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EP 221: 2026 Predictions: Branding, Direct Booking & Personal Brands

Branded & Booked

Release Date: 12/16/2025

EP 224: What I Outgrew in 2025: Business Growth, Family-First Decisions, and Redefining Success as an Entrepreneur show art EP 224: What I Outgrew in 2025: Business Growth, Family-First Decisions, and Redefining Success as an Entrepreneur

Branded & Booked

This final episode of Branded and Booked is a year-end reflection on what I outgrew in 2025 and what I’m intentionally carrying into 2026. I talk about finishing a 12-cabin micro-resort and what it really feels like to build something big when the risk is real and personal. I share lessons from growing The Weber Co. and Hosted by the Webers, including getting clearer on alignment, pricing our expertise with confidence, and saying no to opportunities that don’t fit. A major theme of this episode is family-first decision making. I share how becoming more present with my kids reshaped my...

info_outline EP 223: We Built a 12-Cabin Micro Resort: Here’s What It Really Took show art EP 223: We Built a 12-Cabin Micro Resort: Here’s What It Really Took

Branded & Booked

It’s done. Cabins on the Cumberland is officially complete. In this episode, I’m sharing what it really took to build a 12-cabin micro resort with an event venue, game center, and year-round amenities — from construction milestones and financing lessons to direct bookings, full buyouts, and what’s next. We talk through: How the build unfolded over 2.5 years What I’d do differently with underwriting and reserves How we’ve maintained 30–50% direct bookings Why full property buyouts (weddings, retreats, church groups) are the future The unglamorous realities no one...

info_outline EP 222: Short-Term Rental Investing: What I’d Do Differently Now show art EP 222: Short-Term Rental Investing: What I’d Do Differently Now

Branded & Booked

If I were starting over in short-term rentals today, I wouldn’t rush into the first deal just to say I owned one — and I definitely wouldn’t invest where everyone else is telling you to. In this episode, I’m walking you through our real journey: buying our first STR, building a six-figure co-hosting business, and realizing pretty quickly what wasn’t the right long-term play for us. We talk about market selection, cash flow vs. equity, why I’d avoid certain oversaturated markets now, and what I wish I had understood sooner about renovations, contracts, and boundaries. If you’re in...

info_outline EP 221: 2026 Predictions: Branding, Direct Booking & Personal Brands show art EP 221: 2026 Predictions: Branding, Direct Booking & Personal Brands

Branded & Booked

2026 is not the year to play it safe — and it’s definitely not the year to keep relying on Airbnb alone. In this episode of Branded and Booked, I break down what I see coming next for short-term rentals, boutique hotels, micro-resorts, and the investors behind them — and why branding, direct strategy, and personal visibility are no longer optional. From platform changes and rising fees to the growing gap between checkbox amenities and truly curated guest experiences, this conversation is a wake-up call for hosts who want longevity, leverage, and real brand value. In this episode, we...

info_outline EP 220: 2025 Wrapped: Explosive Growth, Hard Truths, and Our Wild Plan for 2026 show art EP 220: 2025 Wrapped: Explosive Growth, Hard Truths, and Our Wild Plan for 2026

Branded & Booked

2025 has been one of the biggest years of growth I’ve ever had — across three hospitality businesses, inside my personal life, and in the direction I’m heading for 2026. I’m breaking down what worked, what stretched me, and what I’m changing moving forward. I walk through each business — The Weber Co., Hosted by the Webers, and Cabins on the Cumberland — and share the real numbers, the mindset shifts, the growing pains, and the wins. I also open up about the conversations Colin and I have been having about our boys, school, where we want to live, and why “camper life” is the...

info_outline EP 219: How We Drove $40K in Direct Bookings for Tremont Lodge Using an Integrated Marketing Strategy show art EP 219: How We Drove $40K in Direct Bookings for Tremont Lodge Using an Integrated Marketing Strategy

Branded & Booked

In this bite-sized solo episode, I’m breaking down the insane results we’ve helped our client, Tremont Lodge, achieve since partnering in spring 2025. From stock photos and low engagement to over $40,000 in tracked direct bookings, you’ll hear exactly how an integrated marketing strategy — blending social media, email, influencer collaborations, and automation — completely transformed their results. I’ll walk you through the story from the very beginning: where Tremont was when they came to us, the first steps we took to revamp their brand presence, and how each piece of the...

