What truly sets apart a vacation rental that’s always booked from one that simply gets browsed? In this episode, I’m sitting down with industry veteran Kiera McGrath, a real estate investor and marketing expert who was filling calendars long before Airbnb even existed.

We talk about:

1. Kiera’s signature framework for diving into the mindsets and motivations of your ideal traveler.
2. Why trading generic descriptions for emotional, sensory language is the key to resonating on a deeper level.
3. How to analyze your feedback (and your competitors') to uncover the unique value gaps in your market.
4. Why the "vibe" between your photos and your words is the silent deal-breaker for most guests.

But this isn’t just about marketing tricks. It’s about becoming a master of the guest experience. Kiera pulls back the curtain on how to bridge the gap between a generic house and a sought-after brand. You’ll hear why managing expectations and crafting personal touches before a guest arrives is the secret to scaling a rental business that guests actually rave about.

If you’ve ever felt like your property is just a commodity in a crowded sea of listings, this conversation will give you the blueprint to stand out. Get ready to stop hoping for bookings and start engineering them, evolving from a passive host into a strategic market leader.

HIGHLIGHTS AND KEY POINTS:

[00:51] A short introduction about our guest Kiera McGrath, and how she got started in the short-term rental industry

[05:29] Kiera shares her methodology for turning lookers into bookers by applying guest psychology, neuroscience, and deep guest–listing alignment

[09:18] Kiera’s perspective on attracting broad audiences through shared emotional triggers rather than marketing to everyone

[11:13] Kiera’s framework for turning guest emotions into bookings through data, reviews, and booking psychology

[15:20] Kiera’s perspective on using sensory language, mental imagery, and guest fears to strengthen booking psychology

[17:52] Kiera dives into the nuts and bolts of booking psychology, emphasizing that understanding a guest’s mindset involves both logic and emotion

[22:55] Kiera’s approach to listing precision through careful language, proofreading, and attention to detail

[25:14] Kiera’s approach to crafting exceptional guest experiences across the entire journey from booking to post-stay

[28:54] The importance of setting realistic expectations to prevent negative experiences and reviews

[32:43] Kiera stresses the importance of ensuring that the guest experience aligns with expectations set by the listing, even when elements outside the property

[34:45] Kiera’s strategy for leveraging competitor reviews to identify market gaps while staying true to guest demographics

[41:23] Kiera’s perspective on resisting one-size-fits-all strategies and focusing on unique listing value

[43:44] The lightning round

Golden Nuggets:

1. “Guests make booking decisions using both sides of their brain, so both logic and...

Have you ever felt trapped in the whirlwind of your own business, wishing it could run itself so you could finally breathe, and maybe even enjoy a family dinner? That’s not just a dream. That’s a system at work.

In this episode, I’m joined by the powerhouse Marisa Grover—a mom of two toddlers who manages over 50 properties and has mastered the art of the "enough is enough" pivot.

We talk about:

1. How Marisa went from "accidental" host to a systems-driven entrepreneur managing 50+ units
2. The raw reality of handling guest requests while literally in labor (the spark that changed everything)
3. The "Progress over Perfection" method—why a Loom video or a notebook is better than a perfect manual

But this isn't just about automation. It’s about reclaiming your humanity.

Marisa pulls back the curtain on the grit required to scale, from navigating licensing hurdles to building a team aligned with your values rather than just their resume. You’ll hear why letting go isn't a loss of control—it’s the key to leading, creating, and enjoying the life you’ve worked so hard to build.

If you’ve ever wondered if you’re "doing it right" or felt buried by the daily grind, this conversation will give you the blueprint to step out. Get ready to rethink your role in your business, and evolve from an overwhelmed operator into a confident CEO.

