EP 226: How Personal Branding Drives Trust, Bookings, and Growth in Hospitality

In this episode, I'm talking honestly about wealth, real estate, and the parts of the journey that usually get left out online. The "we went from nothing to millions" stories can make it feel like you're behind, when in reality, a lot of those results were shaped by timing, market conditions, and decisions that can't be duplicated today. Colin and I walk through our actual financial path, from student loan debt and modest incomes to buying and selling homes, paying off debt, and building equity in ways we never could have predicted. I share what worked, what I would do differently, and why I'm much more cautious about short-term rentals in today's market, with more focus now on long-term strategy, boutique hotels, and micro-resorts. We also talk through our upcoming camper life decision and what that really looks like financially. This is all about intentional choices, clear boundaries, and understanding risk. If you've ever questioned your progress or felt behind because of what you see online, this episode is meant to bring perspective, not pressure. Connect with me: 📸 @theweberco 🌐 theweberco.com

In this episode, I'm breaking down the real ROI of marketing for boutique hotels, micro resorts, and short-term rental owners, and I'm doing it with actual numbers, not fluffy marketing talk. One of the biggest questions I hear from owners is, "What's my ROI on marketing?" And the truth is, most hospitality businesses are looking at marketing the wrong way. It's not an expense you justify month to month. It's an income-producing asset that impacts revenue, margins, and the long-term value of the business you're building. I walk through a realistic boutique hotel example and show how marketing assets like branding, email marketing, social media, and a direct booking ecosystem can conservatively add around $300,000 per year in revenue, and potentially $800K to $1M in valuation when it comes time to sell. No unicorn assumptions. No perfect markets. Just simple math and strategy that most owners are (unfortunately) not leveraging. We talk about what marketing assets actually are, why relying solely on OTAs leaves you with no leverage, and how things like pricing power, owned demand, and direct bookings give you more control over your business. I also break down why social media is not just about visibility, but credibility and conversion, and why an email list is one of the most overlooked assets in hospitality. This episode also covers what to realistically expect from a marketing agency, how to evaluate ROI beyond just "new bookings," and why sometimes the biggest win is reclaiming profit you're currently giving away in OTA fees. If you're building a boutique hotel, micro resort, STR portfolio, or even a single high-performing property and you care about long-term growth, cash flow, and exit value, this conversation will help you rethink how marketing fits into the bigger picture of your business. Connect with me: 📸 @theweberco 🌐 theweberco.com

In this episode, I'm diving into why personal branding in 2026 is no longer optional, especially if you're in boutique hospitality. If you're building short-term rentals, a co-hosting or property management business, a boutique hotel, or a micro resort, your personal brand is becoming one of the biggest drivers of trust, connection, and bookings. We talk through what a personal brand actually is (and how it's different from your property or business brand), why people connect to people (not logos), and how personal story builds trust long before a booking ever happens. I share real examples from my own journey building The Weber Co. and Cabins on the Cumberland, including how showing up online consistently helped us find partners, grow our audience, and create deeper loyalty with guests. I also break down what I've observed from brands in the hospitality space that are doing this well, why we're in a trust recession, and how human connection is becoming a major differentiator in a crowded market. This episode is for anyone who feels hesitant about showing up online, unsure what to share, or worried about blending personal and business in a way that still feels aligned. If you want to grow bookings, attract the right guests or owners, and build something that lasts beyond algorithms and trends, this conversation will help you rethink how your personal brand fits into the bigger picture. Connect with me: 📸 @theweberco 🌐 theweberco.com

We're kicking off 2026 with a decision that has nothing to do with quarterly goals and everything to do with the kind of life we want to live. In this episode, I'm pulling back the curtain on why our family is planning a full year of camper life — how the idea started, what finally pushed us to commit, and why this felt like a now-or-never moment. I share a glimpse into the planning process, the routes we're dreaming about, and the realities of doing this with two kids, two businesses, and a lot of unknowns. I also talk honestly about the tension that comes with choosing something outside the "normal" path — especially when your decisions shape your kids' childhoods. The excitement, the fear, the opinions, and the very real questions that come up when you step away from routine in pursuit of more freedom, flexibility, and presence. This episode isn't about RV hacks or minimalism. It's about lifestyle design, making bold choices before life makes them for you, and asking the hard question: why are we working so hard if we're not actually living the life we want? If you've ever felt that itch for something different — this one's for you. Connect with me: 📸 @theweberco🌐 theweberco.com

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 goals, my pace, and even who I look to as role models. I'm still ambitious — but I'm no longer chasing growth that competes with the life we want. I also reflect on what I deprioritized this year, including my health and marriage, and what I'm recommitting to moving forward. This episode is about choosing alignment over comparison, staying rooted in your own definition of success, and giving yourself permission to celebrate how far you've come. If you're closing out the year questioning what still fits and what you're ready to release, this episode will resonate. Connect with me: 📸 @theweberco🌐 theweberco.com

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 posts about — dead season, cash flow, and learning as you go This is a raw, behind-the-scenes look at building a destination property — not just something that looks good online, but something designed to last. If you're building, scaling, or dreaming about a micro resort or event-driven STR, this episode will give you real context, not theory. Connect with me: 📸 @theweberco 🌐 theweberco.com

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 the "should we buy?" or "what's our next move?" phase — or you're thinking bigger than single-family STRs — this episode will help you slow down and make smarter, more intentional decisions. We cover: The investing choices I'd change if I started over Why market selection matters more than ever Cash flow vs. long-term equity (and how I think about it now) What co-hosting actually looks like behind the scenes Why we're focused on micro resorts and boutique hotels moving forward Connect with me: 📸 @theweberco 🌐 theweberco.com

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

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 plan for next year. If you're building something big, navigating pivots, or trying to figure out how to scale without losing yourself in the process… this one's for you. Connect with me: 📸 @theweberco🌐 theweberco.com  If this episode was helpful, I'd love you to leave a 5-star review and share it with another business owner who's ready to take control of their business and bookings.

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 strategy now works together to drive measurable growth. What You'll Learn How we turned uninspired, stock-driven content into a story-driven brand experience that connects The 3 C's we use with every client: Content, Conversations, and Collaborations The power of ManyChat funnels and promo codes for tracking real ROI on organic content How influencer partnerships drove more than $16K in direct bookings — and how to choose the right creators for your season Why timing matters for influencer stays and how to shift focus in slower seasons Ways to integrate organic, paid, and email marketing so they all amplify one another Key Takeaways If you're a boutique hotel, short-term rental, or small business wondering how to actually track what's working in your organic marketing — this episode gives you the blueprint. From codes to lead funnels, I'll show you exactly how to build a strategy that drives bookings, builds your list, and grows your brand all year long. Connect with me: 📸 @theweberco 🌐 theweberco.com  If this episode was helpful, I'd love you to leave a 5-star review and share it with another business owner who's ready to take control of their business and bookings.