Best Short Term Rental Strategist Podcasts (2025)

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VRS643 – How Voice AI Can Elevate Hospitality Without Losing the Human Touch – with Eliseo Palous 46:58

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1d ago46:58

46:58

What if artificial intelligence could actually enhance the human touch instead of replacing it? In this episode, Heather speaks with Eliseo Palous, co-founder of Short Stay Media, to explore how AI - especially voice AI - is revolutionizing guest communications in the short-term rental industry without sacrificing what matters most: hospitality, re…

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VRS642 - How Stacey St. John Built a High-Performing STR Portfolio From Scratch 56:53

8d ago56:53

56:53

What happens when a corporate professional takes a chance on short-term rentals in the middle of a global pandemic? In this inspiring episode, Heather sits down with Stacey St. John - real estate investor, property manager, and community builder - to unpack her incredible journey from cautious investor to powerhouse property manager with a portfoli…

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VRS641 - The Insurance Housing Opportunity: What Every STR Operator Should Know with Jake Mast 57:21

17d ago57:21

57:21

When disaster strikes - whether it's a fire, flood, or even a bat infestation - families are often left scrambling for safe, comfortable housing. That's where Jake Mast steps in. In this episode, Heather Bayer sits down with Jake, founder of Rapid Response AI Housing, to explore how his company is disrupting the traditional insurance housing model …

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EP 130 - How Much Can I Save from a Cost Segregation Study? 33:30

16d ago33:30

33:30

Send us a text Cost Segregation can save you tens of thousands, or even hundreds of thousands, in taxes. But here's the problem: most investors have no clue how much they're actually leaving on the table. After personally reviewing hundreds of cost seg studies for our clients at Prosperl CPA, I'm pulling back the curtain and showing you EXACTLY how…

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VRS640 - Why the FIFA World Cup 2026 Starts NOW for Your Vacation Rental with Mark Simpson 52:27

22d ago52:27

52:27

📌In this power-packed episode, Heather Bayer is joined once again by vacation rental marketing guru Mark Simpson of Boostly. Mark returns for his fifth appearance on the podcast - and this time, he's bringing an urgent message for vacation rental professionals across North America: The FIFA World Cup 2026 doesn't start in June... it starts on Decem…

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EP 129 - Meet the Woman Behind America’s Top Tax Planners 43:44

27d ago43:44

43:44

Send us a text We trace the “domino decision” that turned corporate burnout into a calling and show how timing, not tricks, drives real tax savings. Dominique Molina joins us to reveal practical ways to choose your tax rate and stack permanent advantages without gimmicks. • Why timing beats complexity in tax strategy • Permanent savings versus simp…

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VRS639 - Optimizing for AI: What Short-Term Rental Brands Need to Know About GEO and the Future of Search with Neely Khan 52:54

29d ago52:54

52:54

This week I'm welcoming back one of my favourite guests, Neely Khan, founder of the storytelling agency Artwork Creative. This is her second time joining me in less than six months - and there's a good reason for that. Neely is at the forefront of one of the most important shifts we're seeing in vacation rental marketing: the rise of AI-powered sea…

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VRS638 - Democratizing Genius: How Dr. Rachel Gainsbrugh Uses AI to Supercharge Short-Term Rental Success 52:39

1M ago52:39

52:39

In this episode, Heather sits down with Dr. Rachel Gainsbrugh from Short Term Gems to explore how artificial intelligence is changing the way short-term rental businesses operate. Rachel shares how she moved from being a pharmacist to building a real estate education company focused on medical professionals, and how AI is now a core part of that mi…

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EP 128 - The BIG Lie About One-Time Tax Plans 25:38

1M ago25:38

25:38

Send us a text If you're a high-income earner, real estate investor, or business owner, the answer is almost always no—and in this video, I break down exactly why. I’m walking you through the BIG lie behind one-time tax plans, the opportunities most people miss after Year 1, and why ongoing tax strategy can unlock six- and seven-figure savings over…

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VRS637 - AI in Action: What STR Hosts Can Learn from the AI for Business Summit 48:10

1M ago48:10

48:10

In this packed episode, Heather Bayer shares her biggest takeaways from the AI for Business Summit in Las Vegas - and how short-term rental hosts and property managers can take immediate, practical steps to adopt AI tools in their business. Heather reveals how she used a Plaud NotePin to record and summarize every session, giving her powerful insig…

