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...

How do you rebuild your life and create extraordinary success after everything falls apart?

In this episode, I sit down with Ashley Freeman, a former tennis pro who turned the pain of divorce into the fuel for a thriving 115-property short-term rental business—all in just three years. Her journey is a testament to resilience, reinvention, and the power of daring to believe in something bigger for yourself.

Ashley opens up about the pivotal moment she discovered Airbnb, transforming her four-acre property into a surprising income stream. What started as a survival strategy quickly became a passion-driven business that redefined her career and her sense of purpose.

We dive into the entrepreneurial strategies that fueled her rapid growth—from scaling one unit into 115, to building a powerhouse team of predominantly women, to designing systems that keep her business thriving. Alongside the practical insights, Ashley shares the mindset shifts, faith, and intuition that became the foundation of her success.

This is more than a business story—it’s a masterclass in courage, vision, and personal growth. Ashley’s journey will inspire you to see challenges as stepping stones, trust your intuition, and embrace the kind of bold thinking that can transform both life and business.

HIGHLIGHTS AND KEY POINTS:

[00:56] A short introduction about our guest Ashley Freeman and her unexpected journey from tennis pro to scaling a 115-property management company in under three years

[06:37] Ashley shares her mission-driven approach to short-term rentals and her passion for helping others after finding purpose again

[11:28] Ashley’s journey from her first client to managing 135 properties, and how she learned to grow with humility, faith, and adaptability

[15:38] How surrendering control to God after Ashley’s divorce transformed her life and taught her to recognize His guidance

[18:48] Ashley shares how a trip to Africa ignited her mission to reach “broken women” and how she learned to trust whispers from God

[25:10] Ashley’s approach to starting simple and building her property management growth one step at a time

[26:49] Ashley’s team growth and systems that transformed her property management business

[30:18] Ashley’s share her intentional decision to keep cleaning in-house as part of building a trusted team and aligning hospitality with her deeper mission to serve guests with excellence

[35:10] How building systems and processes early allowed Ashley’s business to scale smoothly and avoid breakdowns during rapid growth

[38:44] Ashley’s biggest challenges as she has grown her property management company to now well over 100 units and how she navigated them

[43:12] How I sustain my team by focusing on open communication, removing roadblocks, and empowering them to contribute solutions that strengthen the company

[49:39] The lightning round

Golden Nuggets:

• “I do think there's a sense of faith that you have to have in business, regardless if you believe in the Lord or not. You know you have to have faith. It's that leap of faith that you're taking to even get started.”
• "God is talking to each of us; we have to be willing to open our ears to listen.”
• “Cleaning, to me, is like the most important part of the experience, and so we've never even considered trying to go...

What if standing out in the short-term rental industry isn’t just about the property—but the experience you create?

In this episode, I sit down with Candice Menard, the powerhouse behind Rent It Like a Saint, to explore the transformative philosophy of “Unreasonable Hospitality.” Candice isn’t just managing rentals—she’s redefining modern hosting by crafting heart-centered guest experiences that turn first-time visitors into lifelong fans.

Candice shares her inspiring journey from long-term property management to becoming a visionary in short-term rental hospitality. She breaks down how understanding her ideal guests—hardworking professionals who crave comfort, connection, and care—helped her anticipate needs before they were spoken, setting a new gold standard for guest experience.

We also dive into Travel Like a Saint, her complementary travel service that elevates the guest journey from start to finish. Candice reveals how she blends technology with personal touch through AI-assisted communication, community partnerships, and holistic brand storytelling that keeps guests coming back.

This episode is a must-listen for hosts and entrepreneurs ready to elevate their hospitality game. Candice’s story is a masterclass in business growth, intentional service, and brand differentiation—proving that true success comes from serving with heart, purpose, and a touch of the extraordinary.

HIGHLIGHTS AND KEY POINTS:

[01:00] A short introduction about our guest Candice Menard and how did she get into short-term rental business

[02:57] Candice’s approach to embracing unreasonable hospitality and gaining clarity on her ideal guest to elevate the guest experience

[06:24] Candice talks about how an unexpected Airbnb booking helped her discover her ideal guests and shape the future direction of her rental business

[08:42] How Candice brings “unreasonable hospitality” to life by anticipating guest needs through fast communication, personalization, and gratitude

[12:33] Candice explains how she blends AI with human communication to deliver efficient yet personal guest experiences

[15:43] How the idea of “unreasonable hospitality” inspired Candice to expand from Rent It Like a Saint into a full travel service with Travel Like a Saint

[18:35] Candice explains how she promotes Travel Like a Saint across multiple channels and the enthusiastic feedback she’s received from guests

[20:33] Candice details the foundational systems she built within Rent It Like a Saint to free up her time and focus for launching Travel Like a Saint

[23:23] How Candice’ involvement in the Louisiana Travel Summit unexpectedly turned into an opportunity to build stronger ties within her local community

[28:06] Candice offers thoughtful, grounded advice for anyone who wants to infuse the spirit of “unreasonable hospitality” into their business

[32:00] The lightning round

Golden Nuggets:

• “Providing excellent world class customer service is the best way to get those five star reviews.”
• “The most valuable asset you can have in your hosting arsenal is your speed of communications.”
• “Relationships are where referrals come from.”
• “What's important to you, what's important to your guests, find your who's that can make that connection to get your puzzle piece...

