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

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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/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

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/

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

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/

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/

Your STR business is worth more than you think—if you build it the right way.

In this episode, we break down the difference between operators who burn out… and operators who build real companies that survive, scale, and eventually sell for life-changing money.

We also cover the hard lessons from companies that grew too fast, collapsed, or went bankrupt—and how to avoid their mistakes.

In this episode you’ll learn:

• Why your STR business already has real enterprise value

• What happens if everything lives in your head (and how to fix it)

• The operational mistakes that bankrupted a fast-growing STR company

• How to build systems that survive without you

• What buyers REALLY look for in an STR business

• The path to a 7–8 figure STR exit

If you want help building an STR business that actually runs without you — and is worth something one day — click the link below:

https://go.strsecrets.com/podcast?utm_source=Podcast&utm_medium=Captivate&utm_campaign=T033&utm_content=STRS

00:01:41 - Sonder going bankrupt

00:03:15 - talking about exits / long hold / vision

00:05:09 - private equity, Blackstone, KKR, etc.

00:06:47 - Vacasa, hyper-local focus, selling to PE

00:08:47 - SOP playbook, fear of death, what happens if you’re gone

00:10:20 - CEO role, brand, numbers, game plan

00:12:00 - not as easy as it looks, 70% with PMs 20+ units

00:13:19 - PE criteria, churn, “can somebody else run my business?”

00:14:55 - Built to Sell, books, contracts, “you not being the system”

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

The STR industry is shifting — and this episode marks the beginning of a new era.



Recorded LIVE inside the brand-new Freedom Factory, Mike, E., Chris, and Reilly break down the mindset, seasons, strategy, and direction that will define the next 5 years of short-term rentals… and your future in it.

• The story behind building the Freedom Factory

• Mike’s “origin moment” and how it shaped everything

• The dark seasons every entrepreneur must push through

• Why property management will create more millionaires than arbitrage

• The new PM roll-up and what it means for exits

• How STR Secrets is evolving with 3 new shows & deeper curriculum

00:01:41 – The Freedom Factory: How This All Started

00:04:52 – Mike’s Full Circle Moment at the Old Staples Desk

00:08:35 – The “Dark Seasons” of Entrepreneurship

00:12:48 – The Four Phases of Growth Every Operator Goes Through

00:16:55 – Chris’s Story: Going Broke to Buying His First STR

00:20:33 – Riley’s Risk: Payroll on a Credit Card & Buying His First Property

00:24:40 – The Identity Shift Needed to Enter Your Next Season

00:28:53 – Why Property Management Will Create More Millionaires

00:32:41 – The PM Roll-Up & Hotel Fund Vision

00:37:58 – The New Era of STR Secrets: Three Shows + Bigger Vision

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

AI isn’t the threat — it’s the opportunity most hosts are ignoring.



In this episode, we walk through how top operators are using AI and automation to scale smarter, simplify operations, and outpace the competition.

• How AI is transforming pricing, operations, and marketing

• The biggest mistake hosts make when “trying” automation

• Tools that save hours per week without losing the human touch

• Why your business model must evolve in 2025

• The new advantage: data-driven decision-making

Get the full AI Automation Playbook at strsecrets.com/ai

00:00:18 – Why AI Is the Next Big Shift in STR

00:02:12 – What Hosts Get Wrong About Automation

00:05:09 – The Tools Replacing Busywork in STR Operations

00:08:47 – How AI Enhances the Guest Experience

00:11:38 – Dynamic Pricing and Predictive Data in Action

00:15:22 – Building Systems That Learn While You Scale

00:19:10 – How to Combine AI With a Human Team

00:23:38 – Avoiding the “Set It and Forget It” Trap

00:27:41 – The STR Playbook for 2025 and Beyond

00:30:52 – Final Take: Use AI Before It Uses You

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/