaneously while helping his hometown of Houston attract over $5 Billion in job-creation investments. Rick's volunteer service also includes stints as a Director of a college in the middle east and Chairman of a $250 Million charitable foundation. His 3:30 AM wake-up call helps fit everything in. 
Rick hosts a podcast to help multi-domain leaders learn well - and has interviewed friends, who also happen to be world-class leaders, such as billionaires, musicians, members of the President's Cabinet, US Senate, US Congress, and great thinkers. The podcast is hosted inside a 13,000-square-foot mansion, which was the former party mansion of a Fortune 500 CEO, which Rick restored and uses for his family office, charitable events, and podcasts. 
Rick lives in Houston with his wife and 3 girls, where he spends much of his time serving alongside the best team members in his commercial real estate private equity firm. 
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People will save for four years, eat less, and travel across the world to watch their team play. Kris and Michael walk through Berlin during the World Cup and ask what that spending really buys.
This is the first episode of the Walking Masterclass. Filmed in Berlin a few hours from the Switzerland and Canada match, the conversation moves from the cost of the World Cup to the experience economy, tribal economics, and the human need to belong. Kris and Michael discuss why people spend to be part of a tribe, why travel often works as an escape from the life you built, and why the two most important decisions you make are whether you marry and whom you marry.
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For this episode, let's revisit a strategy skills classic interview with the author of Job Therapy: Finding Work That Works for You, Dr. Tessa West. In her book, Dr. Tessa West helps you figure out the real reason you're unhappy and shows you how to find a new position in which you'll thrive, whether in a different role, company, or new industry altogether.
Dr. Tessa West is Professor of Psychology at New York University, where she is a leading expert on the science of social relationships. Her academic research and writing for the media focuses on how to improve communication between employees, bosses, and hiring professionals across workplace settings.  She has over 100 academic publications and is a regular contributor to the Wall Street Journal. Her work has been covered by Scientific American, the New York Times, Financial Times, The Guardian, CNN, CNBC, ABC World News, TIME, Bloomberg, HBR, Fast Company, and the US Supreme Court. Her first book Jerks at Work published to rave reviews.
Get Dr. Tessa's book here: https://rb.gy/e1iwmg
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For this episode, let's revisit a strategy skills classic interview with the author of Uptime: A Practical Guide to Personal Productivity and Wellbeing, Laura Mae Martin. In her book, Laura shows how to thrive no matter where you're working, giving concrete steps that help you focus on your priorities and keep good systems, routines, and tactics in place. Uptime explains how to make technology work for you and make "feeling on top of it" your new normal. It's a blueprint for operating at the highest levels of productivity while enhancing your own personal well-being.
Laura Mae Martin is the Executive Productivity Advisor in the Office of the CEO at Google. She coaches Google's top executives on the best ways to manage their time and energy and sends out a weekly productivity newsletter that reaches tens of thousands of employees. During her 13-year tenure at Google, she has worked in sales, product operations, event planning, and now executive coaching. Laura holds a Bachelor of Science in business administration from the University of North Carolina at Chapel Hill and lives in Charlotte, NC, with her husband and three children.
Get Laura's book, Uptime: A Practical Guide to Personal Productivity and Wellbeing, here: https://rb.gy/nu5qr6


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