Short-Term Rental Tax Loophole: 100% Bonus Depreciation with Madeleine Raiford-Holland

S6:E17 Everyone wants the shortcut. No one wants to hear there isn't one. Queue Up Episode This week on Small Business Stories, Dr. LL sits down with technical advisor and business coach Matthew Mamet to unpack what AI is actually changing and what it is not. If people don't trust you, they won't buy from you. If they can't distinguish your expertise from a bot, they won't remember you. Matthew brings perspective from the dot-com era through today's LLM shift, explaining why growth hacks fail and why authority now matters more than ever. 👤 Guest Matthew Mamet Technical Advisor & Business Coach Former Java engineer | Growth strategist Core Problems Discussed AI content saturation and declining SEO returns Confusing automation with innovation Decision paralysis in the age of infinite tools Practical Takeaways Authority beats automation Human-in-the-loop content preserves differentiation Most business decisions are reversible — act accordingly Timestamps 00:02 The shift from SEO to AI discoverability 05:45 Why backlinks no longer move rankings alone 08:10 Google's EEAT and authority signals 11:50 Human-in-the-loop content creation 26:30 Type 1 vs Type 2 business decisions Who This Episode Is For Digital entrepreneurs navigating AI Founders building long-term authority Small businesses questioning growth hacks Invisible brands don't make money. Invisible expertise doesn't scale. Season 6 continues decoding the patterns that undermine credibility. ✅ Subscribe for weekly conversations on entrepreneurship 🔁 Share this episode with someone who needs to be heard Follow STEERus on social media: YouTube: https://www.youtube.com/@Midlifesuccess Instagram: https://instagram.com/steerus Facebook: https://facebook.com/steerus LinkedIn: https://www.linkedin.com/company/steerus    #ai #digitalmarketing #seo #entrepreneur #smallbusiness  

S6:E16 If you keep hearing about the short-term rental tax loophole but it feels confusing, this episode makes it easy-peasy to understand. We unpack how 100% bonus depreciation can create big paper losses that may offset active income when structured correctly. Loralyn Mears, PhD, aka "Dr. LL," brings you thoughtful conversations with entrepreneurs and small business leaders navigating visibility, leadership, and growth. Thank you for being here. Overview A lot of smart, high-earning people are trying to "do the right thing" financially, but they are quietly stuck in analysis paralysis, platform dependence, or bad assumptions about what's actually possible. This episode sits inside that tension: you want real assets and real leverage, but you also want clarity, guardrails, and a plan that does not take over your life. That's the difference between buying a property and building an asset that actually performs. 👤 Guest Madeleine Raiford-Holland The Lux and the Short of It (podcast) | Short-term rental investor + educator Based in Athens, Georgia Follow her on Instagram: https://www.instagram.com/madeleineraifordholland ⚠️ Core Problems Discussed People want wealth-building options but get stuck in market selection and "where do I even start?" Regulations and HOA rules can quietly kill a deal if you do not check early Running a short-term rental can become chaotic without systems, coverage, and a boots-on-the-ground team 🧠 The Bigger Pattern Dr. LL Sees Invisibility pattern: Rented Audience Dependence When your revenue engine relies on platforms you do not control, you can look "successful" while your leverage stays fragile. You are visible inside someone else's ecosystem, but you are not building an asset that reliably compounds for you. 🥡 Practical Takeaways Start with your constraints first (cash, time, support), then reverse-engineer the market Treat regulations, HOA docs, and insurance as part of deal quality, not admin paperwork Build an owned book of business (direct booking, repeat guests, referral loops), not platform-only volume ⏱️ Timestamps (key moments) Short-term rentals as a wealth strategy under current macro pressure How the short-term rental tax "loophole" works in real life Picking markets: hidden gems within an hour, plus when distance is fine Systems that keep the property from "running you" Regulations, HOAs, and coverage: how to reduce ugly surprises 🔖 Who This Episode Is For Small business owners trying to diversify income without chaos High earners exploring real estate but overwhelmed by complexity Operators who want systems, not another hustle Hashtags #shorttermrental #realestateinvesting #taxplanning #realestate #investing #taxes