Could a tiny glamping dome really be the first step toward a thriving real estate empire?

In this episode, I sit down with Zoey Berghoff, a young entrepreneur who’s redefining what’s possible in the short-term rental industry. Six years ago, she launched her journey with a 300-square-foot dome and a bold vision. Today, she’s mastered land development, ground-up builds, and extensive renovations—all while staying focused on equity, cash flow, and lifestyle investments that work for her family.

Zoey opens up about the strategies that set her apart, from leveraging forced appreciation to uncovering hidden potential in overlooked properties. She shares how she’s built a reliable team, the importance of outsourcing effectively, and the lessons she’s learned while scaling her portfolio—all while raising a toddler and building a business that supports her life.

What makes Zoey’s story so powerful is her ability to challenge the traditional path of real estate investing. Instead of chasing trends, she’s built a portfolio rooted in long-term value, strategic growth, and resilience. Her approach is a blueprint for anyone who wants to build wealth on their own terms.

This conversation will inspire you to see opportunities where others see obstacles. Zoey’s insights prove that with the right mindset, systems, and strategy, ordinary properties can become extraordinary investments.

HIGHLIGHTS AND KEY POINTS:

[01:03] A short introduction about our guest Zoey Berghoff, and her journey in short-term rentals

[04:18] How Zoey’s first short-term rental was a 300-square-foot glamping dome that she and her husband partly lived in before deciding to rent it out while traveling

[07:34] Zoey explains how freelancing income, self-education, and trial-and-error opened the door to real estate investing

[12:34] Zoey shares her approach to telling her story on social media and encourages others to start small, stay consistent, and focus on impact over perfection

[15:49] Zoey highlights the dangers of comparison on social media and shares how focusing on slow, intentional growth in real estate helped her define success on her own terms

[19:13] How Zoey’s first ground-up construction project taught her the value of delayed gratification, forced appreciation, and learning the hard way through trial and error

[24:00] Zoey’s advice for vetting contractors and builders to protect your investment and avoid costly mistakes

[29:38] Zoey’s philosophy on pay structure to protect yourself and maximize value in contractor agreements

[33:07] The concept of forced appreciation in real estate and how buying undervalued properties can create massive equity gains in a short time

[36:50] How forced appreciation doesn’t always require major renovations—sometimes strategic cosmetic updates are enough to build equity and long-term wealth

[40:45] Zoey explains how equity and forced appreciation play a central role in scaling short-term rental portfolios

[44:38] Zoey reflects on her biggest mistake of trying to do everything herself instead of outsourcing sooner

[49:14] The lightning round

Golden Nuggets:

• "Just share what you're doing. It doesn't have to be perfect. People want the behind the scenes. They want to know the challenges.”
• “You, as the investor, need to be logical about...

What if the biggest obstacle to financial success isn’t strategy or hard work—but the beliefs you hold about yourself?

In this episode, I sit down with Esmeralda Alba to explore the inner work of abundance and how simple mindset shifts can create profound changes in your financial life. She shares her personal journey from struggle to transformation, and how a powerful practice called Intensati helped her rewrite her inner dialogue and step into a new reality of possibility.

Esmeralda opens up about moving from a scarcity mindset to one of abundance, showing how even small adjustments in thought patterns and daily practices can unlock growth. She also shares practical tools—from gratitude to intentional language—that helped her transform her relationship with money and opportunity.

We dive into the wisdom of her spiritual mentor, Patricia Marino, who taught her that abundance isn’t something you chase, but something you cultivate within yourself. Esmeralda’s raw and vulnerable stories reveal how doing the inner work can lead to breakthroughs that ripple into every area of life.

Whether you’re building a business, investing in real estate, or simply seeking more alignment in your personal journey, this episode will inspire you to reset your mindset. Esmeralda’s story is proof that financial success starts on the inside—and grows outward from there.

