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The Rise and Fall of Trust

The Rise and Fall of Trust

Written by: Cashflow Podcasting
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The Rise and Fall of Trust dives deep into the defining moments when trust is earned, shattered, or put on the line. In each episode, hosts Anne Claessen and Pete Mockaitis sit down with bold, honest professionals–from wealth advisors and legal experts to executive coaches and thought leaders–who’ve seen trust tested in real time.


Through real-world stories of extraordinary follow-through and shocking betrayal, you’ll gain powerful insights into how trust shapes reputations, relationships, and results. Discover the traits that elevate someone from good to unforgettable, and the red flags that signal a fall from grace.


Whether you’re leading teams, advising clients, or navigating your own high-stakes path, this podcast helps you master the art of trust in business AND in life.


New episodes drop every other week. Tune in to uncover what makes trust thrive, and what causes it to collapse.


© 2026 The Rise and Fall of Trust
Economics Leadership Management & Leadership
Episodes
  • Building Trust Through Transparency and Risk: Lessons from Market Losses with Larry Kriesmer
    Jan 7 2026

    What happens when trust in the financial system collapses inside your own family?

    In this episode, Measured Risk Portfolios Chairman and Chief Compliance Officer Larry Kriesmer shares the story that shaped his lifelong commitment to transparency, risk management, and investor education. After witnessing his father lose nearly everything due to financial fraud following early retirement, Larry saw firsthand how devastating broken trust can be.

    He reflects on how that experience guided his approach through the tech bubble, the 2008 financial crisis, and ultimately into building structured, math-based investment strategies designed to limit catastrophic loss. This conversation explores how trust falls, how it can be rebuilt, and why better often requires being different.



    What You’ll Learn:

    • Why catastrophic financial loss can permanently change how people relate to risk and trust.
    • How the tech bubble and 2008 financial crisis exposed the limits of traditional diversification.
    • The real role options play in modern risk management.
    • Why education is one of the strongest trust builders in financial advising.
    • How mathematical structure can reduce emotional panic during market downturns.
    • What synthetic equity is and why it was created.
    • The difference between trusting people vs. trusting systems and transparency.


    Ideas Worth Sharing:

    • “Different isn’t always better, but better is always different.” - Larry Kriesmer
    • “Math is not going to let us down. And that's what this story's really about.” - Larry Kriesmer
    • “If it does well, we'll do well. If it does poorly, we'll do kind of poorly. If it does really bad, we won't be really bad.” - Larry Kriesmer


    Resources:

    • Measured Risk Portfolios
    • MRP SynthEquity ETF


    About Larry Kriesmer:

    Larry Kriesmer, CLU, ChFC, is the Chairman and Chief Compliance Officer at Measured Risk Portfolios, a registered investment advisory firm he co-founded in 2007. After growing frustrated with traditional portfolio diversification and exposure to large losses, Larry set out to build a more controlled, risk-managed investment approach rooted in structure and transparency.

    Born and raised in Saudi Arabia, Larry now lives in Rancho Santa Fe with his wife, Carol, where they enjoy travel, outdoor sports, fine wine, and international cuisine.


    Connect with Larry:

    LinkedIn: Larry Kriesmer


    Connect with Anne:

    LinkedIn: Anne Claessen


    Connect With Us

    If you enjoyed this episode, follow The Rise and Fall of Trust wherever you get your podcasts. And if you’re thinking about launching a podcast that builds trust and drives results, that’s our jam. Schedule a free call at Cashflow Podcasting to learn more.

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    31 mins
  • Trust Is the Business: Transparency, Risk, and Proactive Communication with Tom Kelly
    Dec 17 2025

    Trust in wealth management isn’t built on returns. It comes from how you show up when things get messy.

    When markets rise and fall, strategies shift, and emotions run high, that’s when trust is really put to the test.

    In this episode, Tom Kelly, Chief Investment Officer and Senior Advisor at SJS Investment Services, shares how transparency, patience, and emotional intelligence shape real confidence between advisors, clients, and investment partners.

    Through two contrasting stories of rising and falling trust with third-party asset managers, Tom reveals what he has learned about strengthening long-term relationships, as well as what can quickly unravel them.