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VRS636 - Scaling Smart: How to Spot the Owners Who'll Sabotage Your Growth 55:57

2M ago55:57

55:57

Dennis Goedheid is back on the show, and we dive deep into one of the most overlooked yet mission-critical aspects of running a property management company - identifying and saying no to the wrong owners. We also chat about his journey with Casiola's international expansion, his team's DEI award win at VRMA, and why scaling means getting crystal cl…

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S9 Ep28: This is the Short Term Rental episode you've been waiting for - PART TWO 18:06

2M ago18:06

18:06

PART TWO: We're thrilled to have Verenice Leon back on the show with new adventures and amazing tips for all our Savvy listeners. If you've been thinking about a short-term rental investment but are unsure if you can do it on your own, this episode is for you. Reach out to Verenice on IG: @cafecito.homeloans…

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EP 127 - The Hidden Limits to Tax Deductions (and How the Wealthy Work Around Them) 29:09

2M ago29:09

29:09

Send us a text You’ve heard the stories: jets written off, million‑dollar refunds, zero taxes on millions in income. But are those strategies fundamental? And more importantly, do they apply to you? In this video, Mark Perlberg (CPA + Tax Strategist) breaks down the truth about these “too good to be true” tax moves. He pulls back the curtain on ded…

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VRS635 - From Tinkering to Transformation: Building an AI Adoption Strategy for Your Vacation Rental Business 45:25

2M ago45:25

45:25

While everyone's been playing around with AI tools like ChatGPT, few in the short-term rental industry have taken the next step - turning experimentation into strategy. In this episode, Heather shares a clear, step-by-step framework to help you move from random tinkering to thoughtful implementation, drawn straight from her AI Ambassador Program. W…

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S9 Ep27: This is the Short Term Rental episode you've been waiting for - PART ONE 19:59

2M ago19:59

19:59

We're thrilled to have Verenice Leon back on the show with new adventures and amazing tips for all our Savvy listeners. If you've been thinking about a short-term rental investment but are unsure if you can do it on your own, this episode is for you. Reach out to Verenice on IG: @cafecito.homeloansBy Natalie Torres-Haddad

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VRS634 - The Direct Booking Mindset Shift: What Every Host Needs to Hear Right Now 55:59

2M ago55:59

55:59

In this episode, I'm joined by the brilliant Jenn Boyles, founder of the Direct Booking Success Summit and host of the Direct Booking Success Podcast. Jenn is a passionate advocate for empowering hosts and property managers to take back control from the OTAs - and she did it herself with an incredible 80% direct booking rate. We go deep into why di…

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EP 126 - High-Income W-2? Do THIS Before December 31st to Unlock Massive Tax Savings 25:05

2M ago25:05

25:05

Send us a text We show high‑earning W‑2s how to cut taxes now, not months from now, and convert savings into immediate cash flow. We walk through year‑end tactics, stacking limits, overlooked credits, and why adjusting your W‑4 can supercharge wealth growth. Ready to slash your tax bill? Schedule your free consultation and let's strategize your tax…

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VRS633 - The Trustology: The Secret to a Successful Direct Booking Strategy with Chris Maughan 51:25

2M ago51:25

51:25

In this penultimate episode in our series on Direct Booking, this is an episode you can't afford to miss. Heather is joined by long-time industry leader Chris Maughan, the founder of i-PRAC and a pioneer in the trust movement for short-term rentals. This conversation isn't about OTAs, algorithms, or the latest booking engine. It's about what really…

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VRS632 - How to Transform Your Short Term Rental Business with Google's NotebookLM 58:51

3M ago58:51

58:51

In this solo episode, Heather shares her enthusiasm for Google's NotebookLM. If you've ever wished for a research assistant who knows your business inside and out - an assistant who can analyze guest reviews, SOPs, market data, and spit out insights without hallucinating - this one's for you. Heather walks through how NotebookLM works, why it's dif…

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EP 125 Maximizing “Use It or Lose It” Tax Breaks for High Earners 30:05

