STR Like The Best

Michael Chang
  • 5.0 (67)
  • ENTREPRENEURSHIP
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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.

  1. 23H AGO

    You're Smart Enough to Figure This Out Alone. That's Exactly Why You're Stuck.

    You've built a successful career by outworking and outthinking everyone around you. So why does building wealth outside your W2 feel so hard? In this episode, Michael and Liz sit down to talk about the one thing that actually accelerated their journey from a few properties to a 30+ unit portfolio: community. They share how a corporate "zero-sum" mindset kept them isolated early on, and what changed when they started asking for help, showing up at conferences, and surrounding themselves with people a few steps ahead. This isn't a fluffy conversation about networking. It's a real look at how one introduction, one conversation, or one piece of advice from the right person can unlock years of progress. We break down: How meeting one person at a conference in 2016 led to virtual assistants, better systems, and eventually the entire STR Like The Best education business The mindset shift from "figure it out alone" to building a network that compounds over time Why high earners often struggle to ask for help and how cultural and personality factors play into it What their mentorship community actually looks like with 150+ investors, 20 team members, and resources at every stage from search to operations The give-and-take dynamic that attracts the right people and filters out the ones who only take Why trying to do this solo is like playing on "super hard mode" and what to do instead The bottom line: The fastest path to building wealth isn't figuring it out alone. It's finding the right people who've already done it and learning from them. LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb

    30 min

  2. JAN 16

    When to Walk Away From Your Best Asset (A $600M Real Estate Lesson)

    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 is about market timing, discipline, and deal selection principles that apply whether you're buying your first Airbnb or your tenth apartment building. We break down: Why Eli stopped buying. The Fed said "we no longer have your back." Eli listened and shut down acquisitions. Groups that kept buying are now facing capital calls and wipeouts.The controversial REIT take. Public REITs are cheaper than private multifamily deals right now. You get diversification, liquidity, no promote fees, and better debt costs. "Why would anyone pay more for an illiquid private deal?"When Eli DID buy in 2024. San Francisco off a major REIT, well below pre-COVID pricing. Denver dramatically below seller's cost basis. Both below replacement cost with strong fundamentals.Michael's deal selection story. "I looked at dozens of STR deals. One came up with crappy iPhone photos. We knew it was different. Made an offer the next day. Strong cashflow and appreciation followed. You need the reps to develop conviction."The fast food arbitrage. Operating businesses and real estate trade at different multiples. If you own both, you can shift value between them. Eli's developing chicken restaurants across Texas using this strategy.The power of showing up. Michael drove up with his daughter in a stroller. The sellers were grandparents. They gave her a teddy bear. "That teddy bear is worth a million dollars now."Whether you're buying short-term rentals, multifamily, or restaurants, the principles are the same. Do the reps so you recognize the right deal. Know when the market doesn't justify the risk. Walk away when it doesn't make sense. Move fast with conviction when you see the right one. This isn't your typical STR episode, but the lessons on market timing and deal selection apply to any real estate investor. LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb

    39 min

  3. JAN 3

    Why We Started STR Like The Best (And Why We're Teaching You Everything We Know)

