The Rise and Fall of Trust

Cashflow Podcasting
  • 5.0 (4)
  • ENTREPRENEURSHIP

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.

  1. 5D AGO

    Commitment Over Balance: Why Strong Partnerships Aren’t 50/50

    What makes a partnership last decades when most business relationships fracture under pressure? In this episode, Anne speaks with financial advisor and True Success Podcast co-host Daniel Friedman, whose 30-plus-year partnership with his business partner offers a rare long-term view on trust in business. Daniel’s philosophy challenges the common idea that partnerships should be “50/50.” Instead, he believes each person must bring 100%, even when their contributions look different in a given season. Trust is reinforced not just through character, but through systems: open financial transparency, clear expectations, and a willingness to test partnerships before fully committing. As you listen, consider where trust in your own partnerships depends not on balance, but on commitment. What You’ll Learn: Why strong partnerships don’t operate on 50/50.How transparency inside a firm reinforces trust among partners and teams.Why testing partnerships before full commitment reduces long-term risk.The warning signs when values around money begin to diverge.What difficult seasons reveal about real partnership trust.Why clear values make difficult business decisions easier.How redefining success changes the way trust is built in business relationships. Ideas Worth Sharing: “When your values are clear, your decisions are easy.” - Daniel Friedman"Our relationships… are 100/0. You give a hundred, I give a hundred. None of this 50/50 stuff." - Daniel Friedman"We always know how much money we have. We don't know how much time." - Daniel Friedman About Daniel Friedman: Daniel Friedman is the CEO and Co-Founder of WMGNA, which he has led since 1995. He pioneered the firm's Tax-Out Financial Solutions™ model, built around the philosophy that tax planning and financial planning are inseparable. Under his leadership, WMGNA introduced a subscription-based model, integrated CPA partnerships, and developed innovative concepts like Restylement™, a reimagined approach to retirement planning. Today, the firm serves subscribers across more than 35 states. Daniel is also the co-host of the True Success Podcast. A graduate of Denison University with a degree in History, he lives in West Hartford, CT and serves on the Advisory Board for The Miracle League of Connecticut. Resources: The Gift of Fear: And Other Survival Signals That Protect Us from Violence by Gavin de BeckerWMGNA.comTrue Success Podcast Connect with Daniel: LinkedIn: Daniel Friedman 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.

    27 min

  2. MAR 4

    Consistency, Candor, and Client Loyalty: How Trust Is Built in Financial Advice

    What if the biggest threat to your client relationships isn’t market volatility but a poorly handled referral or an unanswered question? In this episode, Anne sits down with Larry Ginsburg, a seasoned financial advisor who has built decades-long client loyalty primarily through referrals. At the heart of his approach? Disciplined communication. Larry believes trust isn’t built through performance alone. It’s built through consistency, clarity, and immediate responsiveness. Questions are answered promptly. Jargon is eliminated. Mistakes are addressed directly. His core message: you’re not just in the investment business; you’re in the anxiety-reduction business. And reducing anxiety requires a deliberate, disciplined commitment to trust-building at every interaction. What You’ll Learn: Why your clients stay and why it has little to do with returns.How immediate responsiveness changes client perception.The cost of using jargon in high-stakes conversations.What happens when advisors admit mistakes openly.Why giving a single referral can create unintended liability.How structured processes protect both trust and responsibility.Why every interaction shapes long-term loyalty. Ideas Worth Sharing: “The only way to build trust is to deliver a consistency of effective communication that clients can determine for themselves is true, accurate, and respectful.” - Larry Ginsburg“There's no such thing as a foolish question when it comes to [your] money.” - Larry Ginsburg“If you're not consciously choosing to move the relationship forward, you are making a decision to deteriorate the quality of that relationship from the client's perspective." - Larry Ginsburg About Larry Ginsburg: Larry Ginsburg is a CFP professional with more than four decades of experience in personal financial planning. He has held senior leadership roles including Branch Manager, Regional Director, Board Member, and firm owner, and has served in leadership positions within the Financial Planning Association. Larry joined Wealth Enhancement Group in 2022 through the acquisition of Ginsburg Financial Advisors. His work focuses on helping clients reduce financial anxiety while keeping long-term goals clearly in view. Connect with Larry: LinkedIn: Larry Ginsburg 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.

