loader from loading.io

Estate planning, the stock market, and the potential downside of wealth, with John M. Jennings

Measure Success Podcast

Release Date: 09/19/2023

AI and Data Strategies for E-Commerce Success show art AI and Data Strategies for E-Commerce Success

Measure Success Podcast

On this episode of the Measure Success Podcast, Carl J. Cox welcomes Matthew Stafford, co-founder of Build Grow Scale. Matt shares how he turned a $1,000 investment in analytics into a billion-dollar path in e-commerce. They dive into the mindset shifts leaders need, how AI transforms data into action, and why profitability matters more than revenue growth. You’ll hear how one client scaled from $10,000 to a $60M run rate in just three years. Tune in for insights you can apply to your business today. 🎧 Listen to the full episode now

info_outline From Chaos to Clarity: Cash Flow Tools show art From Chaos to Clarity: Cash Flow Tools

Measure Success Podcast

Cash flow is more than money in the bank—it’s about clarity, planning, and purpose. In this episode of the Measure Success Podcast, Carl J. Cox talks with Michelle Röse, COO and co-founder of Breakaway Bookkeeping and Advising. Michelle shares how her team helps businesses forecast cash weekly, align budgets with reality, and make faster, smarter decisions. She also dives into why success isn’t only about profit—it’s about purpose, balance, and measuring what truly matters. 🎧 Tune in to learn how to strengthen cash flow and measure success in business and life.

info_outline Thriving in Uncertain Times with Mark Murphy show art Thriving in Uncertain Times with Mark Murphy

Measure Success Podcast

On this episode of the Measure Success Podcast, Carl J. Cox talks with Mark Murphy, CEO of Northeast Private Client Group and top-ranked financial security professional. Mark explains why wealth is created not by holding assets, but by investing in your business, real estate, and smart financing. He shares how leaders can strengthen culture, improve liquidity, and turn volatility into opportunity. Whether you’re building wealth, scaling your business, or seeking financial freedom, this conversation offers practical insights for entrepreneurs and executives. Listen to the full episode now!...

info_outline Scaling Innovation Without Wasting Time show art Scaling Innovation Without Wasting Time

Measure Success Podcast

Innovative ideas often die inside large companies — not because they lack potential, but because they don’t fit the organization’s existing priorities and processes. On this episode of the Measure Success Podcast, Carl J Cox speaks with Jim Bodio and Stephen Rich of BRI Associates, creators of Growth Forge. They share how their platform helps companies de-risk innovation by guiding teams through strategy definition, market evaluation, and execution planning. You’ll hear lessons from their time leading Intel’s new business incubator and discover how to overcome internal friction that...

info_outline Break the $30M Ceiling Using AI Strategy show art Break the $30M Ceiling Using AI Strategy

Measure Success Podcast

Professional services firms often face a growth ceiling — struggling to scale without losing client relationships or service quality. In this episode of the Measure Success Podcast, Carl J Cox sits down with Mohan Rao of KnownWell to discuss how AI can help break through that barrier. Mohan explains how their platform turns everyday communication data into actionable insights, helping firms identify client risks, spot expansion opportunities, and strengthen account management. We also explore the “Playing to Win” strategy framework and how it applies to service-based businesses. Tune in...

info_outline The Curious Leader Mindset show art The Curious Leader Mindset

Measure Success Podcast

What if curiosity was the secret to getting unstuck? In this episode, Jon Bassford — CEO of Lateral Solutions and author of The Curious Leader — shares how leaders can overcome fear, break unhelpful habits, and create a culture of growth. We explore his TEDx talk, how to create operational excellence, and the difference between being busy and being effective. ✅ How to stop doing everything yourself ✅ Why psychological safety unlocks innovation ✅ Simple strategies to save time and money in operations Listen now and start building a more curious, effective organization.  

info_outline How Losing Her Business Launched Her Career show art How Losing Her Business Launched Her Career

Measure Success Podcast

What if a business disaster was the exact push you needed? Nicole Cramer’s story starts with a total digital wipeout: her Facebook group hacked, Instagram accounts stolen, website taken down. Instead of folding, she turned it into fuel for her long-delayed goal—becoming a full-time speaker. In this episode of the Measure Success Podcast, Nicole shares how she pivoted, what she learned from professional speaking training, and how to build trust in an AI-saturated sales world. Key takeaways: How to rebuild after a tech breakdown Building a repeatable, profitable speaking business ...

info_outline AI is Here. Lead Like It. show art AI is Here. Lead Like It.

Measure Success Podcast

Trey Taylor returns to discuss what CEOs are getting wrong about AI—and why lazy usage is worse than no usage at all. From productivity tools to people leadership, this episode challenges leaders to take full ownership over how AI is integrated in their organizations. You’ll also hear how AI is being used in construction, insurance, and even quoting systems—and why quality control still starts with the CEO. 🎧 This is strategy for the future—listen now.  

info_outline How to Create Culture That Actually Works show art How to Create Culture That Actually Works

Measure Success Podcast

Ken Rusk, author of Blue Collar Cash, started in the trenches—literally. Today, he’s built a company where success means everyone wins. In this episode, Ken shares: The power of “timed pathways” vs. vague goals Why blue-collar jobs are an untapped goldmine How culture, transparency, and shared purpose drive retention If you want practical advice on building wealth, culture, and freedom (without a college degree), this one’s for you. 🎧 Tune in and rethink what it really means to succeed.  

info_outline Stop Surviving, Start Scaling with Idan Shpizear show art Stop Surviving, Start Scaling with Idan Shpizear

Measure Success Podcast

What’s more powerful than a strategy? Belief. In this episode, Idan Shpizear—CEO of 911 Restoration—shares how he helps entrepreneurs move from fear and doubt to clarity and execution. He unpacks: The difference between belief and knowing Why your inner world shapes your business results How simple mindset shifts unlock new revenue This is one of our most mindset-driven, actionable conversations to date. 🎧 Tune in and discover how your mind may be the key to your next level.  

info_outline
 
More Episodes

Money 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: 

 

  • More info about what John’s organization does, and what differentiates them from other competitors

  • The power of “ridiculous customization”, plus why John’s company starts with the “unsexy” things (like cash flow) before anything else related to investment

  • Why having major wealth isn’t always “puppies and butterflies”

  • 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

  • Some of the biggest insights from John’s book, “The Uncertainty Solution” — and why it’s not actually just an investment book

  • Why John didn’t buy Amazon stock — and what that says about the overall stock market

  • What John prioritizes when it comes to his physical and mental health, and why those habits help him perform his best

  • Why John’s measure of success in his personal life is related to naptime

  • More about the journey it took for John to finally write his book despite a lot of self-doubt 

  • Several of John’s top book recommendations

 

Resources Mentioned in This Episode: