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