The Luxe and The Short of It

Madeleine Raiford-Holland

What if you could swap burnout for freedom? Host Madeleine Raiford Holland—military wife, mom, and 7-figure entrepreneur—escaped the 9-5 grind by building a short-term rental empire. Now, she teaches you how to reclaim your time, income, and joy through short-term rentals and real estate investing, mindset shifts, and systems that align with your priorities. Each week, get no-nonsense strategies for scaling rentals, overcoming fear, and designing a life where work fuels your passions (not the other way around). With solo episodes, expert guests, and raw stories of wins and mistakes, this podcast is your roadmap to financial freedom and intentional living. Ready to trade burnout for a legacy? Hit follow—your "Luxe Life" starts now. Discover more here: https://www.madeleineraifordholland.com/podcast-insider

  1. 1d ago

    Investing in Artists, Not AI | Meredith Raiford Akins

    Madeleine is joined by her lifelong best friend and sister, artist and muralist Meredith Raiford Akins. It's a true family affair as the two discuss the sweet privilege of navigating the "golden season" of life, raising their kids just minutes apart, and building dynamic businesses side-by-side in Athens, Georgia. While Madeleine thrives on systems, delegation, and scaling real estate, Meredith’s world revolves around custom, handcrafted artistry. They dive into these contrasting entrepreneurial styles, discussing the growing pains of transitioning from a solo "jack of all trades" to a systemized business owner, and how your business ultimately becomes a mirror for your own limiting beliefs. For short-term rental investors looking to stand out in a crowded market, this episode is packed with insider design knowledge. Meredith breaks down the true value of custom murals and original art versus mass-produced decor. Discover exactly what goes into commissioning a mural, how pricing works (from square footage to clear-primed linen textures), and why investing in original, human-made art creates the ultimate "stop-the-scroll" moment to boost your bookings and elevate your property's value. Key Takeaways & Highlights: Navigating the "golden season" of motherhood and family entrepreneurship.The stark differences between scaling a systemized real estate business and a custom creative studio.Overcoming the limiting beliefs holding back your business growth.The step-by-step process of commissioning, prepping, and pricing a custom mural.Why original, handcrafted art is the ultimate return on investment for short-term rental hosts. Connect with Meredith: 💼 Portfolio: https://meredithraifordart.com/ 📸 Instagram: https://www.instagram.com/meredithraifordart/ Resources: 🔗 Streamline Workshop Sales Page: https://www.streamlinededucation.co/streamline-your-str-journey-workshop-podcast 🚀 Elevate Workshop Sales Page: https://www.streamlinededucation.co/elevate-your-str-workshop-podcast 💼 Connect with Madeleine on LinkedIn: http://linkedin.com/in/madeleine-raiford-holland/ 🎙️ Join Madeleine's Podcast Insider: https://www.streamlinededucation.co/subscribe-to-podcast-email-list 📸 Follow Madeleine on Instagram: https://www.instagram.com/madeleineraifordholland/ 🌐 Explore Madeleine’s Work & Coaching Programs: https://www.streamlinededucation.co/ 💡 Turn on notifications so you never miss a strategy that could change your life. Disclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Luxe & the Short of It podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

  2. Sep 14

    Demystifying STR Accounting

    In this episode, Madeleine dives deep into the financial side of short-term rentals (STRs). Following up on last week’s conversation with tax strategists Andrew Khubiar and Kirby Kwok from Imperium Advisory, Madeleine shares actionable advice on how to interview tax professionals, adopt the right accounting mindset, and leverage the exact tech stack she uses to manage her multi-figure STR portfolio. Key Takeaways Mindset Shift: Accounting isn't life or death—the numbers on a spreadsheet don't define your self-worth. View business taxes as a partnership with the tax code rather than a penalty.How to Interview a Tax Professional: Avoid asking yes/no questions (e.g., "Do you work with real estate investors?"). Ask open-ended, leading questions like:"What specific real estate investor experience do you have?"Price vs. Value: Paying $10k–$20k for tax strategy doesn't guarantee better advice. Focus on finding professionals willing to educate and empower you.Essential STR Financial Tech Stack:QuickBooks Online: The industry standard for tracking property expenses and collaborating with your preparer.Relay Financial: The ultimate banking platform for STR owners that seamlessly integrates with QuickBooks.Hostfully: Property management software (PMS) to streamline operational automations.Recommended Reading: Profit First by Mike Michalowicz—the essential baseline guide for learning how to structure payments and plan for business profit. Resources & Links Mentioned Book: Profit First: Transform Your Business from a Cash-Eating Monster to a Money-Making Machine by Mike MichalowiczBanking: Relay Financial (Listen to our previous interview with the Relay team in the archives!)Accounting Software: QuickBooks Online (Check link below for host discount code)Property Management Software: HostfullyPrevious Episode: Episode w/ Andrew & Kirby on STR Tax Strategy 🔗 Work With Madeleine's Team - https://strsuccess.typeform.com/podcast 💼 Connect with Madeleine on LinkedIn – http://linkedin.com/in/madeleine-raiford-holland/ 🎙️ Join Madeleine's Podcast Insider: https://www.madeleineraifordholland.com/podcast-insider 📸 Follow Madeleine on Instagram: https://www.instagram.com/madeleineraifordholland/ 🌐 Explore Madeleine’s Work & Coaching Programs: https://www.madeleineraifordholland.com/ 💡 Turn on notifications so you never miss a strategy that could change your life. Disclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Luxe & the Short of It podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk. Subscribe & Review Enjoying The Luxe and The Short of It? Hit the follow button or the + sign on your podcast app so you never miss an episode. Leave us a review and share this episode with a fellow real estate investor!

  3. Sep 7

    What Your CPA Isn't Telling You About Short-Term Rentals | Andrew Khubiar and Kirby Kwok

    In this episode of The Luxe and the Short of It, Madeleine is joined by tax strategists Andrew Khubiar and Kirby Kwok from Imperium Advisory. Together, they pull back the curtain on short-term rental (STR) tax loopholes, common CPA blunders that cost investors hundreds of thousands of dollars, and why educating clients to take control of their financial picture is the ultimate path to long-term wealth. Key TakeawaysThe $400k+ CPA Mistake: Many traditional tax preparers default to marking real estate losses as "passive" out of over-caution or lack of STR knowledge. Working with a specialized STR tax strategist can uncover massive missed deductions—like bonus depreciation.The 7-Day Rule: Under IRS tax code, if the average guest stay is seven days or less, it is not classified as a traditional rental activity. This unlocks unique tax strategies distinct from long-term rentals.Setup Time Counts Toward Material Participation: You don't need to spend hours managing guests every week to hit the 100-hour threshold. Time spent on the initial physical and digital setup, interior design, and system automation counts toward your material participation for that initial tax year.The Aggregation Election Power: If you own multiple STR properties and have automated systems in place, taking the aggregation election allows you to treat all properties as a single activity—making it much easier to meet the material participation hour requirements across your entire portfolio."Imperium" Mindset: Financial freedom isn't about giving total control away to an outside firm. True wealth creation comes from educating yourself (and passing that knowledge to your children) so you remain in the driver's seat of your financial empire. Resources:🔗 Work With Madeleine's Team - https://strsuccess.typeform.com/podcast 💼 Connect with Madeleine on LinkedIn – http://linkedin.com/in/madeleine-raiford-holland/ 🎙️ Join Madeleine's Podcast Insider: https://www.madeleineraifordholland.com/podcast-insider 📸 Follow Madeleine on Instagram: https://www.instagram.com/madeleineraifordholland/ 🌐 Explore Madeleine’s Work & Coaching Programs: https://www.madeleineraifordholland.com/ 💡 Turn on notifications so you never miss a strategy that could change your life. Disclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Luxe & the Short of It podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

