Wall Street Doesn’t Care If You Lose Money

Send us Fan MailIn 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 & CEOWhy he built Stirlingshire to better align advisors and clientsWhat losing seven figures in a day teaches you about riskWhy finance often stays opaque and who benefits from thatThe biggest money assumption most people get wrongHow AI is improving advisor decision-making and efficiencyThe mindset shift beginners need to start investing soonerLessons elite institutions don’t teach about running real businessesConnect with Steven Woods - Stirlingshire:LinkedIn: https://www.linkedin.com/in/stirlingshireinvestments/ Website: https://www.stirlingshire.com/ _________Want to clip long-form content into shorts in one click? Receive 25 % off OpusClip, the same tool we use to turn episodes into shareable clips. support the show and save: https://www.opus.pro/?via=93d640 The Business Game is proud to be an official OpusClip affiliate. _________Thanks to Smoothx for sponsoring this episode.  Smoothx, your global power connector, Visit  https://www.smoothx.com/ to get started.  _________This episode is for educational purposes only and does not constitute financial advice.This post contains affiliate links. By clicking and purchasing through these links, we may receive a small commission at no additional cost to you. Thank you for supporting our work.Support the showThank you for listening to The Business Game, where real founders break down the real levels of business.Whether you're building at Level 1 ($0–$1M) or scaling through Level 6 and beyond, this show is designed to help you understand exactly where you are, and what it takes to level up.If you enjoyed this episode, please subscribe, follow and leave a review. It helps more founders find the roadmap.For full episodes, level breakdowns and behind-the-scenes content, follow us on YouTube, TikTok, LinkedIn, Facebook and Instagram.Want to identify your level or learn more about The Business Game framework?Visit www.thebusinessgamegroup.comIt's time to Level Up!We’ll see you at the next level.