info_outline EP 218: How Strategy-Driven Interiors Are Winning in Today’s STR Market with Jordan from Somerled Designs show art EP 218: How Strategy-Driven Interiors Are Winning in Today’s STR Market with Jordan from Somerled Designs

Branded & Booked

Three years ago, it was enough for your Airbnb to have cute décor and a decent location. Today? The game has changed. In this episode, Steph sits down with Jordan, co-founder of Somerled Designs, to talk about what it really takes to compete in the 2025 short-term rental market. You’ll learn how Somerled has scaled from a college-friend side hustle to 50+ design projects per month, why they pair market research with creative interiors, and how their signature approach—“where strategy meets design”—helps investors turn underperforming listings into high-return assets. Whether...

info_outline Ep 217: What 5 STR Owners Changed in Their Marketing—And the Direct Booking Results They Saw show art Ep 217: What 5 STR Owners Changed in Their Marketing—And the Direct Booking Results They Saw

Branded & Booked

You don’t have to stay stuck on the OTA hamster wheel. 👏 In this episode, I’m pulling back the curtain on real short-term rental owners who decided enough was enough—and took control of their marketing. You’ll hear from five amazing hosts who implemented the exact strategies I teach inside and saw direct booking results they didn’t think were possible: ✨ Kathleen in the Poconos, who clarified her guest avatar (big groups celebrating milestones) and used content pillars to launch a direct booking site. ✨ April in Lake Tahoe, who leaned into lifestyle photography and a...

info_outline EP 216: Are direct bookings just a trend? show art EP 216: Are direct bookings just a trend?

Branded & Booked

Don’t forget — kicks off today (Sept 23–25)! It’s a free 3-day workshop where I’ll walk you through how to rely less on OTAs and build a marketing system that works. Save your seat (or catch the replays if you can’t make it live). 👉  Are direct bookings just a trend… or the future of your short-term rental business? In this episode of Branded and Booked, I’m diving into one of the most important conversations I’ve had with STR hosts over the last two years: should you go all in on a direct booking strategy, and if so, when? Airbnb isn’t going anywhere, but the...

info_outline EP 215: The 3 C’s of Social Media Strategy for Short-Term Rentals show art EP 215: The 3 C’s of Social Media Strategy for Short-Term Rentals

Branded & Booked

If you’ve ever wondered how to make social media actually work for your short-term rental, boutique hotel, or micro resort—this episode is for you. I'm breaking down my 3 C’s of Marketing on Social Media Strategy that I've been teaching since 2020. These tried-and-true pillars have helped businesses across industries grow their brands, book more clients, and build genuine connections. In this episode, you’ll learn: How to develop a content strategy rooted in your brand stories and guest experience. Why conversations (and engagement funnels like ManyChat) are essential to boost...

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More Episodes

2026 is not the year to play it safe — and it’s definitely not the year to keep relying on Airbnb alone.

In this episode of Branded and Booked, I break down what I see coming next for short-term rentals, boutique hotels, micro-resorts, and the investors behind them — and why branding, direct strategy, and personal visibility are no longer optional.

From platform changes and rising fees to the growing gap between checkbox amenities and truly curated guest experiences, this conversation is a wake-up call for hosts who want longevity, leverage, and real brand value.

In this episode, we cover:

  • Why more investors are shifting away from single-family STRs and toward boutique hotels, micro-resorts, and larger experiential projects

  • The real cost of relying solely on Airbnb — and why 2026 is the year direct booking strategies become essential

  • Why design alone isn’t enough (and what real brand strategy actually includes)

  • How brand clarity directly impacts the guests you attract — and the problems you avoid

  • The rise of personal branding for hosts, operators, and real estate investors with bigger visions

  • What it actually looks like to leverage your personal brand to attract partners, clients, and opportunities

  • Why the guest experience gap is widening — and how curated rituals, storytelling, and intentional touchpoints win

  • The evolution of influencer marketing (no more random trades, ever)

  • Why hospitality brands are becoming media brands — and how content now drives demand

  • How strong branding and marketing directly increase the exit value of your properties

Connect with me:
📸 @theweberco
🌐 theweberco.com