The EntreLeadership Podcast

Host: Dave Ramsey, Ramsey Network

Episode: My Uncle Was Stealing From Our Business for Years

Date: October 27, 2025

Episode Overview

This episode of The EntreLeadership Podcast, hosted by Dave Ramsey, centers on the real-world complexities of family businesses, integrity at work, leadership transitions, and setting culture within organizations. Calls from business leaders explore tough decisions, such as handling theft by a family member, fostering company culture in large, distributed organizations, and leading across generational divides. Dave delivers his signature direct, no-nonsense business advice, laced with empathy and humor.

Key Discussion Points & Insights

1. Navigating Family Business Dilemmas: Dealing with Theft by a Relative

Caller: Lee, North Dakota
(00:55-15:12)

• Background: Lee, transitioning 4th generation owner of a $4M/year service business, inherited difficult consequences from his father's leadership decisions, notably rehiring an uncle (by marriage) after years of theft.
• Lee’s Dilemma: Struggles to trust the uncle, who is a visible company figure and is facing lifelong medical challenges.
• Options Discussed:
  • Forgive & Move On: Dave stresses the personal, internal decision: “One is get over yourself and forgive him. If he's not stealing anymore, and it was five years ago, it's in the rearview mirror.” (04:01)
  • Terminate Compassionately: Alternatively, Lee can choose to part ways: “Or fire him... and here's some severance pay and you're on your way, dude. And you know, you can be kind and a little bit more flamboyant about it than that…” (04:39)
• Revelation: The Thief is Family:
  When Lee reveals the relative is his uncle, not by blood but by marriage, Dave reassesses the emotional complexity:
  “Well, that's different information. Okay… There are two options... Can I gracefully help him exit and take care of him...” (05:58, 07:43)
• Comprehensive Context:
  • 30-year employee, 60-ish, serious medical needs
  • Theft was “skimming off the till... repeatedly in small amounts” (07:27)
• The ‘Price of Admission’ for Family Business:
  • Dave reiterates: “You get all the benefit of the wonderful story of being fourth generation and you get all the downside of being fourth generation. And this is one of [those situations].” (12:42)
• Recommended Approach:
  • Generosity with Severance/Retirement: “When in doubt, I up it… You’ve got a lot of reasons to be crazy generous.” (09:42)
  • Initiate Retirement Conversation: Suggests framing the exit as a retirement, possibly with two to three years’ pay, for dignity and closure. (13:20)
  • Leadership Lesson: “There’s a lot of days when leadership has to… have the shovel out with the manure and nobody else shovels but leaders.” (14:41)
• Final Thought: Clean up problems in your tenure so you don’t hand off a mess:
  “Note to the generation before: if you clean the stable, you don’t have to ask your kids to do it when you hand it off next.” (15:05)

Notable Quotes

• Dave Ramsey:
  “You would not hire this guy in a million years if he wasn't already working there.” (11:19)
• Dave Ramsey:
  “The price of admission to be me is I got to deal with this uncle.” (13:01)

2. Building Company Culture at Scale & Across Locations

Caller: Natalie, NY
(16:58-24:39)

• Background: Chief of Staff at a large multi-regional non-profit organization. Impressed by Ramsey Solutions’ unified culture, seeks advice to build similar cohesion despite not starting early and being spread out.
• Dave’s Strategy for Culture-Building:
  • “It’s a Herculean task... but it’s going to be worth the trouble to get there.” (18:48)
  • Start with core leadership (top 100–200), define honest, actual core values (“not what we wish they are”), and incrementally cascade through the organization.
  • Use “hydrostatic pressure” analogy: steady, incremental build-up will eventually break through and create change. (19:55)
  • Emphasizes learning from both your company and outside examples (e.g. Alan Mulally at Ford): Core principle—“If you want to be a ‘we,’ you have to align with these core values.” (20:46-22:46)
  • Warns against “aspirational values”—focus on what you actually ARE when at your best, not what you wish to be. (23:24)
• Practical Steps:
  • Workshops with leadership, iterative value refinement (“It’s actually a pretty emotional exercise.” (24:10))
  • Embed values into hiring, onboarding, and regular conversations.
  • Anticipate a 5-year timeline for significant culture transformation.

