STR Like The Best

Your CPA says you make too much money. They say you work too many hours at your job. They say you need to be a real estate professional. All three of those statements are wrong. In this episode, Michael sits down with Amanda Han and Matt MacFarland from Keystone CPA, two of the leading tax experts in the short-term rental space, to break down exactly how the STR tax loophole works, why most CPAs g...

LEARN HOW I ANALYZE IF A PROPERTY WILL WORK AS A STR 🔥 https://strlikethebest.com/strlitmustest?utm_source=pod You're about to wire $150K for a down payment based on a revenue projection. But three different platforms just gave you three different numbers. Which one is real? In this episode, Michael sits down with Jae Seok An, founder of AirBtics and former Meta software developer, to pull b...

USE MY 5-STEP LITMUS TEST TO SEE THE PROFITABILITY OF A POTENTIAL PROPERTY: https://strlikethebest.com/litmuspod Q4 2025 Market Update: What's Actually Working Right Now Most people think high-income professionals are buying Airbnbs for cash flow. They're wrong. In this episode, Michael and Liz reveal the real reason why employees at Meta, Amazon, Blackstone, and Goldman Sachs are aggres...

LEARN MY STR INVESTING & STRATEGIES 🔥 https://coaching.strlikethebest.com/7figureexit?utm_source=yt Part 4 — Taipei Series Part 3 explored how mentorship, consistency, and STR tax strategy turned business growth into leverage and legacy. Part 4 dives into how those same principles shape parenting, raising kids with judgment, integrity, and emotional intelligence in an AI-driven world. 1. From...

LEARN MY STR INVESTING & STRATEGIES 🔥https://strlikethebest.com/wealthyt Part 3 — Taipei Series Episode 2 showed how humility, metrics, and defined roles turned conflict into scale, systems + a global team protecting marriage and ROI; Episode 3: dives into building our media/education engine (mentors, consistency) and how STR tax strategy (incl. 100% bonus depreciation) lets high-earners buy...

LEARN MY STR INVESTING & STRATEGIES 🔥https://strlikethebest.com/wealthyt Part 2 — Taipei Series In the previous episode, Michael and Liz shared how systems, tech, and a global team let them run ~40 STRs remotely. In this part of the series, they continue the conversation, diving into how they work together as a married team, balance decision-making with data, and turn early conflicts into a s...

LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthyt From Taipei, Michael and Liz show how systems, tech, and a global team let them run ~40 STRs remotely, reclaim family time, and help clients save taxes while scaling.  Episode Highlights: 1. Hands-off weekly hours, kids immersed with family and mandarin 2. Staff across 5 continents and working collectively to run 95% of...

In this episode of STR Like the Best , I sit down with John from Topkey—a financial operating system built specifically for property managers—to talk about the “unsexy” but absolutely essential side of running a short-term rental business: cash flow, expense tracking, and financial controls. We cover why cash (not revenue) is the single source of truth in your business, how to capture every reimbu...

In this episode of STR Like the Best , I sit down with Alex Alioto, Co-Founder and Head of Growth at Whimstay, an OTA built specifically to fill your last-minute and gap-night inventory. We break down why relying solely on Airbnb is like owning a stock portfolio with just one stock, how to think strategically about OTA distribution, and why last-minute travelers aren’t just bargain hunters—they’re...

In this episode, I sit down with JJ King—STR operator, ex-product lead, and serial entrepreneur—who scaled from answering Craigslist ads to running a 300-unit property management company. We dive deep into the early rental arbitrage days in NYC, how a cold outreach strategy turned into a SaaS acquisition, and what it takes to scale a property business sustainably in today’s market.  LEARN MY STR I...

In this week's episode, Michael Chang and Avery Carl, CEO of The Short-Term Shop, break down the brutal reality of today’s short-term rental market and why that’s exactly where the opportunity lies. If you want to thrive in today's market and position yourself for outsized returns, this episode is a must-listen. Subscribe for more STR investor strategies every week. JOIN MY PRIVATE COMMU...

JOIN MY FREE INVESTOR COMMUNITY FOR MONTHLY COACHING & DAILY WEALTH-BUILDING STRATEGIES 🔥  https://www.strlikethebest.com/insider In this episode, Michael Chang and Philip Kennard discuss the evolving landscape of short-term rentals, focusing on the importance of direct bookings versus relying solely on online travel agencies (OTAs) like Airbnb. They explore the benefits and challenges of bot...