    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 both working in investment banking showed them there was a different path than the 9-to-5 grindWhy they started teaching. Friends and family kept asking "how do you do that?" They started sharing online. The community response surprised them. Seeing student success became more rewarding than doing deals themselvesThe transformation stories. From stay-at-home moms launching their first property remotely (Philadelphia to Dallas) to couples quitting their jobs to run 18+ units. The self-confidence people develop is the real winThe four core values that guide every decision: (1) Family first, (2) Long-term thinking, (3) Numbers not feelings, (4) Responsibility to their communityLiz's immigration story. Coming to the US at 16, working in fashion for 9 years, feeling stuck in paycheck-to-paycheck cycles, and only seeing family once a year for one week. The lack of time freedom drove her to real estate meetups every weekMichael's "brainwashed" moment. Investment banking taught him nothing about tax strategy, cost segregation, or building wealth outside of a W2. "We're brainwashed to think we have to work a job till 65 and pay our taxes. But no, there's a different way."The 6 weeks in Taiwan. How they achieved the level of freedom to spend July and August abroad with their kids, something impossible when working in banking, proving location independence is realThe vision for the community. It's not just about buying one property and saving on taxes. It's holistic financial planning: estate planning, insurance, tax-efficient investing for your kids, building generational wealth. Real estate is one piece of the puzzleWhy abundance mindset works. "There's so much opportunity out there. We don't have enough money or time to hit it all. We want to teach you so you can have this for yourself." When you share knowledge, it comes back in unexpected ways (deal flow, partnerships, connections)If you've ever wondered why high-income professionals are leaving stable careers to build STR portfolios, or why hundreds of people trust Michael and Liz to guide them through this strategy, this episode gives you the unfiltered answer. LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb

    20 min

  4. 12/19/2025

    How AI Automates 90% of My Guest Messages (And Why Hosts Who Don't Adapt Will Get Left Behind)

    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, detect guest problems, and make decisions about review removals, whether you know it or notWhy Michael went from highly skeptical to running his entire company on HelloHost in 2-3 weeks (started with 3 lowest-performing listings, now uses it for all 30+ properties)The multi-agent system that makes 90% automation possible. It's not just a chatbot, it's multiple AI agents debating in real-time to get the answer right before respondingWally, the operations AI agent that lives in your WhatsApp/Slack and handles maintenance coordination, guest info lookups, and mass messaging ("Hey Wally, tell all my guests Merry Christmas")How ChatGPT is becoming a discovery platform and why Airbnb's negotiating with OpenAI over who controls the booking flow (and what this means for your listings)Why AI costs are subsidized right now and won't stay cheap. The Uber pricing trajectory from $2 rides in 2010 to $45 for 10 minutes todayAI Engine Optimization (AEO): The new SEO for getting your property discovered on ChatGPT and LLMs, not just GoogleWhy review removal is now AI-assisted and the default answer is "no." Understanding how platform decisions are being automated AI is not coming to short-term rentals. It's already here. Airbnb is using it. Your competition is using it. Michael uses HelloHost for all 30+ of his properties because if you're not using AI to handle guest communications and operations, you're working 10x harder for the same results. The subsidized learning period is now. Costs will go up dramatically in the next few years. Try HelloHost free for 30 days at strlikethebest.com/hellohost LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb

    30 min

  5. 12/12/2025

    How We Manage 30+ Short-Term Rentals, 2 Kids Under 5, and Actually Like Each Other

    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 money solved more problems than therapy ever could. We break down: The one non-negotiable rule about how they talk about each other (in public and private) that's kept their partnership strongWhy "you can't manage what you can't measure" applies to marriage just as much as business, and the KPIs they actually trackHow they built the business before kids and why that timing gave them an unfair advantage when babies arrivedThe delegation framework that works for both business and home (virtual assistants, cleaners, postpartum nannies, and why there's no pride in doing dishes)Why Liz was pregnant for 12 of the last 60 months and how they structured support during postpartum recovery (hint: it wasn't just "tough it out")The mindset shift from "no one can do it like me" to trusting a global team of 20+ people they've never met in personHow making more money isn't about working more, it's about hiring out everything you're not good at or don't want to doWhy working with your spouse means no operating agreements, no distribution fights, no tax headaches, just two people rowing in the same directionThe transferable strengths they've borrowed from each other (EQ, design thinking, analytical skills) and how they've covered each other's weaknessesBeing married and working together is either your biggest asset or your biggest liability. The difference comes down to alignment, delegation, and one critical rule about how you treat each other when things get hard. LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb

    18 min

  6. 12/05/2025

    Why Most Hosts Are Slaves to Their Airbnb (And How to Break Free) w/ Shaun Shirazian from Lodgify