Notable Quotes

• Dave Ramsey:
  “If you’re going to work here, you’re going to be a ‘we.’” (20:46)
• Dave Ramsey:
  “People just want to know where they stand. They don’t want to be coddled.” (38:54)

3. Multi-Generational Teams: Leadership through Clarity and Consistency

Listener Question: Austin, NC
(24:50-38:54)

• Context: How to lead teams spanning multiple generations, respecting different “expectations about work, communication, and leadership.”
• Dave’s Response:
  • “Their expectations... are not a concern. That’s a nice way of saying, I don’t care what their expectations about those things are. What I care about... is what your expectations are.” (24:50)
  • Core values and clarity beat coddling or accommodating generational quirks. Use strengths of each generation for project-specific value, but maintain uniform standards for culture and execution.
  • Leaders should set expectations and be unwavering in upholding them—regardless of age differences.

Notable Quotes

• Dave Ramsey:
  “Bosses push, leaders pull. Leader’s job is to serve.” (26:09)
• Dave Ramsey:
  “Otherwise you’re running a freaking beauty parlor and you’re having to treat the blondes different than the redheads... You cannot figure this out.” (29:42)
• Dave Ramsey:
  “People just want to know where they stand. They don’t want to be coddled… You don’t fit in here, you’re not a ‘we’ if you want to be coddled.” (38:54)

4. Practical Business Finance: Managing Savings/Retained Earnings

Caller: Alex, Birmingham
(41:46-48:12)

• Background: Small business owner, 25 employees, $6–9M revenue, $3M “savings” and $1M “emergency fund,” wants to ensure solid financial strategy for idle funds.
• Dave’s Advice:
  • Emergency fund remains in high-yield savings (~4%+).
  • Retained earnings ($3M) should not be making just 2% ($60K a year): “There’s nothing that should have made 2%. Crap. You could have got that on a high-yield savings account.” (44:59)
  • Recommends conservative growth stock mutual funds (e.g., S&P 500 index), citing better historical returns for business retained earnings that aren’t needed immediately.
  • Encourage learning the basics, comparing current advisors with a Ramsey SmartVestor Pro, and not abdicating financial understanding.

Notable Quotes

• Dave Ramsey:
  “Don’t ever... Close your eyes and trust that they’re driving the car well. Don’t ever do that again. You want to know what’s going on.” (47:40)

Memorable Moments & Language

• Dave’s Signature Tone: Forthright, sometimes blunt, often leavened by humor (“micro-barbecued microwave... that’s not the sign of a good barbecue!” (30:58)).
• Compassion & Realism: Encourages generosity but stays pragmatic about business needs and boundaries.
• Leadership Truths: Consistently highlights that hard, sometimes unpleasant conversations are intrinsic to good leadership (“That’s one of the days when leadership sucks.” (14:41))

Summary Table of Notable Quotes & Timestamps

| Timestamp | Speaker | Quote | |-----------|--------------|----------------------------------------------------------------------------------------| | 04:01 | Dave Ramsey | “One is get over yourself and forgive him. If he's not stealing anymore... forgive him.” | | 11:19 | Dave Ramsey | “You would not hire this guy in a million years if he wasn't already working there.” | | 13:01 | Dave Ramsey | “The price of admission to be me is I got to deal with this uncle.” | | 18:48 | Dave Ramsey | “It’s a Herculean task... but it’s going to be worth the trouble to get there.” | | 20:46 | Dave Ramsey | “If you’re going to work here, you’re going to be a ‘we.’” | | 29:42 | Dave Ramsey | “Otherwise you’re running a freaking beauty parlor... You cannot figure this out.” | | 38:54 | Dave Ramsey | “People just want to know where they stand. They don’t want to be coddled.” | | 44:59 | Dave Ramsey | “There’s nothing that should have made 2%. Crap. You could have got that on a high yield savings account.” | | 47:40 | Dave Ramsey | “Don’t ever... Close your eyes and trust that they’re driving the car well. Don’t ever do that again.” |

Timestamps for Important Segments

• Lee’s Family Business Dilemma: 00:55–15:12
• Building Company Culture at Scale: 16:58–24:39
• Leading Across Generations: 24:50–38:54
• Financial Management of Retained Earnings: 41:46–48:12

Final Leadership Takeaways

• Leadership requires balancing compassion with clarity and accountability—even (especially) in family businesses.
• Culture is shaped by living out real values, not aspirational ones, and develops through relentless, patient, top-down effort.
• Lead with consistency, set clear standards, and leverage generational strengths—but don’t let shifting expectations dictate your core culture.
• Financial stewardship is a leadership responsibility—understand where your money is parked, and don’t shy from seeking better returns.

“Better a weary warrior than a quivering critic. This world needs more high quality leaders, so take courage and lead.” – Dave Ramsey (closing)

End of summary.