Short Term Rental Secrets Podcast

Ep 272 - How AI Will Replace Most STR Ops Work (And What Operators Should Do) with Shahar Goldboim

AI isn’t a tool anymore — it’s infrastructure. In this episode, Chris and E sit down with Shahar Goldboim, founder of BOOM, to break down how AI is fundamentally changing short-term rental operations, exits, and scale. From selling a property management company to building tech that replaces broken workflows, this conversation dives deep into why fragmented tools are failing and why operators who don’t adapt will fall behind. Inside this episode: * Why “tech-enabled” STR businesses still fail * The biggest mistakes operators make when exiting * Why one company can’t do funds, PM, design, and tech well * How AI eliminates 80% of guest communication (without killing hospitality) * Why fragmented STR software stacks are breaking ops * How AI becomes the new infrastructure for scale 00:00 – Why Solving Everything Breaks Most Tech-Enabled STR Companies 03:05 – “Business as a Service” vs Traditional STR Software Stacks 06:20 – From Operator to Platform Builder: Shahar’s Real Estate Path 10:10 – Why Tech-Enabled PMs Fail Without Focus 14:30 – The Hidden Cost of Fragmented PMS + Tools 18:05 – Why AI Fails Without Full Operational Data 22:40 – How AI Can Eliminate 80% of Guest Communication 27:15 – The Real Bottleneck: Scaling Ops, Not Software 32:10 – Why All-in-One STR Platforms Are the Future 38:20 – The Direction of AI, Automation, and STR Businesses Guest Bio: Shahar Goldboim is the Co-Founder and CEO of Boom, the world’s first Autonomous Property Management System (AiPMS)—a platform redefining how real estate assets are operated through AI. Before founding Boom, he built DesignedVR, a hospitality management company overseeing more than $150 million in assets. This extensive experience gave him a firsthand understanding of the intricate, day-to-day challenges property operators face. Throughout his career, Goldboim has been involved in hundreds of millions of dollars in real estate transactions as an investor and broker, and has deployed over $50 million in syndication funds. That deep operational and financial experience shaped his belief that the future of property management lies in automation, intelligence, and human-centered design. Today, Boom merges hospitality, real estate, and AI to help operators around the world manage smarter, scale faster, and unlock the full potential of their assets. Guest Link: https://www.linkedin.com/in/shahar-goldboim-80820b95?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app [https://www.linkedin.com/in/shahar-goldboim-80820b95?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app] Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/ [https://group.strsecrets.com/]

Ep 271 - Why Your STR Isn’t Making What It Should — And How to Fix It with Mark Lumpkin

Your STR isn’t underperforming by accident — it’s underperforming because of decisions. In this episode, Chris and E sit down with Mark Lumpkin from STR Cribs, the company behind 500+ STR setups, to break down the real reasons properties fail and what the best operators do differently. If you’re buying, designing, furnishing, or managing STRs — this is a masterclass in thinking like a pro instead of an amateur. Inside this episode: • The biggest mistakes investors make when buying or furnishing STRs • Why “more amenities” isn’t the answer — strategic amenities are • How to work with (and filter out) bad owners • The 80/20 rule for projects, clients, and portfolio performance • Why elite STR teams operate like “SEAL Team 6” • How culture, tension, and standards lead to scale • The future of STR Cribs and Mark’s next business moves Guest Bio: Mark Lumpkin helps investors set up highly profitable STRs all over the country. 00:00 – How STR Cribs Started & Grew to 500+ Setups 00:04:45 – Why High-Net-Worth Investors Still Make Rookie Mistakes 00:09:10 – The Amenities Strategy That Actually Drives Bookings 00:13:55 – Institutional Investors vs Mom-and-Pop Operators 00:18:25 – The Problem With Owners Who Want to “Test It First” 00:22:40 – The 80/20 Rule, Pumpkin Planning & Firing Bad Clients 00:27:05 – Sniper vs Machine Gun: How to Focus Your Time as an Operator 00:31:30 – The STR Cribs Hiring Philosophy: SEAL Team 6 00:36:15 – Creating a High-Performance Culture Through Healthy Tension 00:41:50 – What’s Next for STR Cribs & Mark’s Personal Vision Guest Link: https://www.linkedin.com/in/mark-lumpkin-84b173142/ [https://www.linkedin.com/in/mark-lumpkin-84b173142/] Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/ [https://group.strsecrets.com/]

Ep 270 - Why Most STR Hosts Stay Broke — And How Bernie Broke Out

Your business can’t outgrow the identity you’re stuck in. In this episode, Bernie Cesareo reveals the mindset and identity shifts that transformed his life, his confidence, and his STR businesses — from shrinking portfolios to scaling multiple companies with clarity and purpose. This episode breaks down the real reason most hosts stay stuck, how to think and act like a CEO, and the inner work required to grow a business that matches the life you want. Inside this episode: • The identity upgrade that changed Bernie’s life • How self-image controls your STR results • Why talking about your vision attracts the right people • The shift from operator → leader → CEO • How Bernie built multiple businesses by delegating • Why gratitude, belief, and clarity fuel massive growth 00:01:12 – Bernie’s Big Mindset Shift: Stop Doing Everything Yourself 00:04:07 – “Assume the Wish Fulfilled”: Rewriting Your Identity 00:08:10 – Manifesting the Dream Jeep: Breaking 30 Years of Beliefs 00:11:20 – Running Multiple STR Businesses Through Identity Upgrades 00:14:36 – Lifestyle Freedom: Why Bernie Never Misses His Son’s Games 00:17:00 – The Elder-Care Village Vision: Thinking Bigger Than STR 00:20:12 – From Player to Coach to CEO: Letting Go of Control 00:24:18 – Correcting Systems, Not People: Real Leadership 00:28:55 – How Speaking Your Vision Attracts the Right Opportunities 00:33:42 – Gratitude, Belief, and the Identity That Builds Your Future Guest Bio: Bernie Cesareo and his wife Courtney started the company by turning a long-term rental in their hometown into a short-term rental and doing everything themselves from guest support to cleaning and maintenance. Happily surprised with the success and popularity of this property, they decided to turn this side hustle into a primary business. They loved providing quality accommodations and creating great value for their guests and felt they could do this on a larger scale. They started growing the business by becoming co-hosts for other property owners and have added team members to help make everything run smoothly. After several years, they have a team of 8 that manages anywhere from 20-40 properties. Guest Link: https://eaglestays.com/ Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

