Most operators think better tech will fix their problems. It won’t.

In this episode, Frank Bosi (Hostfully) joins the show to unpack the real challenges STR leaders face as they scale—pressure, decision fatigue, emotional weight, and the constant tension between automation and hospitality.

Drawing from years inside luxury hotels like Ritz-Carlton and Four Seasons, Frank breaks down what most operators get wrong about tech stacks, leadership, hiring, and guest experience—and how to build systems that create confidence instead of doubt.

Inside this episode:

1. Why tech stack decisions are emotional, not logical
2. How disconnected tools quietly create leadership stress
3. The difference between automating tasks vs removing hospitality
4. What luxury hotels get right about training and consistency
5. Why leaders must absorb pressure instead of passing it down
6. How to hire people who protect your brand when you’re not watching

This is a must-listen for any STR operator building a team, scaling systems, or feeling the weight of leadership.

00:01 – Why Tech Stack Decisions Are Emotional, Not Logical

03:45 – Automation vs Hospitality: Where Operators Go Too Far

07:10 – The Weight of Leadership Most People Aren’t Ready For

11:00 – Why Disconnected Tools Create Doubt and Stress

15:20 – Lessons STR Operators Can Steal From Luxury Hotels

19:10 – Why Leaders Can’t Have “Bad Days” Publicly

23:30 – Hiring People Who Protect Your Brand When You’re Not There

27:40 – Training, Standards, and Why Consistency Beats Luxury

31:50 – Using Tech to Create Confidence, Not Complexity

36:40 – The Real Role of a Leader in Scaling STR Operations

Guest Bio:

Frank Bosi is the Senior Director of Partnerships at Hostfully, a leading platform supporting short-term rental operators around the world. He drives strategic relationships across the STR ecosystem; working with technology partners, influencers, coaches & thought leaders to help property managers scale and deliver great guest experiences.

Frank also actively contributes to industry conversations through webinars, events and podcasts (such as this) designed to help operators grow smarter, faster, and more profitably.

Outside of work, Frank prioritizes faith, fitness, and family; spending his free time with his wife and kids, training CrossFit, and staying focused on overall wellbeing.

Guest Link:

https://www.instagram.com/frank_bosi/

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https://group.strsecrets.com/

Your goals aren’t failing — your calendar is.

In this episode, E and Chris break down why most people start the year motivated… then quietly drift back into old patterns. The problem isn’t strategy, tools, or ambition — it’s misalignment between who you say you want to become and how you actually spend your time.

This conversation dives deep into identity, courage, time audits, consistency, and the hidden habits that either compound your growth or quietly sabotage it.

Inside this episode:

1. Why your calendar tells the truth about your real priorities
2. The “perfect week” exercise that exposes misalignment fast
3. Why every new level requires letting go of your old identity
4. How fear, comfort, and ego silently slow your progress
5. The power of small, consistent actions over big intentions
6. Why courage often means saying “no,” not “yes”

If you’ve ever felt busy but stuck — this episode will hit home.

00:00 – Why New Year Motivation Dies Faster Than You Expect

02:05 – The Reality Check: When Goals Collide With Real Life

04:20 – The Calendar Test: Do Your Actions Match Your Goals?

07:40 – Designing Your “Perfect Week” (And What It Exposes)

10:55 – Your Dreams Are Expensive — Here’s the True Cost

14:30 – Killing the Old Version of Yourself to Level Up

17:55 – Faith vs Fear: Making Decisions Without Freezing

21:30 – Small Habits That Quietly Compound Massive Change

25:10 – Letting Go of Ego to Create Space for Growth

29:05 – Enjoyment, Consistency, and Becoming Your Best Self

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The STR game has changed—and most operators haven’t caught up.

In this episode, we break down what actually separates top-performing short-term rentals from the ones stuck in the middle. From design and amenities to operations, leadership, and systems—this is a real look at how elite STR businesses are built and sustained in hyper-competitive markets.

This isn’t theory. It’s what’s working right now.

Inside this episode:

- Why “good enough” STRs are getting crushed

- The amenity arms race (and how to win without wasting money)

- What guests notice that most hosts completely miss

- How ops and hospitality matter more than design long-term

- Why disciplined systems protect profit—even in down years

- The leadership mindset required to scale without chaos

If you want longevity in this industry, this episode is required listening.

00:06:15 – Becoming “The Guy” in a Hyper-Competitive STR Market

07:45 – Why Copying Competitors Is a Losing Strategy

09:15 – The New Minimum Standard for STR Design & Amenities

11:40 – Why Half-Upgraded Properties Always Underperform

18:50 – The Amenity Arms Race: What Actually Moves Revenue

20:00 – When Design Stops Mattering and Ops Take Over

26:10 – Building Teams and Systems That Don’t Break Under Stress

30:45 – Leadership Lessons from Military and STR Operations

34:05 – How Efficiency Protects Profit in Down Revenue Years

39:35 – The Long-Term STR Play: Scale, Discipline, and Longevity

Guest Bio:

Shane O’Connor is the CEO & Founder of Alchemy Real Estate & Alchemy Hosting. Alchemy is based in Tampa, FL, building a portfolio of Short-Term Rental assets primarily focused in Central Florida. By delivering vertically integrated, top-tier service from beginning to end in the investment process, Alchemy has grown from a single property (and single employee) to 11 properties & a team of four in less than a year. In that same time, Alchemy will have also delivered more than $3M in closed real estate deals for its clients.

