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. Jun 24

    Trust Is a Commodity. Here's How You Earn It with Dan Brothers

    You might think trust takes months to build. Dan Brothers earned it in a single conversation… by saying almost nothing. In this episode, Pete sits down with Dan Brothers, CFP and co-founder of Brothers Wealth Management at Edward Jones. Dan brings a rare dual perspective to the conversation: he's spent decades building trust with clients as a financial advisor, and he's also experienced firsthand what it feels like to be on the receiving end of that process for better and for worse. Through two vivid stories (a personal trainer who showed up in slacks instead of gym shorts and a real estate agent who missed the point entirely), Dan reveals what separates advisors who build loyalty from those who quietly lose it. His central lesson: trust isn't automatically given. It's earned through curiosity, consistency, and the willingness to ask one more question than most people bother to ask. What You’ll Learn: Why trust is an earned commodity and what it actually takes to build it fast.How listening before advising creates an immediate foundation of confidence.Why asking "dumber" questions leads to deeper understanding and better outcomes.How vulnerability in leadership and advising signals sincerity, not weakness.Why consistency without ego is one of the fastest trust-builders in any relationship.How technology and instant gratification have made trust harder to build. Ideas Worth Sharing: "Trust is earned, and it's not automatically given." - Dan Brothers“As I get older and I learn more, I actually find myself asking dumber questions because it helps me understand better, not only from a conceptual perspective, but from an intent perspective.” - Dan Brothers“If you're showing that you can be comfortable in your vulnerable state, then it allows them to understand that there's a lot of sincerity and meaning behind what you're trying to do.” - Dan Brothers About Dan Brothers: Dan Brothers is a CFP® professional and co-founder of Brothers Wealth Management at Edward Jones in Danvers, Massachusetts, where he works alongside his wife and fellow CFP® Ashley Brothers. After losing his father at 58 and witnessing the financial fallout his unprepared family faced, Dan built his practice around one central question: "What happens when my paychecks stop?" Resources: Dan Brothers | Edward JonesStart with Why: How Great Leaders Inspire Everyone to Take Action by Simon Sinek Connect with Dan: LinkedIn: Dan Brothers, CFP® 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, that’s our jam. Schedule a free call at Cashflow Podcasting to learn more.

    29 min

  2. Jun 10

    Building Your Health Account: A Guide for Financial Advisors with Stevyn Guinnip

    What happens when the advice people need most goes against everything they have been taught to believe about health? In this episode, Anne sits down with Stevyn Guinnip, founder and CEO of Grow Wellthy, to explore why trust is essential in health conversations shaped by fear, vulnerability, and long-standing habits. Stevyn helps financial advisors treat health like a long-term asset rather than a short-term fitness problem. She explains why many high performers struggle to trust a slower, more sustainable approach to wellness, especially when the broader industry keeps telling them to push harder and do more. Through a story of rising trust with a client facing pre-diabetes and another of falling trust in a respected public figure, Stevyn shares what helps people feel safe enough to change. What You’ll Learn: Why doing less can get better health results.What finally calms clients who feel health panic.How to make people trust your advice faster.Why sleep may matter more than another workout.What happens when a trusted expert disappoints you.Why people trust systems more than random advice.How imperfection can make you more credible. Ideas Worth Sharing: “Trust is everything because the currency that I work in, which is people's health, is very personal.” - Stevyn Guinnip“ Actually, you need to work with your body and you need to listen to it, and sometimes you do less instead of more.” - Stevyn Guinnip“Whatever the image is, you have to stop and say, what is the real person, and are those things aligned with each other?” - Stevyn Guinnip About Stevyn Guinnip: Stevyn Guinnip is the founder and CEO of Grow Wellthy, a health and wellness advisory firm focused on financial professionals. She is an exercise physiologist, certified wellness coach, author, and speaker who helps advisors protect their health with the same intentionality they bring to building wealth. Resources: Grow WellthyTake the Quiz to Find Out Your Wellth ScoreWell-Advised NewsletterGet-Up! ChallengeGrow Wellthy: The Financial Advisor's 4-Step Plan to Protect Your Health Like an Asset by Stevyn Guinnip Connect with Stevyn: LinkedIn: Stevyn Guinnip 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. May 27

    The Breadwinner’s Partner: Empowering Women Through Financial Trust with Bridget Grimes