S6:E15 What happens when the thing you built your identity around disappears? Queue Up Episode This week on Small Business Stories, Dr. LL sits down with former professional skier turned Denver real estate agent Athena Brownson. She's incredible! Introspective, resilient, and inspirational. Follow her on Instagram: https://www.instagram.com/athenabrownsonrealtor_/ If people don't trust you, they won't hire you. If they don't see the real you, they won't connect with you. Athena's journey moves from elite athletic performance through devastating injuries and chronic Lyme disease to building a thriving relationship-based real estate business. 👤 Guest Athena Brownson Denver Realtor Former Professional Skier ⚠️ Core Problems Identity loss after physical setbacks Building trust in a saturated real estate market Managing discipline without self-destruction 🥡 Practical Takeaways Resilience is trained, not inherited. Trust compounds faster than transactions. Discipline must evolve from punishment to promise. Invisible brands don't make money. Invisible leaders don't scale. Season 6 continues decoding the patterns that keep capable entrepreneurs unseen. ⏱️ Timestamps 00:01 Athlete-to-entrepreneur mindset and fear 00:07 When identity gets forced to change 00:12 Mentorship and relationship-based real estate 00:24 Lyme disease, capacity, and self-kindness 00:32 Building a team that holds the business steady 🔖 Who This Episode Is For Small business owners who feel stretched thin Consultants building trust online Solopreneurs who feel unseen or misread Hashtags #RealEstate #DenverRealEstate #Entrepreneurship #olympics #resilience

S6:E14 Loralyn Mears, PhD, aka "Dr. LL," brings you thoughtful conversations with entrepreneurs and small business leaders navigating visibility, leadership, and growth. Thank you for being here. Most founders are carrying more than they admit, and still trying to look "put together" while the ground shifts underneath them. In 2026, it is easy to confuse polish with progress, and busyness with momentum. This episode lives in that quiet gap between how entrepreneurship is pictured and how it is actually lived. It is also a reminder that the story people see is rarely the full story. 👤 Guest Jennifer Johnson True Fashionistas (Naples, Florida) and The Confident Entrepreneur (platform offering a popular podcast, coaching, and motivational speaking for women business owners) Luxury resale retail founder, small business coach, speaker, and author ⚠️ Core Problems Discussed The hidden operational load behind running a retail resale business that looks "fun" from the outside How image, wardrobe, and self-expression affect confidence and presence for entrepreneurs The "overnight success" myth and how curated visibility creates false expectations 🧠 The Bigger Pattern Dr. LL Sees: Curated Confidence When entrepreneurs feel pressure to appear effortlessly successful, they start performing confidence instead of building it. The result is a public story that looks stable, while the private reality stays unspoken, making it harder for customers, partners, and even the founder to trust what is real. 🥡 Practical Takeaways Confidence is often less about style rules and more about removing doubt from what you wear and how you show up. Business ownership can be deeply fulfilling and still require sweat-level effort that rarely makes it into the highlight reel. Reframing hard seasons as "what can I learn from this?" helps restore agency when things feel chaotic. ⏱️ Timestamps 00:01:07 True Fashionistas: what a "lifestyle resale store" really is 00:03:14 "Dress for the job you want" and why presence matters 00:08:59 Fashion myths that keep people second-guessing themselves 00:10:48 The romanticized business-owner story vs reality 00:24:23 The "say your name" reset for finding the lesson 🔖 Who This Episode Is For Small business owners who feel stretched thin Consultants building trust online Solopreneurs who feel unseen or misread Hashtags: #SmallBusinessOwner #ResaleFashion #Entrepreneurship #consignment #shopping

