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The Luxe and The Short of It

Madeleine Raiford-Holland
The Luxe and The Short of It
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  • How to Build Your Kick-Ass Team by Ditching the Resume
    Madeleine reveals her superpower: connecting people, building kick-ass teams, and cultivating a winning company culture.Madeleine dives deep into her unconventional yet highly successful hiring strategy, revealing why she’d rather look for innate skills and culture fit over a resume. If you’re ready to scale your business by finding the perfect people—the "who" instead of the "how"—this episode is a must-listen.Key Takeaways from This EpisodeCulture Fit Over Credentials: When growing her team, Madeleine prioritizes culture fit and innate skills over an impressive resume. In fact, she often hires from established relationships or referrals.Longevity is Key: She looks for candidates who have been in a position or with a company for a long time—they aren't "bouncing around."Focus on Teachability and Leadership: Seek out people who are teachable, pick things up quickly, and have the ability to train and lead others.Hiring from Within Your Orbit: Three of Madeleine’s coaches have come directly from her mentorship program. This strategy serves as the "best long interview they didn't know they had," giving her deep insight into their work ethic, ability to handle adversity, and how they interact with her existing team.Ditch the Resume, Build Relationships: For small businesses, Madeleine encourages listeners to ditch the resume and instead have conversations and see what people do "out in the real world" to ensure everyone is united toward a common goal and shares the right team mentality.Resources MentionedBook: Who Not How: The Formula to Achieve Bigger Goals Through Accelerating Teamwork by Dan Sullivan and Benjamin Hardy (https://urlgeni.us/amzn/whonot)If you've enjoyed this episode of The Luxe & the Short of It podcast, be sure to leave a review and subscribe today!Enjoy!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.Mentioned in this episode:Pricing Bootcamphttps://www.madeleineraifordholland.com/str-pricing-bootcamp
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  • Scaling Your Business with Financial Clarity and Less Stress
    Madeleine welcomes Robyn Myer, a standout member of the direct acquisition team at Relay: a business and money management platform specifically designed for small and mid-sized businesses.Implementing the Profit First MethodRobyn explains that the Profit First system flips the traditional accounting formula (Revenue - Expenses = Profit) to Revenue - Profit = Expenses. This crucial mindset shift ensures you pay yourself first, forcing your business to operate within the remaining expense budget.The Problem with Traditional Banks: Many banks make it difficult and expensive to open the multiple accounts needed for the Profit First method.Automation is Key: Utilize auto-transfer rules to automatically move funds between accounts based on percentages. This ensures consistent allocation for profit, owner's compensation, taxes, and operating expenses, even during busy periods.Frequency: While Profit First recommends twice a month, Relay users can set transfers to run daily or weekly, especially when starting out or receiving frequent, inconsistent deposits like those from STR platforms like Airbnb.Gaining Cash Flow Visibility and OrganizationA common blind spot for STR hosts is feeling "in the dark" about their cash flow, even if they track revenue well.Stay Organized from the Start: It’s critical to know what you're making, what’s tied to specific expenses, and what is your actual profit. This requires setting up systems and processes.The Danger of Commingling Funds: Robyn emphasizes the number one rule: do not commingle personal and business finances.Scaling with Clarity: As you grow from one property to several, keep funds separate:Multiple Properties, Single Entity: Use Relay's accounts to separate funds for Property A, Property B, etc., even under a single LLC, and utilize tools like Airbnb to direct payments to these specific accounts.Multiple Entities: If you have separate LLCs, Relay allows you to manage all of them under a single secure login, easily transferring funds and maintaining a consolidated view.Common Blind Spot: Business owners often lack a clear view of which properties are truly profitable, sometimes allowing one to cover the losses of another.Tools and Systems for ScalingAs a business scales, it's essential to outsource and bring on experts.Securely Collaborating with Your Team: Relay offers different permission levels to invite bookkeepers, CPAs, or virtual assistants (VAs) without sharing your bank login credentials (a major security no-no).The Power of Virtual Cards: Relay allows you to create physical or virtual cards that are tied to a specific checking account. You can set spending limits (daily, weekly, monthly) and assign cards to specific team members (like VAs or property managers) or even specific properties for easy expense tracking.Streamlined Payments and Tax Reporting: Relay simplifies 1099 reporting by requesting payment details (like W-9 info) via text or email, ensuring all necessary tax information is accurately collected from the recipient.Building Your Reserve Fund for Peace of MindBeing prepared for unexpected expenses (water heater breaks, property damage, floods, etc.) is crucial for long-term success.Start Small: It can feel impossible to start a reserve fund, but Robyn encourages...