    What does it cost to trust someone who publicly champions your success but privately limits it? In this episode, Anne Claessen speaks with Bridget Grimes, CFP and president of WealthChoice, a fee-only financial planning firm serving high-earning breadwinner women. After a decade in an industry that repeatedly asked her to shrink, Bridget’s perspective on trust is shaped by both the damage that experience caused and what she chose to construct afterward. Listen in as she shares what she learned about trust from both sides of professional betrayal. You’ll learn why stated values without supporting structures are not values at all, what intentional succession planning actually requires, and how the wrong firm became the reason she built the right one. What You’ll Learn: Why fiduciary responsibility and personal trust are not the same thing.The real cost of the gender pay gap in financial planning and advisory firms.How fee-only RIAs can build stronger advisor partnerships through clear expectations.What intentional succession planning looks like inside a family-owned firm.How structured communication helps Gen Z advisors transition into financial services.What women in finance need from firm leadership beyond stated support. Ideas Worth Sharing: "I think a client's only going to take the steps that you suggest if they really believe that you are trustworthy." - Bridget Grimes"Whoever your tribe is, you have to have this group of people." - Bridget Grimes"If you are surrounded by folks you trust, who you know are interested in sharing and helping each other succeed, then far more women will succeed in this industry." - Bridget Grimes About Bridget Grimes: Bridget Venus Grimes is a CFP Board Ambassador and founder of WealthChoice, a fee-only financial planning firm built around the financial lives of breadwinner women. She co-founded Equita Financial Network, a community and RIA platform designed to keep women-led advisory firms in the industry on their own terms. Her work as an advisor, speaker, and mentor is shaped by her own experience navigating financial discrimination and rebuilding professional trust from the ground up. Resources: WealthChoiceEquita Financial Network Connect with Bridget: LinkedIn: Bridget Venus Grimes, CFP® 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. May 13

    Radical Transparency: How Financial Advisors Can Build Team Trust and Reduce Turnover

    Most firms invest heavily in client relationships while quietly neglecting the internal ones. The result is predictable: talented people leave, institutional knowledge walks out the door, and the cost rarely shows up on a single line item. In this episode, Anne speaks with Zack Hubbard, Director of Financial Planning at Sargent Investment Group, an independent fee-only RIA based in Bethesda, Maryland. He has spent his career building financial planning teams from the ground up inside firms where the role didn't exist before he arrived. Tune in as Zack shares what he has learned about trust from both sides of the manager-employee relationship, including why direct feedback compounds over time, what makes a young hire genuinely bought in, and why routing criticism through a third party quietly destroys what took months to build. What You’ll Learn: Why financial advisory firms lose good employees they never meant to lose.The feedback structure that quietly predicts employee retention.What indirect feedback signals to the team members receiving it.How trust in a financial planning team moves from credentials to genuine loyalty.What a new hire's feedback quality reveals about their commitment.Why the honest hiring conversation most managers avoid is also the best retention tool.The cost of waiting for an annual review to say what needed saying months ago. Ideas Worth Sharing: "If you're not building that relationship with your employees the same way you think about your relationship with your clients, you're not going to keep them." - Zack Hubbard"The more trust you have with your employees, the more they will stick around and weather some hard times." - Zack Hubbard"If you can build that level of trust where they have an unwavering belief that it's going to work out, you can weather a lot." - Zack Hubbard About Zack Hubbard: Zack Hubbard, CFP®, is the Director of Financial Planning at Sargent Investment Group, an independent fee-only RIA based in Bethesda, Maryland. Before joining SIG, he built the centralized planning practice at Greenspring Advisors and developed its training program for incoming financial planners. He holds the CERTIFIED FINANCIAL PLANNER® designation and is an active member of NAPFA. Resources: Sargent Investment Group Connect with Zack: LinkedIn: Zack Hubbard 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.

    29 min

  5. Apr 29

    Trusting Yourself at the Bottom: Promises, Small Clients, and Long-Term Loyalty

    What holds a relationship together when outcomes are uncertain, mistakes are inevitable, and incentives begin to shift? In this episode, Anne speaks with Brett Danko, president of Danko Education and a financial advisor at Main Street Financial Solutions. Working in both financial education (where students place their future in his hands) and in advisory work (where clients do the same with their money), Brett has seen that trust grows through candor, responsibility, and relationship.  Tune in as Brett shares what he has learned about trust through the years, including the value of saying “I don’t know,” owning mistakes quickly, and treating people as more than transactions. As you listen, consider where trust in your own work depends less on being flawless and more on being transparent, steady, and willing to stick around when things get difficult. What You’ll Learn: Why saying “I don’t know” can build more trust than pretending certainty.How a spouse’s belief and a clear time boundary helped Brett bet on himself.The cost of treating early, “small” clients as disposable once you’ve grown.What broken business promises reveal about someone’s true reliability.How transparent communication can preserve trust in failure.Why many younger investors no longer trust traditional markets and what that signals.How real conversation, not online conflict, restores trust across differences. Ideas Worth Sharing: “In the end, it comes down to relationships, and I found that when people actually talk to one another, even from different viewpoints, they tend to understand one another.” - Brett Danko“When you’re working with clients, it’s all about trust. They have to know that you are a fiduciary. They have to know that you have their best interests at heart.” - Brett Danko“You can have a business that doesn’t work out, but yet the trust still remains because it’s about the longer-term relationship. That’s what really matters.” - Brett Danko About Brett Danko: Brett R. Danko, CFP® is the Founder and Managing Partner of Main Street Financial Solutions, LLC, where he actively advises clients on complex financial planning and investment issues. He also leads Danko Education, teaching CFP® Certification Education and exam prep courses nationwide, bringing real-world planner experience into the classroom. A graduate of the University of Pennsylvania, Brett grew up in Pittsburgh, PA and now lives in Newtown, PA with his wife and two children. Resources: Brett Danko | Danko EducationMain Street Financial Solutions Connect with Brett: LinkedIn: Brett Danko 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.

