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/

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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...

In this episode, I sit down with Robin Spires, a designer with over 20 years of experience who has mastered the art of creating unforgettable short-term rental spaces. What began as a challenging divorce became the spark that launched her into the world of STR design, where she discovered that the real magic isn’t just in style—it’s in crafting an experience guests can’t stop talking about.

Robin shares some of her most creative strategies, from handcrafting hot pink gumballs to drilling vintage statues so they blow bubbles—quirky touches that have become signature features in her rentals. These unique design choices don’t just look cool—they turn guests into raving fans who leave glowing reviews and spread the word far beyond Airbnb.

We also dive into the practical side of design. Robin reveals how she studies the competition to identify what’s standard versus what will make a property stand out. She breaks down her philosophy on balancing creativity with budget, proving you don’t need a massive overhaul to create impact—a little spray paint, resourcefulness, and vision can completely transform a space.

From the psychology behind guest experiences to the marketing power of Instagram-worthy design, Robin’s approach is both refreshing and actionable. Her story of reinvention and her practical tips will inspire you to rethink your own short-term rental and see design as more than décor—it’s the key to creating a business that thrives.

HIGHLIGHTS AND KEY POINTS:

[01:05] A short introduction about our guest Robin Spires and shares how her journey from marketing to motherhood, vintage retail, and interior design led her to being an STR host

[03:58] Robin explains how her divorce became the push she needed to finally bring her vision for her farmhouse guest cottage to life, creating a whimsical and one-of-a-kind short-term rental

[06:37] Robin’s approach to setting realistic budgets before deciding what investments are truly necessary

[08:44] How Robin layers intentional design, playful details, and guest-centered research to create spaces that spark emotional connections

[15:43] Robin’s shares the the most missed marketing opportunities when it comes to design

[17:20] How phasing updates and reusing quality pieces can create a polished design without overspending

[20:01] Robin shares how she reimagines overlooked pieces with creativity while balancing budget, durability, and design vision

[24:11] Robin shares the important pieces that she likes to invest in from a design perspective

[26:36] What are Robin’s go-to places for sourcing commercial-grade products and unique design pieces

[30:23] Robin shares some of the quirky and unconventional design choices she’s incorporated into her projects

[32:06] Robin shares her favorite tips and hacks for designing small spaces on a budget

[34:46] What are the key questions to ask before hiring a designer

[37:43] Robin’s guidance on deciding whether to design yourself or hire a professional

[40:14] The lightning round

Golden Nuggets:

• "It's so important if this doesn't come naturally for you, partner with someone, collaborate with someone who it is their natural, God given talent.”
• “Even if you don't have all the money in the world, don't be afraid to engage a professional, because this is business for most of...

Are you worried that partnering with family in real estate will strain your relationships?

In this episode, I sit down with Annchen Knodt, a neuroscience researcher who joined my STR Accelerator program during its very first beta launch. Annchen’s story is a powerful example of how building an Airbnb business with family can work—even when things get messy.

She opens up about the reality of partnering with her parents: the disagreements that got heated, what it felt like to be outvoted, and the boundaries they created to protect family dinners from turning into business meetings.

Annchen also faced another challenge—having a spouse who wasn’t sold on the time and energy she was putting into real estate investing. She shares the loneliness of being the only one in her circle excited about Airbnb and short-term rentals, and how finding a community of like-minded women gave her the courage to keep moving forward.

From waking up early to analyze deals before heading into the lab, to answering Airbnb guest messages between experiments, Annchen’s dedication shows what’s possible when you refuse to let excuses hold you back. She even reveals the breakthrough moment she realized she was much closer to financial freedom than she thought.

Her journey proves that success in Airbnb and real estate isn’t always about scaling fast or building an empire—it’s about creating a business that supports the life you truly want. With the right systems, boundaries, and support, both family and business can thrive side by side.

HIGHLIGHTS AND KEY POINTS:

[01:06] A short introduction about our guest Annchen Knodt and what she does outside the short-term rental space

[05:38] Annchen shares how she overcame the common fear of partnerships especially when working with her parents

[08:59] Annchen recounts the process of deciding to sell one of the long-term properties she co-owned with her parents in Texas

[11:11] How a major challenge tested Annchen’s family partnership and revealed the importance of balancing values with business decisions

[14:45] Annchen shares how blending business with family creates harmony rather than conflict

[17:30] Annchen opens up about the challenges of pursuing real estate when her spouse shows little interest and how she found strength through community and mindset

[21:44] How accountability pods provided the structure, support, and community Annchen needed to set goals, stay consistent, and feel less alone in her real estate journey

[26:20] How redefining success beyond rapid portfolio growth allowed Annchen to embrace financial independence more holistically and prioritize family, passive investing, and a fuller life

[30:05] Annchen shares how embracing pivots and diversification clarified her dream life, strengthened harmony at home, and renewed her joy in the process

[35:59] How finding and building community has been essential for overcoming isolation in real estate investing and hosting

[38:02] The lightning round

Golden Nuggets:

• “Life is way too short not to enjoy what you're doing.”

