The Luxe and The Short of It

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 your Virtual Assistant (VA) to log every expense (property name, amount, receipt upload, description) on the backend for easy reconciliation by the bookkeeper.Year-End Financial Checklist (Mid-November to December)Hounding Your Tax Strategist: Check in almost weekly toward the end of the year to discuss expected income ranges, tax liability, and options to reduce taxes (e.g., strategic spending).Monthly Reconciliations: Ensure your books are reconciled, clean, and up-to-date.Prepare for 1099s: Gather W9s for all contractors now to avoid a scramble in January...

Madeleine and Abby are bringing back the fun with a special game episode, this time playing the classic "Kiss, Marry, Kill" with Short-Term Rental twist! Get ready for Madeleine's unfiltered, gut reactions to scenarios covering everything from booking platforms and guest behavior to pricing strategy and the eternal quest for peace over burnout in the short-term rental (STR) business.Kiss, Marry, Kill:Airbnb, Direct Bookings, Vrbo. (01:43)A Superhost Badge, a guest who actually reads the house manual, or a neighbor who minds their own business. (03:09)Midstay cleaning, late checkout, and bachelorette parties. (03:55)AirDNA, Price Labs, and Praying. (05:04)A guest with kids, a guest with dogs, or a guest with an emotional support reptile. (06:15)100% occupancy and total burnout, sixty percent occupancy and peace, or eighty five percent occupancy but you forgot to file taxes. (07:17)A guest who messages 'Ready' when you are an hour before check-in, a guest who says 'We left it how we found it', or a guest who books and asks zero questions (so they're suspiciously quiet). (08:33)A 5 star review with no text, a four star review that's basically a love letter, or a three star review that ends with would absolutely stay again. (09:56)Key Takeaways & Actionable Advice:Take Control of Your Revenue: Being the Merchant of Record (like on Vrbo or Direct Bookings) gives you more control over your payments, which is why Madeleine prioritizes these channels over Airbnb.Prioritize Peace Over Perfection: Aim for 70-80% occupancy. 100% occupancy often means you are undercharging, and it will lead to quicker burnout and excessive wear and tear on your property.Educate Your Guests on Reviews: Clearly communicate what a 5 star review means for your business, as guests may not understand the massive difference between a 4 star and a 5 star rating.Resources:🚀 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.

Join Madeleine for a crucial episode on her personal and professional practice of reflection and vision casting—the cornerstone of her career and personal success. This is a companion episode to two essential free resources designed to guide you through a thorough 2025 business audit and strategic 2026 vision planning.Madeleine emphasizes a shift from emotionally reacting to data to interpreting it strategically to set yourself up for a bold and successful year.Free Companion Resources (Get Them Now!)Madeleine has created two free resources to accompany this episode. Pause the podcast and download them to work through your audit and vision casting:Audit and Vision Workbooks - https://www.madeleineraifordholland.com/audit-and-vision-workbooksKey Areas of the 2025 STR Business AuditMadeleine walks through the specific data points and questions she reviews for her own portfolio, encouraging listeners to approach the numbers as information, not judgment.Revenue & Occupancy:Monthly revenue and occupancy rate, best/underperforming months, and pattern shifts.Average booking window (how far in advance guests book).Pricing Strategy:Highest/lowest Average Daily Rate (ADR) and nightly rate charged.Percentage of nights discounted.Identifying where you underpriced or overpriced based on 2025 data.Guest Experience & Reviews:Common positive and negative mentions (in public or private feedback).Where guests are finding your listing (reliance on OTAs vs. direct/other sources).Team & Operations:Identifying MVP team members.Pinpointing problem areas (staff, vendors, property issues).Defining your Zone of Genius and roles you need to delegate.The first process or SOP to systematize in Q1 2026.Tech Stack & Automation:Reviewing all tools used (PMS, pricing, AI, etc.) - what worked, what to drop, and how to negotiate better contracts in Q1.Identifying new automations for 2026.Listing Photos, Copy, & SEO:Checking for outdated photos and optimizing titles/captions for keywords.Reviewing listing performance data (views, saves, conversions).End-of-Year Tax Preparation:Reconciling income/expenses and collecting 1099s.Reviewing deductions (travel, mileage).Identifying capital vs. regular expenditures and confirming property classification (material participation, real estate professional status).Considering a cost segregation study if a property was purchased or put into service in 2025.Strategic Reflection: Ask yourself: "What actually made me money? What just kept me busy? And what do I want to feel like running my STR in 2026?"Creating Your 2026 Vision & Action PlanUse the insights from your audit to strategically plan your next year with the Vision Planner.Revenue & Occupancy Strategy: Use if-then statements to guide your focus (e.g., If strong occupancy but low profit, then focus on raising ADR and auditing expenses).Pricing & Profit Strategy: Set clear minimum night stay targets for peak and slow seasons, and define your core pricing rules.Guest Experience: Turn guest feedback...