HIGHLIGHTS AND KEY POINTS:

[01:20] A short introduction about our guest Esmeralda Alba and shares how an exercise class introduced her to the power of affirmations and an abundance mindset

[05:19] Esmeralda explains how shifting her money mindset during tough times transformed her family’s business journey

[09:21] Esmeralda outlines the daily practices she uses to cultivate an abundance mindset and describes how she actively shifts from fear to gratitude when facing life’s toughest moments

[14:15] How solitude and daily discipline support Esmeralda’s shift toward an abundance mindset

[16:33] Esmeralda shares how she shifted her money mindset from scarcity to abundance through daily language changes and affirmations

[21:26] Esmeralda explains how repeating present-tense affirmations like “I am a money magnet” programs the subconscious to attract financial abundance

[25:23] How mindset practices, abundance beliefs, and reframing money stories transformed Esmeralda’s life

[33:00] Esmeralda credits her late mentor for reshaping her money beliefs and emphasizes that abundance requires consistent daily practice

[36:58] How intuition and leaning on a trusted community helps Esmeralda vet opportunities within an abundance mindset

[41:47] Esmeralda credits Alicia for pushing her out of her comfort zone and helping her step into the spotlight

[43:17] The lightning round

Golden Nuggets:

• "What you put out, or what you say, or even what you think is what you're attracting, these are the things that you're going to attract.”
• “We're able to set fuel to our fire and power behind ourselves when we train our brain to work for us.”
• “The more grateful you are for the things that you have, the more abundance that you attract into your life.”
• “Having an attitude of gratitude helps you, not only again organically begin to see shifts in your life, but it also makes life

What does it take for a young entrepreneur to turn a family’s real estate legacy into a thriving vacation rental business?

In this episode, I sit down with Allison Bayley, the powerhouse behind Bayley Vacation Rentals, for a conversation that blends business strategy with personal transformation. Allison’s story proves that passion and grit—not age—are the true drivers of success.

From summers working at her grandparents’ campground to becoming a scuba diving master in California, Allison never followed a straight line. When her mom, a real estate agent, called her home with a bold business proposition, Allison took a leap of faith. While bartending at night and working out of a tiny 600-square-foot office by day, she built the foundation of a company that now dominates her market.

Allison’s journey hasn’t been without challenges. As a young, tattooed, non-traditional professional, she often faced judgment in an industry that loves to size people up by appearances. But she turned those doubts into fuel, building not just a successful business but a women-owned, women-operated powerhouse spanning generations With a cutting-edge tech stack and an obsession with guest experience, she’s redefining what a family business looks like in the modern era.

This episode is more than a success story—it’s a masterclass in resilience, mindset, and the power of bold risks. Whether you’re a seasoned entrepreneur or just dreaming of your first venture, Allison’s journey will inspire you to rethink what’s possible when family, vision, and courage come together.

HIGHLIGHTS AND KEY POINTS:

[01:08] A short introduction about our guest Allison Bayley and how she got into short-term rentals

[03:14] How Allison’s mom’s phone call felt like the right moment to return home and take on more responsibility

[04:47] Allison shares how she and her mom set up the vacation rental business in the early days

[07:43] Allison reflects on the early fatigue and mental strain of building her business while juggling long shifts in hospitality

[10:52] Allison shares how she faced misjudgments for her tattoos, piercings, and colored hair and the way she navigated those perceptions

[15:41] How Allison’s early responsibility and guidance from her sister and therapist shaped her emotional resilience and wisdom

[18:26] Allison’s perspective on what makes a good boss and recalls lessons from a former mentor about keeping doors open and not burning bridges

[19:47] Allison talks about her all-female, close-knit team and the challenges of balancing friendship with leadership in her seasonal business

[28:42] Allison describes her evolving use of systems and technology to streamline operations and manage growth

[32:54] Allison shares her evolving perspective on team feedback, communication tools, and embracing growth through discomfort

[37:15] Allison’s post-season shift in strategy and vision for guest experience and future concierge services

[39:46] The lightning round

Golden Nuggets:

• "They say, mind over matter, and that's where I really just had to often remind myself, is mind over matter. And having a good mindset around it is what is required to continue on.”
• “The grass is only greener where you water it.”
• “Training our brains to actually recognize when those...

Ever wondered how to turn your short-term rental into more than just a stay—but a shopping experience?

In this episode, I sit down with Nisha Franklin, co-founder of From Where, a platform that turns your STR into a fully shoppable experience. Imagine your guests falling in love with your mattress, coffee table, or artwork—and then being able to purchase those exact items through your personalized digital storefront.

Nisha’s path to entrepreneurship is anything but typical. From her days as a marketing maven in Los Angeles to running a cheese education business, she and her husband David stumbled on a brilliant idea while vacationing in Hawaii. Their lightbulb moment? Creating a platform where hosts can effortlessly monetize the items guests constantly ask about, earning commissions on every single sale.