• “If you really want to achieve something that's beyond your comfort zone, that's pushing the boundaries of what you've done in the past.”

• “At the end of the day, living your best life is knowing what you want.”

• “Look for a coaching program. Join a coaching program. It's always worth the investment. Talk to other people who are already in the program to get some feedback. From them, you can learn pretty quickly whether it's worth the investment.”

• “Live below your means, something that I had been taught growing up, basically, but it's what's put me in the position, to be able to invest fairly early in life, and then to be able to...

What if the career you’d worked decades to build was the very thing holding you back from the life you actually wanted?

In this episode, I sit down with Kerri Gibson, a former CPA who built a thriving hospitality empire in Quebec. After 22 years in tax and accounting software, Kerri’s breaking point became her breakthrough when a simple house flip spiraled into seven renovated ski chalets—and eventually a full-scale motel transformation. Kerri opens up about the toll of burnout and the moments she missed with family because work always came first. She shares how she and partner Philip navigated the tricky shift from colleagues to business partners to spouses working side by side, and how a few uncomfortable conversations ultimately strengthened both their relationship and their business. Most impressively, Kerri has achieved what many hospitality owners dream of: 70% direct bookings through her own website—without relying on OTAs. She walks us through the exact strategies she built from the ground up, plus how she infused their signature “hygge” concept into a roadside motel, transforming it into a place where guests connect and create lasting memories. Packed with real-world advice and hard-earned wisdom, this episode is a must-listen for anyone feeling stuck—whether you’re plotting your escape from corporate life or striving to build a hospitality business that truly reflects your values.

HIGHLIGHTS AND KEY POINTS:

[01:16] A short introduction about our guest Kerri Gibson and how she got into the world of short-term rentals [03:27] Kerri shares her journey from from CPA to tech leader in tax and accounting software [06:28] Kerri’s breaking point that pushed her to leave the corporate world [13:20] Kerri reveals her two-question strategy for making big decisions without a support system [21:06] Kerri recounts her journey from renovating distressed chalets to revitalizing a roadside motel [25:39] Kerri outlines her vision to reinvent the roadside motel experience through Scandinavian-inspired design and communal spaces [30:17] The challenges and growth that come from defining roles when running a business with a spouse [38:04] How Kerri shifted from relying entirely on OTAs to achieving 70% direct bookings [45:15] The power of starting early with a strategy and evolving it over time [48:08] Kerri talks about her self-taught marketing journey and how she strategically brought in outside expertise [52:39] The lightning round

Golden Nuggets:

• “Find coziness, comfort and the simplicity of the small moments of life surrounded by those that you love the most.” • “I had to learn to find space for him to be a part of the business and flourish. And as we've defined, find our swim lanes, which is super important. It's allowed us to find, like these great things that go in sync together. You know, the Ying and the Yang.” • “Never, ever, ever build your house on someone else's land, no matter how small you are.” • “You have to create the strategy, then go implement the strategy. But without that strategy-first approach, it's just like throwing spaghetti at the wall and hoping that something works.” • “There's nothing you can't do, or nothing you can't be, there's only what you're willing to work for.”

This episode is brought to you by ⁠⁠⁠⁠⁠⁠Lodgify⁠⁠⁠⁠⁠⁠!

👉 Use the code STRSH20 at checkout for 20% off any yearly plan and start owning your bookings today.

🔗 ⁠⁠⁠⁠⁠⁠Visit Lodgify.com

Let’s Connect!

LinkedIn: https://linkedin.com/in/kerri-gibson-cpaInstagram: https://www.instagram.com/kerri_reinventedEnjoyed the show? Subscribe, Rate, Review, Like, and...

In this mind-opening episode, I sit down with Dawn Asher, the creative force behind The Olive Jar, to explore the powerful intersection of neuroscience and hospitality marketing. Dawn isn't your typical branding expert—she’s a master of emotional design, turning short-term rentals into sensory-rich experiences that guests rave about (and return to).

We dive into the science of human behavior, breaking down how neurochemicals like dopamine and oxytocin shape memory, emotion, and connection. Dawn reveals how to harness these neurological triggers through intentional design choices, subtle surprises, and personalized moments that leave a lasting impact.

This episode is packed with practical strategies that go far beyond throw pillows and curated art. We’ll challenge the traditional idea of luxury and explore why true hospitality is about making guests feel understood, valued, and emotionally engaged. You’ll walk away with fresh inspiration—and a toolkit rooted in science—to turn your property into a story your guests won’t stop talking about.

Tune in now and discover the neuroscience behind next-level guest experiences!

