Inner Circle
← Back to Listen
Content

Ep 128. Can You Really Take a Vacation When You Own the Business?

⏱️ 1:00:39 🎀 Jason Lee, Jordan Upcavage, Chris
AUDIO EPISODE
Ep 128. Can You Really Take a Vacation When You Own the Business?
0:00
0:00

Chapters

Click to jump to section

  • 0:00
    Vacation Edition Intro
    Jason and Jordan introduce the 'Vacation Edition' of their podcast, setting the stage for discussions about taking time off as business owners.
  • 0:13
    Jordan's Mountain Adventure
    Jordan recounts his family's trip to the Tennessee mountains, including visits to Dollywood, Forbidden Caverns, and the Bush's Baked Bean Factory.
  • 23:39
    Jason's Beach Getaway
    Jason shares details of his family beach vacation in Sea Grove, Florida, highlighting fishing and crabbing experiences.
  • 52:07
    Business While Away
    The hosts discuss how their businesses function (or don't) while they are on vacation, comparing past struggles with current improvements in team and culture.
  • 57:27
    Team and Culture Changes
    Jordan elaborates on the positive changes in Skyfrog Landscape's culture, attributing improved vacation experiences to better hiring and employee fit.
  • 1:10:00
    Work Vacations & Trade Shows
    Jason describes his 'work vacation' at the Tree Florida conference, involving his kids in fundraising, and both hosts discuss upcoming industry trade shows.
  • 1:29:10
    Rookie Vacationer
    Jason playfully calls himself a 'rookie vacationer' compared to Jordan, highlighting the difficulty of truly disconnecting as a business owner.
  • 1:38:56
    No Clocking Out
    Jordan takes a work call during the podcast, illustrating the constant demands of business ownership, and discusses the inability to 'clock out' mentally.
  • 2:55:27
    Switchy AI Success
    Jordan shares an impressive story of how 'Switchy' (Live Switch AI) accurately diagnosed a problem with his boat motor.

Speakers

J
Jason Lee
Host
J
Jordan Upcavage
Host
C
Chris

Key Takeaways

✦

Prioritize building a strong team and positive company culture, as this is crucial for enabling owners to take vacations without business collapse.

✦

Be proactive in addressing problematic employees; 'hire slower and fire faster' to ensure your team aligns with your company values and goals.

✦

Implement systems and delegate responsibilities to trustworthy employees to minimize day-to-day interruptions while you're away.

✦

Utilize 'work vacations' strategically for networking and industry engagement, but ensure there's still personal time integrated.

✦

Invest in tools and technology that can assist with remote management and problem-solving, like AI, to maintain operations even when you're not physically present.

✦

Recognize that disconnecting entirely as a business owner is challenging, but strive for opportunities for strategic thinking and planning during downtime.

✦

Create clear communication channels and protocols for emergencies with your team so you know critical issues are being handled while you're out of office.

Want the full experience?

Join the Inner Circle for full access to every episode, AI-powered insights, personalized coaching, and a network of industry leaders.

Join Inner Circle β†’

Inner Circle Membership Portal © 2026 Power100. All rights reserved.

power100.io