David Waddell

David Waddell – The Power of Vulnerability and Fast Decision-Making in Business Growth

David Waddell is the CEO and Chief Investment Strategist at Waddell & Associates, an SEC-registered investment advisory and wealth management firm. He leads the firm’s investment committee, using macroeconomic forecasting, market analysis, and risk assessment to guide clients’ portfolio strategies. With over two decades of experience, David is a recognized economic and investment expert and has been featured in major media outlets like Forbes and The Wall Street Journal.

Here's a Glimpse of What You'll Learn

[3:47] The benefits of long-term EO forum relationships and how members build trust over time
[8:21] David Waddell’s early career journey from college to working at NFL Films and Charles Schwab
[12:48] David talks about returning to Memphis to take over his father’s firm
[17:17] The decision to shift from asset management to financial planning
[21:18] How overconfidence and market shifts led to a difficult period of underperformance and self-reflection for David
[31:54] Common financial mistakes entrepreneurs make, including a lack of professionalization and poor deal strategy
[35:45] David discusses the future of his business and why embracing AI and human connection is key to growth

In This Episode

Success in business often looks like confidence, certainty, and control — but the reality is often far messier. Behind strong outcomes are moments of doubt, difficult decisions, and the willingness to admit what isn’t working. Sometimes, the advantage isn’t having the answers, but knowing when to question them.

As an investment strategist with decades of experience guiding entrepreneurs, David Waddell’s journey was shaped as much by missteps as by wins. From humble beginnings — sleeping in a sparse apartment while working at Charles Schwab — to stepping into his father’s firm and challenging its core business model, David learned early that conviction comes with risk. Years later, after a long stretch of success, shifting market dynamics exposed flaws in his approach, forcing him into a difficult period of reflection and reinvention. That experience reshaped his leadership style, grounding it in humility and decisiveness.

In this episode of The Decision, Robert Hartline and Eric Jackson sit down with David Waddell, CEO and Chief Investment Strategist at Waddell & Associates, to discuss decision-making and growth as an entrepreneur. David explains the importance of vulnerability in EO forums, lessons from shifting a business model, and how market changes forced a strategic reset.

Quotable Moments:

“I think the vulnerability is the power.”
“I think truth and getting to sort of transparency and authenticity fast in EO is endearing.”
“I’d much rather be at the bottom of the mountain looking up than being at the top.”
“If I learned one thing, it’s make decisions. If they’re the wrong decisions, make other decisions.”
“Overpay your advisor, overpay your accountant, and overpay your lawyer.”

Action Steps:

Embrace vulnerability in professional relationships: Being open about challenges and uncertainties builds trust and accelerates meaningful connections. This creates stronger support systems and leads to better decision-making through shared experiences.
Make decisions quickly and adjust as needed: Delaying decisions can stall progress and create unnecessary friction within a business. Acting decisively allows you to learn faster and adapt before small problems become major setbacks.
Challenge your own assumptions regularly: Long-term success can create blind spots that prevent you from seeing changing conditions. Continuously questioning your approach helps you stay adaptable and avoid complacency.
Invest in expert advice during critical moments: Trying to cut costs on advisors during major financial decisions can lead to costly mistakes. Paying for high-quality expertise ensures better outcomes and more strategic execution.
Integrate technology while prioritizing human connection: Leveraging tools like AI can improve efficiency and free up time for deeper client relationships. Focusing on the human element ensures your business remains relevant and differentiated in a rapidly evolving landscape.