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Rethinking Wall Street: Why Conventional Investment Advice Fails

Theodore Hicks · September 17, 2026

Author · Financein

Interview with Theodore Hicks

Rethinking Wall Street: Why Conventional Investment Advice Fails — Theodore Hicks

Podcast: Invest in You

September 17, 2026 · 48 min

In this episode, Fredrik sits down with Theodore Hicks, a registered investment advisor and author of Evidence-Based Investing. Drawing from over two decades of financial experience, including navigating the dot-com bubble and the 2008 global financial crisis, Theo breaks down…

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Key topicsStarting My Career in a Market That Kept Proving the Textbooks WrongTheodore began his career determined to become a financial planner rather than a stock picker, only to enter the profession as markets delivered three consecutive years of losses during the dot-com crash. When the global financial crisis followed several years later, he discovered that faithfully applying conventional industry guidance still did not protect investors from severe portfolio damage. That experience forced him to question the theories he had been taught and begin searching for an approach that responded to real market evidence rather than assuming diversification would eventually solve every problem. This conversation gives investors and financial professionals an honest look at how difficult market periods can reshape a career, challenge accepted wisdom and lead to a more defensive way of thinking about wealth. Protecting wealth requires guardrails before growthThe financial industry often celebrates the highest returns, but for people in their fifties, sixties and beyond, avoiding a devastating loss may matter more than capturing every market gain. Theodore’s approach begins with protecting the wealth a client has already spent decades accumulating before deciding how aggressively it should grow. He describes this as “guardrails and growth”, a priority shaped by seeing traditional strategies fail during major market shocks. Listeners gain a practical framework for judging investment decisions by whether they protect the life the money must support, not simply whether they outperform in a good year. The investment advice most professionals still follow was never designed for today's marketsFinancial advisors, planners, and finance students are still taught Modern Portfolio Theory as the foundation of investing, despite it being built on assumptions developed decades ago. Theodore examines where the theory succeeds, where it falls short in real-world markets, and why practitioners should question long-held industry beliefs rather than treating them as untouchable doctrine. This is a conversation about improving investment thinking rather than defending financial orthodoxy. View all topics →

About Theodore Hicks

Theodore Hicks, podcast guest

Wealth Management Author, Financial Planner and Market Strategist

20+ years Financial planning and portfolio management2 awards Winner for Evidence-Based Investing3 credentials CFP®, CKA® & CMT®MoneyShow Masters Symposium Industry speaker

Theodore Hicks is a financial planner, author and speaker whose approach to wealth management was shaped by experiencing some of the most difficult market periods of the past three decades.

He entered the profession determined to help people build thoughtful financial plans, only to begin his career during the dot-com crash and later guide clients through the global financial crisis. Despite following the established guidance promoted by major firms and academic theory, Theodore saw how quickly even a well-constructed financial plan could be undermined by severe market losses at the wrong stage of an investor’s life. That experience led him to question the industry’s default assumptions and develop a more defensive, evidence-based approach to portfolio management.

Today, Theodore helps investors navigate the point at which accumulated wealth brings greater complexity, higher stakes and less room for error. His work is particularly relevant to business owners, senior executives, professionals and retirees who have spent years building their assets but no longer want the responsibility of managing every investment decision themselves. He challenges the idea that investors must simply accept major losses, ride out every downturn and trust that markets will recover on a timetable that suits their lives.

Theodore is also the author of a highly regarded book written for both experienced investors and the next generation of financial professionals.

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About this episode

In this episode, Fredrik sits down withTheodore Hicks, a registered investment advisor and author of Evidence-Based Investing. Drawing from over two decades of financial experience, including navigating the dot-com bubble and the 2008 global financial crisis, Theo breaks down why conventional financial advice and Modern Portfolio Theory often fail investors during real-market drawdowns.

KEY TAKEAWAYS

The Importance of "Sell Discipline": Everyone knows the phrase "buy low, sell high," but few practice the discipline of actually trimming winning positions to lock in gains and mitigate portfolio risk.

The Reality of Portfolio Math: Recovering from market drawdowns is asymmetric: a 50% loss requires a 100% gain just to break even. Protecting capital on the downside is far more effective than trying to catch up later.

Salespeople vs. Portfolio Managers: A large portion of the retail finance industry consists of sales professionals driven by product commissions rather than trained managers actively hedging risk.

Strategy-Based Diversification: True diversification isn't just owning different stocks; it involves diversifying entry and exit strategies, rules, and risk guardrails to withstand bear markets.

Wealth and Health are Intertwined: Accumulating financial wealth is meaningless if you lack the physical health to enjoy it, play with future generations, or pursue your life goals.

BEST MOMENTS

"We have to trim every once in a while... You actually have to have that sell discipline."

"I'm trying to give people permission to question what they hear from the news media, the financial news media, Wall Street, etc."

"The majority of the people that are managing money for retail... they're not trained portfolio managers, they're trained sales professionals."

"In order to win the poker game, you got to survive each hand."

"A smart man learns from his mistakes, but a wise man learns from others."

GUEST LINKS

Theodore Hicks

https://www.linkedin.com/in/theodore2hicks/

https://www.theodorehicks.com/

Book Evidence-Based Investing

About the Podcast

Invest in You is a global podcast where entrepreneur and investor Fredrik Sandvall shares practical ideas and conversations with founders, investors, and operators. Episodes focus on investing, entrepreneurship, and building long-term control and freedom.

Occasionally joined by his sons Ivan and Charlie, the show offers both experience-based insight and a next-generation perspective.

Listeners in 155+ countries tune in to think clearer, act smarter, and build with intent.

Community & Contact

Podcast community: https://bit.ly/4jxF94k

Fredrik Sandvall

LinkedIn: ⁠https://www.linkedin.com/in/sandvall/⁠

Facebook: ⁠https://www.facebook.com/FredrikinLondon/

YouTube: https://www.youtube.com/@FredrikSandvall

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