3M ago30:05

30:05

Send us a text We challenge the idea that lower is always better for taxes and show how “use it or lose it” deductions and credits vanish when income is either too high or too low. We map the sweet spots that unlock SALT, QBI, and child credits, and share moves to land there on purpose. • standard vs itemized deductions and why timing matters • SAL…

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VRS631 - Are You a Digital Sharecropper? Taking Back Control with Humphrey Bowles 53:52

3M ago53:52

53:52

In this bold and thought-provoking episode, Heather sits down with Humphrey Bowles, the founder of Truvi and who has adopted the term "digital sharecropping" within the short-term rental industry. Together, they explore the illusion of entrepreneurship in the short-term rental world - especially when you build your business entirely on platforms li…

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VRS630 - Build Trust, Book Direct: Lessons from Louis Andrews of OVO Network 55:50

3M ago55:50

55:50

In this first episode of a special 5-part series on direct booking, Heather Bayer sits down with Louis Andrews, Director at OVO Network, to explore what it really takes to win the battle against OTAs and build a successful direct booking strategy. With OVO Network reaching 75-80% direct bookings, Louis shares the secrets behind their platform, the …

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EP 124 - How to find Cash Flowing Short-term Rental Investments with John Bianchi 42:03

3M ago42:03

42:03

Send us a text The short-term rental loophole offers incredible tax-saving opportunities but requires careful market research and property selection to be profitable in today's competitive landscape. While the tax incentives can be life-changing, many Airbnbs have become money pits due to changing market conditions and lack of proper analysis. Take…

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VRS629 - From Digital Guides to Donut Walls: Inside a Next-Gen Guest Experience 54:14

3M ago54:14

54:14

I first met James Rubino at a VRMA conference in Orlando two years ago. He was there at the start of his journey in short term rentals, to learn and network and I mentioned to him then I would have him as a guest on the podcast down the road. So two years later here we are and what a story it is . At just 26, James launched Rubino Home Ventures and…

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EP 123 - Social Security Benefits and Planning w/ Mike Skrynecki 48:14

3M ago48:14

48:14

Send us a text Take our free Tax Planning Checklist & learn about what tax savings may be available for you in our minicourse at https://taxplanningchecklist.com Take our free Tax Planning Checklist & learn about what tax savings may be available for you in our minicourse at https://taxplanningchecklist.com At the very least, get on our newsletter …

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EP 122 - Offshore Asset Protection & International Tax Strategies 36:15

4M ago36:15

36:15

Send us a text Mikkel Thorup, an offshore consultant with 25 years of international experience, shares legal strategies for reducing U.S. tax burden through international relocation and asset protection. He explains how these approaches can potentially save six figures annually while remaining fully compliant with tax laws. Checkout the Expat Learn…

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VRS628 - Why Local Wins: The Five Pillars for Success You Must Follow - with Ashley Ching 54:48

4M ago54:48

54:48

Have you ever found yourself wondering why so many large-scale property management companies rise quickly… and then fall just as fast? In this episode, I'm joined by Ashley Ching, Founder and CEO of Inhaven, who brings a fresh - and deeply researched - perspective to this question. Ashley recently published an eye-opening report, "A 25-Year History…

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EP 121 - How Timing Your Cost Segregation Studies Can Save You Millions in Taxes 31:56

4M ago31:56

31:56

Send us a text Strategic timing is the unsung hero of tax planning, especially when it comes to cost segregation studies for real estate investors. The difference between performing these studies at the optimal time versus the wrong time can mean hundreds of thousands of dollars in tax savings. PS. Whenever you're ready, here are some ways we can h…

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VRS627 - Thriving in the Age of AI and Short-Term Rentals with Bart Sobies 55:02

4M ago55:02

55:02

In this episode, Heather Bayer welcomes back a long-time friend and industry innovator, Bart Sobies, founder of iBooked.Online and the creative mind behind the Strive to Thrive events in Australia and beyond. Bart joins Heather (from tomorrow, no less - Australia time!) to share insights on: The power of in-person connections and how conferences ca…

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EP 120 - What is Cost Segregation & When do we Use It? 25:50

4M ago25:50

25:50

Send us a text Cost segregation stands as the most powerful tax strategy for real estate investors, allowing identification of property components that can be depreciated faster than the standard 27.5 or 39-year schedules. • Typical cost segregation studies reclassify 25-30% of a property's value for immediate write-off through bonus depreciation •…