We dive into the nuts and bolts of how From Where works, including how to set up your storefront, source forgotten items, and start generating new income streams. Nisha also shares insider tips on promoting your digital store, the types of products guests love most, and how even local furniture finds can be made shoppable.

Beyond the tech and strategy, this conversation is a refreshing look at entrepreneurship, time management, and building a community-driven platform. Whether you’re a seasoned host or just getting started, Nisha’s insights will inspire you to see your short-term rental not just as a place to stay—but as a goldmine of untapped opportunity.

HIGHLIGHTS AND KEY POINTS:

[00:46] A short introduction about our guest Nisha Franklin and including how she first got started in the short-term rental space and what drew her into the industry

[05:17] Nisha explains what From Where is — a unique platform designed for hosts to share, recommend, and earn from the products they use in their properties — and why it’s becoming a valuable tool for the STR community

[07:25] How hosts without receipts or with locally purchased items can still participate on FromWhere and create storefronts that reflect their property’s style

[10:04] Nisha talks about the items that are trending on FromWhere storefronts

[10:48] Nisha walks us through the From Where sign-up process, explaining how pricing works, what commissions look like, and how hosts can leverage promotions to boost their earnings

[14:08] Nisha describes how timing for sales varies depending on host engagement and promotion

[16:09] How Nisha juggles multiple businesses and family life through planning and time blocking

[18:00] Nisha shares her vision for From Where’s growth over the next five years and how she relies on her tech-savvy team to power the backend

[20:37] The lightning round

Golden Nuggets:

• "Don't be afraid to make mistakes.”
• “The biggest failure is not the mistake itself. It's failing to learn from that mistake.”
• “When we have that one thorn in our side, that one pain point, if we ignore it and we just say, Oh, it'll go away; It might, but it might come back to bite you in the future. So take care of that pain point, solve the problem.”

Lets Connect:

Website: https://fromwhere.com/

Facebook:

Are you ready to discover how one woman walked away from a six-figure tech career to build a 25-property short-term rental empire in just one year?

In this episode, I sit down with Chelsea Cutrer, whose story is as bold as it is inspiring. Chelsea started like many hosts—frustrated with a management company that was nickel-and-diming her while neglecting her property. After uncovering mysterious charges and damage to her property that had been ignored for months, she made the gutsy decision to take control of her rentals herself.

Using her tech background and determination, Chelsea streamlined operations with tools like OwnerRez and PriceLabs—all while still working her full-time job. Her success was immediate, and soon other property owners were asking her to manage their rentals. What began as self-preservation quickly grew into a thriving business.

Chelsea opens up about scaling from managing two properties to 25, the challenges of rapid growth, and the lessons she learned about delegating to a virtual assistant. She also shares why she only takes on properties and owners that align with her vision, maintaining high standards across her portfolio.

Losing her father to cancer shifted her perspective, inspiring her to pursue work that truly excites her rather than staying in a high-paying but unfulfilling career. Chelsea’s journey is proof that pairing systems with passion and courage can lead to extraordinary results. Her insights on owner relationships, property selection, and building a values-driven business are packed with actionable strategies for anyone looking to grow in the short-term rental space.

HIGHLIGHTS AND KEY POINTS:

[01:13] A short introduction about our guest Chelsea Cutrer and how she got into short-term rentals

[03:30] Chelsea explains how lack of transparency and repeated issues with her property manager pushed her to take over and self-manage her rentals

[07:49] How Chelsea’s tech background and sales experience made the transition to self-managing her rental portfolio smooth and manageable

[09:48] Chelsea shares how quickly expanding from two to four properties convinced her to pursue short-term rentals full time

[10:49] Chelsea explains how leaving her tech job and helping others with their setups naturally grew into a co-hosting business that evolved into full-time property management

[12:22] Chelsea shares how mentoring others on tech and self-management grew into co-hosting, which later transitioned into full-time property management

[14:45] How shifting from coaching to full-service management led Chelsea to refine her offerings and streamline her business model

[16:18] Chelsea talks about her owner acquisition process and how her established business attracts more leads than she can handle, allowing her to be selective with owners based on fit, quality, and revenue goals

[18:07] How Chelsea evaluates potential properties for revenue, condition, and fit, while being honest with owners about whether she can take them on

[19:38] How Chelsea vets owners to gauge their openness to upgrades and alignment with delivering a great guest experience

[21:12] Chelsea shares how she’s growing her team with tech tools, a VA, and a real estate license while evaluating the best path for future expansion

[22:29] Chelsea reflects on how losing her father shifted her perspective from chasing money to pursuing passion and fulfillment in real estate and...