What does it really take to build a multi-billion-dollar real estate enterprise, raise a family on your own terms, and still have the energy to show up as the face of your brand every single day? Most people think it requires sacrificing your personal life; Avery Carl is proof that it requires a better system.

In this episode, we’re skipping the basic tactics and going deep on the woman behind the empire—the one who went from a $37,000 salary to leading the country’s largest STR-focused real estate team.

We talk about:

1. How Avery and her husband structured a massive business so that, to their kids, it feels like they have two stay-at-home parents
2. Avery’s intentional prioritization filter—how she decides what stays on her plate and what gets delegated to her team
3. Why telling a client not to buy a property is the secret to building a decade of trust (and a billion-dollar legacy)
4. How Avery dominates Instagram, YouTube, and TikTok when she’d actually rather not be on camera at all.
5. The relentless focus on what actually moves the needle versus what just feels like "busy work."

Avery pulls back the curtain on the hard conversations, the fear of letting go, and why she insists on writing every word of her books herself. You’ll hear how she transitioned from "doing it all" to becoming a leader who empowers a team, all while maintaining the boundaries that protect her family time. If you’ve ever felt torn between your ambition and your afternoon with the kids, this conversation is your blueprint.

Get ready to rethink your role and learn how to build a business that supports your life instead of consuming it.

HIGHLIGHTS AND KEY POINTS:

[01:05] A short introduction about our guest Avery Carl, a seasoned real estate investor and short-term rental expert

[03:23] Avery explains how consistency, lived experience, and transparency shaped her cohesive personal brand

[06:43] Avery shares her experience on encountering shiny object syndrome without abandoning her strategy

[08:17] Avery reflects on losing focus, learning fast, and recommitting to her core business

[09:46] How Avery Carl decides what deserves her attention inside a growing business and shares how delegation, focus, and integrity guide her leadership style

[18:19] Avery explains how fluid boundaries help her balance business demands and family life

[19:45] Avery shares how virtual assistants and AI reduce the constant demands of short-term rental hospitality

[23:57] How Avery develops content ideas, refines the message, and publishes with consistency

[26:23] Avery looks back on when she realized content creation mattered and why she started later than most

[28:06] Avery explains how she evaluates content performance beyond likes, views, followers and how her platform strategy evolved from a few core channels to everywhere

[30:47] What are the biggest lessons Avery learned about focus, credibility, and follow-through from writing multiple books

[33:38] Avery’s advice to anyone dreaming of writing a book and emphasizes...

Ever felt like you’re building an empire on an island, carrying the entire mental load of your business while wondering why there isn’t a roadmap for women like you? Scaling to the top of this industry requires more than just strategy; it requires the grit to go first and the heart to bring others with you.

In this episode, I’m joined by the legendary Lisa Roads, a trailblazer who grew a UK property portfolio into a powerhouse managing over 175 luxury villas in Cyprus, all while pioneering a movement for women in hospitality.

We talk about:

1. How Lisa spotted a gap in the Cyprus market and scaled to 175+ luxury units before the industry had a manual.
2. The raw reality of the loneliness and lack of support that often comes with rapid growth.
3. Why Lisa is dedicated to solving the representation crisis and lifting the "unique burdens" women face in property management.
4. The essential boundaries you must set to ensure your business doesn’t consume your life.

But this isn't just about property counts or profit margins. It’s about reclaiming the narrative of the female entrepreneur. You’ll hear why true success isn’t just about the daring leaps you take for yourself, but about the space you carve out for others to be heard, supported, and celebrated.

If you’ve ever felt the weight of being the "only one" in the room or are ready to scale a business that aligns with your deepest values, this conversation is your blueprint. Get ready to move beyond the grind and start leading with legacy.