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EP 119 - Financial Freedom through Passive Investing w/ Joey Mure 44:01

4M ago44:01

44:01

Send us a text Start Your Journey to Financial Freedom through passive income NOW! In this episode, I break down how to reduce your tax bill, grow passive income, and rethink what freedom with money really looks like. Here’s what you’ll take away: • How to stop overpaying taxes by adjusting W-4s and using smart tax planning. • Simple ways to create…

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VRS626 - Tech-Enabled Hospitality with Jessica Gillingham of Abode Worldwide 52:56

4M ago52:56

52:56

What does it really mean to run a tech-enabled hospitality business - and how do we do it without losing the human touch? In this episode, Heather sits down with Jessica Gillingham, founder of Abode Worldwide and author of Tech-Enabled Hospitality, to talk about how property managers can embrace technology to improve guest experiences, operations, …

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EP 118 - Tax Showdown: Oil & Gas Investing vs. Retirement Account Investing 30:21

4M ago30:21

30:21

Send us a text Ready to slash your tax bill? Schedule your free consultation and let's strategize your tax savings together! Book now at: https://www.prosperlcpa.com/apply Or, if you still need more time, here are some other ways to begin winning the tax game... Take our free Tax Planning Checklist & learn about what tax savings may be available fo…

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VRS625 - Five Quick Wins to Start Using AI in Your STR Business Today 47:05

4M ago47:05

47:05

In this solo episode, Heather Bayer returns to the mic for an approachable explanation of the transformative power of AI in short-term rental operations. With over 600 episodes under her belt, Heather has seen just about every trend in this space - but few as game-changing as this. Whether you're a solo host or run a multi-property management compa…

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VRS624 - Trust, Tech & Storytelling: The Keys to a High-Converting STR Website 56:04

5M ago56:04

56:04

In this fun and super insightful episode, I'm joined once again by vacation rental marketing expert Jodi Bourne, and we're diving headfirst into something that's never been more important - your website. With all the recent changes to the big OTAs, more and more hosts are waking up to the power of direct bookings. And at the heart of that? Your web…

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EP 117 - Short-Term vs Long-Term Rentals from a Tax Perspective 23:24

5M ago23:24

23:24

Send us a text Short-Term vs. Long-Term Rentals: Tax Benefits Explained Understand the tax differences that can make or break your rental strategy when choosing between long-term rentals and short-term rentals for tax savings, profit, cashflow and wealth. In this video, we break down how each property type impacts your deductions, cash flow, and lo…

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EP 116 - Tax Benefits of Passive Real Estate Investing 27:23

5M ago27:23

27:23

Send us a text Ready to slash your tax bill? Schedule your free consultation and let's strategize your tax savings together! Book now at: https://www.prosperlcpa.com/apply Or, if you still need more time, here are some other ways to begin winning the tax game... Take our free Tax Planning Checklist & learn about what tax savings may be available fo…

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EP 115 - What the Big Beautiful Bill Means for Short-Term Real Estate Investors 26:23

5M ago26:23

26:23

Send us a text Ready to slash your tax bill? Schedule your free consultation and let's strategize your tax savings together! Book now at: https://www.prosperlcpa.com/apply Or, if you still need more time, here are some other ways to begin winning the tax game... Take our free Tax Planning Checklist & learn about what tax savings may be available fo…

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VRS623 - Safety Sells: Why STR Leaders Are Putting Protection First 49:22

5M ago49:22

49:22

In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down for a summer Sunday chat with Justin Ford from Breezeway, to discuss how prioritizing safety can transform your short-term rental business. Not just in protecting reputations, even boosting bookings, but in saving lives. Justin has been on the show just a few times…

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EP 114 - How Passive Real Estate Investors Save Big on Taxes WITHOUT Real Estate Professional Tax Status 23:22

5M ago23:22

23:22

Send us a text Ready to slash your tax bill? Schedule your free consultation and let's strategize your tax savings together! Book now at: https://www.prosperlcpa.com/apply Or, if you still need more time, here are some other ways to begin winning the tax game... Take our free Tax Planning Checklist & learn about what tax savings may be available fo…