JOIN MY FREE INVESTOR COMMUNITY FOR MONTHLY COACHING & DAILY WEALTH-BUILDING STRATEGIES 🔥  https://www.strlikethebest.com/insider In this episode of STR Like the Best, Michael Chang sits down with Jeff Illoulian, CEO of HostGPO, to explore how short-term rental operators can save money and streamline their furnishing process. Jeff shares his journey from managing 150 STR units to founding Hos...

JOIN MY FREE INVESTOR COMMUNITY FOR MONTHLY COACHING & DAILY WEALTH-BUILDING STRATEGIES 🔥 https://www.strlikethebest.com/insider ⭐ In this conversation, Michael Chang interviews William Lucas, the chairman of Mint House, a leading company in corporate housing and short-term rentals. William shares his entrepreneurial journey, the inception of Mint House, and the challenges & strategies i...

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider     In this episode, I sit down with Sarah and Emily — better known as the Karwells — two best friends turned powerhouse STR investors who’ve raised over $5.5 million from everyday investors, built a thriving portfolio of uniquely designed Airbnbs, and launched a brand that span...

In this episode, Michael Chang and Thomas Castelli, CPA, break down essential tax strategies for short-term rental investors. Learn how to leverage the "short-term rental tax loophole" to offset W-2 income, maximize depreciation benefits, and avoid common tax pitfalls. They also discuss material participation rules, bookkeeping best practices, and key deductions to optimize your financia...

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider   In this episode, host Michael Chang interviews Federico Zimmerman, a seasoned property manager operating a short-term rental management company with 65 properties across 12 states in the U.S. Federico shares his inspirational journey of transitioning from a corporate career in...

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider  In this episode, Michael Chang interviews Pierre-Camille Hamada, CEO of hospitable.com, discussing the transformative impact of AI technology on short-term rental management. Pierre shares his unique journey from a law career to founding a leading property management software,...

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider  02:54 Understanding the Value of Cost Segregation 06:03 The Role of CPAs in Real Estate Investing 08:55 Short-Term Rentals and Tax Benefits 14:45 The Future of Cost Segregation and Legislative Changes 17:57 Real-Life Examples and Case Studies 20:47 When Cost Segregation May Not...

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES 🔥 -https://www.strlikethebest.com/insider  In this episode, Michael Chang interviews Jonathan Farber, a successful real estate investor and entrepreneur. Jonathan shares his journey from a sales software company to building a diverse real estate portfolio, including short-term rentals. He discusses creative financing st...

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES  🔥  -https://www.strlikethebest.com/insider  In this episode of STR Like the Best, Michael Chang sits down with Shahar Goldboim, CEO of Boom AI, to explore how artificial intelligence is reshaping the way short term rental hosts and property managers operate. From centralizing tasks to boosting efficiency and increasing...

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES  🔥  -https://www.strlikethebest.com/insider  In this episode of STR Like The Best, Michael Chang sits down with leading hospitality entrepreneur Isaac French to discuss thriving in the ever-evolving short-term rental market. Michael and Isaac dive into the dynamics of scaling a traditional rental business versus craftin...

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES  🔥  -https://www.strlikethebest.com/insider  In this episode of STR Like The Best, host Michael Chang sits down with industry expert Caleb Shore to reveal strategies for scaling your short-term rental business in the evolving landscape of 2025 and beyond. Tune in to learn how to: - Leverage advanced revenue management t...

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES  🔥  -https://www.strlikethebest.com/insider  Today, I'm thrilled to be joined by STR Like The Best coaching member Jaime Cabal! In less than a year after joining the program, Jaime has scaled his Airbnb business into a thriving global operation and investment portfolio. He’ll be sharing the strategies, pivotal deci...

JOIN MY PRIVATE COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES  🔥  -https://www.strlikethebest.com/insider  In this episode of 'STR Like The Best,' host Michael Chang interviews seasoned investor Michael McKay about advanced real estate negotiation strategies and the evolution from Airbnb to property flipping. They discuss McKay's focus on solving sellers' probl...