The Luxe and The Short of It

Madeleine Raiford-Holland
  • 5.0 (35)
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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. 6D AGO

    RECAST: Brianna Amigo | Hospitality Hacks: Creating Spaces Guests Love

    This is a a recast from 2/2/25. 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 Brianna Amigo of Brianna Michele Interiors. During the conversation, Madeleine and Brianna explore the intersection of creativity and practicality, emphasizing the importance of balancing style with functionality. They discuss how attention to detail and thoughtful choices can transform a space, creating unique experiences that leave lasting impressions. You'll discover the evolving landscape of design and how emerging tools and resources are reshaping the way professionals approach their work. With a focus on efficiency and innovation, Brianna shares strategies for simplifying processes while maintaining high standards. Brianna's journey demonstrates how thoughtful planning and a clear focus on values can lead to meaningful opportunities and sustainable success. This dynamic discussion offers a refreshing perspective on blending artistry with practicality, leaving listeners motivated to explore their own creative possibilities. 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: Brianna's transition from marketing to design, highlighting her 10 years of experience in the corporate marketing space. The importance of relying on data to identify use cases and design strategies that outperform competitors. The challenges of running a business and the fulfillment of creating her own path. Brianna's must-have features for short-term rentals, including white linens and sheets, full-length mirrors, luggage racks, and universal chargers.And much more... Guest Bio: Brianna Amigo is the founder of Brianna Michele Interiors, a design firm specializing in transforming short-term rental (STR) properties into standout spaces that drive increased revenue through strategic, scroll-stopping design. With a background in corporate marketing and a deep understanding of target demographics, Brianna blends creativity with data-driven insights to craft memorable guest experiences that enhance brand visibility. Her passion for design stems from a childhood immersed in creativity, influenced by her father, a chef and musician. After identifying a significant gap in the STR design market, Brianna pivoted her focus in 2020, leveraging her skills as an interior designer and Airbnb Superhost. Today, she collaborates with her dedicated team on STR, residential, and commercial projects nationwide. https://www.madeleineraifordholland.com/streamlined Resources: Brianna's Instagram Brianna Michele Interiors 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...

    52 min

  2. FEB 10

    RECAST: Successful Habits of the Purposeful Mind

    This is a a recast from 2/2/25. We will be back next week with a regular episode. Madeleine reflects on the practices and tools that have shaped her journey from a stressed-out nine-to-fiver to a thriving entrepreneur with time and financial freedom. Drawing from personal experiences, she shares the value of intentional goal-setting, effective habit formation, and practical strategies to maintain focus and balance in the midst of a busy life. From planning quarterly goals with the Epic Life Planner to incorporating small but meaningful habit stacks inspired by Atomic Habits, Madeleine explains how these methods create lasting change without overwhelming your day-to-day routine.   You'll discover the importance of creating space for reflection and recalibration. By sharing her own experiences with yearly planning alongside her husband, Madeleine emphasizes how aligning personal and professional goals has helped set the trajectory for their life and business. She introduces the concept of the "sacred pause," a deliberate practice of stepping back to assess priorities, avoid burnout, and reconnect with purpose.  Whether it’s rethinking how you set goals, simplifying your daily habits, or carving out time for self-reflection, this episode serves as a reminder that the life you envision starts with the choices you make today.  If you've enjoyed this episode of the The Luxe and the Short Of It podcast, be sure to leave a review and subscribe today! In This Episode You'll Learn: How tools like the Epic Life Planner and quarterly goal-setting can help you focus on specific areas of your life while embracing the idea that you can’t do everything all at once.  How small, actionable changes—like pairing new habits with existing ones—can simplify routines and make it easier to achieve your goals consistently.  Why stepping back to reflect on your priorities and align them with your larger purpose is essential for avoiding burnout and driving personal and professional growth.  Why breaking down ambitious goals into smaller, manageable steps leads to long-term success, with examples of practical tips for building momentum.And much more... 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.

    16 min

  3. FEB 2

    35 Lessons on My 35th Birthday

    It’s a double celebration! In this episode, Madeleine rings in her 35th birthday while also celebrating the one-year anniversary of The Luxe and the Short of It. Reflecting on the contrast between her 30th birthday and where she stands today, Madeleine shares the wisdom gained from a year of "evolving in public." From breaking into the Top 75 Business Podcasts to the quiet grit of consistency, this episode is a heart-to-heart on what it truly means to build a life and business of freedom. Inside the EpisodeThe Power of One Year: A look back at the milestones, the guest experts like Amy Pierce and Brianna Michelle, and the lessons learned from showing up consistently.The Birthday Contrast: Why 35 feels lighter than 30, and the shift from "surviving" to "actively creating" a life you love.Evolving in Public: Navigating the "not-so-fun" moments of failing out loud and why the internet rewards honesty over polish. 35 Things I Know for SureMadeleine counts down 35 life and business lessons that have shaped her journey. Here are a few highlights: On Presence: You do not need to be louder to be heard; calm confidence is magnetic.On Growth: You are allowed to evolve in public without having it all figured out.On Consistency: Showing up when no one is watching builds more trust than being perfect.On Boundaries: You can love your business without centering your whole life around it.On Joy: Joy is allowed now, not just later when you hit a certain milestone. Are you ready to start your own year of evolution? If you enjoyed this episode, please hit the follow button or the (+) sign on your app so you never miss a weekly drop. 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.