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VRS622 - Navigating Growth, Change, and True Hospitality with Jackie Norde from Casago 50:02

5M ago50:02

50:02

When change hits fast and hard, what keeps a company grounded? In this episode, Heather welcomes Jackie Norde, who shares her remarkable journey from vacation rental software onboarding to her current role helping Casago franchisees succeed - especially in the wake of Casago's rapid expansion via Vacasa acquisitions. Jackie offers rich insights int…

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VRS621 – The Power of Storytelling: How Hospitality Brands Can Stand Out in a Sea of Sameness 54:49

5M ago54:49

54:49

In this inspiring episode, Heather Bayer sits down with storyteller and copywriter Neely Khan to explore how hospitality businesses can set themselves apart through powerful, purpose-driven storytelling. Neely shares her journey from aspiring writer to founding AWC, a story-branding agency that helps short-term rental businesses create meaningful c…

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VRS620 - Staying Human: The Power of Vulnerability in Vacation Rental Leadership 57:44

6M ago57:44

57:44

In this episode, Heather Bayer sits down with Heather Fillmore, co-founder of Utah-based StayLuxe Properties, for an honest and inspiring conversation about resilience, growth, and leadership in the short-term rental space. Heather shares her remarkable journey from surviving a catastrophic flood in Baton Rouge to launching a successful luxury vaca…

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EP 113 - Alternative Investment Strategies w/ Dan Holmlund 45:41

6M ago45:41

45:41

Send us a text Ready to slash your tax bill? Schedule your free consultation and let's strategize your tax savings together! Book now at: https://www.prosperlcpa.com/apply Or, if you still need more time, here are some other ways to begin winning the tax game... Take our free Tax Planning Checklist & learn about what tax savings may be available fo…

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EP 112 - Navigating Complexities in Tax & Wealth Planning w/ Ryan Sweet 35:51

6M ago35:51

35:51

Send us a text Mark Perlberg and Brian Sweet discuss strategies for building and protecting wealth beyond tax savings, with an emphasis on what to do with cash after receiving tax refunds from bonus depreciation and other tax benefits. They explore holistic wealth planning approaches that balance immediate tax benefits with lifetime tax minimizatio…

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VRS619 - Making AI Work for You: Insights, Use Cases, and a New Industry Survey with Fred Bassili of Hostfully 50:55

6M ago50:55

50:55

In this episode of the Vacation Rental Success Podcast, host Heather Bayer sits down with Fred Bassili from Hostfully to discuss the evolving role of AI in vacation rental businesses and how short-term rental managers can use AI tools and workflows to scale operations, improve guest communication, and boost owner acquisition. Fred Bassili, a season…

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EP 111 - Tax Planning for Pivoting OUT of Real Estate 21:34

6M ago21:34

21:34

Send us a text The dream of mailbox money through real estate investing often collides with the reality of demanding property management, leading many investors to seek alternative wealth-building paths while maintaining tax advantages. • Hire property managers to maintain real estate professional tax status benefits while reducing workload • Inves…

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EP 110 - Why You Should (or should not) Defer Taxes 20:22

6M ago20:22

20:22

Send us a text Tax deferrals can be a powerful tax strategy when implemented properly and at strategic times, as demonstrated by a client who missed an opportunity that will cost them approximately $100,000 in taxes. We explain why timing your tax deferrals between high and low-income years creates massive tax savings despite common objections. • C…

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VRS618 - Legacy, Leadership & AI: Inside the Evolution of Cottage Connection of Maine with Alexis Miller 44:21

6M ago44:21

44:21

Some of the strongest brands in the vacation rental business have been around for decades and are rooted in tradition, family values and local knowledge. As the next generation stepping into a decades-old family-run vacation rental business, Alexis Miller personifies this legacy as she shares how she's honoring her family's rich story while usherin…

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EP 109 - The Consumption Tax - The Hidden Cost Making You Broke! 16:25

6M ago16:25

16:25

Send us a text Ready to slash your tax bill? Schedule your free consultation and let's strategize your tax savings together! Book now at: https://www.prosperlcpa.com/apply Or, if you still need more time, here are some other ways to begin winning the tax game... Take our free Tax Planning Checklist & learn about what tax savings may be available fo…