  4. Aug 31

    How Vulnerability & True Connection Drive Business Success

    Following up on her conversation with business bestie Jake Sasseville, Madeleine unpacks what it truly takes to move past transactional networking and build deep, transformative professional relationships. She discusses how opening up, active listening, and treating your business as a mirror for personal growth can unlock your true entrepreneurial potential. Key TakeawaysListen to Listen, Not to Respond: True connection requires active presence and genuine curiosity without rushing to solve every problem.Support How They Need It: Shift the dynamic by asking, "How can I best support you right now?" whether that means sounding board, problem-solving, or just holding space.Go a Layer Deeper: Real breakthroughs happen when you ask the extra question to uncover what subconsciously drives surface-level challenges.Business is a Mirror: Your short-term rental business directly reflects the internal mindset and personal growth work you are doing on yourself.In-Person Connection Matters: While digital communities are great, real vulnerability and lasting friendships often spark in face-to-face, intimate environments. Upcoming Events & RetreatsAthens Mini-RetreatDates: May 13th – 14thWhat to Expect: Connect with 250–300 entrepreneurs to build meaningful networks and foster deep business relationships.Costa Rica RetreatDates: March 9th – 14thWhat to Expect: An exclusive, intimate retreat (capped at 20 participants) focused on deep internal work, uncovering your ultimate motivation, and alignment. Connect & SubscribeIf you enjoyed this episode, make sure to hit the Follow button or + sign on your favorite podcast app so you never miss an episode. Resources: 🔗 Streamline Workshop Sales Page: https://www.streamlinededucation.co/streamline-your-str-journey-workshop-podcast 🚀 Elevate Workshop Sales Page: https://www.streamlinededucation.co/elevate-your-str-workshop-podcast 💼 Connect with Madeleine on LinkedIn: http://linkedin.com/in/madeleine-raiford-holland/ 🎙️ Join Madeleine's Podcast Insider: https://www.streamlinededucation.co/subscribe-to-podcast-email-list 📸 Follow Madeleine on Instagram: https://www.instagram.com/madeleineraifordholland/ 🌐 Explore Madeleine’s Work & Coaching Programs: https://www.streamlinededucation.co/ 💡 Turn on notifications so you never miss a strategy that could change your life. Disclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Luxe & the Short of It podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

  5. Aug 24

    What Has the Mirror Taught You? | Jake Sasseville

    Madeleine sits down with truly incredible human being, entrepreneur, and "business bestie," Jake Sasseville. What starts as a reflection on the loneliness of the entrepreneurial journey quickly goes deep into the power of finding genuine community without the pressure of competition. Jake shares his personal evolution from building transactional relationships to fostering regenerative ones, and reveals the deeply emotional inspiration behind his upcoming book, 'A Million Little I Love Yous'. If you've ever struggled with small talk or felt isolated at the top, this conversation will completely shift how you approach human connection. Key Takeaways & Highlights The Business Mirror: How your business acts as a mirror, forcing you to confront your truest self and shed the "suits" or identities you thought you had to wear.Community Over Competition: Why finding your "business bestie" is crucial, and how to build a relationship that is supportive rather than extractive.Asking for What You Need: The simple but profound act of acknowledging when you need support and actively asking for it, rather than accepting the narrative that "it's lonely at the top."A Million Little I Love Yous: Jake opens up publicly for the first time about his upcoming book, detailing the miraculous and emotional three days he spent reuniting with his mother after 16 years apart.The Rollercoaster of Conversation: How leaning into genuine curiosity can instantly transform awkward small talk into meaningful connection. Connect with Jake Sasseville: Book Pre-order | A Million Little I Love Yous by Jake Sasseville (Coming this Fall)Imiloa Institute | Costa Rica-based retreat center founded by Jake Sasseville: https://imiloainstitute.com/Website: https://www.jakesasseville.comInstagram: https://www.instagram.com/jakesasseville/?hl=enTikTok: https://www.tiktok.com/@jakesasseville1YouTube: https://www.youtube.com/@jakesasseville1 Resources: 🔗 Streamline Workshop Sales Page: https://www.streamlinededucation.co/streamline-your-str-journey-workshop-podcast 🚀 Elevate Workshop Sales Page: https://www.streamlinededucation.co/elevate-your-str-workshop-podcast 💼 Connect with Madeleine on LinkedIn: http://linkedin.com/in/madeleine-raiford-holland/ 🎙️ Join Madeleine's Podcast Insider: https://www.streamlinededucation.co/subscribe-to-podcast-email-list 📸 Follow Madeleine on Instagram: https://www.instagram.com/madeleineraifordholland/ 🌐 Explore Madeleine’s Work & Coaching Programs: https://www.streamlinededucation.co/ 💡 Turn on notifications so you never miss a strategy that could change your life. Disclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Luxe & the Short of It podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

  6. Aug 17

    The Myth of the "Right Time"