    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 change how small operators compete. We break down: The three types of independence STR investing unlocks (financial, location, and time) and why diversification across OTAs is the only real protection against platform riskWhy 86% of hosts have 7 listings or below, and why software built for 100-unit operators doesn't work for the long-tail marketHow Lodgify helps hosts go from Airbnb-only to multi-channel distribution with a direct booking website in minutes, not weeksThe mental model shift from managing one OTA to managing a real business through a PMS system, and why the calendar is the most important visual elementAI's role in guest messaging (90% automation is now possible with tools like HelloHost) and why pricing optimization is the next frontier no one has solved yetWhy properties with just one distribution channel struggle to fill weekdays, and how multi-platform presence dramatically lifts occupancy ratesTechnology is just the how. The what hasn't changed in 20 years. Hosts want passive income, peace of mind, and independence. The right tech stack makes that possible. The wrong one (or no tech stack) keeps you trapped. Try Lodgify free at www.lodgify.com For direct questions, email Shaun at shaun.shirazian@lodgify.com LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb

    38 min

  7. 11/28/2025

    What Your CPA Gets Wrong About The STR Tax Loophole w/ Amanda Han & Matt MacFarland from Keystone CPA

    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 material participation tests that actually matter (500 hours, 100 hours with no one else having more, and more hours than everyone combined) and why married couples have a major advantageThe grouping election that most CPAs miss entirely because it's a paragraph, not a form, and why this one oversight can destroy your audit defense when you scale to multiple propertiesWhat actually counts toward your hours (hint: it starts when you go under contract) and what doesn't count no matter how much time you spend on itA real IRS audit case study where the auditor automatically disallowed all losses because the properties were out of state, and how it ended with zero changes after proper documentationWhy properties with lower land value create significantly larger tax benefits and which markets give you the best depreciation potentialThe three red flags that signal your CPA does not understand the STR loophole (if you hear any of these, it's time to find a new accountant)Best practices for documentation including RepsTracker, separate phone systems, dedicated email addresses, and why showing up as an "A plus student" changes everything in an auditWith bonus depreciation now permanent at 100%, this is the most meaningful window for high-income W2 earners to legally offset substantial income through short-term rental investing. But only if you do it right. Check out Keystone CPA: https://strlikethebest.com/keystonecpa Follow Amanda on Instagram: https://www.instagram.com/amanda_han_cpa LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb

    42 min

  8. 11/21/2025

    Can You Really Trust That Revenue Projection? Inside How STR Data Actually Gets Made

    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 the numbers you're betting your money on are accurate or fantasy. We break down: The review-matching verification method that reveals when a property claiming 80% occupancy only has two reviews (the simple check sophisticated investors use before trusting any data)Why scraped data can actually be more comprehensive than first-party PMS data, and the real tradeoffs between accuracy and coverage that most investors don't understandHow 36 months of historical data reveals seasonality issues and bad comps that annual snapshots completely miss (this is why monthly breakdowns matter more than you think)The technical truth behind how platforms collect, process, and present your numbers, from data scrapers to cleaning algorithms to the alerts that catch when things go wrongWhy averaging three different data points guarantees you the wrong answer, and what to do instead when platforms give conflicting projectionsData confidence is the difference between taking action on great deals and second-guessing yourself into paralysis. When you understand how the numbers actually get made, you can finally trust your analysis enough to pull the trigger. LEARN MY STR INVESTING & STRATEGIES 🔥 https://strlikethebest.com/wealthpod Apply to work with Michael: https://strlikethebest.com/applypod Follow Michael on Instagram: https://www.instagram.com/michaelchangbnb

    28 min
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5
out of 5
67 Ratings

About

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.

Information

  • Creator
    Michael Chang
  • Years Active
    2023 - 2026
  • Episodes
    76
  • Rating
    Clean
  • Copyright
    © 2026 STR Like The Best
  • Show Website
    STR Like The Best

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