HIGHLIGHTS AND KEY POINTS:

[00:51] A short introduction about our guest Marisa Grover, and how she got started in the short-term rental industry

[03:36] Marisa’s early trial-and-error journey and the wake-up call that systems are what make a short-term rental business sustainable

[07:48] Marisa’s approach to building systems by starting small, documenting in real time, and valuing her time as a business owner

[12:31] Marisa’s perspective on team-building rooted in self-belief, leadership mindset, and intentional delegation

[15:22] Marisa shares her mindset evolution through support, delegation, and gradual practice

[21:14] Marisa’s strategic approach to building a team around culture, outcomes, and intentional hiring

[25:34] How Marisa’s local team member who started as a cleaner naturally advanced to lead cleaner and eventually Operations Manager

[26:17] Marisa shares the first task she delegated, driven by a desire to reclaim personal time and be fully present with her family during meals

[29:29] Marisa’s approach to next-level business growth by aligning with personal values, focusing on what she enjoys, and improving existing services

[35:13] The lightning round

Golden Nuggets:

1. “I think a common misconception about building systems is that it is gonna suck your soul for a full year of your life, like there's no alternative, right? And so I just started, yes. I just started.”
2. “Having belief in yourself and believing that you have value is the start of a domino effect that's much bigger.”
3. “You have to believe that you are the valuable and the most...

Ever scroll past a vacation rental photo and feel like you had to stay there—like, yesterday? That’s not an accident. That’s story-driven strategy at work.

In this episode, I’m joined by the incredible Nicole Alexander—a woman who’s mastered the art of making STRs look so inviting, guests can’t help but click “Book Now.”

We talk about:

1. How Nicole went from wedding photography to capturing the soul of spaces
2. Her three-month adventure across Europe, camera in hand, documenting dreamy cabins
3. Why cozy corners, golden light, and personal touches matter more than you think

But this isn’t just about pretty pictures. It’s about creating an emotional connection.

Nicole walks us through her process—how she uncovers what makes a property special and translates it into visuals that spark curiosity, desire, and trust. You’ll hear why professional photography isn’t just a “nice to have.” It’s a brand builder. A booking booster. A guest experience enhancer.

If you’ve ever wondered whether great photos really move the needle in your STR business... this conversation will open your eyes.

Get ready to rethink how you show up online—and how guests see your property through the lens of story.

HIGHLIGHTS AND KEY POINTS:

[01:03] A short introduction about our guest Nicole Alexander, and how she got started in the short-term rental industry

[03:01] Nicole’s shift from wedding photography to cabin photography, and her approach to translating storytelling and vision into impactful property photography

[07:46] Why it's so important for hosts to invest in high quality story driven images, instead of just hiring a real estate photographer, or snapping their own pictures with their iPhone

[12:22] Nicole’s emphasis on atmospheric moments as the emotional bridge that turns a property into an experience guests can already feel themselves living

[14:51] Nicole’s commitment to honest, accurate photography as a trust-building tool rather than a marketing illusion

[18:15] What are some of the biggest mistakes that Nicole sees when hosts rely on subpar or non-experiential photography

[20:34] Nicole emphasizes that while professional photography is essential for listings, candid and non-professional shots play a crucial role in storytelling, particularly on social media

[22:42] Nicole talks about the common styling mistakes and preparing a property for photography

[25:32] Nicole’s advice on finding a creative photographer beyond traditional real estate specialists

[28:06] Nicole’s insights on vetting photographers to ensure they can deliver on your vision

[29:56] Nicole breaks down realistic photography investment ranges and what hosts should expect in return

[35:18] How investing in professional, story-driven photography directly drives stronger cash flow, higher nightly rates, and better guest alignment

[37:39] Nicole’s guidance on prioritizing hero images that quickly communicate space, amenities, and setting to drive booking decisions

[39:18] The lightning round

Golden Nuggets:

Building a successful vacation rental portfolio isn’t just about numbers—it’s about strategy, intuition, and having the confidence to trust both. In this episode, we explore what it really looks like to invest with intention, think long-term, and build a business rooted in education rather than hype.

In today’s episode, I sit down with the incredible Parker Borofsky, whose passion for lending and vacation rental investing shines through every story she shares. From her early days as Avery Carl’s lender to becoming a seasoned investor herself, Parker offers a behind-the-scenes look at a journey shaped by curiosity, courage, and thoughtful decision-making.

