STR Like The Best

Most high earners are winning the income game and losing the wealth game. They make great money, hand half to the government, park the rest in a savings account that doesn't beat inflation, and wonder 10 years later why they don't have more to show for it.

In this episode, Michael and Liz debrief their first-ever client conference, Architect Your Wealth, held in New York City with almost 100 clients flying in from across the country, and break down the exact wealth framework they've built over 10 years of STR investing.

They also share the full origin story of STR Like The Best, the moment in a cold Chicago conference room that changed everything, and the new wealth management platform they just launched to help clients manage their money the right way.

We break down:

The Make, Keep, Grow framework and why focusing only on your income is the reason most high earners fall behind

The 4-bucket wealth system Michael and Liz use personally to organize every dollar that comes in

Heirmont Wealth, their new wealth management platform and how it manages their core stock and bond portfolio on a quarterly basis

The Architect Your Wealth conference recap with almost 100 clients in one room in New York City and why the energy in that room felt like a milestone

Why proactive financial planning at the start of the year beats reactive tax-time panic every single time

The origin story of STR Like The Best from a cold February conference in Chicago to almost 30,000 LinkedIn followers and 100 podcast episodes

The bottom line: Building real wealth isn't about working harder. It's about making more, keeping more, and growing what you have with a real plan.

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

Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

If you're earning good money and still handing a massive chunk of it to the IRS every April, there's a better way. We built it the hard way so you don't have to.

In this episode, Michael sits down with his partner Liz to pull back the curtain on how they built STR Like The Best from zero followers in May 2023, why they finally launched their education programs, and what 10 years of trial and error actually taught them about building real wealth through short-term rentals.

This isn't a highlight reel. It's the real story of posting to 3 views, hiring mentors when they had no idea what they were doing, and building a business that now helps high-income W2 investors stop overpaying taxes and start building generational wealth.

We break down:

How one conference in Chicago changed everything and led to launching STR Like The Best with zero followers and no roadmap

Why hiring a mentor is the single fastest way to compress 10 years of mistakes into months, and what to actually look for when choosing one

The STR Concierge program: how Michael and Liz guide high-income investors through market selection, property analysis, tax strategy, and operations from start to finish

Why earning $400K a year means paying $125K in taxes, and how buying an Airbnb with 100% bonus depreciation back in 2025 changes that equation completely

Why building a personal brand is no longer optional in the age of AI, and why waiting even one more year makes it harder

What's next: the Elite group coaching program, future fund plans, and how they're scaling to help more investors build real wealth

The bottom line: Ten years of figuring it out the hard way is only worth something if someone else gets to skip the hard part.

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

Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most high-income W-2 professionals are leaving six figures on the table every year because their accountant doesn't fully understand the short-term rental tax loophole. And with 100% bonus depreciation now back permanently, the stakes have never been higher.

In this episode, I sit down with Amanda Han and Matt from Keystone CPA to give the most comprehensive breakdown of the STR tax loophole we've done on this show, covering material participation tests, audit defense, and what the new tax law means for high-income investors right now.

Amanda and Matt are CPAs by day and real estate investors by night. They've helped investors across the country legally offset W-2 income using this part of the tax code, and they've seen firsthand how often good investors lose serious money simply because their accountant doesn't understand the rules. This episode fixes that.

We break down:

The 3 material participation tests that unlock the STR loophole (the 500-hour rule, the 100-hour rule, and the majority test most people don't know exists) and how married couples can combine hours to qualify faster

The grouping election that most CPAs miss and why not having this one paragraph on your tax return is an audit risk waiting to happen once you scale beyond one property

What activities count toward your hours and what don't including whether flying to your property, driving to the airport, and doing bookkeeping actually qualify

How to audit-proof your STR strategy with RepsTracker, a separate phone number, a dedicated email address, and the documentation habits that make the IRS move on without a fight

Why 100% bonus depreciation being permanent makes the STR loophole 2.5x more powerful than it was before the Big Beautiful Bill passed in July 2025

3 phrases that signal your CPA doesn't understand this strategy and what to do if you hear "you make too much," "you work too much at your job," or "you're not a real estate professional"

The bottom line: The STR tax loophole is one of the most legitimate and powerful tools available to high-income W-2 earners, and the new tax law just made it more powerful than ever. The only thing standing between you and six figures in annual tax savings is having the right team and the right strategy.

