Madeleine dives deep into a powerful, yet often misunderstood, strategy for high-income earners: the Short-Term Rental (STR) Tax Loophole. It's legal, written into the tax code, and can significantly reduce your tax liability by allowing you to offset active income with real estate losses.

Tax Code Rewards Certain Investments: High earners often pay tens or hundreds of thousands in taxes, believing it's unavoidable. The U.S. tax code actually rewards certain investments, and STRs offer a powerful way to reduce taxes and build wealth.

The Four Pillar Profit Strategy: When investing in STRs, focus on winning in four areas simultaneously:

• Equity: Someone else (the guests) pays your mortgage, building your equity.
• Appreciation: The property gains value over time.
• Cash Flow: Underwriting for a minimum of $2,000 per month in cash flow.
• Tax Savings: Leveraging the tax code to pay less.

STRs are NOT Passive: Unlike most rental properties (which only allow losses to offset passive income), STRs with an average guest stay of less than 7 days fall under a different tax code section. Meeting "material participation" requirements allows you to use paper losses to offset your active (W-2) income.

The Power of Depreciation and Cost Segregation: Buying and furnishing an STR allows for a Cost Segregation Study. This study, conducted by an engineer, accelerates the depreciation of components like furniture, appliances, flooring, decks, and landscaping (which normally depreciate over 5-15 years) into one year. This creates a huge paper loss that can be applied against your active income if you qualify.

It's NOT Too Late: Even if you acquire and open a property late in the year (like the last week of December), your first guest stay allows you to utilize the entire year's depreciation and bonus depreciation for the property!

You must meet all three of these requirements to materially participate and qualify for the loophole:

1. Average Guest Stay is Less than 7 Days: STRs with an average stay of <7 nights are considered a business, not a rental property, by the IRS. (Total nights rented/Number of bookings = Average Stay Length)
2. The Property is Actually Rented: Set-up time alone doesn't count. You must have guests/bookings during the year to qualify.
3. Material Participation: You must be actively involved in the business.

• Self-Management is Key: Hiring a property manager typically disqualifies you. You can self-manage with the appropriate systems/automations.
• The 100-Hour Rule: You worked at least 100 hours on the property, and no one else worked more hours than you. (The alternative is 500+ hours).
• Qualifying Work Examples: Guest messaging, cleaning/turnovers, repairs, restocking, managing listings/pricing, buying/setting up furniture, and bookkeeping. (Time spent thinking or reviewing reports does not count.)

STR Tax Loophole:

• Core Requirement: Avg. rental period $< 7$ days & Material Participation (100+ hours/year).
• Who Qualifies: Busy professionals, W-2 earners, business owners, or a household with a flexible spouse.
• Time Commitment: Moderate (typically 100-500 hours/year).
• Loss Offset Potential: Can offset active income if material participation is met (REPS is not needed).
• Documentation: Hour logs, proof of operational involvement, booking records. Hours can be provided in a narrative form.
• Scalability: Must qualify participation for each STR individually.
• Best For: People wanting to keep their career but still use real estate to offset taxes.

Real Estate Professional Status (REPS):

• Core Requirement: 750 hours/year in real estate activity AND it must be more than half of your total working time.
• Who Qualifies: Full-time investors or agents with flexible schedules.
• Time Commitment: Very high (typically replaces full-time work).
• Loss Offset Potential: Can offset active income if REPS is qualified for.
• Documentation: Requires contemporaneous hour logs, activity breakdowns, and proof of majority time spent in real estate.
• Scalability: Once achieved, applies to all rental properties owned that year.
• Best For: People ready to commit their career to real estate.

• Watch the Land Value: You cannot depreciate the land itself. Avoid high-value vacation markets where most of the property's value is in the land.
• Strategy for Success: Target markets with high revenue potential but lower land costs. This ensures a higher depreciable value in the physical property, maximizing your tax benefit.
• Work with Professionals: Consult your CPA/Tax Strategist year-round to determine the target loss needed. Use a Cost Segregation Specialist before you purchase a property to get an Estimated Analysis of Benefits so you know the exact bonus depreciation potential.