    Madeleine gives an insider look at what’s in store for this season—including a mix of expert guest interviews recorded on location in Athens and deep-dive reflection episodes. In this reflection episode, Madeleine unpacks a core theme from the latest coaching round-table: why true business growth requires getting comfortable being uncomfortable. From setting self-imposed launch deadlines to "front-loading the hard" with systems and automations, Madeleine shares candid insights on why waiting for the "right time" will hold you back from achieving real freedom. Key Takeaways & HighlightsSeason 3 Structure: Expect a two-part cadence each week—one interview episode featuring industry-leading experts, followed by a solo recap episode where Madeleine breaks down key takeaways and actionable perspectives.The Myth of the "Right Time": Whether it's economic shifts, election years, or global events, there will always be an excuse to wait. The top performers are those who took action anyway and are now reaping the rewards.Front-Loading the Hard: Building systems, setting up automations, and training a team takes upfront time and effort, but doing the hard work early saves you years of manual labor later.Drawing a Line in the Sand: Growth rarely feels comfortable. Setting firm, self-imposed deadlines forces progress and prevents analysis paralysis when launching short-term rentals.Practicing Discomfort in a World of Convenience: Modern life offers endless convenience (DoorDash, Instacart, telehealth), making intentional discomfort rare—and even more essential for personal and business growth. Resources: 🔗 Streamline Workshop Sales Page: https://www.streamlinededucation.co/streamline-your-str-journey-workshop-podcast 🚀 Elevate Workshop Sales Page: https://www.streamlinededucation.co/elevate-your-str-workshop-podcast 💼 Connect with Madeleine on LinkedIn: http://linkedin.com/in/madeleine-raiford-holland/ 🎙️ Join Madeleine's Podcast Insider: https://www.streamlinededucation.co/subscribe-to-podcast-email-list 📸 Follow Madeleine on Instagram: https://www.instagram.com/madeleineraifordholland/ 🌐 Explore Madeleine’s Work & Coaching Programs: https://www.streamlinededucation.co/ 💡 Turn on notifications so you never miss a strategy that could change your life. Disclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Luxe & the Short of It podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

  7. Aug 11

    Progress Over Perfection | Streamlined Coaching Team

    Madeleine is joined by some of the Streamlined coaching team—Alex Akins, Sara Hug, and Mo Harris — to discuss the rapidly evolving landscape of the short-term rental (STR) industry. From the professionalization of property listings to the rise of wellness amenities and AI technology, the coaches break down exactly what it takes to stand out in today's market. Whether you're a seasoned host or just trying to overcome the fear of buying your first property, this conversation is packed with insider expertise, mindset shifts, and the push you need to finally take action. Key Takeaways & Market Trends The Market is Professionalizing: Gone are the days of throwing up listing photos taken on an iPhone without any styling. Success today requires a professional approach, including high-quality interior design, professional photography, and dynamic pricing platforms.Wellness Amenities are Booming: To stand out and increase ROI, hosts are moving beyond basic hot tubs and adding barrel saunas, cold plunges, red light mats, and dedicated yoga/workout spaces to their properties.Tech Makes it Easier Than Ever: While the market is more competitive, advancements in technology and AI API integrations have made managing businesses and streamlining hosting operations much more accessible for newcomers.Action Takers Find Success: The clients who see the most success aren't necessarily the ones with the most experience; they are the ones who commit to making imperfect progress and putting in the work every single day.Give Yourself a Deadline: Overcome "analysis paralysis" and perfectionism by setting strict deadlines for yourself when setting up a property or launching a listing. Resources 🔗 Streamline Workshop Sales Page: https://www.streamlinededucation.co/streamline-your-str-journey-workshop-podcast 🚀 Elevate Workshop Sales Page: https://www.streamlinededucation.co/elevate-your-str-workshop-podcast 💼 Connect with Madeleine on LinkedIn – http://linkedin.com/in/madeleine-raiford-holland/ 🎙️ Join Madeleine's Podcast Insider: https://www.streamlinededucation.co/subscribe-to-podcast-email-list 📸 Follow Madeleine on Instagram: https://www.instagram.com/madeleineraifordholland/ 🌐 Explore Madeleine’s Work & Coaching Programs: https://www.streamlinededucation.co/ 💡 Turn on notifications so you never miss a strategy that could change your life. Disclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Luxe & the Short of It podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

