Builders of Authority

This is what Serial Entrepreneurship ACTUALLY Looks Like | Jen Dempsey-Blakely

Adam McChesney Episode 203

In this episode of the Builders of Authority Podcast, I sit down with Jennifer Dempsey-Blakely to talk about building authority while running multiple businesses across hospitality, short-term rentals, and experiential brands.

Jennifer is a lifelong entrepreneur and Hazelwood Central graduate who built her education through hands-on experience, conventions, and continuous learning. With 30 years in management and merchandising at Marshalls, a decade running a commercial cleaning company, and extensive experience in short-term rentals, she and her husband Shane combined their expertise to create The Landing Hub, a unique hospitality concept that blends the best of hotels, Airbnbs, and large group travel.

Designed for independent travelers, families, and groups, The Landing Hub was built to be a clean, safe, and community-focused space where guests can connect, relax, and truly feel at home.

What we cover in this episode:

  • Running multiple businesses without chaos
  • Dividing responsibilities and staying in your lane
  • Branding unique experiences people talk about
  • Why community beats traditional marketing
  • Building businesses that do not fit into one box
  • Knowing when to jump on opportunities and when to wait
  • Delegation, systems, and freeing up mental bandwidth
  • Long-term authority versus short-term tactics

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