🚀 Your STR Workshop - https://madeleineraifordholland.com/elevate

🔗 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:

Elevate Your STR Workshop

https://madeleineraifordholland.com/elevate

Madeleine takes a high-level view of the different roles - or hats - that every business owner must wear. If you’re a successful professional transitioning from the 9-to-5 world, this is crucial: the shift to wearing multiple hats in your own business can feel like being hit by a freight train.

Madeleine breaks down the three core roles, explaining why understanding each one is the key to scaling your business with grace and ease - and avoiding total chaos.

• The Three Hats: As a business owner, you are typically wearing one of three hats: the Operator, the Marketer, or the CEO.
• The Chaos Zone: Stuff hits the fan when you try to wear all three at the same time. Learning to identify and prioritize which hat you need to wear, and when, is essential for growth.
• The Ultimate Goal: The secret is learning how to quickly move out of the Operator and Marketer roles and elevate yourself to wearing the CEO Hat as much as possible.

Operator

• Daily Operations: guest interaction, scheduling cleaners, maintenance, building SOPs, and ensuring the business runs smoothly.
• Understand, Automate, and Delegate: The mistake is camping out here because it feels productive or thinking, "nobody can do it as well as me."

Marketer

• Driving Business/Sales: Optimizing listings (OTAs), building a direct booking website, email marketing, collecting emails, consistent social media, and personal brand building.
• Automate and Delegate: Many STR owners rely on OTAs (like Airbnb/Vrbo) and fail to graduate to this role, missing out on significantly more revenue from direct bookings.

CEO

• Strategic Thinking: Focusing on new projects, property acquisition, new partnerships, business development, analyzing reports, and giving high-level strategic input.
• Wear This Hat Most Often: This is where the creativity and magic lives, allowing you to work on your business instead of in it. 

Document Everything: Anytime you are working on a repeatable task, focus on documenting the process. Documentation is the foundation for eventual automation and delegation.

Tool Spotlight: Madeleine shares her favorite documentation tools:

• Loom: Great for creating screen-recording videos of processes.
• Scribe: Captures keystrokes and screenshots to automatically generate step-by-step guides you can export. (Madeleine often uses both simultaneously!)

Catch Yourself: Bring awareness to which hat you are wearing. Catch yourself when you're in the weeds of the Operator or Marketer roles, and ask: "What can I do to automate or delegate this so I can wear the CEO hat more often?"

If you're an STR owner ready to shift into that CEO role, build time freedom, and stop wearing all three hats at once, Madeleine's entire mentorship is based on giving you the tools and SOPs to do exactly that.

🔗 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:

Elevate Your STR Workshop

https://madeleineraifordholland.com/elevate

Madeleine welcomes back her Director of Marketing, Abby Dickerson (who was previously on Episode 18 discussing AI), to talk about the crucial shift toward authentic marketing. They dive into why raw, unfiltered content is outperforming ultra-curated feeds and how to leverage AI to make your marketing sound more genuinely you.