In this conversation, Parker shares:

1. How her early career in lending gave her an “under the hood” view of what truly makes a short-term rental successful—and how she used that insight to build a portfolio spanning the Smokies and Florida’s Panhandle
2. The remarkable story behind acquiring a bona fide Frank Lloyd Wright home in Kentucky, including the family connections and moments of serendipity that led her there
3. What it’s really like to invest during uncertain and unpredictable times, and why balancing solid research with gut instinct allowed her to seize opportunities others overlooked
4. The unique challenges and rewards of restoring and short-term renting a historic home, from navigating appraisals to thoughtfully weaving the property’s history into the guest experience
5. Why putting heart and education above hype—and surrounding yourself with the right community—is essential to building a more meaningful, sustainable business

Parker’s insights and grounded enthusiasm make this episode a must-listen for anyone looking to build a smarter, more intentional vacation rental portfolio. It’s filled with practical takeaways, mindset shifts, and real-world lessons for scaling with clarity and purpose.

HIGHLIGHTS AND KEY POINTS:

[01:00] A short introduction about our guest Parker Borofsky, and how she got into investing in short-term rentals

[03:00] Parker walks through her growing short-term rental portfolio across Tennessee, Florida, and Kentucky, highlighting a pivotal purchase in Townsend, Tennessee

[08:43] Parker explains how intuition, timing, and storytelling led her to an unexpected Kentucky purchase

[13:01] Parker shares how stewardship and storytelling shape the experience of owning a Frank Lloyd Wright home

[18:56] Parker reflects on the emotional full-circle of stewarding a historic Frank Lloyd Wright home

[21:24] Parker dives into the complexities of securing a mortgage for a one-of-a-kind Frank Lloyd Wright home, emphasizing that unique properties often create appraisal challenges

[26:51] How to handle appraisal challenges for unusual properties, emphasizing preparation, collaboration, and clear communication

[31:24] Parker talks about the mortgage options that are trending for real estate investors, particularly for self-employed borrowers or those with complex income streams

[34:57] The importance of connecting with experienced loan officers as a critical first step for anyone looking to grow their property portfolio in 2026

From corporate hustle to hospitality powerhouse, Janel’s story is the kind every host needs to hear.

In this episode, I sit down with the inspiring Janel Gallucci, who walked away from a high-pressure San Francisco career to build a short-term rental business on her own terms. What began with a single Lake Tahoe cabin quickly evolved into a thoughtfully scaled portfolio — each property designed with intention, creativity, and an unwavering commitment to delivering a true 5-star guest experience.

You’ll hear how Janel shifted from “one-property owner” to savvy portfolio builder, the systems and mindset she used to scale sustainably, and the decisions that helped her create guest-loved stays while protecting her time and energy. This conversation is a powerful reminder that a purpose-driven business can grow without sacrificing the life you’re building it for.

Janel shares:

1. The pivot point: How a moment of burnout prompted her and her husband to leave the corporate grind and dive head-first into STRs.
2. Taking control: Why early missteps with property managers forced her to self-manage—and how applying her corporate skills dramatically boosted her returns and created unforgettable stays.
3. Guest-Magnet Strategies: The exact systems she uses to turn listings into best-in-class properties, from leveraging market data and building local partnerships to offering dog-friendly welcome baskets and locally sourced amenities.
4. The Blueprint for Growth: Why defining your ideal guest and implementing robust systems is essential for managing properties confidently, whether they're nearby or across the country.

Janel’s story is a powerful blueprint for building a richer, more flexible life through short-term rentals. It's packed with actionable tips, mindset shifts, and the courage required to build an intentionally successful business. Tune in now to unlock the strategies for your own STR success!

HIGHLIGHTS AND KEY POINTS:

[01:15] A short introduction about our guest Janel Gallucci, and how she got into the short-term rental industry

[04:24] Janel reveals how miscommunication and poor property care pushed her to replace her property manager with direct self-management

[08:04] Janel’s approach to shifting into self-management to enhance confidence and control in her short-term rental

[11:02] How Janel handles tough guest situations to enhance satisfaction and protect reviews

[14:23] I share my experience at Airbnb headquarters and unpack why hosts have seen a dramatic shift in Airbnb’s willingness, and ability to remove unfair reviews

[17:12] Janel’s thoughts about the challenges of subjective guest ratings to highlight the flaws in Airbnb’s value and accuracy metrics

[20:12] Janel outlines her strategy for breaking past her revenue ceiling by elevating her property into the luxury tier

[22:06] How small luxury touches elevate the guest experience and reinforce premium positioning

[23:27] Janel outlines the intentional upgrades and guest-avatar strategy that fueled her jump from average earnings to six-figure revenue

[27:20] How low-cost, locally sourced, and thoughtfully branded welcome baskets enhance the guest experience while

Are you ready to stop relying on a single platform and take true control of your bookings, brand, and profits?

