The EntreLeadership Podcast

Episode: "My Employees Keep Wanting More Time Off (Bad Sign?)"

Host: Dave Ramsey, Ramsey Network
Date: September 29, 2025

Episode Overview

In this episode, Dave Ramsey hosts a wide-ranging Q&A with small business owners tackling critical leadership challenges. The main focus kicks off with managing employee time-off expectations in a post-COVID culture, especially in small businesses where operational coverage is crucial. Additional segments include advice on timing and strategy when selling a successful business, handling disengaged team members, and systems for scaling up an e-commerce venture. Throughout, Dave infuses tough love, clear policy recommendations, and hard-earned wisdom from his decades leading Ramsey Solutions.

Segment Breakdown & Key Insights

1. Navigating PTO Expectations in Small Businesses

(00:50 - 10:27)
Caller: Denise from Philadelphia

• Denise’s Situation:

  • Husband-and-wife pest control company, grown from 2 to 13 employees, $2.3M revenue.
  • PTO policy: 5 days after one year, increasing with tenure.
  • Facing pressure from younger employees to allow unpaid time off beyond allotted PTO.
  • Employees are burning through PTO early in the year and expecting additional unpaid time off for non-emergencies.

• Dave’s Advice:

  • Draws the line against casual unpaid time off: “I hired you to get a job done. If you don’t get the job done, I don’t need you.” (04:00)
  • Strict policy: Only unpaid leave for medical emergencies, not leisure.
  • Highlights organizational impact: If many employees did this, essential work wouldn’t get done.
  • Importance of upfront communication: “We do a better job at onboarding explaining this is not gonna happen. So before it even comes up...we’re saying, OK, here's how we do things. We do not do unpaid time off.” (08:01)
  • Use difficult conversations and enforce consequences to uphold culture and standards.

• Notable Quotes:

  • “This is grown up time now. You’re no longer in high school, you no longer get summers off. Your mommy isn’t doing your laundry anymore. And you’re now a grown up. So it's time to do that. Time to step up.” — Dave Ramsey (09:25)
  • “If you have a crisis, we’re probably gonna give you what we call grace period... You just want to go on a hike? Sorry, it’s not an option.” — Dave Ramsey (08:01)

Memorable Moment:
Denise and Dave commiserate on shifting generational expectations, with a humorous exchange about the rise of paternity leave and the “old-school” attitude toward work.

2. When Is the Right Time to Sell My Business?

(12:55 - 20:40)
Caller: Savannah from Baltimore

• Savannah’s Situation:

  • Spa owner, 18 years, thriving post-COVID.
  • Business is maxing out profitably ($2.5M revenue, $800K+ net).
  • Now semi-absentee, working 4–6 hours/week, strong delegatable team.
  • Considers selling but is unsure whether to cash in now or keep reaping high profits.

• Dave’s Insights:

  • Urges against premature sale solely out of fear or “timing the market.”
  • “Let’s fast forward a year and a half. You’re putting a million dollars a year in your pocket. Why would you sell it?” (16:10)
  • Suggests selling only if work becomes unenjoyable or a truly attractive offer arises (high multiplier, $5M+).
  • Dispels fear of “missing the top” — the business is worthwhile as long as it continues providing satisfaction and strong income.

• Notable Quotes:

  • “There’s no universal wisdom that says you got to get out just because you’re on top.” — Dave Ramsey (16:55)
  • “This idea that everything should be built so that it can be sold and I can maximize my profits at the top is a very utilitarian view of business, and it doesn’t have much soul.” — Dave Ramsey (20:20)

Memorable Moment:
Dave celebrates Savannah’s success: “I’m proud of you. Well done.” (19:59)

3. Confronting Disengaged Employees (“Quiet Quitting”)

(20:40 - 31:37)
Q&A from Tanya in California

• Situation:

  • Tanya suspects a team member has checked out, doing only the basics.
  • Unsure how to address the issue without seeming petty.

• Dave’s Approach:

  • Engagement and initiative are non-negotiable cultural values; minimum effort isn’t enough.
  • Immediate, direct “difficult conversation” to surface issues, with openness to underlying causes (personal struggles, etc.).
  • Makes it clear: “If your spirit leaves the building, you should take your body with it or I’ll help you.” (23:30)
  • Do not tolerate disengagement, or it will infect company culture.

• Notable Quotes:

  • “No one wants to work with people who are mailing it in... If you’re excellent at your job, but you work with a doofus who’s mailing it in, then you don’t... your team doesn’t look good.” — Dave Ramsey (25:40)
  • “When you tolerate someone checking out... you are tolerating lack of productivity, lack of care... and it will spread through your organization.” — Dave Ramsey (27:07)

Memorable Moment:
Dave recounts confronting an employee who rolled her eyes during a staff meeting—emphasizing a leader’s obligation to address disengagement head-on.

4. Scaling an E-commerce Side Hustle: From Treadmill Operator to Pathfinder

(31:37 - 39:55)
Caller: Scott from Houston, TX

• Scott’s Situation:

  • Side e-commerce business ($1M sales, $170K projected profit), plus day job.
  • Operates with two virtual assistants; wants to hire an inventory manager.
  • Uncertain about how to split profits between personal pay, new hires, and retained earnings.

• Dave’s Playbook:

  • Systematically build retained earnings (suggests 10–20% profit set aside).
  • Hire for the right reasons and train meticulously: “They’re not going to produce any results that you wouldn’t have produced by yourself in the first six months, because you’re going to be sitting in their lap anyway.” (37:00)
  • Consider incentivizing growth (e.g., $20K bonus if sales hit $1.5M).
  • Path to growth: one solid hire at a time, build outwards, don’t relinquish control prematurely.

• Notable Quotes:

  • “You can delegate to someone easily when you trust their competency and their integrity. And the only way a sane person can trust someone’s competency and integrity is by hanging out with them and observing them.” — Dave Ramsey (37:49)
  • “Go from owning a job to owning a business, right?” — Scott (39:31)
    “That’s the one, man. That’s the one.” — Dave Ramsey (39:33)

Notable Quotes Recap

• “I hired you to get a job done. If you don’t get the job done, I don’t need you.” (04:00, Dave Ramsey)
• “This is grown up time now. You no longer get summers off.” (09:25, Dave Ramsey)
• “Let’s fast forward a year and a half. You’re putting a million dollars a year in your pocket. Why would you sell it?” (16:10, Dave Ramsey)
• “If your spirit leaves the building, you should take your body with it or I’ll help you.” (23:30, Dave Ramsey)
• “Go from owning a job to owning a business, right? ... That’s the one, man.” (39:31–39:33, Scott & Dave)

Key Takeaways

• Set Clear Boundaries: PTO and work attendance policies must be clearly stated, enforced, and communicated both in writing and verbally.
• Hold Firm on Culture: Leaders have both the right and obligation to address disengagement and quiet quitting — it’s not nitpicking.
• Sell Only for the Right Reasons: Don’t feel pressure to sell a thriving business unless you want to, or the offer significantly outweighs ongoing value.
• Systems Fuel Growth: Building retained earnings and extensively training hires form the foundation to transition from “operator” to business owner.
• Leadership Requires Difficult Conversations: Enforcing standards, even when uncomfortable, is crucial to maintaining team performance and company health.

Useful Episode for:

• Small business owners struggling with PTO requests post-COVID
• Leaders worried about disengaged staff
• Entrepreneurs debating selling at a perceived "peak"
• Operators wanting to scale from solo act to sustainable business