• The Power of Raw Content: Both Madeleine and Abby agree that the market has shifted away from pristine, ultra-curated feeds. Ads and affiliate products perform best when they are raw and unfiltered, such as a video of Madeleine simply sipping coffee on her back porch with no makeup. This relatability drives connection and conversion.
• Simple Scales, Complicated Fails: They discuss A-B testing for co-hosting outreach, finding that a plain-text, two-to-three-sentence email with a direct question and call-to-action is converting better than "beautiful tied with a bow" emails. Simple content feels less manufactured and less like bulk spam.
• TikTok's "Don't Try Too Hard" Rule: When discussing growing on platforms like TikTok, the key is to appear effortless. If you're "trying at all, you're trying too hard." Simple things like a great "hook" at the beginning (like the sound of a toilet flushing) or an unexpected element (like a massive plant) are often the secrets to going viral.
• Authenticity Over Perfection: Madeleine highlights an unexpected viral moment—a picture of the pitcher top on her 64-ounce mason jars in her fridge—proving that relatable, authentic moments resonate far more than perfectly staged content. The new mantra for marketing is "Better authentic than perfect."
• Leveraging AI for Authentic Ideas: Abby explains that she uses "trained bots" to capture Madeleine's unique voice, tone, and specific knowledge of her properties. This allows them to use AI for idea generation, like meme remixes and video concepts, that feel completely authentic and personal, not "manufactured."
• The "Crazy Enough" Content Rule: Madeleine shares her tip for identifying content: if it's "somewhat crazy enough to extend beyond the family group chat," it's generally interesting enough to create content around. Real-life absurdities, like a guest leaving 100 Jesus statues or a controversial toilet paper roll debate, make the best engaging content.
• The Fun Factor in Marketing: Ultimately, both Madeleine and Abby emphasize that you must "have fun" creating content. If you're not enjoying it, your audience can tell, and they won't engage. The goal is to connect, be engaging, and have fun doing it!

AI Bootcamp: Learn how to leverage AI to create authentic content by training your own bots!- https://www.madeleineraifordholland.com/str-pricing-bootcamp

Episode 18 - Abby Dickerson | Unlock Your Creative Genius with AI Collaborators - https://player.captivate.fm/episode/0a2338c8-35a7-406c-b12e-20075ef91029/

🔗 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:

Elevate Your STR Workshop

https://madeleineraifordholland.com/elevate

Madeleine opens up about how she tackled a negative multi-week spiral by choosing to take radical responsibility for her attitude and actively creating positive momentum in her life and business.

She dives into powerful mindset shifts and actionable business strategies, encouraging listeners to stop feeding their fears and instead, focus on cultivating gratitude and clarity to own their success.

• Your Attitude is Your Responsibility: You are accountable for how you show up and respond, which has ripple effects on your family, team, and business leadership.
• The Power of Three Laws for Momentum: Madeleine breaks down three psychological/business laws and how she uses them to regain control:
• Murphy's Law: The more you fear something happening, the more likely it is to occur. Stop feeding your fears and fixating on what's going wrong. Cultivate an attitude of gratitude and focus on positive outcomes.
• Gilbert's Law: Your success is in your hands. Take responsibility, find solutions, and own the outcome. This is the shift that moves you away from a victim mentality.
• Kidlin's Law: Write a problem down clearly, and that is half the solution. Clarity equals power. Brain dump your situation to gain the confidence to solve it.
• Focus on Gratitude: Even in challenging moments, shift your focus to what you are thankful for, such as financial freedom and time to be present.
• The Best Things in Life are Free: When feeling stuck, get back to the free things in life that bring you joy. Put your phone down, spend time outside, cook, and be present with your family.
• Build Q4 Momentum: Madeleine goes "pedal to the metal" during Q4, building momentum into the new year. She encourages listeners to have next year's personal and professional goals planned by mid-December.
• Reverse Engineer Your Year: Use a calendar to plot birthdays, known travel, and special events, and then plan business goals around those anchors.
• Create Focus Time: Close off company calendars for new meetings during the last two weeks of the year to allow the team to focus on year-end goals and plan initiatives for the new year.

• Write Yourself into Your Dreams by Teri Wade (https://urlgeni.us/amzn/writedreams)
• Madeleine's Momentum Spotify Playlist (https://open.spotify.com/playlist/7fWiP86DNnU5DzkuW2NPLd?si=3I570277RniCZV509DH55A&nd=1&dlsi=1157d8f103dd4448)

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:

Elevate Your STR Workshop

https://madeleineraifordholland.com/elevate

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.

• Culture 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.

• Book: 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:

Elevate Your STR Workshop

https://madeleineraifordholland.com/elevate

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.

Robyn 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.

A 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.

As 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.

