Claim OwnershipSTR Like The Best
Subscribed: 9Played: 73
Subscribe
© 2026 STR Like The Best
Description
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.
81 Episodes
Reverse
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-...
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 th...
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 ...
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...
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 conversati...
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 p...
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...
Comments
Download from Google Play
Download from App Store
United States