The EntreLeadership Podcast

Episode: The Best Calls of 2025
Date: December 29, 2025
Host: Dave Ramsey
Description:
Dave Ramsey shares real-life business and leadership coaching moments from 2025, highlighting practical advice, tough-love leadership, and problem-solving for business owners in challenging situations.

Overview of Main Theme

This “Best Calls” episode features impactful listener calls from 2025, showcasing business and leadership challenges faced by real entrepreneurs. Dave Ramsey applies over 30 years of experience as CEO of Ramsey Solutions, providing unfiltered advice on debt management, profit sharing, explosive business growth, and family business succession. The episode centers on what it takes to lead with integrity, resilience, and clarity amid uncertainty and pressure.

Key Discussion Points & Insights

1. Rescuing a Debt-Ridden Remodeling Business (Matt, Lansing, MI)

(00:54–20:59)

• Matt, 24, owns a remodeling business with $260,000 in debt and liquidity problems.
  • Revenue: $150,000/year; 6 full-time employees.
  • Debt: $185,000 (bank loans, credit cards, trucks), $72,500 (vendors).
  • Buried by poor project estimating & using client deposits to float business.
• Dave’s Approach:
  • Dissects each project, emphasizing finishing what’s already started.
  • Advises prioritizing quick-turn, high-margin small jobs to generate fast cash.
  • Stresses job costing and not misusing future deposits.
  • Guidance on triaging creditors: payroll/trucks first, vendors next, banks last; credit cards at the bottom.
  • Emphasizes tough lessons, accountability, cash flow discipline, and picking the right pain.

Notable Quotes:

• “[Y]ou run these jobs as separate standalone businesses. They're separate P&Ls. Your job cost everything back to the job and you keep all the money in the job that's on the job until the job is done. And only then if there's money laying there, do we clear it and move it onto general fund.” (13:13) Dave Ramsey
• “I want you to kill rabbits, not elephants. I want you to turn stuff in two week turns and let's just start generating cash at 40% margin.” (11:33) Dave Ramsey
• "You have learned your lesson. You'll never do the misuse of the deposit again, right?" (13:09) Dave Ramsey
  “Absolutely not. Absolutely not.” (13:11) Matt
• “If you go make half a million dollars, that's 200 grand. 200 grand gets you out of this mess because you could clear your vendors and you can finish the 256 [job]. The bank is still going to be sitting there looking at you, but…that's a longer term issue.” (14:14) Dave Ramsey

2. Scaling Back Profit Sharing and Handling Entitlement (Mike, Philadelphia, PA)

(21:25–32:46)

• Mike leads a $15M industrial distribution company with a large veteran staff.
  • Company tradition: distributing all profits among staff and ownership yearly.
  • Economic shifts and tight margins lead to reduced profit sharing, causing backlash among long-tenured employees.
• Dave’s Approach:
  • Advises clarity—profit sharing should be tied directly to actual profits.
  • Urges firm boundaries: pushback and entitlement are unacceptable, even from longtime team members.
  • Stresses the importance of continuously communicating (and re-communicating) that profit sharing is a discretionary, not guaranteed, benefit.
  • Provides scripting and concrete steps to reset expectations at company meetings.

Notable Quotes:

• “If you ever do that again, I'll walk out. Is the last conversation I have with that person... You don't freaking threaten me. I own this. You are confused.” (25:05–25:24) Dave Ramsey
• “We are sharing what our family owns with you. We are not obligated to give it to you, but we have chosen as an act of kindness to share with the people that run the business with us.” (26:42) Dave Ramsey
• “When sales are down, we. We don't have an ice cream party. We only celebrate when sales are up. This is like adult stuff. It's not a freaking kindergarten. It's a business.” (28:40) Dave Ramsey
• “You are not due a thing. This is a gift. I am sharing some of my money with you. It's not your money. I want to reframe who owns it.” (30:01) Dave Ramsey

3. Taking the Leap from Side Hustle to Full-Time Construction (Isaac, Sacramento, CA)

(32:47–40:42)

• Isaac’s small residential construction company exploded from $70k to $3M in revenue in a single year.
  • Net profit projected at $350,000.
  • Balances a remote project manager job and fatherhood to a newborn; struggles with security concerns around benefits.
• Dave’s Approach:
  • Cuts through self-doubt: "You're a stud, man. Act like it."
  • Do the math: giving up a $110K salary when earning $350K+ makes the leap a "no-brainer."
  • The real risk: keeping the sales pipeline full, not personal capability or market potential.
  • Challenges limiting beliefs and celebrates Isaac’s wins.