    What You’ll Learn:

    • Why wealth management is ultimately a trust-based business.
    • How transparency around both wins and losses strengthens long-term confidence.
    • What red flags appear when investment managers avoid discussing risk.
    • Why proactive communication matters most when things go wrong.
    • How emotional intelligence shapes trust during market volatility.
    • The role diversification plays in balancing excitement and long-term stability.
    • Why knowing the person behind the portfolio matters more than just performance.


    Ideas Worth Sharing:

    • “I always say I'm an investment advisor or work in the wealth management industry, but truly… it's a trust business at the end of the day.” - Tom Kelly
    • “Everyone loves to talk about everything that’s good and the potential good that can come, but people are oftentimes very short on the risks.” - Tom Kelly
    • "Trust oftentimes takes a long time to build and can be destroyed instantaneously with one wrongdoing.” - Tom Kelly


    Resources:

    • SJS Investment Services


    About Tom Kelly:

    Tom Kelly is the Chief Investment Officer and Senior Advisor at SJS Investment Services, an independent registered investment advisory firm with nearly 30 years of history. He leads with a long-term investment philosophy focused on diversification, discipline, and client-first decision making. Tom is known for pairing institutional-level investment rigor with relationship-driven service rooted in transparency and trust.


    Connect with Tom:

    LinkedIn: Tom Kelly, CFA


    Connect with Anne:

    LinkedIn: Anne Claessen


    Connect With Us

    If you enjoyed this episode, follow The Rise and Fall of Trust wherever you get your podcasts. And if you’re thinking about launching a podcast that builds trust and drives results, that’s our jam. Schedule a free call at Cashflow Podcasting to learn more.

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    26 mins
  • Building Trust Through Competence and Compassion: Insights from the Military to Financial Advisory with Phillip Hulme
    Dec 10 2025

    What separates leaders who earn trust effortlessly from those who struggle, even with all the right qualifications?

    In this episode, Stars & Stripes Financial Advisors founder Phillip Hulme reflects on why understanding someone’s language, background, and lived experience isn’t just a nice-to-have. It’s often the difference between trust that grows easily and trust that never forms at all.

    Phillip grew up in a military family, enlisted at 17, and spent over 7 years in service before transitioning into corporate America—and later financial planning. In our conversation, he shares how competence and compassion work together to build trust, why reliability is a superpower anyone can develop, and how one painful leadership experience taught him what not to replicate.

    Listen in to hear stories about showing up fully, even when your time in an organization is coming to an end, and why listening without defensiveness is one of the most underrated trust-building habits a leader can have.

    What You’ll Learn:

    • How cultural competence creates immediate trust with military clients.
    • Why reliability is one of the strongest signals of character.
    • How compassion and competence work together in trust-building.
    • What Phillip learned from a leader who lacked emotional intelligence.
    • Simple habits he uses to invite feedback and strengthen relationships.


    Ideas Worth Sharing:

    • “One of the biggest components of trust is competence. And if I'm coming from a similar background—if I know your language, I know your culture—it allows me to be competent.” - Phillip Hulme
    • “Competency is a part of trust, but competency is not all-encompassing… It is necessary, but insufficient.” - Phillip Hulme
    • “Allowing people to speak their truth, to be honest, to operate with integrity requires that you have enough compassion to hear somebody out.” - Phillip Hulme

    Resources:

    • Stars & Stripes Financial Advisors: Blog | Services

    About Phillip Hulme:

    Phillip Hulme is the founder and Chief Financial Advisor at Stars & Stripes Financial Advisors, where he serves military members and veterans through culturally competent, accessible financial planning. A U.S. Army veteran himself, Phillip spent over 7 years in active service before moving into corporate America and ultimately discovering that financial advising was the perfect intersection of his love for personal finance and his desire to serve the military community. Phillip built his firm with a model that works for real military households — focusing on pensions, disability, healthcare, and GI Bill benefits rather than traditional asset-based requirements. Today, he helps clients navigate life transitions, build financial clarity, and make confident decisions rooted in trust and shared understanding.

    Connect with Phillip: Website | LinkedIn | Facebook | YouTube

    Connect with Anne: LinkedIn

    Connect with Us

    If you enjoyed this episode, follow The Rise and Fall of Trust wherever you get your podcasts. And if you’re thinking about launching a podcast that builds trust and drives results, that’s our jam. Schedule a free call at Cashflow Podcasting to learn more.

    Show More Show Less
    31 mins
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