S6:E13 Loralyn Mears, PhD, aka "Dr. LL," brings you thoughtful conversations with entrepreneurs and small business leaders navigating visibility, leadership, and growth. Thank you for being here. Overview A lot of founders are stuck because their identity is still anchored to safety, approval, and "the responsible choice." So the goalposts keep moving. The bank balance is never enough, the timing is never right, and the dream stays theoretical. This shows up as overwork, over-functioning, and businesses that look "successful" but feel misaligned and unsustainable. 👤 Guest Jenna Harrison The Uncommon Way Life coach for women entrepreneurs (identity, nervous system, and business redesign)   ⚠️ Core Problems Discussed  -Why people keep postponing the leap, even when the numbers look "ready" -Over-functioning as a learned survival strategy that becomes a business model  -The hidden cost of building a business that does not match your real life   🧠 The Bigger Pattern Dr. LL Sees: Identity Safety Loop When your identity equates safety with external structures (titles, paychecks, "the right way"), you keep re-negotiating your own goals to avoid the discomfort of change. Across founders, this loop creates a visibility problem too: your message stays cautious, your offers stay diluted, and your decisions stay reversible, which makes trust harder to earn.   🥡 Practical Takeaways  -If you keep adding "just one more condition," it is probably an identity issue.  -Overwork can feel like virtue, but it quietly shrinks creativity, clarity, and staying power. -Your business gets easier to explain when your decisions stop hedging and start matching the life you actually want.   ⏱️ Timestamps  00:01 Moving to Mallorca and choosing the uncommon path 03:30 The "moving goalposts" trap (savings, salary, safety) 06:10 Over-functioning and why it stops being sustainable 09:45 The "fishbowl" metaphor for limited possibility thinking 14:50 Going off social media and growing anyway 🔖 Who This Episode Is For Small business owners who feel stretched thin Consultants building trust online Solopreneurs who feel unseen or misread   👉 Learn more about Jenna and the Uncommon Way here: https://www.theuncommonway.com/   ✅ Subscribe for weekly conversations on entrepreneurship 🔁 Share this episode with someone who needs to be heard Follow STEERus on social media: YouTube: https://www.youtube.com/@Midlifesuccess Instagram: https://instagram.com/steerus Facebook: https://facebook.com/steerus LinkedIn: https://www.linkedin.com/company/steerus #WomenEntrepreneurs #BusinessCoach #EntrepreneurMindset #entrepreneur #smallbusiness

S6:E12 Loralyn Mears, PhD, aka "Dr. LL," brings you thoughtful conversations with entrepreneurs and small business leaders navigating visibility, leadership, and growth. Thank you for being here. Overview Sometimes the issue is not your talent. It is that people cannot verify it fast enough to feel safe choosing you. In a world where AI can generate endless output, the quiet problem becomes trust, proof, and what feels "real." This episode sits inside a recurring Season 6 thread: capable people getting overlooked because their credibility is not legible at first glance. If you have ever felt like the work is strong but the market still hesitates, there is more going on here than effort. 👤 Guest Name: Tim Packer Company: Tim Packer Art Academy Area of expertise: Professional artist and educator helping artists build skill and income. He's earned his own place in the world, but many people consider him as "the Bob Ross of the 21st Century."   ⚠️ Core Problems Discussed -Why many creators try to sell before they have visible proof of results or outcomes -How complex offers require longer-form trust-building, not quick ads and quick claims  -What AI changes about visibility, and why human-made work still matters to buyers    🧠 The Bigger Pattern Dr. LL Sees Invisibility pattern: Credibility Gap When proof is missing, unclear, or hard to find, people default to caution, even if the work is excellent. Across industries, this is why strong operators get underpaid: credibility is present, but not legible in the formats people and algorithms actually trust.   