By the end of 2022, it is Shane’s goal to have a blended Direct Ownership & Co Hosting portfolio of 30 properties centered in Florida, to then begin expanding to other markets. Shane is a graduate of the United States Naval Academy and served as an Officer in the U.S. Navy for 9 years. He received an M.S. Degree in Real Estate from the University of Florida. He runs the company with his brother, Captain Devin O’Connor, who is an active duty Marine Corps helicopter pilot in addition to being the Director of Operations for Alchemy.

Guest Link:

https://www.instagram.com/oc_dreams19/

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https://group.strsecrets.com/

Most people don’t fail because they lack discipline — they fail because they’re trying to grow without changing who they are.

In this episode, Chris and E break down why goals alone don’t create change, how identity drives momentum, and the real reason most people stall out by February. This is a deep, practical conversation on discipline, accountability, emotionalized goals, and how to build habits that actually stick.

If you’ve ever felt stuck despite “doing all the right things,” this episode will reframe how you think about growth — personally and professionally.

Inside this episode:

• Why identity matters more than motivation

• How emotionalized goals create automatic discipline

• The “never two days in a row” rule that builds momentum

• Why most people sabotage themselves without realizing it

• How to design accountability that actually works

• Turning small daily actions into long-term transformation

👉 If this episode resonated, share it with someone who’s setting big goals this year — and subscribe for more real conversations on growth, leadership, and execution.

00:00 – Why the Point of a Goal Is Growth, Not the Outcome

02:05 – Identity vs Outcomes: The Real Way to Set Goals

04:20 – Emotionalizing Goals to Create Immediate Action

06:10 – Going Deeper on “Why” Using the Seven Layers Exercise

08:35 – Shifting from “I Have To” to “I Get To”

10:15 – Building Momentum with Small, Non-Sexy Wins

12:40 – Vision First: Thinking Big Enough for the Next Level

15:05 – Quarterly Sprints and the Power of the 12-Week Year

17:40 – Time Blocking Life, Family, and Business (In That Order)

20:30 – Accountability, Never Missing Twice, and Staying in Motion

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Most entrepreneurs focus on tactics — but the real breakthroughs happen internally first.

In this episode, Stacey St. John breaks down how self-awareness, intuition, mindset, and values-driven leadership shape long-term success in business and life. From recognizing limiting beliefs to building aligned teams and managing energy, this conversation goes far beyond surface-level motivation.

If you’ve ever felt stuck, overwhelmed, or pulled in too many directions — this episode explains why and what to do about it.

Inside this conversation:

1. How intuition and body awareness guide better decisions
2. Why identity drives action (and keeps people stuck)
3. The difference between excitement and misalignment
4. How to hire and lead based on values, not resumes
5. Practical mindset tools to reset stress and overwhelm
6. Why self-image and internal stories affect performance
7. How high performers accept feedback without ego

00:00 – Why Most Entrepreneurs Stay Stuck (It’s Not Strategy)

03:45 – Introducing Stacey & Why Mindset Drives Everything

07:20 – Front Pocket vs Back Pocket Decisions Explained

10:50 – Learning to Trust Intuition Without Second-Guessing

14:30 – Energy, Stress, and Showing Up as a Leader on Bad Days

18:10 – Building the Right Team: Values Over Skills

22:40 – Why Misaligned Hires Quietly Kill Momentum

27:05 – Identity Shifts Required to Reach the Next Level

31:20 – Rewriting Internal Stories That Limit Growth

35:50 – Integrating Mindset Work Into Daily Business Life

Guest Bio:

Stacey St. John is a visionary real estate entrepreneur who is reshaping the short-term rental industry for women on Airbnb. She founded the Female Short-Term Rental Investors Facebook Group, The STR Sisterhood, and The Short-Term Rental Virtual Summit for Women. Stacey began her short-term rental journey on Airbnb in 2020; she quickly realized the industry’s potential and the opportunity to empower women through real estate investing to help them create successful, profitable “Airbnb businesses.” She has since built a 7-figure portfolio and left her corporate career to focus on her mission. Stacey is a strong advocate for women in business and is committed to creating a more equitable and inclusive industry. She is a frequent speaker at short-term rental and Airbnb industry events and is a regular contributor to industry publications.

Guest Link:

https://www.instagram.com/stacey_st.john/

Get FREE Access to our Community and Weekly Trainings:

https://group.strsecrets.com/

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

Get FREE Access to our Community and Weekly Trainings:

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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/