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:

1. “Photos truly are the only thing that are consistently working for you, 24/7.”
2. “Your photos sell the charm of the space. It's history, it's personality, the feeling of the location.”
3. “There's nothing worse than walking into a space and being like this doesn't look like what I was sold.”
4. “Ask to see galleries, ask to see their work, because social media can be fake.”

Let’s Connect:

Website: www.cabinhunter.com

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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

[37:13] Genuine appreciation for Parker’s commitment to giving back to the short-term rental industry, and Parker’s role as a speaker at the upcoming Short-Term Rental Virtual Summit for Women

[38:30] The lightning round

Golden Nuggets:

1. "It's not always perfect when you're finding properties in the market. So, go and see and feel and trust your gut feeling.”
2. “It's so important that we balance the numbers with our intuition.”
3. “Look ahead of what's coming.”

Let’s Connect:

Website: wealthbuildersmortgage.com

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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 supporting efficiency and local partnerships

[31:54] The importance of building systems and delegating tasks to free up a host’s time and prevent burnout

[34:44] Janel explains how she found and acquired her second property—the number one most wish-listed property in the state

[42:03] How Janel’s Mississippi property became the most wish-listed in the state

[47:18] The value of sharing expertise and mentoring, regardless of portfolio size

[49:13] The lightning round

Golden Nuggets:

1. “If we just show up really compassionately and empathetically and try to understand what's going on, and like, make our best effort to fix that issue, people actually really appreciate that, and that can end up leading to a five star review.”
2. "If you talk to a rep at Airbnb and something doesn't seem right, or you feel like they don't have your back, just hang up and call again and get another rep, and then that ends up solving the problem.”
3. “We tripled our revenue. What led to that one? I think just me owning the full guest experience, and not having to pay a commission to a property manager obviously made a huge difference.”
4. “The systems are what give you freedom.”
5. “When you actually understand the value of your time, it makes it so much easier to delegate work and to make decisions.”
6. “Look at your own experience, your own knowledge, and look for opportunities to pay it forward, to help other people, because we learn so much by helping others.”

Let’s Connect:

Instagram: https://www.instagram.com/sevensummershostacademy/

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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 Connect:

Instagram: https://www.instagram.com/thehostapproach/

Website: https://www.thehostapproach.com/

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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 is what closes clients. Clients are what build your business.”
• “Successful co-hosts don't need to reinvent the wheel; they document the wheel.”
• “Setting boundaries and managing expectations with your owners is absolutely important.”
• “You need to know your numbers.”
• “You need to have confidence in yourself, and confidence is built through action. Confidence is built sometimes by borrowing courage from other people.”

Let’s Connect:

Website: staceystjohn.com

Reference Mentioned:

The Co-Host Code https://tinyurl.com/y2tpruen

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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 to not know all the things. You learn as you go along, and you educate yourself every day.”

Let’s Connect:

Website: https://www.strjumpstart.com/

Instagram: https://www.instagram.com/distilleddestinations/

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Ever feel like scaling your STR biz means sacrificing your sanity?

Jessica Hill is living proof it doesn’t have to be that way.

In this episode, we chat with the inspiring mama, healthcare pro, and STR entrepreneur behind Jet Setter Property Management — where intentional design meets boutique profitability. With just 12 hand-picked properties, Jessica has built a wildly successful short-term rental business that’s rich in personality and profit… without managing dozens of doors or burning the candle at both ends.

She gets real about:

• Designing properties that connect emotionally (hello, custom murals and curated guest experiences)
• Balancing a demanding W-2, motherhood, and business ownership
• The systems, boundaries, and support that make her model sustainable

This convo is a masterclass in doing STRs differently — and doing them on your terms.

If you’re craving a business that feels good and does good, this episode will remind you that “more” isn’t the goal — meaning is.

HIGHLIGHTS AND KEY POINTS:

[00:56] A short introduction about our guest Jessica Hill and how she got into the world of short-term rentals

[03:32] Jessica talks about her company and explains why she intentionally operates a boutique, hands-on property management model instead of scaling into a large, volume-driven portfolio

[05:19] Jessica emphasizes the importance of intimate, hands-on management that boutique operators provide compared to large-scale property managers

[09:55] Jessica’s active involvement in the guest experience and daily operations despite having a team

[11:03] Jessica shares about her W-2 job and what she has pulled over from her W-2 into her short term rental business

[12:35] Jessica explains explains why strategic design is a performance lever, not just aesthetics, in driving bookings and brand demand

[16:11] Jessica talks about how she monetizes design and listing optimization as value-add services within her boutique hosting model

[17:31] Jessica shares the key foundations smaller hosts should prioritize to deliver a high-touch guest experience through a boutique-style approach

[20:11] How Jessica balances a full-time W2 career, motherhood to a special needs child, and her co-hosting business through intentional time management