    11 min

  4. JAN 26

    Ditching the Guru Advice: A Realistic Morning Routine for Busy Entrepreneurs

    In this episode, Madeleine breaks down her actual morning schedule as a seven-figure business owner, mother of two, and military wife. She pulls back the curtain on why she ignores some common "expert" advice—like staying off your phone—and how she uses "habit stacking" to ensure her team is supported while she prioritizes her own mental and physical health. Key TakeawaysReject the "All or Nothing" Mentality: You don't need a two-hour meditation session to be successful. Three minutes of reading or one minute of gratitude is better than zero.The "Zero Bottleneck" Strategy: Madeleine spends 12 minutes on her phone early in the morning specifically to clear hurdles for her team so they aren't waiting on her to start their day.Hydrate Before You Caffeinate: One of Madeleine's non-negotiables is 16oz of electrolyte water before the first cup of coffee. What does your morning look like? Reach out to Madeleine on Instagram or leave a comment in the show notes to share your routine! Resources:Project Management: Monday.com Communication: Slack Wellness: Electrolytes and Pilates 🔗 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.

    13 min

  5. JAN 19

    Built for Freedom, Not Burnout: Why Most STR Businesses Break Their Owners

    In this episode, Madeleine dives deep into the "invisible cost" of the short-term rental (STR) industry: burnout. While many people enter the space for financial freedom, they often neglect the systems required for time freedom. Madeleine explores why hobby hosting is no longer viable in 2026 and introduces her "Freedom First Framework"—a strategic roadmap designed to help you build a business that supports your life rather than one you need to escape from. Key TakeawaysThe Emotional Failure: Most STR businesses don’t fail because of the numbers; they fail because the owner burns out from being "on" 24/7, dealing with decision fatigue and reactive problem-solving.Professionalization is Mandatory: The "Airbnb Bust" is really just the industry professionalizing. Hobby hosts who refuse to treat their rentals as a real business with systems will struggle to survive.Automate Before You Scale: The biggest mistake hosts make is trying to "retrofit" systems after they already have multiple properties. The complexity of guest messaging and logistics snowballs—build the foundation with property one.The Marble Analogy: Prioritize your "big things" (family, health, relationships) first. If you fill your life with the "sand" of business busy-work first, there will be no room for what matters most. The Freedom First FrameworkDesign Before You Scale: Know exactly what you want out of life and business. Focus on quality over quantity to command premium prices.Automate Before Adding Doors: Use Property Management Software (PMS) from day one. Build the framework first, then "plug and play" new properties into it.Build a Team Sooner Than Feels Comfortable: Hire a Virtual Assistant (VA) around the 4–5 property mark to handle guest messaging and coordination.Standardize Everything: Aim for operational efficiency. Use the same linens, towels, and even the same TV brands (e.g., Samsung) across all properties to simplify troubleshooting.Let Go of Control Without Losing Quality: Create SOPs (Standard Operating Procedures) for everything you do more than twice. Get the information out of your brain and into a shared system (like monday.com). Resources:Costa Rica Retreat: (March 3rd–8th, 2026) A pause for conscious operators to evaluate their work-life integration. https://www.madeleineraifordholland.com/accelerate-your-str-retreat Monday - https://try.monday.com/madeleine 🔗 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...

    20 min

  6. JAN 12

    The "Airbnb Bust" Myth

    Welcome to 2026! To start the New Year, Madeleine tackles the controversial "Airbnb Bust" narrative head-on. While headlines and major real estate influencers claim the market is oversaturated, Madeleine argues that the industry isn't dying—it’s professionalizing. The era of "hobby hosting" and "half-assing it" is over. The hosts who are being squeezed out are those who failed to treat their properties like a business. For the serious investor, Madeleine explains why there has never been a better time to enter the space, provided you have the right systems, brand standards, and data-driven mindset. Key TakeawaysThe "Bust" is a Filter: The market isn't crashing; it's shedding low-quality hosts who entered during the "cheap money" era of COVID.Brand > Listing: Successful hosts in 2026 focus on building a recognizable brand (like Westin or Four Seasons) rather than just individual listings.The Power of Direct Booking: Owning your book of business and direct booking websites is essential for long-term stability.Data is Information, Not Emotion: To survive saturation, you must be "emotionally regulated" and pivot based on what your numbers are telling you.The Four Pillars of a Winning Deal: Every investment should win on Equity, Cash Flow, Appreciation, and Tax Depreciation. 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.