In this episode, I sit down with Jennifer Spencer— who left her corporate career to master the world of direct bookings. Jennifer’s journey from a single property in the Canadian Rockies to a diversified portfolio in Maui taught her one powerful lesson: you need to own the guest relationship.

We dive deep into her proven, anchor strategies for success:

• Crafting property brands that guests instantly recognize and remember.
• Leveraging email marketing to drive loyalty and repeat, direct bookings.
• Implementing smart automations that scale income without sacrificing the personal, top-notch guest experience.

If you feel overwhelmed by the thought of shifting from one platform to multiple channels, Jennifer offers a practical, step-by-step roadmap for taking manageable action, discovering your unique hosting style, and building a supportive network.

Tune in to learn how to brand boldly, optimize smarter, and turn casual stays into lifelong fans.

HIGHLIGHTS AND KEY POINTS:

[01:03] A short introduction about our guest Jennifer Spencer, and how she got into the short-term rental industry in the Canadian Rockies to expanding to Maui

[03:53] Jennifer shares how her transition from corporate sales and marketing into the vacation rental space happened almost unexpectedly

[06:08] Jennifer highlights the mindset shift required to move from an Airbnb-only approach to a diversified, business-driven booking strategy

[10:16] Jennifer shares her go-to tools and guest-experience strategies that reliably drive repeat direct bookings

[12:19] Jennifer outlines a balanced, human-first approach to using AI in guest messaging without sacrificing authenticity

[16:05] Jennifer shares her compliant, subtle strategy for priming guests for direct bookings without violating platform rules

[18:28] Jennifer’s top strategies for helping a property go from staying afloat in the market to truly outperforming its competitive set

[21:31] Why dynamic pricing tools only work when paired with proactive revenue management

[25:20] Jennifer explains why a defined, memorable brand is critical for driving direct bookings and standing out in a saturated market

[29:13] The critical role of guest communication and proactive problem-solving in creating memorable experiences and earning five-star reviews

[34:54] Jennifer highlights that the biggest challenge in shifting to a diversified direct booking strategy

[39:15] The lightning round

Golden Nuggets:

• “If you're really wanting to grow, whether it's one or two or an empire, you need to have a diversified strategy.”
• “I'm also super passionate about making sure that we are doing the work– number one that is within our genius zone. But it's also work we enjoy. If you don't enjoy that, don't just not do it. Delegate it to someone else.”
• “If there's nothing unique about you, it can be very difficult to stand out.”
• “You can turn any negative situation into a positive if you handle it properly.”
• “Find the support that matches what you need and what you're looking for.”

Let’s...

Are you accidentally making one of the five deadly mistakes that could be sabotaging your short-term rental co-hosting dreams?

In this candid episode, I pull back the curtain on the real pitfalls that derail even the most ambitious hosts. These errors are far more common than people admit, and they quietly chip away at your confidence, your profits, and your ability to grow.

We’re breaking down the 5 critical errors that hold co-hosts back:

• Lacking the non-negotiable systems that keep your business running smoothly and efficiently
• Undercharging for your services just to land your first client
• Believing every client is the right client for your co-hosting business
• Tying your professional worth and boundaries to your constant availability
• Not knowing exactly what to say to owners when it matters most

This is more than just spotting mistakes—it's about transforming missteps into momentum. I detail the clear professional standards, streamlined systems, and mindset shifts that will elevate you from busy to unstoppable.

Plus, discover The Co-Host Code—my step-by-step guide packed with templates, scripts, and proven strategies to build your business the right way from day one.

Tune in now to start charging your worth, setting boundaries, and building a sustainable co-hosting empire!

