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Proven strategies and insights from successful STR investors and wealth-building experts. We share methods that help high-income earners protect their income, build lasting wealth, and compound their finances for the long term.
75 Episodes
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Usually we focus on short-term rental investing, tax strategy, and how high-income professionals can offset W2 income through STRs. Today's different. Michael sits down with his college friend Eli Cohen, who's acquired $600 million in multifamily real estate over 15 years, to talk about something every investor needs to understand: knowing when to walk away. In 2022, Eli stopped buying. Not because he ran out of capital. Because the returns didn't justify the risk anymore. This conversation i...
Most people ask us: "Why would you teach this? Why not just keep it to yourself and do more deals?" Fair question. In this episode, Michael and Liz sit down to answer that question and share the real story behind STR Like The Best, the core values that drive everything they do, and why they've helped hundreds of high-income professionals build STR portfolios from scratch. We break down: The $10K/month origin story. How one apartment in Queens making $5,000/month in cashflow while they were bo...
If you're manually responding to guest messages at 11pm, you're competing with one hand tied behind your back. In this episode, Michael sits down with Annie, co-founder of HelloHost (the AI platform Michael uses in his own STR business), to break down how AI is fundamentally changing short-term rental operations and why hosts who don't adapt will get left behind by operators who are 10x more efficient. We break down: How Airbnb is reading every message you send with AI to enforce policies, ...
Most couples can't work together without wanting to kill each other. Add two kids under five, 30+ properties across multiple states, and a seven-figure business to the mix, and you've got a recipe for disaster. Except it's not. In this episode, Michael and Liz pull back the curtain on how they actually make it work. Not the Instagram highlight reel. The real stuff. The 2:30 AM wake-ups, the fights they avoided by hiring smart, the one rule that's saved their marriage, and why making more mone...
If you're only on Airbnb, you don't have a business. You're a vendor to Airbnb. And if they change the algorithm, spike their fees, or suspend your account over a bad review, your entire income disappears overnight. In this episode, Michael sits down with Shaun Shirazian, CEO of Lodgify, to break down why property management systems are non-negotiable for anyone serious about STR investing, how the right tech stack creates three types of independence, and why AI is about to fundamentally chan...
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 get it wrong, and how to protect yourself if the IRS ever comes knocking. We break down: The three...
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 back the curtain on how short-term rental data actually gets built and more importantly, how to know if ...
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 aggressively buying $750K-$1.5M short-term rental properties and it has everything to do with the tax code. We br...
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...
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