HIGHLIGHTS AND KEY POINTS:

[01:01] A short introduction about our guests Lisa Roads, and shares her journey from long-term investor to industry leader while explaining her mission to elevate and support women in the short-term rental space

[05:31] Lisa Rhodes and I reflect on the power of women-centered communities to build confidence, visibility, and leadership in short-term rental businesses

[11:38] Lisa shares the realities of scaling a property management business to 175 high-performing properties by prioritizing alignment, systems, and long-term profitability

[14:22] Lisa emphasizes the importance of intentional, systems-driven growth over chasing door count and scaling chaos in large property management portfolios

[16:29] How intentionally defining the ideal guest, designing for that audience, and building strategic partnerships allowed Lisa to create demand in an undeveloped short-term rental market

[18:11] Lisa on creating high-trust travel agent partnerships and the operational systems that made them scalable

[20:51] Lisa explains how she built custom systems to manage bookings, property operations, and service delivery in a market without established short-term rental technology

[22:31] How building a support network was essential to managing the invisible mental load of running a business and caring for family

[25:50] Lisa emphasizes the importance of setting boundaries, protecting mental and physical health, and intentionally scheduling downtime to prevent burnout as an entrepreneur

[29:19] Lisa reflects on growing up in an entrepreneurial, nomadic family, and emphasizes the importance of self-belief and having a solid...

Have you ever fantasized about quitting your corporate job to buy a run-down motel and turn it into a boutique empire—even if you have zero experience in hospitality or design? Most people keep that dream in their head; April and Sarah actually did it.

In this episode, I’m joined by the visionary co-founders of The June Motel, April Brown and Sarah Sklash, two friends who traded their steady city lives for power drills, YouTube tutorials, and a lot of pink paint.

We talk about:

1. The "Wine-Fueled" Leap: How a casual brainstorm in Toronto turned into the bold acquisition of an aging roadside motel.
2. The Reality of "DIY" Hospitality: From learning to use power tools on the fly to handling mountains of laundry and mid-reno panic.
3. Building an Instagram Icon: Why "Instagrammable" was just the hook, and how they built a deep, meaningful brand culture to back it up.
4. The Netflix Pivot: The behind-the-scenes chaos and courage required to scale a business while the cameras are rolling.

But this isn't just a story about pretty renovations. It’s about the grit behind the glamour. April and Sarah pull back the curtain on the financial hurdles, the steep learning curves, and the power of a partnership built on radical trust.

If you’ve ever felt like you’re waiting for "enough experience" to start your dream project, this conversation will be your wake-up call. Get ready to stop playing it safe and start building your own version of "The June Way."

HIGHLIGHTS AND KEY POINTS:

[01:05] A short introduction about our guests April Brown and Sarah Sklash, how they met, and what got them thinking about the world of hospitality

[04:20] April and Sarah’s mindset shift from cautious transition to shared conviction while building a new hospitality vision

[07:14] April and Sarah’s transformation of a no-frills fishermen’s motel into a visually driven, experience-led boutique destination

[10:06] April and Sarah’s perspective on how “Instagrammable” has evolved from bold backdrops to cohesive, authentic storytelling

[12:38] April and Sarah talk about their ability to see potential and design guest experiences beyond technical renovation skills

[16:14] April and Sarah’s reckoning with the reality of hospitality and the doubts that come with it

[18:53] The expansion journey of April and Sarah, and the behind-the-scenes challenges of opening new properties while launching a Netflix show

[26:37] April and Sarah discuss the necessity of creating repeatable systems to maintain the quality and character of their properties when they couldn’t be on-site every day

[29:19] The importance of hiring for cultural alignment and understanding the “why” to foster team buy-in and preserve the vision of their properties

[31:14] April and Sarah share their hands-on, values-driven approach to hiring and staff retention to ensure cultural alignment and long-term team growth

[33:02] April and Sarah reflect on managing perfectionism and making collaborative decisions while keeping the big picture in focus

[36:45] April and Sarah discuss collaborative decision-making and how differing perspectives strengthen their...

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