    39 min

  6. Apr 15

    Trust Under Pressure: Accountability in High-Stakes Relationships

    What does trust actually depend on when the stakes are high and something goes wrong? In this episode, Anne speaks with Eric Stein, partner at East Bay Investment Solutions, whose work sits inside one of the most trust-sensitive environments there is: investment decision-making. When advisors rely on your judgment to serve their clients, credibility is built in the details. Eric shares two stories from his career that reveal opposite sides of trust. One shows how taking full ownership after a major mistake actually strengthened trust. The other shows how unclear expectations and misaligned incentives slowly weakened it. As you listen, consider whether trust in your own work is being built by what you promise, or by what people experience when pressure arrives. What You’ll Learn: Why owning a mistake can build more trust than avoiding one.How people decide whether you are reliable under pressure.The cost of delayed communication in high-trust relationships.Why incentives can quietly weaken trust over time.How better expectation-setting prevents unnecessary friction.What strong handoffs require when relationships change.Why follow-through matters more than good intentions. Ideas Worth Sharing: “Trust is not only in what you say, but it’s in how you act and react to different things.” - Eric Stein“You want to certainly limit the number of mistakes you make, but if you do make them… let's make sure that we're accountable for them and how we fix them.” - Eric Stein“You need to trust that they're actually going to respond to you and that the relationship they have with you is as important as the relationship that we have with them.” - Eric Stein About Eric Stein: Eric Stein, CFA, is Partner and Senior Investment Strategist at East Bay Investment Solutions, where he serves as an outsourced Chief Investment Strategist for select financial advisory firms. With prior leadership roles at Goldman Sachs Asset Management and RSM U.S. Wealth Management, Eric brings deep experience across portfolio construction, risk analysis, asset allocation, and advisor support. He has been quoted in The Wall Street Journal and writes regularly on markets, due diligence, and investment strategy. Resources: East Bay Investment SolutionsServices & PricingSchedule an Intro CallJoin the Email ListLearn How East Bay Helps Connect with Eric: LinkedIn: Eric Stein 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

  7. Apr 1

    Trust Begins Where Assumptions End

    What actually earns trust: expertise or evidence of care? In a world full of information and increasing complexity, the real tension is not access to answers, but confidence in who is giving them. In this episode, Anne sits down with Eric Ludwig, a retirement income specialist, researcher, and advisor who operates at the intersection of practice and academia. His work centers on helping individuals deal with increasingly complex financial decisions with clarity and precision. At the core is a simple but often overlooked idea: trust is what makes information possible. Expertise alone is insufficient. It must be paired with care, curiosity, and the willingness to revise assumptions. In medicine or finance, specialization can help you feel more confident, but only if it is based on listening instead of being sure. Tune in to learn where trust in your own decisions comes from and whether it is rooted in credentials, care, or something deeper. What You’ll Learn: Why trust determines whether information is accepted or ignored.How specialization signals credibility in uncertain decisions.What happens when incentives shift from people to metrics.The cost of treating clients as accounts instead of relationships.Why asking better questions builds more trust than giving answers.How AI changes access to information but not the need for human trust.What distinguishes expertise from perceived expertise in practice. Ideas Worth Sharing: “Trust is… the oil in the process. If there's no trust… there's no way of really transferring information.” - Eric Ludwig“There's 252 different designations… How the heck do you know who to go to?” - Eric Ludwig“If you and I are client/advisor and there's no trust, it doesn't matter what either one of us has. The information isn't going to land.” - Eric Ludwig About Eric Ludwig: Eric T. Ludwig, PhD, CFP®, RICP®, is an associate professor of Retirement Income and Director of the RICP® program at The American College of Financial Services, where he also leads the Center for Retirement Income. He is the CEO of Stockbridge Private Wealth Management, bringing over a decade of advisory experience into his academic work. A nationally recognized researcher and speaker in behavioral finance and retirement planning, Eric focuses on helping individuals achieve long-term financial security through specialized, evidence-based advice. Resources: Professional Designations | FINRA.orgEricTLudwig.comThe Retirement Specialist BookThe Financial Insights ShowThe Influence of Risk, Financial Literacy, and Trust on Financial Advice-seeking Behavior in a Cross-racial Examination Connect with Eric: LinkedIn: Eric Ludwig 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

  8. Mar 18

    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
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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
    25
  • Rating
    Clean
  • Copyright
    © 2026 The Rise and Fall of Trust
  • Show Website
    The Rise and Fall of Trust