HIGHLIGHTS AND KEY POINTS:

[00:00] Co-hosting – the smartest way to grow and scale an STR business in 2026, and the quote that inspires me about ambition and believing in yourself

[01:34] Introducing my e-book The Co-Host Code – a step-by-step guide for building a profitable co-hosting business, and where to grab it

[02:29] Why do I believe co-hosting is one of the best ways to start and scale your short-term rental business

[04:42] How co-hosting allows me to support both guests and fellow real estate investors

[06:26] The First and the Biggest Mistake in Co-hosting: Lacking systems

[10:04] The Second Mistake: Undercharging for your services just to land your first client

[11:49] The Third Mistake: Every client is the right client for your co-hosting business

[15:22] The Fourth Mistake: Tying your worth to your availability

[17:36] The Fifth Mistake: Not knowing what to say to owners

[19:50] What are the things that you need to have in place for success in co-hosting

[24:49] The importance of building confidence through systems and action to scale a co-hosting business

Golden Nuggets:

• “Ambition is not a dirty word, it's just believing in yourself and your abilities.”
• “Co-hosting is a way for you to grow your portfolio without having to invest cash.”
• “If you are looking to grow a co-hosting business, or launch a co-hosting business, you absolutely need systems that are outside of what you are utilizing in your day to day.”
• “When you undercharge for your services, it is the fastest way to begin resenting your business.”
• “Not all owners are created equal.”
• “Your value is so much greater than the time you have for your business.”
• “The right words when you're selling your co-hosting services create confidence in your owners, and confidence...

How can you turn your dreams into a profitable real estate strategy that builds both wealth and freedom?

In this episode, I sit down with Sandy Lee, who pivoted from a 30-year career in oil and gas engineering to become a savvy short-term rental investor with properties across four different states. Sandy’s story is about reimagining what’s possible when you combine strategic thinking, personal passion, and a relentless drive to learn.

What started as a family joke about buying a ski condo her son dreamed of turned into a thriving investment portfolio that now generates meaningful retirement income. Sandy’s approach is rooted in intentional, long-term wealth building—where every property reflects both financial foresight and lifestyle design.

We dive into how Sandy leveraged her engineering mindset and financial modeling skills to build a short-term rental business that delivers more than just cash flow. From managing remote teams to identifying the financial metrics that truly matter, she shares the systems and mindset shifts behind her success.

This episode is a powerful reminder that it’s never too late to reinvent your career or your financial future. Sandy’s journey proves that with clarity, structure, and purpose, your investments can become more than assets—they can become the foundation for the life you’ve always envisioned.

HIGHLIGHTS AND KEY POINTS:

[00:50] A short introduction about our guest Sandy Lee, and how she got into the short-term rental industry

[05:10] Sandy shares how she went from doubting property ownership to building a multi-state portfolio that fuels her retirement

[08:04] How aligning Sandy’s investments with her personal mission brings both joy and purpose to her real estate journey

[10:44] Sandy talks about how continuous learning shaped her mindset shift toward early retirement and business reinvention

[14:37] How leadership and appreciation elevate Sandy’s short-term rental business

[18:12] The importance of building genuine, caring relationships with the cleaning team and how Sandy found them in four different locations

[20:35] Sandy shares the challenges and lessons of managing teams across multiple short-term rental locations

[24:06] Sandy talks about the realities and rewards of managing short-term rentals from afar

[26:40] The key financial metrics that Sandy uses to evaluate short-term rental investments

[28:20] Sandy discusses the importance of tracking data-driven performance metrics after purchase to guide strategic decisions

[32:08] Sandy discusses the importance of moving away from “ego pricing,” and trusting experts to strengthen business performance

[34:42] Sandy shares her enthusiasm for bringing fresh energy into the short-term rental, and emphasizes the importance of thinking beyond the “get rich quick” mentality

[35:38] The lightning round

Golden Nuggets:

• “It's really important to figure out who you are, what you want from life, put that together and then make it happen.”
• “Don't wait for an opportunity, create it.”
• “You've got to keep learning, or you're paced out.”
• “People are your business, no matter how tiny your business is.”
• “It's okay