Arbitrage vs. Co-Hosting: The Real Winner Isn’t Even Close | The STR Scale Show with Mike Reilly | Ep 34

The arbitrage era is cracking — fast.  With Sonder filing bankruptcy and operators across the country getting crushed by fixed leases, the truth is clear: the STR model you choose determines whether you scale… or sink. In this episode, we break down why arbitrage is failing, what Sonder’s collapse teaches every host, and why co-hosting remains the most profitable, low-risk, scalable model in 2025 and beyond. Inside this episode:  • Why arbitrage collapses under pressure  • The hidden costs operators never calculate  • Why co-hosting produces higher margins with lower risk  • How boutique operators beat centralized “big brand” models  • What the fastest-growing hosts are doing differently  • The shift every STR operator must make in 2025 Message me to get a free resource and see how the program could fit your goals. Click the link below: https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T034&utm_content=RESOURCE [https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Youtube&utm_campaign=T033&utm_content=STRS] 00:01:00 – The Real Cost of Arbitrage: Leases, Debt & Cash Burn 00:02:30 – Why Arbitrage Margins Collapse in Today’s Market 00:03:45 – Co-Hosting vs. Arbitrage: The Risk Difference 00:05:10 – Arbitrage at Scale Becomes a Cash-Flow Death Trap 00:06:15 – Real Examples of Small Operators Losing Money 00:07:10 – The Tiny Margin of Error That Kills Arbitrage Deals 00:08:30 – Why Co-Hosting Wins: Low CAC, High Lifetime Value 00:10:20 – How Operators Are Scaling Co-Hosting With $0 Spend 00:12:20 – Centralized vs. Local: Why Guest Experience Matters 00:15:00 – Why Arbitrage Can’t Keep Up With Industry Changes 00:17:00 – The Bankruptcy Wave: Small Operators Getting Hit 00:18:30 – How to Pivot Out of Arbitrage Before It’s Too Late 00:20:10 – What a Healthy Co-Hosting/PM Business Looks Like 00:22:00 – No Get-Rich-Quick: The Reality of STR Success Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/

Ep 269 - How to Scale Your Property Management Business with Brooke Pfautz

In this episode, Chris and E sit down with the founder of Vintory to uncover the real reason PMs fail, what the top managers are doing differently, and how to build a predictable machine for owner acquisition. Whether you're starting with 5 doors or aiming for 500, Brooke breaks down the playbook that actually works. Inside this episode: • Why most PMs never break past 50–100 properties • The REAL reason owner acquisition is so difficult • Brooke’s formula for predictable PM growth • Why marketing is now non-negotiable for property managers • What the top PMs are doing differently • How the industry is shifting — and where the opportunity is 00:02:11 – Brooke’s Story: How He Scaled to 500 Properties 00:06:34 – Why Most Property Managers Plateau at 50–100 Doors 00:09:58 – Owner Acquisition: The Hardest Part of PM Growth 00:13:22 – Why Homeowners Don’t Convert (And What They Really Want) 00:17:45 – The Data Behind Fast-Growing PM Companies 00:21:18 – Why Marketing Is No Longer Optional for PMs 00:25:40 – Building a Real Sales Pipeline for Property Management 00:30:12 – Brooke’s Predictable Growth Formula Explained 00:34:49 – Industry Shifts: Consolidation, Competition, and Opportunity 00:38:27 – The Future of PM Growth (And How to Win the Next Wave) Guest Bio: Brooke Pfautz is one of the industry's foremost experts in growing vacation rental inventory. He literally wrote the book on inventory growth – and it’s already a three-category Amazon bestseller. Brooke got his start in the industry in 2007 when he co-founded Vantage Resort Realty in Ocean City, MD, and took an idea on a napkin to more than 500 properties in just five years. After a successful exit, he went on to grow inventory for other major vacation rental brands as a Chief Business Development Officer in multiple destinations. Most recently, as an executive at a leading vacation rental software company, he saw first-hand through MasterMind groups that he launched and facilitated what worked and what didn’t for the 20 largest and most successful companies in the country. Today, Brooke leads Vintory, the first and only CRM & Sales and Marketing Automation Platform designed exclusively for Vacation Rental Managers to grow their inventory. At Vintory, a team of over 50 growth experts is laser-focused on one thing: helping VRMs hit or exceed their inventory growth goals. Guest Link: https://www.instagram.com/vintoryhq/ Get FREE Access to our Community and Weekly Trainings: https://group.strsecrets.com/ [https://group.strsecrets.com/]