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. 3D AGO

    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

  2. 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

  3. 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

  4. 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

  5. 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

  6. 11/26/2025

    Trust, Presence & the Cost of Broken Promises with Charlie Horonzy

    In a world full of constant distractions, the people who choose to make time for us stand out — and for Charlie Horonzy, founder of Focused Up Financial, that simple act has become one of the clearest measures of trust. Across his career, Charlie has experienced both the steady confidence that comes from a generous mentor who always shows up, and the frustration that emerges when communication breaks down and leadership disappears. Those two contrasts shaped his entire understanding of trust, not just in financial planning, but in parenting, teamwork, and everyday relationships. In this episode, Charlie reflects on why mentorship mattered so deeply early in his career, how availability builds confidence for clients and colleagues, and what he learned from an experience where shifting expectations and unclear communication caused trust to fall apart. What You’ll Learn: How simple availability can become a powerful trust-building habit.Why presence matters more than ever in a distraction-heavy world.How inconsistent communication erodes trust even without malicious intent.What leaders often overlook when hiring, mentoring, or promising career progression.How Charlie uses early lessons (good and bad) to shape the way he serves clients and raises his kids. Ideas Worth Sharing: “What's really neat about this in this day and age is people who can make the time for you. I view it as it's even more important because there's so many other distractions—whether it's work, family, whatever it is—away from time.” - Charlie Horonzy"You can't really trust someone if they're telling you one thing and then they're doing another. You gotta be true to your word.” - harlie HoronzyC“Every day, children are watching and they're looking for us to be leaders. And through that, they're gonna have the biggest trust in us, especially when they're young. And we can either develop that trust… or we can start to break that trust.” - Charlie Horonzy Resources: Focused Up Financial, LLCCareless People by Sarah Wynn-Williams About Charlie Horonzy: Charlie Horonzy is a fee-only financial advisor, CPA, and Certified Financial Planner™ who founded Focused Up Financial to help individuals and families align smart planning with meaningful life goals. With a background in public accounting and a passion for integrating tax strategy into long-term financial decisions, Charlie now supports clients in building clarity and confidence around their finances. Outside of work, he enjoys exploring Chicagoland with his wife and three children, biking the Salt Creek trail, and volunteering in his community. Connect with Charlie: Website: Focused Up Financial LinkedIn: Charlie Horonzy, CFP®, CPA Facebook: Focused Up Financial YouTube: Focused Up Financial 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

  7. 11/12/2025

    Trust Isn’t a Final Exam — It’s a Pop Quiz: How Preparation Shapes Reliability with Levi Anderson

    Trust in financial planning isn’t built in the big moments — it’s revealed there. Most people think of trust as something you prepare for like a final exam, with a clear date and time on the calendar. But what if the real tests come without warning? What if trust works more like a pop quiz, where the only thing that matters is whether you’ve been doing the work all along? For Levi Anderson, a financial planning manager at EP Wealth Advisors, this idea became clear through two very different experiences: guiding clients through major life decisions and attempting a 51-mile Grand Canyon run he thought he was prepared for. Both moments taught him the same thing: trust is shaped by the work you do long before anyone is watching. What You’ll Learn: Why trust is less like a scheduled exam and more like a surprise test.How proactive communication reduces “blind trust” moments for clients.Why small actions (taking notes, creating templates, doing the basics well) create disproportionate trust dividends.How unrealistic “business as usual” messaging erodes trust during organizational change.What personal failure can teach us about rebuilding trust through ownership and integrity.The crucial role of preparedness in high-stakes financial conversations. Ideas Worth Sharing: “I think building trust is a lot more like a pop quiz where you don't find out when the big test of your knowledge is until it's too late to go back and do the studying that you should have done.” - Levi Anderson“You kind of have to honor what somebody is worried about by communicating well and being transparent.” - Levi Anderson“It makes it so much easier to trust somebody when they’ve given you every bit of information that they can.” - Levi Anderson Resources: EP Wealth AdvisorsLevi Anderson, Senior Financial Planner in San Diego | EP Wealth Advisors About Levi Anderson: Levi Anderson is a fee-only financial planner and Financial Planning Manager at EP Wealth Advisors, based in San Diego and serving clients nationwide. He holds the CFP®, CPWA®, and Enrolled Agent designations, specializing in retirement planning, tax strategy, and real estate financial planning. Outside of work, Levi is an avid trail runner, a passion that has shaped some of his most impactful lessons on trust, preparation, and personal integrity. Connect with Levi: LinkedIn: Levi Anderson, CFP®, CPWA®, EA - EP Wealth Advisors 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

  8. 10/29/2025

    Setting Expectations: How Transparency Builds Financial Trust with Ian Bloom

    Trust in financial services isn't built through credentials or polished sales pitches. It’s earned through transparency, consistent communication, and a genuine willingness to help—even when there's nothing in it for you. But what happens when those elements are missing? The contrast can be stark, stressful, and leave you wondering if you got a fair deal. Ian Bloom, a financial life planner, knows this better than most. Through two vastly different mortgage experiences (one that exemplified trust-building at its finest, and another that left him scrambling in the dark), Ian reveals what separates professionals who inspire confidence from those who create chaos. What You’ll Learn: How transparency during complex processes builds lasting trust.Why starting from a place of trust doesn't mean blind faith.The danger of being "salesy" versus providing genuine value first.How trust transfers (and weakens) when passed between people.The power of the "preview-review" method for guiding clients through complicated work. Ideas Worth Sharing: “People want to be heard. So if you ask them about themselves — if you have a real back-and-forth conversation — that builds trust really quickly.” - Ian Bloom“The mark of a good professional is someone who can take a very difficult process and make it seem simple.” - Ian Bloom“I think actually one of the errors that early career professionals make is you meet with a client for the first time and you just talk the whole time about what you do... instead of just asking the client, so what are you hoping to get from this meeting? People want to be heard.” - Ian BloomResources: Achieving Accumulation: A Gamer's Guide to Money: Level 2  by Ian BloomA Gamer’s Guide to Money: Level 1 by Ian BloomEp. 04: Earning vs. Building Trust: What Really Creates Psychological Safety — Cashflow Podcasting About Ian Bloom: Ian Bloom is a financial life planner and founder of Open World Financial Life Planning, where he helps clients achieve financial literacy through long-term planning. Combining his certifications as a CFP® (Certified Financial Planner) and RLP® (Registered Life Planner), Ian specializes in making complex financial processes simple and approachable. He's the author of the "Gamer's Guide to Money" series, with his latest book, Achieving Accumulation, recently released. Connect with Ian: LinkedIn  Open World Financial Life Planning: Website | LinkedIn | YouTube | Facebook | X 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.

    28 min
See All (15)

Trailer

Ratings & Reviews

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
    15
  • Rating
    Clean
  • Copyright
    © 2026 The Rise and Fall of Trust
  • Show Website
    The Rise and Fall of Trust