Radical Hospitality Show

How Storytelling Builds Boutique Hotel Brands That Last with Steph Weber

In this episode, Zeke Freeman sits down with Steph Weber, a branding and marketing leader in the short-term rental, boutique hotel, and micro resort space. Steph shares the origin story behind her move from fashion and influencer marketing into hospitality, and why story-led branding is no longer optional as platforms shift and competition tightens.

They unpack what “owning your brand” really means for STR and boutique operators, how to build a brand before construction is even finished, and why strong marketing systems (email lists, content, direct bookings) become part of the business asset itself, especially when it’s time to exit.

What you’ll learn

  • How Steph went from fashion branding and influencer work to hospitality investing and development
  • Why storytelling is the competitive edge in modern STR and boutique hotels
  • The difference between “good design” and a stay that creates emotion (and loyalty)
  • How to define a target guest profile that guides everything from amenities to messaging
  • What it looks like to market a property while it’s still under construction
  • Why relying on OTAs alone can cost you loyalty, margin, and long-term business value
  • The real-world journey of building Cabins on the Cumberland: partnerships, financing, surprises, and lessons learned
  • How to think about event venues, capacity, and the economics of full-property buyouts


Connect with Steph Weber:

Website: theweberco.com

Instagram : @theweberco

Connect with Zeke Freeman:
Instagram: @zekefreeman_rootarchitecture and @rootarchitecture
YouTube: @rootarchitecture
Facebook: @RootArchitectureandDevelopment
LinkedIn: Zeke Freeman
X/Twitter: @zfreemanroot

Ready to get started with your hospitality project?
https://root-ad.com/

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