  8. Mar 2

    RECAST: Ami Pierce | What It Takes To Craft A Vibrant Life

    This is a a recast from 1/29/25. We will be back next week with a regular episode. In today's episode of The Luxe and The Short of It podcast, Madeleine is joined by Ami Pierce, the Founder and CEO of A More Better You. During this conversation, Madeleine and Ami explore the intersection of personal growth, creativity, and the power of intentional design. The conversation begins with stories of unexpected journeys, where embracing change and following intuition led to remarkable transformations. Discover the process of crafting spaces that resonate deeply with those who experience them. The dialogue goes beyond surface-level aesthetics, emphasizing the importance of tuning into the unseen elements that create harmony and evoke comfort. With candid anecdotes about personal struggles, moments of realization, and surprising breakthroughs, the episode paints a vivid picture of how thoughtful design can be a form of self-expression and healing. Whether it’s a last-minute retreat or a chance to collaborate, Ami highlights how stepping into the unknown can unlock new connections, purpose, and inspiration. With heartfelt stories and actionable insights, this conversation invites you to rethink what it means to create a life and work that truly align with your passions. If you've enjoyed this episode of The Luxe and The Short of It podcast, be sure to leave a review and subscribe today! Enjoy! In This Episode You'll Learn: Ami's background in finance and her decision to pursue a career in investment banking despite her passion for design.Her decision to leave Coca-Cola in 2023 after a year of preparation, driven by her desire to focus on her creative passions.The value of creating spaces that make people feel good and the role of essential oils and other design elements in enhancing the guest experience. The importance of creating spaces that feel good to be in, drawing on her sensitivity to light, sound, and texture.And much more... Guest Bio: Ami Pierce is the Founder and CEO of A More Better You and A More Better Home, dedicated to helping individuals overcome limiting beliefs and hidden barriers to achieve fulfilling personal and professional lives. After 22 years in the corporate world, including 19 years of outward success masking inner turmoil, Ami hit rock bottom in 2019. A transformative encounter with Mindset Coach Teri Wade at a meditation course helped her break free from burnout, establish healthy boundaries, and rediscover joy. Inspired by her own transformation, Ami introduced growth mindset workshops at Coca-Cola, fostering connection, collaboration, and success across teams. Following the program’s success and its eventual funding cut, Ami left the corporate world in 2023 to pursue her passion for mindset coaching full-time. https://www.madeleineraifordholland.com/streamlined Resources: A More Better You Ami's Instagram Madeleine's Podcast Insider 🔗 Work With Madeleine's Team - https://strsuccess.typeform.com/podcast 💼 Connect with Madeleine on LinkedIn – http://linkedin.com/in/madeleine-raiford-holland/ 🎙️ Join Madeleine's Podcast Insider: https://www.madeleineraifordholland.com/podcast-insider 📸 Follow Madeleine on Instagram: https://www.instagram.com/madeleineraifordholland/ 🌐 Explore Madeleine’s Work & Coaching Programs: https://www.madeleineraifordholland.com/ 💡 Turn on notifications so you never miss a strategy that could change your life. Disclaimer: The views, information, or opinions expressed during this podcast are solely those of the individuals involved and do not necessarily represent those of The Luxe & the Short of It podcast or its affiliates. The content provided is for informational and entertainment purposes only and is not intended to be a substitute for professional advice. We make no representations as to the accuracy, completeness, suitability, or validity of any information on this podcast and will not be liable for any errors, omissions, or delays in this information or any losses, injuries, or damages arising from its display or use. Listeners should consult with a professional for specific advice tailored to their situation. By accessing this podcast, you acknowledge that any reliance on the content is at your own risk.

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42 Ratings

About

What if you could swap burnout for freedom? Host Madeleine Raiford Holland—military wife, mom, and 7-figure entrepreneur—escaped the 9-5 grind by building a short-term rental empire. Now, she teaches you how to reclaim your time, income, and joy through short-term rentals and real estate investing, mindset shifts, and systems that align with your priorities. Each week, get no-nonsense strategies for scaling rentals, overcoming fear, and designing a life where work fuels your passions (not the other way around). With solo episodes, expert guests, and raw stories of wins and mistakes, this podcast is your roadmap to financial freedom and intentional living. Ready to trade burnout for a legacy? Hit follow—your "Luxe Life" starts now. Discover more here: https://www.madeleineraifordholland.com/podcast-insider

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