Estate planning, the stock market, and the potential downside of wealth, with John M. Jennings
Release Date: 09/19/2023
Why Sales Data is Failing & How to Fix It
Measure Success Podcast
Most sales teams are working with bad data—and it’s costing them revenue. In this episode of the Measure Success Podcast, Robert Kall, CEO of Cien, explains how AI-powered sales intelligence is helping companies clean up their CRM data, improve forecasting, and drive more conversions. Key insights: ✅ How bad sales data hurts revenue growth ✅ Why most CRM data is inaccurate—and how to fix it ✅ How AI helps sales teams improve forecasting and performance If you want to eliminate bad sales data and unlock more revenue, don’t miss...
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Successful Sales Strategies That Actually Work
Measure Success Podcast
Scaling a business takes focus, consistency, and the right people. Gui Costin, founder of Dakota, built a $40 billion sales and marketing firm by staying committed to long-term strategy and execution. In this episode, he shares how he grew his business, built an effective sales team, and created a system that works. Key insights: ✅ Why most sales teams fail and how to fix it ✅ The key to building a business that scales ✅ How private equity firms can raise more capital If you’re serious about growing your company the right way,...
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How to Build a Business That Makes a Difference
Measure Success Podcast
A sock company that changes lives? Yes. John and Mark X. Cronin, the team behind John’s Crazy Socks, prove that a business with heart can also be a business that thrives. In this episode, they share their journey from a small startup to a global brand, all while prioritizing inclusion, impact, and customer happiness. Key insights: ✅ How a simple idea became a multi-million dollar business ✅ Why purpose and giving back drive growth ✅ What businesses can learn from their customer-first approach If you want to build a company that stands for...
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How to Grow Your Startup with Smart Branding
Measure Success Podcast
Small businesses and startups need strong branding to stand out and grow. Jason Sherwood joins the Measure Success Podcast to explain why branding isn’t just about logos—it’s about creating trust, recognition, and customer loyalty. Key insights: ✅ Why branding matters for small businesses ✅ How to build a brand that attracts customers ✅ The biggest branding mistakes startups should avoid If you want to turn your business into a recognizable brand, this episode is packed with insights you can apply today. !
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The Truth About Starting a CPA Firm
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Going from a big firm to building your own CPA business takes courage, strategy, and the right mindset. Frank Milone, co-founder of FML CPAs, shares his journey from working at Ernst & Young to running a successful accounting firm. He explains the key lessons, mistakes to avoid, and how small firms can thrive today. Key insights: ✅ Why he left a major accounting firm to start his own ✅ The biggest challenges in running a CPA business ✅ How small firms can compete and grow If you’ve ever thought about starting your own business, this episode will...
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How to Identify High-Drive Sales Talent
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Hiring a great salesperson isn’t luck—it’s science. In this episode, Dr. Christopher Croner explains how companies can identify high-drive salespeople before they make a bad hire. He breaks down the psychology behind top-performing sales reps and how to build a team of closers. Key insights: ✅ The three essential traits of elite salespeople ✅ Why traditional hiring methods fail in sales ✅ How to predict whether a candidate will succeed If you want to stop guessing and start hiring salespeople who can close, don’t miss this...
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The Four-Leaf Growth Model for Business Leaders
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Growth without purpose leads to burnout and misalignment. In this episode of the Measure Success Podcast, Mark Mears explains why purpose-driven growth is the key to building successful businesses and engaged teams. He introduces the Four-Leaf Growth Model, a framework designed to help leaders create businesses that thrive and leave a lasting impact. Key insights: ✅ Why businesses need a clear purpose to grow sustainably ✅ The connection between leadership, culture, and profit ✅ How the Four-Leaf Growth Model drives long-term success If...
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Why Great Branding Matters for Your Business
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Your brand is more than a logo—it’s the feeling people get when they interact with your business. In this episode, Jason Sherwood shares how businesses can build a bold, recognizable brand that attracts and retains customers. Key insights: ✅ Why branding is the foundation of business growth ✅ How to design a brand that stands out ✅ The biggest mistakes businesses make with branding If your business isn’t getting the recognition it deserves, this episode will help you refine your brand strategy for better results. Interested in being a...
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How to Create a Culture of Trust and Accountability
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You Need to Know Key CFO Strategies
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Growth is exciting—but without strong financial strategy, it can lead to cash flow issues and missed opportunities. Jody Grunden, co-founder of Summit CPA, explains how Virtual CFOs help businesses scale without financial blind spots. Key insights: ✅ How forecasting helps businesses avoid financial pitfalls ✅ The most common cash flow mistakes—and how to fix them ✅ Why strategic CFO planning leads to long-term success If you want to scale with confidence and financial clarity, don’t miss this episode. Need CFO services? ! Connect...
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