Estate planning, the stock market, and the potential downside of wealth, with John M. Jennings
Release Date: 09/19/2023
How Smart Leaders Use AI to Execute Better
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AI is changing how companies grow, how leaders lead, and how strategy gets executed. In this episode of the Measure Success Podcast, Carl J Cox sits down with Klee Kleber, co-founder and partner at Build Group, to discuss what leaders need to understand right now. Klee shares why expertise is becoming a commodity, why implementation is still the biggest challenge, and how operator-led strategy creates real value. They cover how AI is reshaping product development, go-to-market strategy, and leadership, along with why human judgment, trust, and execution still matter. This episode is a clear...
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AI, Sales, and the Power of Human Connection
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In this episode of the Measure Success Podcast, Carl J Cox talks with Gabe Lullo, CEO of Alleyoop, about the real role of outbound sales in today’s market. They discuss how AI is changing sales without replacing human connection, why founders should stay close to revenue early, and how content builds trust before the first conversation ever happens. Gabe shares lessons from scaling a remote SDR organization and explains how fractional sales teams help growing companies create momentum without overspending. This conversation is practical, honest, and focused on strategy over tactics. If you...
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Why AI Is Reshaping Leadership Today
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In this episode of the Measure Success Podcast, Carl sits down again with CEO and author Trey Taylor for a candid conversation on AI, culture, and the future of leadership. Trey explains why AI is no longer optional, how leaders can avoid lazy thinking, and what’s driving the rapid rise of Latino-owned businesses in the U.S. He shares insights on balancing culture, people, and numbers—his signature “three things”—while adapting to tools that change faster than organizations can keep up. Trey also gives practical examples of AI improving operations, decision-making, and customer...
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Where Do Leaders Go For Real Growth?
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In this episode, Carl J. Cox talks with global speaker and executive coach Dona Amelia about why leaders need safe spaces to grow. Dona shares her upbringing in rural Indonesia, her rise as a performer and executive, and how those experiences shaped her belief that leaders can only grow when they have a place to speak honestly, ask real questions, and receive support without judgment. She explains how peer networks, shared experiences, and diverse perspectives help executives make better decisions and avoid isolation at the top. If you’ve ever felt pressure to know everything or carry...
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Get Found in the New AI Economy
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In this episode of the Measure Success Podcast, Carl sits down with digital marketing expert Dave Burnett to unpack the seismic shift happening in search and AI. Dave explains why Google is no longer the only place customers look for answers and how large language models are reshaping discoverability. He shares lessons from his own journey—partnership failures, business resilience, and recovering from a traumatic brain injury—and how those experiences shaped how he leads today. Dave outlines the new rules of digital visibility, why PR is becoming essential, and how companies can position...
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Double Revenue. Cut Costs. One Strategy.
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On this episode of the Measure Success Podcast, Carl J. Cox speaks with Tammy Nam, CEO of The Brief, the AI Agency for marketers. Tammy shares how she doubled revenue at Viki while cutting costs and improving team morale—a rare combination that highlights her strategic clarity and leadership strength. She explains how The Brief helps marketers run smarter campaigns from start to finish using intelligent agents that analyze performance, generate content, launch faster, and learn continuously. Tammy also breaks down how leaders can protect their top performers, remove friction, and communicate...
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The Secret to Elite Business Performance
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In this episode of the Measure Success Podcast, Carl J. Cox talks with Michael Erath, founder of Next Level Growth and author of The Five Obsessions of Elite Organizations. Michael shares his powerful story of losing a multimillion-dollar company to fraud and how that crisis transformed his view of leadership. He explains how elite organizations are built around five obsessions—great people, inspiring purpose, optimized playbooks, performance-driven culture, and sustainable profits. Tune in to learn how you can lead with purpose, build stronger teams, and achieve both a return on investment...
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Radical Clarity: How Founders Lead with Purpose
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Many technical founders find themselves running companies almost by accident. They know their craft — but struggle to lead with clarity. In this Measure Success Podcast episode, Carl J. Cox interviews Pete Steege, author of Radical Clarity, to discuss how “accidental CEOs” can grow their businesses by uncovering their true story. Pete explains why clarity — not more effort — drives growth. He shares how to focus on purpose, align your team, and communicate with meaning so your message connects with customers. 🎧 Tune in to learn how to move from complexity to clarity.
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Leadership alone doesn’t drive success—it’s only part of the equation. In this episode of the Measure Success Podcast, Dr. James Chitwood shares how his TRAC framework—Training, Recognition, Accountability, and Communication—creates lasting organizational transformation. Hear how his military background shaped his leadership philosophy, why capitalism is at risk, and what it takes to build high-performing, people-centered teams. Listen now and learn how to lead through structure, not just inspiration.
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Data Privacy Laws Every CEO Must Know
Measure Success Podcast
In this episode of the Measure Success Podcast, Carl J. Cox talks with Jenny Sheridan, attorney and founder of JL Sheridan Law, about how changing data privacy laws are shaping the way companies operate. Jenny shares insights on how businesses can stay compliant with the California Consumer Privacy Act (CCPA) and similar state laws, the real risks of ignoring them, and how privacy can become a competitive advantage when managed strategically. Listen to learn how to protect your business, reputation, and customers in a data-driven world. 🎧 Stream now at...
info_outlineMoney solves many problems, but it doesn’t solve *all* of them. And in some cases, wealth can actually create some new problems. Here to talk about that dynamic — and how people can get ahead of those issues by proactively managing their wealth — is someone who’s helped dozens of families do exactly that over the last couple of decades.
John M. Jennings is president and chief strategist of St. Louis Trust & Family Office, a $15 billion wealth management firm. His book, “The Uncertainty Solution”, is an engaging dive into investing philosophy and best practices as well as an authoritative, accessible guide for anyone who feels inundated with financial news and data.
Listen to the full episode for more on the “unsexy” task of figuring out cash flow, why having large amounts of wealth can come with its own unanticipated problems, John’s insights into investment, and a lot more.
Here’s a Glimpse of What You’ll Learn:
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More info about what John’s organization does, and what differentiates them from other competitors
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The power of “ridiculous customization”, plus why John’s company starts with the “unsexy” things (like cash flow) before anything else related to investment
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Why having major wealth isn’t always “puppies and butterflies”
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More about the intricacies of estate (and other types of) tax, and when a family or business owner should seek advice in order to minimize how much they pay in taxes
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Some of the biggest insights from John’s book, “The Uncertainty Solution” — and why it’s not actually just an investment book
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Why John didn’t buy Amazon stock — and what that says about the overall stock market
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What John prioritizes when it comes to his physical and mental health, and why those habits help him perform his best
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Why John’s measure of success in his personal life is related to naptime
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More about the journey it took for John to finally write his book despite a lot of self-doubt
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Several of John’s top book recommendations
Resources Mentioned in This Episode:
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“The Uncertainty Solution: How to Invest with Confidence in the Face of the Unknown” by John M. Jennings
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“The Success Equation: Untangling Skill and Luck in Business, Sports, and Investing” by Michael J. Mauboussin
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“The Black Swan: The Impact of the Highly Improbable” by Nassim Nicholas Taleb
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“Thinking, Fast and Slow” by Daniel Kahneman
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“Winning the Loser’s Game: Timeless Strategies for Successful Investing” by Charles Ellis
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“Scale: The Universal Laws of Life, Growth, and Death in Organisms, Cities, and Companies” by Geoffrey West
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Buy a copy of “Lost at CEO: An Entrepreneur’s Guide to Strategy” by Carl J. Cox