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

Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most high earners are stuck paying 40% in taxes year after year, trading time for money, and wondering if there's actually another way. There is. We know because we lived the exact same story.

In this episode, I sit down with my co-founder Liz to share the real origin story behind STR Like The Best, why we left investment banking and a fashion career to build a 30+ property portfolio, and what finally convinced us to start teaching everything we know.

This isn't a pitch. It's the behind-the-scenes conversation we've been meaning to have, covering 9 years of building, the early mistakes we made, and the four core values that drive every decision we make today.

We break down:

How a single Queens apartment generating $5,000 a month in cash flow changed everything in 2016

Why Liz and I left high-paying corporate careers to go all-in on short-term rentals

The real reason we launched the mentorship program and why we don't just keep the playbook to ourselves

The 4 core values behind every decision at STR Like The Best: family first, long-term thinking, numbers not feelings, and responsibility to our community

Student success stories: from a stay-at-home mom launching her first STR to Julie and Andy scaling to 18 Airbnbs in Dallas

The bigger vision for what STR Like The Best is becoming: a holistic wealth community covering tax planning, estate planning, and investing mindset

The bottom line: Real estate is the tool, but the goal has always been the same. Build a life where family comes first and the money works for you, not the other way around.

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

Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most STR investors spend months finding the perfect market and the perfect property. Then they buy something "turnkey," take their own photos, skip the specialist designer, and wonder why their numbers fall flat.

In this episode, Michael and Liz break down the complete framework for turning a good property into a 90th percentile short-term rental, from design and staging to photography and dynamic pricing.

This is not about buying better. It is about executing better once you own it. Michael and Liz share the exact mistakes they made early in their own portfolio, what they changed, and why doing it right the first time creates a flywheel that compounds for years.

We break down:

Why "turnkey" is a trap and what a properly designed STR actually looks like

The difference between an STR-specific designer and a residential designer, and why it directly impacts your returns

Why we spent $5,000 on a photographer and flew him to Tennessee for 3 full days

The storefront framework: how to think about design, staging, and photography as one complete package

The guest experience details that drive 5-star reviews, from labeled light switches to welcome baskets at check-in

Dynamic pricing and revenue management: the final piece that determines what your property actually earns

The bottom line: Picking the right market and property is only the first 10%. The investors who consistently outperform are the ones who execute the design, the photography, and the operations at a level most people skip.

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

Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most people using AI like a search engine are leaving serious money on the table. If you're typing one-off questions on a free plan and calling it a day, you're running one of the most powerful tools available at about 5% of its actual capacity.

In this episode, I sit down with Liz to break down exactly how we use AI across our 30+ property portfolio, from analyzing inspection reports before we close to solving guest issues without sending a repair person out at 11pm.

These are not theories. These are the exact systems we use every week, and why we spend $500 a month on AI subscriptions without hesitating.

We break down:

Why the free plan is actively working against you and why $25 a month is the best investment you can make this year

How to upload a 60-page inspection report and have AI act as your personal property inspector, pulling the 5 biggest issues, projected repair costs, and best and worst case scenarios

The adversarial AI method: how I pit Claude against ChatGPT on high-stakes decisions to stress test answers and catch hallucinations before they cost me money

Why AI makes you a better client, and how I used it to push back on an attorney who kept giving me hand-wavy answers on our corporate structure

How we build a separate AI project for every property we own, loaded with appliance manuals, vendor contacts, and inspection reports, so our VA team solves guest issues in minutes instead of days

The project context file technique that keeps your AI sharper with every session instead of starting from scratch each time

The bottom line: AI does not replace your expertise. It multiplies it. The operators who figure this out are building a permanent edge over everyone still treating it like a better Google.

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

Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most high-income couples assume getting a real estate license is the shortcut to real estate tax benefits. We made that exact mistake in 2018, and it cost us years of going down the wrong path.

In this episode, I sit down with Liz to break down the real difference between Real Estate Professional Status and the STR tax loophole, and why one works for almost every W-2 couple and the other almost never does.

We recorded this one just the two of us because this question comes up constantly with our clients and we wanted to put the whole framework in one place. No fluff, just the mechanics, the mistakes, and the exact questions you need to ask your CPA before you do anything.