    30 min

  3. FEB 18

    Clarity Beats Cleverness: The Eight Pillars of Trust with David Horsager

    What if your sales problem, leadership challenge, or retention issue isn’t really about strategy at all, but about trust? In this episode, Anne sits down with trust expert David Horsager, founder of the Trust Edge Leadership Institute and author of multiple books on trust, including Trust Matters More Than Ever and Trust at a Distance. David has spent decades researching how trust is built, measured, and repaired inside organizations, from Fortune 500 companies to the U.S. military. Listen in as he explains why trust is the leading indicator behind sales, engagement, referrals, and retention. He also breaks down his eight pillars of trust framework and shares how trust is built in measurable, practical ways. As you listen, consider where trust may be the real issue behind the challenges you’re trying to solve. What You’ll Learn: Why trust is the leading indicator behind sales, engagement, and retention.The eight pillars that determine whether trust rises or falls.Why clarity beats cleverness in leadership and marketing.How to make your message memorable, repeatable, and actionable.The cost of inconsistency in brand and leadership behavior.Why personal connection is regaining importance in a digital world. Ideas Worth Sharing: “Clarity beats cleverness today. People want to be clever, and they want to be cute… No, clarity wins. Just say the thing.” - David Horsager“Every single interaction we have with every single person, we increase or decrease trust a little bit.” - David Horsager“If you want it to matter, it's got to be MRA… Is it memorable? Is it repeatable? Actionable?” - David Horsager Resources: David HorsagerTrust Edge Leadership InstituteTrust Matters More Than Ever by David HorsagerOther BooksThe 8 Pillars of Trust About David Horsager: David Horsager is CEO of the Trust Edge Leadership Institute and a Wall Street Journal bestselling author. He is the inventor of the Enterprise Trust Index™ and director of the global trust study, Trust Outlook®. His books include Trusted Leader, Daily Edge, and The Trust Edge. David works with leaders and organizations worldwide, from Fortune 100 companies to professional sports teams and global governments, to measure, build, and restore trust. Connect with David: LinkedIn: David Horsager 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.

    32 min

  4. FEB 4

    The Seven Rules of Trust: Designing Trust at Scale with Wikipedia Founder Jimmy Wales

    What happens when you shift from a seven-stage approval process that screams “we don't trust you” to a radically open model where almost anyone can edit anything? In this episode, we feature a special conversation (originally hosted by Pete Mockaitis of How to Be Awesome at Your Job) with Wikipedia founder Jimmy Wales. Jimmy shares the story of how Wikipedia went from an intimidating, top-down editorial system to the open-source knowledge powerhouse we know today. This conversation explores how designing systems that assume good faith promotes more trustworthy behavior. Jimmy also connects these principles to real-world examples across industries: subscription dark patterns, pandemic health guidance, social media algorithms, and why Netflix succeeded where Blockbuster failed. As you listen, consider Jimmy’s invitation to take a “trust inventory” and notice where your own organization may be unintentionally signaling mistrust and what could change if you flipped that script. What You’ll Learn: How the Seven Rules of Trust emerged from Wikipedia’s early failures and reinvention.What it really means to design trust at scale inside large, open systems.Why assuming good faith can be more powerful than control in leadership and organizations.How subtle design choices quietly shape whether people feel trusted or policed.Where modern institutions and platforms unintentionally lose credibility.Why transparency and independence still matter in a world driven by metrics and clicks.A simple “trust inventory” you can apply to your own organization or work. Ideas Worth Sharing: "One of the things people first think of when you say ‘what makes an organization more trustworthy?’ … is transparency." - Jimmy Wales“If you approach someone and you trust them—and you make it clear that you're trusting them—they're very likely to reciprocate because humans are like that." - Jimmy Wales“Take a trust inventory. So think about all the different aspects of your work life, your home life, all of that. ‘What are the things that I could do to help people trust me, and what are the things I can do to encourage other people to be trustworthy?’” - Jimmy Wales Resources: The Seven Rules of Trust: A Blueprint for Building Things That Last by Jimmy WalesWikipediaHow to be Awesome at Your JobTrust Café About Jimmy Wales: Jimmy Wales is the co-founder of Wikipedia and a pioneer of the open knowledge movement. In addition to Wikipedia, Jimmy is the author of The Seven Rules of Trust, where he explores how individuals and institutions can earn credibility through independence, respect, and ethical system design. His work continues to shape conversations around trust, media, and the future of the internet. Connect with Jimmy: LinkedIn: Jimmy Wales Connect with Pete: LinkedIn: Pete Mockaitis 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, th