🥡 Practical Takeaways -Build credibility from demonstrated results and recognizable proof, not volume of promotion -Match your marketing format to the complexity of what you sell (short-form is not always honest) -Use AI for support work, but protect your unique voice as the core differentiator   ⏱️ Timestamps 00:04:30 Growth mindset and the turning point that brought Tim back to art 00:16:01 The "30-minute" commitment that gets you past resistance 00:18:49 What makes an online course credible enough to sell  00:21:03 Why long-form content builds trust for complex transformations 00:31:44 AI, human-made work, and why process visibility matters    🔖 Who This Episode Is For Small business owners who feel stretched thin Consultants and coaches building trust online Solopreneurs who feel unseen or misread   ✅ Subscribe for weekly conversations on entrepreneurship 🔁 Share this episode with someone who needs to be heard   Follow STEERus on social media: YouTube: https://www.youtube.com/@Midlifesuccess Instagram: https://instagram.com/steerus Facebook: https://facebook.com/steerus LinkedIn: https://www.linkedin.com/company/steerus TikTok: http://tiktok.com/@steerus #artist #ai #entrepreneur #smallbusiness #bobross

S6:E11 Loralyn Mears, PhD, aka "Dr. LL," brings you thoughtful conversations with entrepreneurs and small business leaders navigating visibility, leadership, and growth. Thank you for being here. Overview There's a subtle moment many business owners miss: when growth doesn't stall because of effort, but because clarity slips. The work still happens, but the signal becomes harder to read. Over time, audiences feel unsure how to describe what you actually do. This episode sits inside a recurring pattern Dr. LL sees across businesses that are active, capable, and quietly misaligned. 👤 Guest Larissa Banting Company: Larissa Banting Publicity Public relations, media visibility, credibility building ⚠️ Core Problems Discussed Pivoting too far away from proven expertise Confusing novelty with strategic growth Losing credibility through scattered offers and messaging 🧠 The Bigger Pattern Dr. LL Sees The invisibility pattern here is Expertise Drift. Across hundreds of conversations, Dr. LL sees capable founders slowly dilute trust by moving away from what audiences already recognize and value. Visibility grows when expertise compounds, not when it constantly resets. 🥡 Practical Takeaways Visibility strengthens through repetition, not reinvention Trust grows faster when your work is easy to name Going deeper often creates more momentum than going wider    ⏱️ Timestamps  00:07:23 Media visibility creates legitimacy 00:14:44 The moment of returning to core expertise 00:18:32 Squirrel brain and scattered focus 00:21:36 Why depth beats breadth 00:27:10 Trust signals in AI-driven search   🔖 Who This Episode Is For  Small business owners who feel stretched thin Consultants and coaches building trust online Solopreneurs who feel unseen or misread  ✅ Subscribe for weekly conversations on entrepreneurship 🔁 Share this episode with someone who needs to be heard Follow STEERus on social media: YouTube: https://www.youtube.com/@Midlifesuccess Instagram: https://instagram.com/steerus Facebook: https://facebook.com/steerus LinkedIn: https://www.linkedin.com/company/steerus TikTok: http://tiktok.com/@steerus  #ai #marketing #entrepreneur #smallbusiness #digitalmedia #trust

S6:E10 Loralyn Mears, PhD, aka "Dr. LL," brings you thoughtful conversations with entrepreneurs and small business leaders navigating visibility, leadership, and growth. Thank you for being here. Overview There is a specific kind of frustration that does not look dramatic from the outside: you are doing the work, you are buying the tools, you are trying to keep up, and somehow things feel harder, not easier. You are not "behind," you are managing a system that is quietly becoming unmanageable. In 2026, the gap between what you know you should do and what you can realistically maintain is where a lot of businesses get misread. And when your backend is messy, your signal gets messy too. 👤 Guest Jennifer Christensen Founder, Spark Story Marketing Marketing strategist focused on small business foundations, AI-informed execution, and practical visibility (including GEO conversations) ⚠️ Core Problems Discussed Small businesses are overwhelmed by disconnected tools, logins, and platforms that do not integrate cleanly AI can amplify confusion when the underlying foundation is inconsistent or broken Many founders chase "viral" outcomes while the basics (listings, website, credibility signals) quietly degrade 🧠 The Bigger Pattern Dr. LL Sees This episode reflects the invisibility pattern Tool Pileup: when a business stacks tools faster than it can integrate or maintain them, and the brand starts leaking trust in small but costly ways. It is not a motivation problem, it is a signal integrity problem. In a world where customers and AI systems scan for consistency, Tool Pileup can make capable businesses look fragmented, unreliable, or harder to verify. 