Being 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 business owners to start with a very small percentage, even 1% of revenue, and utilize automations.
• Madeleine’s Reserve Goal: Madeleine aims for a six-month reserve of all business expenses to ensure the business never relies on personal funds.
• The Unexpected Opportunity: For many customers, the greatest value of implementing these systems is the peace of mind and reduced mental strain, allowing them to focus their energy on their "zone of genius."

Madeleine shares the percentage breakdown they use for their STR business (Note: these are malleable and should be adjusted to your specific business reality):

• Operating Expenses: 53%
• Management: 12%
• Tax: 12%
• Profit: 5%
• Reserve (until six months of expenses is reached): 8%
• Charitable Contribution: 10% (Optional)

Key Advice: Start with smaller percentages for profit and reserves if needed, work to analyze and trim expenses, and gradually increase allocations as you gain clarity and control.

Find Relay Online:

Sign up for Relay: https://join.relayfi.com/partner?referralcode=madeleinerh&utm_source=influencer

YouTube: https://www.youtube.com/channel/UCTmli04_PnCdhnbRvsRRMhg

Instagram: https://www.instagram.com/bankwithrelay?igshid=YmMyMTA2M2Y%3D

Twitter: https://x.com/bankwithrelay

Facebook: https://www.facebook.com/bankwithrelay

LinkedIn: https://www.linkedin.com/company/bankwithrelay/

Relay is a financial technology company and is not an FDIC-insured bank. Banking services provided by Thread Bank, Member FDIC. FDIC deposit insurance covers the failure of an insured bank. The Relay Visa® Debit Card is issued by Thread Bank, member FDIC, pursuant to a license from Visa U.S.A. Inc. and may be used anywhere Visa debit cards are accepted. Certain conditions must be satisfied for pass-through deposit insurance coverage to apply.

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:

Elevate Your STR Workshop

https://madeleineraifordholland.com/elevate

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.

• International Retreats: For more information, email [email protected]
• Streamline Your STR Journey: Two Day Workshop to Start or Optimize Your STR Business (https://www.madeleineraifordholland.com/streamlined)

• Instagram (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 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:

Elevate Your STR Workshop

https://madeleineraifordholland.com/elevate

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.

• Shift 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.

Madeleine outlines three critical, practical steps to prepare for what's coming:

• Show 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)

• AI 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."

• Focus 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 connection and relational experiences, such as retreats and simply "taking walks with them."
• Invest in Travel and Real Estate: Madeleine is doubling down on travel and real estate because it's a physical asset—"you own the land and the land isn't going away"—and is something AI cannot replace.
• Create Connection: Look for business opportunities that lean toward physically being present and creating connection.

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:

Elevate Your STR Workshop

https://madeleineraifordholland.com/elevate

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:

Elevate Your STR Workshop

https://madeleineraifordholland.com/elevate

After a busy summer, Madeleine felt completely burned out, describing it as "pouring from an empty cup." This led to a key realization: she was in a position where she needed to be supported herself, something she wasn't used to. (00:00:44)

Madeleine re-examined a core belief she had held for years: "I do my best work when my back is against the wall." With the help of her team, she realized this was a self-sabotaging lie. She had been subconsciously creating pressure-filled situations to feel successful. She has since shifted this belief to: "I am most successful when I take care of myself, my family, and my business in balance."

Taking this time for herself and shifting her mindset had an incredible impact on her business. Madeleine found that despite working a fraction of the time she used to, her companies were achieving milestones and profitability levels they had never reached before. She realized she was getting in her own way by filling her life with busyness instead of focusing on what truly lit her up.

Madeleine assures her listeners that she is not leaving the short-term rental or coaching space. She continues to find short-term rentals profitable and a great tax strategy, but she focuses on the parts of the business she loves most: finding and underwriting new deals and the initial property setup. The day-to-day operations are handled by her trusted team. For now, she is committed to helping her clients, celebrating their successes, and exploring what the next evolution of her career will be.

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:

Elevate Your STR Workshop

https://madeleineraifordholland.com/elevate