We break down:

Why 99.99% of W-2 couples don't qualify for REPS, and why a real estate license changes absolutely nothing

The 100-hour material participation rule and why it's achievable even when both spouses are working full time

What hours actually count toward material participation, and the investor hours the IRS will never give you credit for

Why your CPA is not your tax strategist, and why that responsibility falls entirely on you

The Schedule C vs. Schedule E test: one question that tells you immediately whether your CPA actually understands this strategy

Why it's still possible to execute the STR loophole this tax year, even if you're starting in August

The bottom line: Taxes are your single largest expense. The STR loophole is the most accessible tool a dual-income couple has to keep more of what they earn, but only if you understand how it actually works.

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

Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most couples don't realize the empty nester transition is three separate problems, not one. And most of them hit all three at the same time, completely unprepared.

In this episode, Liz and I sit down to break down what actually happens when the kids leave, why stay-at-home parents lose more than just a routine, and how short-term rental investing solves all three problems at once.

This isn't just a real estate episode. It's a life design episode. We share what we've learned from building an STR portfolio together, the hard conversations we had along the way, and why we believe this is the single best vehicle for any couple heading into the empty nester phase.

We break down:

The three-part identity crisis stay-at-home parents face when the kids leave and why going back to work isn't the answer for most people

How building an STR business together gives both spouses a separate identity and a shared project at the same time

The 100-hour material participation rule and why married couples filing jointly have an advantage most people completely miss

How Liz and I divide lanes in our business, why the first year is hard, and what we figured out that made it work

Why our kids already have a bigger Roth IRA than I had in my 20s and how we fund it through the STR business

Why waiting until you're 60 to build this life is the one mistake we're glad we didn't make

The bottom line: The empty nester transition doesn't have to mean losing your identity, drifting from your spouse, and hoping your 401k holds. STR gives you all three things back at once.

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

Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most investors think the endgame is to buy, hold, and eventually sell. But selling might be the most expensive decision you ever make.

In this episode, Michael and Liz share a real-time breakdown of their newest short-term rental, a $2.4M Tennessee property launched July 1st, covering the actual cash flow numbers, the tax strategy behind it, and why they plan to hold it for generations.

This is one of the most transparent, numbers-first episodes we've done. No hypotheticals. Just the real performance data, the cost segregation results, and the Section 1014 strategy that changes how you think about real estate as a long-term wealth tool, all recorded while managing the property from 12 time zones away in Taiwan.

We break down:

How the property hit $30K in revenue and 82% occupancy in its very first month, before professional photos were even live

Why the cost segregation study is projecting $800K to $1M+ in protected taxable income from this single property, and how an on-site engineering study could push that number even higher

The Section 1014 strategy that lets you pass real estate to your kids completely free of capital gains tax and depreciation recapture

How Michael and Liz manage 12 properties remotely in about an hour a day each, whether they're in New York or 12 time zones away

Why they only use 30-year fixed-rate debt, never underwrite a refinance, and model a conservative 3% annual appreciation when analyzing a deal

How $370K in projected tax savings effectively returns more than half their original cash investment in year one

The bottom line: The real power of STR investing isn't just the cash flow. It's what happens when you stack cost segregation, bonus depreciation, and Section 1014, and hold the asset long enough to change your family's financial future.

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

Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/

Most people building passive income are chasing a number. We were chasing something else entirely.

In this episode, Michael and Liz sit down together from Taipei, Taiwan, where they're spending their third consecutive summer with their kids, to share the real reason they built their STR portfolio and what time freedom actually looks like in practice.

This isn't a theory episode. It's a behind-the-scenes look at how two former investment banking and fashion professionals designed a life where the portfolio works while they're sleeping, the kids are in $45 swim lessons four days a week, and the whole family is under one roof for seven weeks straight.

We break down:

How 8 short-term rentals generate $200K+ in July revenue while Michael and Liz are 12 time zones away

The real cost breakdown of 7 weeks in Taiwan, including flights, summer camp, and personal training, and why it costs a fraction of what it would in New York

The daily schedule that lets them work 8 to 12, spend afternoons with their kids, and still meet their 500-hour material participation requirement for the STR tax benefit

How a team of nearly 10 specialists provides 24-hour client support across Slack so their mentorship program never misses a beat while they sleep

Liz's golden handcuff story and why 10 vacation days a year was never going to be enough

The immigrant parent story that became the North Star for everything Michael has built

The bottom line: The STR portfolio isn't the point. The time it buys you is.

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

Track your STR hours the right way. STR Tax Loophole is our time tracking app built specifically for short-term rental investors. Document your qualifying activities, maintain clean records, and simplify your STR tax qualification. Start your free trial at https://www.thestrtaxloophole.com/