🥡 Practical Takeaways Before adding a new tool, confirm your "foundation layer" is clean: access, ownership, listings consistency, and one source of truth Use AI to support execution, not to compensate for a broken system underneath Measure success by real outcomes (referrals, qualified leads, conversions), not vanity metrics or follower counts ⏱️ Timestamps 00:08:27 – Why misalignment shows up in health, energy, and performance 00:16:24 – The real-world panic founders feel after buying tools that do not work together  00:19:13 – Why "basic info cleanup" can create a real business boost  00:22:31 – Why limiting your core tools can protect your clarity 00:35:12 – Reframing "a few thousand followers" as real trust, not a small number 🔖 Who This Episode Is For Small business owners who feel stretched thin Consultants and coaches building trust online Solopreneurs who feel unseen or misread Potential Next Step: If you're noticing this pattern in your own business, STEERus offers structured clarity for leaders who want to be seen without becoming louder or losing themselves.  ✅ Subscribe for weekly conversations on entrepreneurship 🔁 Share this episode with someone who needs to be heard Follow STEERus on social media: YouTube: https://www.youtube.com/@Midlifesuccess Instagram: https://instagram.com/steerus Facebook: https://facebook.com/steerus LinkedIn: https://www.linkedin.com/company/steerus TikTok: http://tiktok.com/@steerus #ai #entrepreneur #smallbusiness #marketing

S6:E9 Pattern Discussed: Borrowed credibility, unearned trust. A founder attaches themselves to a "known" brand, platform, or business model and assumes it will carry visibility and trust, but the local operator work that actually earns belief (standards, reputation, community proof, consistency) still has to happen. How it keeps good businesses unseen, untrusted, underpaid, or underperforming: it creates a quiet mismatch between what the audience expects and what they experience, so people hesitate, churn, or never refer. Why it shows up across many businesses: I hear this across franchises, startups, and service businesses: people buy "brand" or "marketing," then discover the real differentiator is still execution, clarity, and credibility signals at the ground level. Loralyn Mears, PhD, aka "Dr. LL," brings you thoughtful conversations with entrepreneurs and small business leaders navigating visibility, leadership, and growth. Thank you for being here. Overview There's a quiet frustration many owners do not say out loud: you can do "the right things," spend real money, and still feel like momentum never arrives. Sometimes the issue is not effort, it's the assumption that a name, a model, or a platform will do the trusting for you. Across hundreds of conversations, Dr. LL keeps hearing the same underlying tension: people want a clearer path, but they keep getting sold shortcuts. This episode sits right in that gap. 👤 Guest: Alex Smereczniak Franzy Franchising education, franchise matching, and business ownership pathways ⚠️ Core Problems Discussed: - The myth of "passive" franchise income and what ownership actually requires - How "brand" reduces some risk, but does not remove execution risk - The broken incentives in parts of the franchise-broker ecosystem and how buyers get misled 🧠 The Bigger Pattern Dr. LL Sees: Across business models, a recurring credibility trap shows up: people borrow authority (a brand, a system, a market trend) and assume it will translate into trust, sales, and stability. But customers and communities still decide based on the proof they can feel locally: standards, consistency, reputation, and clarity. Challenges that surfaced in this episode: - Confusing "de-risked" with "effortless" - Underestimating how much operator quality protects (or damages) trust - Following incentives that benefit intermediaries more than the buyer 🥡 Practical Takeaways: - Treat franchising like a major life decision, not an "asset class" shortcut - Evaluate fit as much as brand, your skills and the model must align - Look for transparency in incentives, avoid pathways that hide who profits from your choice ⏱️ Timestamps: 00:02:25 Franchising is not mailbox money 00:04:14 What