Madeleine and her Marketing Director, Abby, switch things up for a fun, spontaneous episode by playing a game of "Smash or Pass: Short-Term Rental Edition." Abby, using her "robot" (AI) to generate a list of "unhinged" scenarios for Madeleine to decide if she would Smash 🔨 (do it) or Pass 👋 (not do it) in her short-term rental business.Scenarios:Cash back incentive for guests who read the house rules: 🔨 Offer a small reward (like $5/coffee) for a secret word in the rules. Rewards action-takers and sets a fun tone.Spend $600 on a neon sign because you saw it on Instagram: 👋 (For Her)Depends entirely on your guest avatar and aesthetic. A Smash for bachelorette/party vibes, but not for her personal brand/guests.Outsource guest messaging to your teenage niece for work experience: 👋Too risky when revenue is on the line. Requires an "extenuating circumstance" for someone super bright.Let your cleaner set their own rates AND booking times just to keep them happy: 👋Madeleine's cleaners set their own flat-rate pricing, but the 4 PM turnover deadline is non-negotiable.Post a TikTok dragging a guest's insane request, then DM them the link: 👋 (on sending link)Posting about it on social media is fine for views/sharing the craziness, but stirring up drama by sending it to the guest is not her style.Build an outdoor shower even if you live in Michigan: 🔨 (if market calls for it)Market analysis is key. Smash if it's a lake/summer market and a good differentiator, provided it can be properly weatherproofed against the elements.Let your ex manage your STR remotely if it meant not dealing with guest drama: 🔨Smash the situation, not the ex! *Abby's answer: Pass hard due to no trust.Use AI to respond to reviews even if it accidentally called someone "bro": 🔨One small casualty is worth it if the AI is generally effective and saves time.Set up a fake security camera labeled "Guest Behavior Monitor" to keep people in line: 👋 (100%)Invades privacy, will get reported to Airbnb, and hosts are not "hall monitors."Reply to a guest's two-star review with a custom Canva graphic that says, "Thank you for your opinion": 👋Review responses are for future guests, not the person who left the review. You must be professional and address the feedback/situation without passive-aggression. (Never call a guest a "filthy liar"!)Create an Airbnb profile just to spy on your local competition's response time and pricing: 🔨Secret shop all day long! Copying communication instructions from a competitor is working smarter, not harder.Copy and paste a guest's rude message into Chat GPT and ask it to "clap back like Cardi B": 🔨 (But don't send it)For emotional release and a good laugh. Humor is the best medicine to clear your head before responding professionally.Use your Airbnb reviews as your dating app profile bio: 🔨Humorous, unique, and a great conversation starter.Name your STR something unhinged like "Bread and Bougie" or "The Moist Manor" just to go viral: 👋Hard pass, especially due to Madeliene's least favorite word ("moist"). Not on-brand, even for a viral moment.Spend more on throw pillows than your monthly car payment and feel zero regret: 🔨(Madeleine's done it!) For large properties with multiple rooms, the cost of quality pillows adds up quickly for the design/comfort factor.Resources:🚀 Your STR Workshop - https://madeleineraifordholland.com/elevate🔗 Work With Madeleine's Team -...

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.Key Takeaways: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!Three Core Requirements for the STR Tax Loophole:You must meet all three of these requirements to materially participate and qualify for the loophole: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)The Property is Actually Rented: Set-up time alone doesn't count. You must have guests/bookings during the year to qualify.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 vs. Real Estate Professional Status (REPS)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...

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.Key Takeaways: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.The Three Roles Defined:OperatorDaily 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."MarketerDriving 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.CEOStrategic 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. Scaling with Grace and Ease: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?"Resources: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:...