[22:32] Jessica shares how motherhood shaped her communication philosophy in short-term rentals

[25:15] Jessica emphasizes the power of over-communicating with her team to build ownership and brand-aligned service

[27:27] Jessica shares her piece of advice for all women who are chasing big dreams while also navigating life, being a mom, working a full time job

[29:51] The lightning round 

Golden Nuggets:

• “Start and make sure that you have the proper systems in place.”
• “I have brought those people on my team to help with those things, so that way I can be a more effective property manager and do the things that I love to do.”
• “When you love what you do, you never work a day in your life.”
• “Don't lose yourself in the day to day of motherhood. Carve out a little time for yourself, because you can't pour from an empty cup.”
• “When we do learn something, it's important that we implement it and execute it and keep our business moving forward.”

Let’s Connect:

Website: https://stayjetsetting.com/

Facebook: https://www.facebook.com/stayjetsetting

Instagram: https://www.instagram.com/stayjetsetting

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Ever wondered how to successfully manage a short-term rental hundreds of miles away—without losing your sanity or your weekends?

In this episode, I sit down with Lydia Patel, a pharmacist who’s mastered the art of remote property management while balancing a full-time career and family life. Lydia’s story proves that you don’t need to live near your investment to make it thrive—you just need the right systems, people, and mindset to make it work.

From setting up her Florida rental property while caring for a newborn to building a trustworthy team of local professionals, Lydia walks us through the practical steps that turned her long-distance investment into a sustainable success. Her journey is a blueprint for anyone looking to create a business that fits seamlessly into real life, not the other way around.

We explore the exact tech tools and strategies that make remote management possible—from noise monitoring and digital locks to streamlined property management software. But at its heart, this conversation is about more than tools—it’s about resilience, resourcefulness, and redefining what freedom looks like in real estate.

Lydia’s insights will inspire you to think differently about investing, scaling, and balancing it all. Her story is proof that with strategy, systems, and heart, you can manage your business from anywhere and still have a life you love.

HIGHLIGHTS AND KEY POINTS:

[00:52] A short introduction about our guest Lydia Patel, how her hosting journey began, and walks us through the long-distance managing her Florida short-term rental while living full-time in Minnesota

[05:59] Lydia opens up about the steep learning curve and operational surprises of managing her Florida rental remotely right after giving birth

[09:45] Lydia details how she built a dependable remote team by combining local expertise, reliable systems, and open communication

[14:02] Lydia shares how smart technology and integrated systems make remote property management seamless and secure  

[19:23] Lydia opens up about overcoming the emotional challenges of managing from afar and learning to let go of control

[24:04] How to turn preventable mistakes into refined systems that strengthen business operations over time 

[29:12] Lydia shares the real challenges of juggling motherhood, work, hosting, and the mindset shift that helped her find balance

[32:24] How sharing Lydia’s journey through content creation became an authentic way to give back and connect with others on a similar path 

[35:22] Lydia shares how she balances creativity and delegation in managing her content creation process 

[39:43] The lightning round 

Golden Nuggets:

• “Never make assumptions; look for those opportunities where slip ups happen, and write a process to fill in a gap so that there's no question.”
• “There's something very rewarding about feeling like you're helping someone else. And so if I can share something that I've done, a tip, a helpful trick, a strategy that's been beneficial for me, if I'm able to pay it forward and help someone else.”
• “Slow months are real. Don't panic over it, just budget for it.”
• “Just stay human. Yes, it's a business, but there's a human aspect to it. Whether it's the relationship with your team members, relationship with your guest and how you're interacting with your own self like you are only human as well. You cannot operate at robot level.”

Let’s Connect:

YouTube: https://www.youtube.com/@lydiapatelll

Instagram: https://www.instagram.com/lydiapatelll/

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How do you turn a single-property hustle into a thriving, purpose-driven business that actually gives you freedom?

Join me as I sit down with Brindy Bringhurst, a trailblazer who transformed her entrepreneurial journey from managing one property to leading a successful multi-property management operation in Arizona. We dive deep into the art and science of building a strategic short-term rental business that goes far beyond just hosting guests.

Brindy shares the pivotal lessons she learned along the way—from defining her ideal owner avatar to building a supportive, high-performing team that became the backbone of her success. Her story is a masterclass in resilience and strategic growth, proving that the key to scaling isn’t just about more properties, but about smarter systems and stronger relationships.

We unpack her early challenges of working solo and feeling stretched thin, and how she intentionally built a team that understands both the business and the heart of hospitality. Brindy reveals how protecting your team’s energy and aligning your business with your values can completely redefine success.

This isn’t just a conversation about rentals—it’s about designing a business that supports your lifestyle, empowers your people, and creates lasting impact. Get ready for an honest, inspiring dialogue that will challenge how you think about entrepreneurship, leadership, and sustainable growth.