happens when a franchisee hurts the brand 00:10:06 The real value of built-in peer community 00:14:42 Why Franzy was built and what it fixes 00:23:14 "Balance" vs "harmony" for founders 🔖 Who This Episode Is For: Small business owners who feel stretched thin Consultants and coaches building trust online Solopreneurs who feel stuck or unseen ✅ Subscribe for weekly conversations on entrepreneurship 🔁 Share this episode with someone who needs to be heard Follow STEERus on social media: YouTube: https://www.youtube.com/@Midlifesuccess Instagram: https://instagram.com/steerus Facebook: https://facebook.com/steerus LinkedIn: https://www.linkedin.com/company/steerus TikTok: http://tiktok.com/@steerus  #entrepreneur #smallbusiness #franchise #growth

S6:E8 Loralyn Mears, PhD, aka "Dr. LL," brings you thoughtful conversations with entrepreneurs and small business leaders navigating visibility, leadership, and growth. Thank you for being here. Core pattern: People assume their capability will speak for itself, then accidentally leave their "first impression story" to chance. When that happens, others decide what you mean, what you're worth, and whether you're credible, before you ever get to show your work. This shows up everywhere: founders, consultants, leaders, job seekers. They are doing real work, but their presence, framing, and positioning are not carrying it. Overview There's a quiet mismatch many business owners and leaders feel but rarely name: you are doing the work, yet people still do not read you the way you intended. You show up sincere, capable, and prepared, and somehow the room lands on a different story. Then you spend the rest of the conversation trying to undo an impression you did not choose. This is a pattern that shows up across industries: when presence is unclear, perception takes over. 👤 Guest: Vernessa Hopkins VHH Consulting Leadership influence, executive presence, and change management ⚠️ Core Problems Discussed: - Why titles do not automatically create leadership, influence does - How appearance, energy, and "approachability" shape credibility in the first seconds - Where people get stuck: limiting beliefs, perceived barriers, and giving away the driver's seat 🧠 The Bigger Pattern Dr. LL Sees: - Across many businesses, visibility breaks down when people expect competence to carry the message without actively shaping the context. - When you do not define your brand in the room, others do it for you, fast. - The result is that good leaders and strong operators get underestimated, misread, or priced below their value. 🥡 Practical Takeaways: - Decide what you want to be known for before you walk in, then make your choices match it - Reduce "interpretation space" by naming who you are and how you work in a grounded way - Use strengths as a strategy tool: build around what you reliably do well, and stop apologizing for what is not you ⏱️ Timestamps (high value moments): 00:03:19 Influence starts with you, and "what got you there won't keep you there" 00:06:53 How "showing up" has shifted, and why brand decisions still matter  00:12:09 The reality of being assessed fast, and how to work with it 00:21:14 The Influence Matrix and building stabilizing statements for hard moments 00:28:10 "Don't be mad at where you're parked when you let someone else drive."   🔖 Who This Episode Is For: Small business owners who feel stretched thin Consultants and coaches building trust online Solopreneurs who feel stuck or unseen A Supportive Next Step This episode highlights a pattern we see often: you are capable and committed, but your credibility is not arriving at the same speed as your effort. You might be getting polite interest instead of clear yeses. You might notice that people "don't quite get it" until you over-explain, over-prove, or over-deliver. That can feel personal, but most of the time it is not. It is a visibility gap: the way your value is framed, found, and understood is not keeping pace with the work you are actually doing. ✅ Subscribe for weekly conversations on entrepreneurship  🔁 Share this episode with someone who needs to be heard Follow STEERus on social media: YouTube: https://www.youtube.com/@Midlifesuccess Instagram: https://instagram.com/steerus Facebook: https://facebook.com/steerus LinkedIn: https://www.linkedin.com/company/steerus TikTok: http://tiktok.com/@steerus #entrepreneur #leadership #smallbusiness #professionaldevelopment #coaching