Most STR investors hit a wall around property 3 or 4. Not because they run out of deals, but because conventional lenders start stacking paperwork, haircuts, and restrictions that make it nearly impossible to keep moving.

In this episode, I sit down with Robin Simon, author of The Book on DSCR Loans, to break down every financing option available to short-term rental investors and exactly when to use each one.

Robin spent years inside the DSCR lending industry, took a year off to write a 715-page book on the subject, and used that same time to buy three STRs himself using the strategies he teaches. This is the conversation I wish I had before I started scaling.

We break down:

What DSCR loans actually are and how they're different from conventional financing, including why they look at the property instead of your W-2

The second home loan trap most new investors fall into, and why the 180-day occupancy rule makes it nearly impossible to cash flow

Why the 5 to 50 property range is the sweet spot for DSCR loans, and when conventional financing still makes more sense

How DSCR loans work with LLCs, partnerships, and trusts, and why serious investors structure it this way from the start

The connection between DSCR loans and the STR tax loophole, and how using both together lets you keep scaling without your tax returns slowing you down

What Robin learned buying three STRs himself, including the paperwork reality that conventional lenders put high earners through

The bottom line: the financing tool you choose determines how fast you can scale, and most high earners are using the wrong one.

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/

You just spent $1M on a property. Now someone is telling you to spend another $200K on design. That fear is real, and it stopped me too.

In this episode, I sit down with Jordan McDonough and Bri West, co-founders of Somerled Designs, the largest short-term rental focused design firm in the country, to break down why professional design is the highest-ROI decision you can make for your STR investment.

Jordan and Bri have worked with hundreds of STR investors and manage over 35 properties of their own. What they've built at Somerled isn't just a design firm. It's a data-first strategy that tells you exactly what to build, who to build it for, and how to make sure it pays for itself.

We break down:

Why design is a revenue driver, not an expense, and how to calculate the ROI before you spend a dollar

The data and comp analysis Somerled uses to forecast revenue and build the right design budget for any market

Why generic design is a losing strategy in 2026 and what "niching down" actually looks like in practice

The amenity stacking strategy that creates hero shots, drives bookings, and separates top 10% properties from everyone else

Why relying on Airbnb alone to sell your property is no longer enough and what a real marketing strategy looks like

The "astrology cabin" case study: how Bri branded a 3-bedroom cabin around a theme guests didn't know they wanted until they saw it

The bottom line: the investors winning in this market aren't spending more. They're spending smarter, and design is where the smartest money goes first.

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 wait until they feel "ready" to build something real. Hailee Marie started at 19, during a pandemic, when everyone else was running the other way.

In this episode, I sit down with Hailie Marie, short-term rental operator and angel investor, to talk about how she scaled a 70-unit remote arbitrage portfolio from scratch and why she's now using that cash flow to build long-term wealth.

Hailie built something most operators never do: a business that runs without her. Nine VAs, a full tech stack, 24/7 coverage, and AI handling guest communications around the clock. She did it starting with three units in Austin at 19 years old.

We break down:

How Hailie scaled from 3 units to 70 using arbitrage as a tool, not a destination, and what she's building toward next

The exact tech stack running her remote portfolio, including HostAway, PriceLabs, TrueV, Bestie AI, Kendo AI, and Phantom AI

Why she uses 9 VAs to run 70 units remotely and how she structured 24/7 coverage without burning out her team

How AI is training her customer service and cold calling teams in real time, and why she says it improves humans rather than replacing them

The one habit every operator should start now: recording everything, because your future AI tools will need that data

Why her tax bill was the wake-up call that's pushing her from arbitrage into ownership, and what bonus depreciation changes everything

The bottom line: Arbitrage can make you cash flow. But the operators who win long-term are the ones using that cash flow to buy assets, build systems, and invest in things that compound.

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/

What 19 STR Properties Taught Me About Finding Deals Nobody Else Can See

Most STR investors buy based on what their realtor tells them, what a random listing looks like, or what their gut says. And then they wonder why the numbers never hit the projection.

In this episode, I sit down with Jeremy Werden, co-founder of BNBCalc, to break down how data-driven underwriting separates the investors who build real wealth from the ones who just get lucky once.

Jeremy started with a $5,600 pontoon boat at 23 years old with no credit and no cash. Today he operates 19 STR listings across multiple states and built one of the most widely used underwriting tools in the industry. This conversation is packed with the kind of hard-won insight you only get from someone who has actually done it at scale.

We break down:

Why your realtor's projections are almost always wrong and what to use instead to underwrite a property in 25 seconds

The 50-comp framework BNBCalc uses to show you exactly where your property stacks up against the competition

Why defensibility is the most overlooked factor when buying an STR and the costly Florida mistake that proved it

How to reverse engineer what top operators are doing to find markets and properties with a real edge

Why the STR tax loophole is only powerful if you buy the right property and hold it for the long term

What the new BNBCalc markets tool does and why it changes how investors identify opportunities before anyone else

The bottom line: the investors winning right now are not smarter than you. They just have better data and they know how to use it.

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/

You bought a great property. You amenitized it. You listed it. And then you priced it with your emotions and left thousands of dollars on the table.

In this episode, I sit down with Julie Brinkman, CEO of Beyond Pricing, to break down why revenue management is the most overlooked lever in your STR portfolio and what the top operators are doing differently.

Julie has been leading Beyond for almost six years, and the data her team sits on is unlike anything else in the industry. This conversation will change how you think about pricing forever.

We break down:

Why 55% of STR hosts are using Airbnb smart pricing or nothing at all, and why that's quietly destroying their returns

The 15 factors Beyond analyzes for every single night of your calendar, and why a spreadsheet can never compete

How Beyond uses guest intent data to see demand shifts before they show up in the market

Why the booking window collapsed in 2025 and what that means for how you price your calendar right now

Why last minute discounting is training your guests to wait you out, and what to do instead

What private equity consolidation in the STR space means for independent operators in 2026

The bottom line: your property is a six-figure asset. It deserves a revenue management system that treats it like one.

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/

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

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/

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

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 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 grind
• Why 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 themselves
• The 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 win
• The four core values that guide every decision: (1) Family first, (2) Long-term thinking, (3) Numbers not feelings, (4) Responsibility to their community
• Liz'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 week
• Michael'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 real
• The 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 puzzle
• Why 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

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 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 not
• Why 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 responding
• Wally, 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 today
• AI Engine Optimization (AEO): The new SEO for getting your property discovered on ChatGPT and LLMs, not just Google
• Why 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

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 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 strong
• Why "you can't manage what you can't measure" applies to marriage just as much as business, and the KPIs they actually track
• How they built the business before kids and why that timing gave them an unfair advantage when babies arrived
• The 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 person
• How making more money isn't about working more, it's about hiring out everything you're not good at or don't want to do
• Why working with your spouse means no operating agreements, no distribution fights, no tax headaches, just two people rowing in the same direction
• The transferable strengths they've borrowed from each other (EQ, design thinking, analytical skills) and how they've covered each other's weaknesses

Being 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

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/