    45 min

  5. JAN 21

    Building Trust in Venture Capital: Leadership When No One Is Watching with Victor Orlovski

    What does real trust look like when pressure hits, incentives shift, and no one is watching? In this episode, venture capitalist Victor Orlovski, founder of R136 Ventures and host of Ventures from the Valley, shares the raw reality of trust in the high-stakes world of startup investing. After backing a promising European startup through years of growth and nearly closing a major acquisition, Victor watched helplessly as the founders executed a legal but devastating betrayal. He reveals how that experience influenced his entire approach to venture capital, shifting his focus from metrics and technology to the character of the people behind the pitch. This conversation explores the delicate balance between authority and democracy in leadership, why consistency matters more than personality type, and what truly happens in the room when you're not there. What You’ll Learn: The three components that define trust in any relationship or business.Why venture capital still requires a human intermediary despite technological advances.How to spot red flags in founders who oversell or avoid discussing their biggest challenges.Why consistency in leadership matters more than leadership style.How organizational culture directly mirrors founder behavior (whether they're present or not).The difference between legal and ethical behavior in business partnerships. Ideas Worth Sharing: "Trust is where you withdraw yourself and people keep behaving like you are in the room." - Victor Orlovski“What comes first is awareness. People should know about you. Then second, people should trust you. And then—only then—you can really get what you want: money. So many founders start from the reverse order. They try to get money without establishing awareness and trust. And I think that's very important.” - Victor Orlovski"I'm not going to invest in a founder who exaggerates and who doesn't really have real good answers to his most challenging matters... If a founder is telling me how great things are, probably my desire to invest will diminish." - Victor Orlovski Resources: R136 VenturesVentures from The Valley About Victor Orlovski: Victor Orlovski is the founder and managing partner of R136 Ventures, an investment firm focused on mid-and-late-stage startups across the U.S., Israel, and Dubai. With decades of experience in venture capital and technology, Victor has led investments across fintech and enterprise platforms and is also the host of the Ventures from the Valley podcast, where he explores leadership, trust, and building companies for the long term. Connect with Victor: LinkedIn: Victor Orlovski 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.

    35 min

  6. JAN 7

    Building Trust Through Transparency and Risk: Lessons from Market Losses with Larry Kriesmer

    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 PortfoliosMRP 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.

    31 min

  7. 12/17/2025

    Trust Is the Business: Transparency, Risk, and Proactive Communication with Tom Kelly

    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.

    26 min

  8. 12/10/2025

    Building Trust Through Competence and Compassion: Insights from the Military to Financial Advisory with Phillip Hulme

    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.

    31 min
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5
out of 5
4 Ratings

About

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.

Information

  • Creator
    Cashflow Podcasting
  • Years Active
    2025 - 2026
  • Episodes
    18
  • Rating
    Clean
  • Copyright
    © 2026 The Rise and Fall of Trust
  • Show Website
    The Rise and Fall of Trust