Wall Street Doesn’t Care If You Lose Money

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In this episode of The Business Game, hosts Steve Plummer and Lisa DeAngelis sit down with Steven Woods, founder and CEO of Stirlingshire, to unpack how the financial system really works and why many everyday investors feel left behind.

Steven shares his journey from Kansas City to Wall Street, walking away from a lucrative advisory career with no safety net, and the hard lessons he learned along the way, including what it’s like to lose seven figures in a single day. He explains why much of modern finance is unnecessarily complex, how incentives inside large firms shape investor outcomes, and why transparency and alignment matter more than ever.

The conversation also explores Steven’s simple “grocery store” analogy for understanding the stock market, why people often underestimate how much money they’ll need in the future, and how technology and AI are changing the role of financial advisors - making them more effective rather than obsolete.

Whether you’re a founder, advisor, or someone trying to build more confidence around money and investing, this episode offers a grounded, honest perspective from inside the industry.

You’ll hear about:

• Steven Wood’s path from Wall Street intern to founder & CEO
• Why he built Stirlingshire to better align advisors and clients
• What losing seven figures in a day teaches you about risk
• Why finance often stays opaque and who benefits from that
• The biggest money assumption most people get wrong
• How AI is improving advisor decision-making and efficiency
• The mindset shift beginners need to start investing sooner
• Lessons elite institutions don’t teach about running real businesses

Connect with Steven Woods - Stirlingshire:
LinkedIn: https://www.linkedin.com/in/stirlingshireinvestments/ 
Website: https://www.stirlingshire.com/ 

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Thanks to Smoothx for sponsoring this episode.  Smoothx, your global power connector, Visit  https://www.smoothx.com/ to get started.  

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This episode is for educational purposes only and does not constitute financial advice.

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