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  • It Can Be Beautiful if You Let It
    Madeline welcomes her longtime collaborator and "business bestie," Kristen Day, to the show. They dive deep into the unexpected journey of their friendship, the power of cultivating meaningful, supportive relationships in the entrepreneurial space, and the transformative power of their mini retreats.Key Takeaways:Business Besties are Essential: Madeleine and Kristen discuss the profound impact their relationship has had on navigating the "messy" and often lonely journey of entrepreneurship. They stress the importance of having a support group for those seasons of self-doubt and struggle.Challenging the Grind Mindset: Kristen encourages listeners to reconsider the attitude that the "grind is the only way forward." She admits that her biggest mistake was being closed off to deeper relationships with business friends, mistakenly thinking they would be a distraction.Work-Life Integration over Balance: For entrepreneurs, the solution to "balance" is often work-life integration, which means enjoying the people you do business with. Madeline notes that their best ideas—including "literal million-dollar ideas"—have come from casual conversations outside of formal work.Don't Let Fear Ruin the Potential: The pair discuss overcoming the fear of "ruining the relationship" by doing business together. Madeline affirms that she valued their friendship more than any business outcome, which allowed them to move past Kristen's typical six-month container and continue working together indefinitely."It Can Be Beautiful If You Let It": Kristen shares Madeline's phrase that deeply resonated with her, emphasizing the need to be vulnerable and open to allowing friendships to flourish in a professional context. Entrepreneurship is already messy, so don't close yourself off to something beautiful and supportive.Three Keys to Finding Your Network:Don't assume the outcome of a relationship.Pay attention to what you enjoy about them.Reject the mindset that growing one relationship takes away from another. The right, aligned relationships will open a wealth of opportunities, both personally and monetarily.Upcoming OpportunitiesInternational Retreats: For more information, email [email protected] Your STR Journey: Two Day Workshop to Start or Optimize Your STR Business (https://www.madeleineraifordholland.com/streamlined)Connect with the KristenInstagram (https://www.instagram.com/thehomegrind)LinkedIn (https://www.linkedin.com/in/kristendayaffinity)If you've enjoyed this episode of The Luxe & the Short of It podcast, be sure to leave a review and subscribe today!Enjoy!Resources:🔗 Work With Madeleine's Team - https://strsuccess.typeform.com/podcast💼 Connect with...
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  • 3 Steps to Future-Proof Yourself
    Madeleine offers a different perspective on change and provides three practical steps to future-proof your life and business amid a rapidly changing economic and technological landscape, particularly with the rise of AI.Mindset: See Change as OpportunityShift Your Perspective: Madeleine stresses that the very first step is adjusting your mindset to view change as an opportunity.Be Proactive, Not Passive: Training yourself to see opportunities during a landscape shift moves you from being passive and reactive to proactive and an early adopter.Solve Problems Efficiently: The people who make the most money are those who position themselves to solve people's biggest problems in an excellent and efficient way.3 Steps to Future-Proof YourselfMadeleine outlines three critical, practical steps to prepare for what's coming:1. Create and Curate a Personal BrandShow Up Online: If you are not online, you are invisible. Start building your network and showing people what you do.Curate Your Bio: Make sure your social media bio clearly shares how you can serve people (e.g., "STR investor and business strategist, helping you start or optimize a seven-figure boutique short-term rental business").Content Pillars: Use content pillars (typically four) to create a relatable personal brand that showcases your service and expertise. Madeleine’s pillars include short-term rental tips and lifestyle content (like her farm and being a mom) to show she is "human."Monetize Your Influence: Start earning money by sharing products you love and use.Affiliates are a must-have: You should be compensated for the marketing you do for a brand. Madeleine recommends Shop My (https://shopmy.us/join/madeleineraifordholland), an affiliate company that is helping smaller creators (without the high follower minimums of platforms like LTK) and offers amazing affiliate percentages.Short-Term Rental Hosts: Make your property shoppable as an easy and essential multiple stream of revenue.Madeleine's Marketing Masterclass: Master more than a decade of marketing experience in less than five hours. This STR-specific course teaches advanced tactics for IG, email, affiliate/influencer marketing, and more. (https://www.madeleineraifordholland.com/STR-Marketing-Masterclass)2. Start Learning AIAI Bootcamp: The proven playbook to streamline, systematize & scale your STR business using AI. (https://www.madeleineraifordholland.com/optimize-your-str-ai-bootcamp-1)Don't Be Left Behind: With the launch of OpenAI's Chat version five (and the anticipation that version seven will replace a large portion of the workforce), you must start learning AI.Learn to Prompt and Create Agents: Focus on learning how to prompt AI and how to create AI agents. This is where many business opportunities are for early adopters.Leverage for Efficiency: Businesses are already training AI to do up to 90% of their team's jobs, making the employee's remaining 10% "secret sauce" more efficient and valuable.Devour Content: Madeleine urges listeners (especially short-term rental hosts) to devour every piece of education and content you can about AI, viewing it as the "wave of the future."3. Invest in Physical Assets and ExperiencesFocus on the Physical: The changing technological landscape will make in-person, physical experiences highly valuable.Relational Shift: People will begin to pay a lot of money for in-person
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  • Is There a Garage Door Instead of a Front Door?
    Madeleine shares how a logistical nightmare turned into an unexpected adventure. What happens when your husband's last-minute trip for a hair transplant in Turkey leaves you with a full plate of work and no childcare? You pivot!This isn't just a story about a spontaneous trip, it's a powerful lesson in creative problem-solving and understanding that the most traditional path isn't always the best one.Key Takeaways:Embracing Reality: Entrepreneurial life isn't all sunshine and rainbows. Your host shares a dose of reality about navigating challenges with grace and humor.The Unconventional Path: Sometimes, the best solution isn't the most obvious one. Learn to recognize when to stop forcing a traditional approach and find an alternative.The Power of "Why Not?": Instead of asking, "Why would I do it that way?" try asking, "Why wouldn't I?" This mindset can unlock creative solutions and new opportunities.If you've enjoyed this episode of The Luxe & the Short of It podcast, be sure to leave a review and subscribe today!Enjoy!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.Mentioned in this episode:Pricing Bootcamphttps://www.madeleineraifordholland.com/str-pricing-bootcamp
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About The Luxe and The Short of It

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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