    16 min

  7. 12/22/2025

    Wealth Mastery for the 99% with Robert Annable

    Madeleine welcomes Robert Annable, President and Wealth Advisor of Wealth Strategies Advisory Group. They dive deep into financial strategies that the ultra-wealthy have used for generations to multiply and protect their wealth. From the mechanics of Infinite Banking to the "Virtual Family Office" model, this conversation is a masterclass in shifting your mindset from a standard investor to a legacy builder. Madeleine also shares a massive announcement for her mentorship community regarding their new partnership with Robert’s team. Key Takeaways The Psychology of MoneyThe Taboo Factor: People are often more comfortable talking about their personal lives than their finances due to insecurity and the complexity of the industry.No Wrong Moves: You’ve done the best you could with the information you had; the goal now is optimization, not regret. Infinite Banking (Privatized Banking)Robert explains a contrarian way of thinking about cash flow that allows your money to work in two places at once. The Concept: Using a specifically structured life insurance policy as a personal bank.Uninterrupted Compound Growth: Unlike a traditional bank or a 401k loan, when you "borrow" against your policy to buy a short-term rental, the original capital continues to earn dividends as if you never touched it.Living Benefits: Shifting the focus from "death insurance" to a "living benefit" that provides liquidity, control, and optionality while you are alive. The "Virtual" Family OfficeMadeleine and Robert discuss how to democratize the financial structures of the ultra-wealthy. What is a Family Office? Traditionally, it’s a dedicated team (CPA, Attorney, Wealth Manager, Real Estate Experts) employed by one family to coordinate every financial move.The Virtual Model: Robert’s firm provides this coordinated "General Contractor" approach to growing investors, ensuring that tax, legal, and investment strategies aren't siloed but working together. Big News for the Mentorship CommunityMadeleine announces that Robert Annable’s team is officially partnering with her mentorship program. Direct Access: Mentorship clients will now have access to Robert’s team of 13+ specialist advisors via Slack and office hours.Holistic Growth: The partnership aims to bridge the gap between "buying properties" and "managing a multi-generational wealth empire." Resources:Explore Robert’s Wealth Strategies Advisory Group: https://www.wsagus.com/ 🔗 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: a...

    53 min

  8. 12/15/2025

    The Money Boss with Rachel Evans

    Madeleine welcomes her CFO, Rachel Evans, to demystify the financial management of a growing short-term rental (STR) business. Rachel, who started as a client in Madeleine's mentorship program, offers a unique perspective blending STR hosting experience with deep accounting and finance expertise. They dive into the critical steps for setting up your business finances correctly from day one, avoiding costly cleanup, and structuring your "money team." Rachel shares practical, actionable advice on technology tools, what to look for in a bookkeeper, and the key financial check-ins you need to be doing monthly, quarterly, and annually to optimize for taxes and true profitability. Key Takeaways & Actionable AdviceAct Like the CEO: The number one takeaway is to get organized financially so you can focus on high-level tasks. Action: Implement QuickBooks and hire a good bookkeeper specialized in STRs. (Madeleine notes a 30% off six months link for QuickBooks in the show notes). Monthly Financial Statements are a Must: If your bookkeeper isn't providing monthly financial statements for your business (not just owner statements), it's a major red flag. You need these to make educated decisions. The Power of Specialized Bookkeeping: Find a bookkeeper who understands the complexity of STRs—especially if you have multiple entities (property management, individual LLCs) and various income streams. They should provide managerial accounting where your statements are actually useful for decision-making (e.g., tracking supplies, maintenance by property). Your Essential Money Team: You need three key roles to succeed: Bookkeeper: Prepares monthly financial statements and reconciles accounts.CPA: Files taxes and handles compliance.Tax Strategist: Looks forward to recommend strategies (like property purchases or renovations) to reduce tax liability. Top Bookkeeper Interview Questions: Do you have experience with short-term rentals (STRs) and understanding the unique income/expense flow?What is your attention to detail? Will you track and log which bank account/card ties to which property? Recommended Tech Stack: QuickBooks: Industry standard, easy bank linking, and CPAs can often log in directly.VR Platform (now VR Trust): Automates STR accounting by pulling in listings, property management, and booking platform data (Airbnb, VRBO) to help reconcile owner statements.Relay Financial: (Madeleine's choice) Recommended for bank account reconciliation and visibility. Scaling Expense Tracking: At scale (5+ properties), using a single ordering card and consolidating expenses can be easier than managing multiple property-specific cards. System: Use a platform like Monday.com for...

    31 min
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Trailer

5
out of 5
35 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

Information

  • Creator
    Madeleine Raiford-Holland
  • Years Active
    2025 - 2026
  • Episodes
    46
  • Rating
    Clean
  • Copyright
    © 2025 MHM Luxury Properties. All rights reserved.
  • Show Website
    The Luxe and The Short of It

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