HIGHLIGHTS AND KEY POINTS:

[01:14] A short introduction about our guest Dawn Asher and introduces her creative studio that enhances the guest experience through immersive marketing and storytelling [03:33] Dawn explains the science behind memorable guest experiences and how hosts can use neurological triggers to build trust and emotional connection [09:32] Dawn and I discuss the myth that five-star reviews stem solely from luxury items and consider where emphasis should be placed to ensure guest satisfaction [13:10] Dawn’s advice to decoding guest identity to create deeper brand resonance [17:10] How hosts can uncover what their ideal guests want and use it to create emotionally resonant experiences [22:30] Why emotional intelligence is the real driver of STR success [29:25] How thoughtful post-checkout nurturing helps to shift from transactional stays to lifelong touchpoints [33:34] Dawn dives into the often-overlooked treasure trove of travel content and inspiration that exists online [36:11] Dawn talks about how to use AI as a brand amplifier [37:47] Dawn reveals how hidden design details spark memorable dopamine hits [42:25] Dawn shares the importance of listening to your turnover team as a key source of insight into what guests actually use and what might just be taking up space [45:53] The lightning round Golden Nuggets:

• “The more that you do to build that trust with your traveler, when those bumps come, there is going to be less friction.” • “If you've been nurturing that relationship long before they arrive, you're activating that hippocampus to tell them you're safe. I've got you. I'm gonna get this taken care of.” • “The best way to get five star reviews, we have to actually provide five star service, and the rest will follow.” • “If you're in this business, you have to invest in yourself personally. You have to care about that traveler that you're serving. And if you don't, you will keep hitting this wall.” • “It's about creating an experience for a guest that they're going to remember and come back to us. And we don't do that through the bottom line of a P& L.”

This episode is brought to you by ⁠⁠⁠⁠⁠Lodgify⁠⁠⁠⁠⁠!

👉 Use the code STRSH20 at checkout for 20% off any yearly plan and start owning your bookings today.

🔗 ⁠⁠⁠⁠⁠Visit Lodgify.com

Let’s Connect! Website: www.theolivejar.co Instagram: https://www.instagram.com/theolivejar.co/ Enjoyed the show? Subscribe, Rate, Review, Like, and Share!

Have you ever wondered if there’s a smarter, more profitable way to rent your property—hidden in plain sight?

In this episode, I sit down with Aisha Govani—a dynamic entrepreneur who turned financial rock bottom into a midterm rental success story. From living in her in-laws' basement with two young kids and zero income during COVID, Aisha and her husband rewrote their future through grit, resilience, and an entirely new approach to real estate.

We dive into the world of midterm rentals, where Aisha reveals how this overlooked strategy can be your golden ticket—especially if you’re battling short-term rental restrictions. She breaks down how she built a thriving platform connecting independent hosts with corporate clients, turning properties into profit through business-to-business bookings.

You’ll get actionable tips on everything from cold calling corporate contacts, networking with relocation agencies, to landing contracts with insurance companies. Aisha peels back the curtain on how to structure deals, vet hosts, and maximize bookings—all while building a sustainable, values-driven business.

This isn’t just a roadmap for better bookings—it’s a blueprint for reinvention. Aisha’s story will challenge you to rethink your strategy and show you what’s possible when you bet on yourself. Get ready to turn resilience into revenue and learn why midterm rentals are the smart investor’s next big move!

HIGHLIGHTS AND KEY POINTS:

[01:01] A short introduction about our guest Aisha Govani and her journey from nonprofit work to real estate entrepreneurship

[06:07] Aisha recalls the tough COVID days living in her in-laws’ basement, where grit triumphed over fear

[09:56] The importance of commitment over hesitation, framing failure as an essential step toward mastery and fulfillment

[13:30] How Aisha’s own entrepreneurial evolution reshaped her view on education to empower her children with personalized, real-world education inspired by her entrepreneurial growth

[17:18] Aisha talks about the intensive work behind securing B2B midterm rental bookings and how her platform simplifies access for independent hosts

[22:45] Aisha explains why cold calling often triggers discomfort and shares the key to overcoming

[25:38] Aisha breaks down how to identify decision-makers for B2B bookings and highlights the mindset and approach needed to succeed in cold calling

[30:49] How Aisha’s midterm rental platform connects hosts to both B2C and B2B bookings with a focus on ease and quality of guests

[32:24] Aisha + details the streamlined vetting process for hosts on her platform and highlights high-demand areas, especially in the Greater Toronto Area

[35:57] The lightning round

Golden Nuggets:

• “Decide and ignore the noise.”

• “I always choose grit over fear.”

• “There are days I wake up and I'm like, should I be doing this? Is this the right choice? What have I decided to do? Can I even do this? Am I capable of doing what I think I can do? And when those questions come into your brain, you're really the only one that can quiet it. So I always try to choose, one foot, one foot, one foot. Don't worry about the rest of the race.”

• “We have to commit to what we want first before we do anything else.”

• “What I would say to anyone who's trying to cold call anything is, when you call that person, you speak to them like you're providing a solution for their problem.”

• “It's going to be harder than you think, but networking is going to be a large part of the answer.”

• “If you work on your mind and your body, all else will align.

This episode is brought to you by