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 business lessons to family values, why reputation, patience, and presence matter more than rule...

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 cash-flowing assets and cut taxes. Episode Highlights: 1. From zero followers to a global brand—...

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 scalable structure. Episode Highlights: 1. Offloading guest comms to a global team + PMS/AI to r...

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 business operation 3. The renewed 100% bonus depreciation spiking client deals. They...

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 reimbursable dollar without adding admin headaches, and how to keep your favorite rewards credit cards i...

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 a fast-growing segment that can boost your weekday occupancy. Alex shares practical tips on integ...

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 INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod Apply to work with Michael...

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 COMMUNITY FOR DAILY WEALTH-BUILDING INSIGHTS & STRATEGIES https://www.strlikethebest.com/insider ⬇️ ...

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 both strategies, emphasizing the need for rentalpreneurs to build trust with guests, mana...

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 HostGPO, a group purchasing organization offering discounted, hospitality-grade furnitur...

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 involved in raising capital and building a scalable team. ⭐ They highlight the importance of...

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 spans education, e-commerce, retreats, and more. We talk about how they e...

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 financial outcomes. Don't miss these expert insights to grow your wealth through smart tax planning! 🚀 JOI...

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 Argentina to starting and scaling a successful short-term rental business in the Unit...

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, emphasizing the importance of automation and technology in enhancing guest experience...

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 Be Beneficial 24:06 The Importance of Control in Real Estate Investing ⬇️ Ap...

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 strategies, the shift to short-term rentals during COVID, and the importance of market...

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 revenue, Shahar shares the innovative strategies behind Boom AI. Shahar...

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 crafting unique accommodations, and what investors should know in order to strike th...

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 to maximize profits. - Master effective hiring techniques for building a stron...