HIGHLIGHTS AND KEY POINTS:

[00:55] A short introduction about our guest Brindy Bringhurst and how she got started in the world of short-term rentals

[04:16] Brindy shares her early experiment in full-home hosting that taught her adaptability, connection, and the trade-offs of earning more while giving up stability

[05:24] Brindy’s reflections on the emotional toll of renting out her own home 

[08:49] Brindy walks us through the long, unpredictable transition from her early hosting hustle to establishing a full-fledged co-hosting business

[15:56] Brindy opens up about the defining moment she stopped “trying” and fully committed to making her business work

[20:29] Brindy reflects on the stark contrast between her early years of nonstop hustle and how she now approaches fear, self-doubt, and confidence

[27:08] How growing Brindy’s team transformed her business from a one-woman juggling act into a well-rounded, collaborative operation powered by trust, learning, and honest feedback 

[36:11] How leading a team transformed Brindy’s purpose in business from proving herself to creating a company built on collaboration, accountability, and genuine care for her people

[40:29] Brindy recalls the pivotal moment when she realized not every property—or owner—was the right fit for her growing business

[43:53] The challenges of dealing with difficult owners and how those moments have shaped Brindy’s approach to leadership

[48:22] The lightning round 

Golden Nuggets:

• “If you have an idea and you think it'll work, just commit to it and it'll work. It will happen.”
• “What we believe, is what we can achieve.”
• “As business leaders, it's critical for us to learn skills about how to be a good business leader.”
• “You don't have freedom unless you have a team.”
• “Don't give advice unless you're asked. People don't like being given advice unless they're asking you for advice. So unless they're asking for advice, you might be better off just listening.”

Let’s Connect:

Instagram: https://www.instagram.com/airbrindy

Website: https://airbrindy.com/

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The right tech stack could give you back your time, your freedom, and the space to focus on what truly lights you up in your business.

In this episode, I sit down with Margot Schmorak, CEO and co-founder of Hostfully, to explore how the right property management software can transform your short-term rental business. Margot isn’t just another tech executive—she’s a visionary leader who believes technology should simplify your operations, elevate your guest experience, and help you reclaim your time.

We dive into what really matters when choosing tools for your rental business—from selecting a property management system that scales with you, to optimizing your workflows, to building a cohesive tech foundation that supports both growth and balance.

Margot also shares her journey from big tech to entrepreneurship, her philosophy on human-centered technology, and how she leads a company rooted in joy, purpose, and personal growth. Beyond business, she opens up about finding harmony as a CEO, mom, and lifelong learner.

This episode is a must-listen for hosts and entrepreneurs ready to use technology intentionally. Margot’s insights will inspire you to design a business that runs efficiently, aligns with your values, and gives you the freedom to focus on what matters most.

HIGHLIGHTS AND KEY POINTS:

[00:58] A short introduction about our guest Margot Schmorak and shares her vision for building Hostfully around human connection, real-world impact, and a culture that uplifts people

[04:07] Margot highlights how hiring for passion and fostering authenticity are key to building a thriving, people-centered culture

[07:15] Margot breaks down the essentials of building a strong tech stack that drives bookings, streamlines operations, and supports long-term business growth

[11:14] Margot emphasizes the importance of starting with the right property management software and choosing tools that can scale with your business through integrations 

[14:22] How to shop smart for property management software and the importance of spotting red flags in emerging technology

[19:39] Margot’s insights on using AI to elevate customer experience, strengthen team efficiency, and personalize communication at Hostfully

[22:35] Margot’s perspective on overcoming “Shiny Object Syndrome” to build a focused, intentional tech strategy 

[24:30] The importance of aligning technology and planning with clear goals to set up a strong start for the new year

[28:06] Margot’s perspective on revisiting annual plans and adapting to change while staying confident in the industry’s long-term growth 

[29:39] Margot’s outlook on the next big shifts shaping the short-term rental industry from AI innovation to a new era of professionalism 

[32:15] Margot’s reflections on rediscovering joy, grace, and the freedom to be imperfect outside of work

[37:55] Margot’s journey toward embracing joy, self-compassion, and the simple art of celebrating life’s small wins

[42:51] The lightning round 

Golden Nuggets:

• “One of the most important things is to make sure that you're hiring people into jobs that they're really excited about.”
• “When you're selecting tech, it's really critical to not only know where your business is today, but where you want to be in the future.”
• “Find something that does grow with you, but also is, like, suitable for your needs.”
• “Having a partner and a team around you that is going to give you support and grace when you need it is really important.”
• "We have to celebrate the small stuff because those small things, when left unattended to, that’s when joy starts to head out of our lives."

Let’s Connect:

Website: https://www.hostfully.com/

Email: [email protected]

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