Notable Quotes:

• “If you make 350k, it's officially not a side hustle.” (37:01) Dave Ramsey
• “All that matters is whether you believe in the future. And...I don't know why, how you could screw this up unless you just don't keep the pipeline full.” (36:57) Dave Ramsey
• “$3 million worth of people bet on Isaac. I don't even know you, but I know people don't give doofuses $3 million. Not much anyway.” (38:32) Dave Ramsey
• “Quit your stinking job and go to work and be a...business guy, man. You're that guy. Get her done.” (38:32) Dave Ramsey

4. Family Succession and Estate Planning (Todd, Portsmouth, NH)

(40:45–54:09)

• Todd seeks advice on transferring a $20M (est. value) family entertainment and lighting business to his daughter, while treating his other two children fairly.
  • Daughter actively works in the business; other children happy in separate careers.
  • Total family estate: $22M (business $10M; $12M in real estate/cash).
  • Raised issues: tax efficiency, ensuring fairness, preventing future sibling conflict, appropriate timeline for leadership hand-off.
• Dave’s Approach:
  • Clarifies estate tax thresholds: couple can transfer up to $28M tax-free (as of 2025), so sophisticated (IDGT, etc.) trusts aren't necessary at current value.
  • Importance of a clear trust/ownership structure; offers both his own family plan and other approaches.
  • Differentiates between leaving business only to those working in it vs. splitting equity among all children.
  • Urges honest, proactive family discussions to avoid resentment and future fiascos.
  • Leadership succession: gradually increase responsibility based on competence and readiness, not simply age or tenure.

Notable Quotes:

• “You run these jobs as separate standalone businesses. They're Separate P&Ls...and you keep all the money in the job...until the job is done.” (13:13) Dave Ramsey
• “There's not really a wrong decision except giving it to them too soon or too late. By not being proactive. There's not a wrong decision.” (50:10) Dave Ramsey
• “Thing one is if you give them something to run before they're competent, well, that hurts everybody, including them. And thing two is when they are competent, you don't give it to them.” (51:28) Dave Ramsey

Notable Quotes & Memorable Moments (with Timestamps)

| Timestamp | Quote | Speaker | | --- | --- | --- | | 13:13 | “You run these jobs as separate standalone businesses...you keep all the money in the job...until the job is done.” | Dave Ramsey | | 11:33 | “I want you to kill rabbits, not elephants. I want you to turn stuff in two week turns and let's just start generating cash at 40% margin.” | Dave Ramsey | | 25:05 | “If you ever do that again, I'll walk out. Is the last conversation I have with that person... You don't freaking threaten me. I own this. You are confused.” | Dave Ramsey | | 26:42 | “We are sharing what our family owns with you. We are not obligated to give it to you, but we have chosen as an act of kindness to share with the people that run the business with us.” | Dave Ramsey | | 37:01 | “If you make 350k, it's officially not a side hustle.” | Dave Ramsey | | 38:32 | “Quit your stinking job and go to work and be a...business guy, man. You're that guy. Get her done.” | Dave Ramsey | | 50:10 | “There's not really a wrong decision except giving it to them too soon or too late. By not being proactive. There's not a wrong decision.” | Dave Ramsey | | 51:28 | “Thing one is if you give them something to run before they're competent, well, that hurts everybody, including them. And thing two is when they are competent, you don't give it to them.” | Dave Ramsey |

Important Segments – Timestamps

• Debt Survival & Turnaround Tactics: 00:54–20:59
• Handling Profit Sharing & Company Culture: 21:25–32:46
• Choosing to Leave the Day Job: 32:47–40:42
• Family Business Succession Planning: 40:45–54:09

Tone & Style

Dave brings his signature blunt honesty, zero-BS realism, and a deep sense of encouragement and empowerment throughout the calls. He mixes hard truths (“You’re not owed profit sharing—this is a gift.”) with practical strategy (“Prioritize small, quick-turn jobs.”), and never fails to champion the courage and growth of each caller.

Summary Takeaways

• Leadership growth demands financial discipline, integrity, and a willingness to face hard truths.
• Overcoming past mistakes (like misusing client deposits) is possible with focus, prioritization, and learning.
• Company cultures must beware entitlement; profit sharing must be tied transparently to real business performance.
• Entrepreneurs facing explosive growth should not let fear or comfort prevent them from committing fully.
• Family business transitions require proactive, open planning—both for tax strategy and for legacy—and honest conversations with heirs.

For Listeners Who Missed The Episode

This “Best Calls of 2025” special is an essential listen for any business leader or entrepreneur. Dave Ramsey delivers raw, actionable coaching to real owners on real problems, illustrating leadership’s highest stakes: survival, legacy, and growth. The episode’s candid insights and memorable tough love offer a masterclass in practical leadership for turbulent times.