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

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.Key Takeaways and Strategies: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.Resources: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...

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.

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...

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 learn@mhmluxuryproperties.comStreamline 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...

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

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.

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)The Shift in Mindset (00:08:05)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."The Surprising Results(00:09:50)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.Future Plans (00:13:10)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.

Today's episode of The Luxe & the Short of It podcast is a recast of a conversation between Madeleine and David Lovejoy, host of the Horizon Search podcast.In this engaging and thought-provoking conversation, you'll hear how Madeleine has turned a personal pursuit into a thriving business with heart and strategy. You'll discover themes of transformation, purposeful risk-taking, and redefining traditional paths. Madeleine’s journey is not just one of financial gain but of intentionally crafting a life that reflects her values, creativity, and desire for meaningful impact.Learn the nuances of scaling a business without sacrificing the personal touch that made it successful in the first place. The conversation highlights unexpected challenges and breakthrough moments, offering a rare behind-the-scenes look at how intuition, process, and people-first thinking can intersect in powerful ways.Whether you're an entrepreneur, a dreamer, or someone looking for a fresh spark, this conversation delivers insight and inspiration in equal measure.If you've enjoyed this episode of The Luxe & the Short of It podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You’ll Learn:Madeleine's background, starting her career in a family government contracting business and traveling extensively, as well as the creation of "Moderately High Maintenance," a lifestyle website.Her transition from building her own portfolio to helping others create thriving short-term rental businesses.The common pitfalls in the short-term rental industry, such as treating it like a hobby and not automating the business.The importance of adding multiple streams of revenue, such as affiliate revenue from shoppable properties. Why entrepreneurs must understand that they can't do it all, as well as the importance of delegating tasks to focus on what they love.And much more...About the podcast:The Horizon Search podcast features in-depth conversations with entrepreneurs and industry experts from around the world, uncovering the real stories, strategies, and lessons behind today’s most compelling business innovations. Each episode offers candid, insightful discussions that go beyond the headlines to explore what truly drives success.https://www.madeleineraifordholland.com/streamlined 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...

Today's episode of The Luxe & the Short of It podcast is a recast of a conversation between Madeleine and Marta Spirk, host of The Empowered Women podcast.During the conversation, you'll hear about Madeleine's remarkable journey as she traces an unconventional career path from a traditional corporate role to a bold reinvention of work and lifestyle. She shares insights on navigating major life transitions, balancing family priorities, and discovering new avenues for both financial success and personal freedom. Along the way, you'll learn how blending creativity with strategic thinking helped unlock opportunities that many might overlook.Get a behind-the-scenes look at the challenges and unexpected twists that shaped a thriving business model — one built on innovation, adaptability, and a refusal to settle for "just a job." From managing multiple ventures to developing systems that free up time, this conversation explores how deliberate choices and entrepreneurial mindset can open doors to a life with more flexibility and fulfillment.Whether you’re intrigued by the idea of creating new income streams, dreaming of escaping the traditional 9-to-5 grind, or simply curious about how to make meaningful change happen in your own life, this episode offers practical wisdom and inspiring stories, and a fresh perspective on the pursuit of freedom — not just financial, but the kind that truly lets you live on your own terms.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.

In today's episode of The Luxe & the Short of It podcast, Madeleine is joined by Dr. Caroline Iscovitz, an entrepreneur, advocate for higher-conscious living, and private wellness consultant.During this fascinating conversation, Madeleine and Dr. Caroline discuss the complexities and rewards of blending personal relationships with professional ventures. You'll hear candid insights about navigating the challenges that arise when business and romance intertwine, emphasizing the importance of communication and clearly defined roles. You're invited to explore how balancing different strengths within a partnership can create a dynamic and thriving business environment.The discussion also highlights the value of intentional pauses and retreats in business life—moments designed not only for rest but for reflection and vision casting. This approach helps prevent burnout and allows entrepreneurs to realign with their purpose, ensuring their passion and motivation remain strong over time. The conversation touches on practical strategies to build sustainable systems that keep daily operations smooth, freeing up space for creativity and growth.The episode offers an inspiring message about trust, growth, and the profound impact of taking risks, making it a must-listen for anyone interested in entrepreneurship, personal development, and the power of partnership.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.

In today's episode of The Luxe & the Short of It podcast, Madeleine discusses the tricky realities of managing challenging situations that come with providing premium experiences. Specifically, "pain in the a$$" guests. You’ll hear a real-life guest story that left Madeleine stunned—and how she handled it with grace, not emotion.Despite best efforts to anticipate and prevent issues, sometimes unexpected obstacles and difficult personalities show up, testing patience and professionalism. Madeleine explores the balance between maintaining high standards and navigating the frustrations that inevitably arise when things don’t go as planned.You'll learn about the mindset behind pricing, guest expectations, and the subtle signals that often predict a complicated interaction. Madeleine shares candid reflections on personal growth as a service provider, emphasizing how experience shifts responses from frustration to gracious problem-solving. Strategies for effective communication and maintaining composure when faced with unreasonable demands offer valuable insights for anyone who deals with customers or clients.Whether you’re in hospitality or any customer-facing role, this episode provides thoughtful tools for managing tough encounters with grace and resilience.If you've enjoyed this episode of The Luxe & the Short of It podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Madeleine's recent experience with difficult guests, and why she usually prices her listings to attract the right type of guests.Case studies of incidents involving difficult guests, including abusive behavior toward her team and unreasonable demands when issues arose. The importance of responding graciously to difficult guests and not letting their behavior affect her personally.How turning the problem back on the guest by asking what solution would work for them can sometimes help to mitigate a challenging situation.And much more...https://www.madeleineraifordholland.com/streamlined 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.

In today's episode of The Luxe & the Short of It podcast, Madeleine answers a series of common yet crucial questions that many aspiring entrepreneurs hesitate to ask. From figuring out the initial steps to overcoming financial hurdles, the conversation will guide you through practical ways to navigate early challenges while emphasizing the importance of mindset shifts. Whether you’re just starting or looking to level up, there’s a thoughtful breakdown of how to strategically approach growth and opportunity.You’ll also be introduced to various pathways that can open doors with different levels of commitment and resources, highlighting the value of building a solid foundation through personalized support. The discussion sheds light on the significance of community, mentorship, and having reliable systems in place to accelerate progress. It’s clear that success is often less about quick wins and more about intentional, well-structured efforts that lead to sustainable results.This episode is a valuable resource for anyone ready to transform uncertainty into momentum.If you've enjoyed this episode of The Luxe & the Short of It podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:The importance of having a top-tier property in your chosen market.How offering furnished midterm stays and listing on platforms like Airbnb, VRBO, and temporary housing directories can help during low seasons.The value of having a cohesive brand standard for guest experience and visual branding. Strategies for finding money for investments, including co-hosting, arbitrage, and owning properties.The benefits of cash flow, equity appreciation, and tax advantages in owning properties.And much more...https://www.madeleineraifordholland.com/streamlined 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.

In today's episode of The Luxe & the Short of It podcast, Madeleine dives into a rarely discussed emotional experience that many entrepreneurs face but don’t often name—a profound mix of exhilaration and unexpected grief that follows the completion of a major project. Drawing on a candid conversation with Chase, an interior decorator she works with regularly, Madeleine explores the intensity of being fully immersed in a mission, the high of focused creativity, and the surprising emptiness that can come once it’s all over. Through personal stories of juggling family transitions and hosting a large community event, she reveals how success can sometimes bring an unexpected pause that challenges even the most driven among us.Beyond the immediate aftermath of achievement, the conversation explores the deeper questions of what comes next—how to find new motivation and direction once initial goals have been met. Madeleine reflects on redefining success, emphasizing the importance of joy, fun, and authenticity over rigid numbers or milestones. This episode invites you to reconsider your own relationship with accomplishment, encouraging a thoughtful balance between striving forward and savoring the journey, even when it feels vulnerable or uncertain.If you've enjoyed this episode of The Luxe & the Short of It podcast, be sure to leave a review and subscribe today!Enjoy!In This Episode You'll Learn:Madeleine's experience of completing a major project and the subsequent grief of completion that occurred immediately afterward.The importance of celebrating achievements and not rushing to the next goal. How Madeleine delegates tasks she doesn't enjoy and instead chooses options that bring her joy.The balance between achieving business milestones and personal growth.  And much more...https://www.madeleineraifordholland.com/streamlined 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.