If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply

If you want to join our weekly free training:

https://www.facebook.com/groups/STRentalsecrets

This one is different.

At our last STR acquisitions event at the Freedom Factory in Beverly, MA, we did something we'd never done before.

We filled a hat with real homeowner objections — things operators hear every day — and had four coaches handle them live on stage in front of 50 operators.

No prep. No script. No safety net.

Coaches Mike Reilly, Dave, Darryl, and E took turns handling objections like "your fees are too high," "you're not local," "I don't want to be locked in," and "I want to take advantage of the STR tax loophole." Each coach handled them differently — because that's the point. There is no single right answer. There's the answer that fits your voice.

This is an hour of live, unfiltered STR sales training recorded in the room. If you're growing a property management or cohosting business, this episode will change how you handle objections.

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Resources mentioned in this episode are available at: strsecrets.com/clinic

If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply

If you want to join these live trainings:

https://www.facebook.com/groups/STRentalsecrets

This is the first episode of the STR Portfolio Clinic. A brand new series where me and Mike Sjogren pull up real STR listings on screen and diagnose what's working and what's not. Live. In front of everyone. No filter.

This episode is all about listings.

We reviewed two real Airbnb properties from operators who volunteered to put their listings on the hot seat.

First up is a brand new beach cottage in Oak Island, North Carolina. Second row from the ocean. Clean listing. But nobody's clicking on it. We broke down why and gave the owner a full game plan on the spot.

Then we pulled up a riverfront property in Murphy, North Carolina. Fly fishing right off the deck. Beautiful area. Went an entire summer with zero bookings. It took about 10 seconds to see what was wrong.

We also break down the ALE framework which stands for amenities, location, and experiences. This is the framework behind how we build listings across 30+ properties that generated over $5M in bookings last year.

If your listing has been sitting or your bookings have slowed down, this episode will show you exactly what to fix and in what order.

Want your listing or business reviewed on a future episode? Drop CLINIC in our DMs

TIMESTAMPS:

0:00 - What is the Portfolio Clinic

0:55 - The ALE Framework: Amenities, Location, Experiences

4:17 - Listing Review #1: Beach Cottage in Oak Island, NC

5:09 - Photo feedback: It's clean but it's too white

6:31 - How to use AI for sunset and lifestyle shots

7:15 - Staging amenities: Reilly's beach property example

8:41 - Who's your avatar and why it changes your photos

9:12 - Sjogren: The wizard room hero image strategy

10:33 - Using ChatGPT to create twilight shots

11:38 - Interior updates vs working with what you have

12:47 - Getting five star reviews on a new listing

13:52 - The combined listing strategy for side by side properties

16:58 - Aerial shot hack to show both properties

17:48 - Listing Review #2: Riverfront A-Frame in Murphy, NC

18:16 - Sjogren's first reaction: "I don't love this first photo"

19:04 - Andy's story: Zero bookings since launch

19:56 - Why you need to relaunch dead listings

20:35 - Phone photos are killing your listing

21:24 - What lifestyle photos this property actually needs

22:47 - Comp analysis: What top properties in Murphy look like

25:02 - Brutal feedback: The photos make it look dark and dated

26:35 - Staging the deck and outdoor space

28:41 - The game plan: Photos, relaunch, pricing, reviews

29:42 - The Airbnb new listing push and why Andy missed it

30:09 - Small changes that pay for themselves in one night

30:47 - Insurance and liability for offering amenities

33:23 - Bonus: Quick review of Christie's listing

35:40 - What's coming next and the Freedom Factory event

YOUTUBE DESCRIPTION

Most people end Q1 the same way they started it.

Behind on goals. Ahead on excuses.

In this solo episode, E breaks down why that happens — and what to actually do about it before Q2 starts.

This isn't a motivational pep talk.

It's a direct, honest look at the real reason you keep self-sabotaging — even when you know exactly what you need to do.

In this episode, E covers:

- Why the brain doesn't perceive time as time — and what that means for how you're living

- Tony Robbins' 3 S's framework: State → Story → Systems (and why you're skipping the first two)

- The 5 core wounds that create self-sabotage: rejection, abandonment, humiliation, betrayal, and injustice

- The difference between being self-centered vs. self-aware — and why it changes everything

- The belief thermostat: why you always reduce yourself back to what you think you're worth

- 3 questions to ask yourself right now as you close out Q1

- The one question E asks himself that "terrifies the shit out of him" — and keeps him moving

If the year hasn't gone the way you planned — this episode is the reset you need.

📲 Connect with STR Secrets:

Free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

Apply to work with us: https://strsecrets.com/apply

STR Secrets Podcast: https://strsecrets.com/podcast

Timestamps:

0:00 - Intro

2:09 - Q1 Check-In: Are You Still Holding Your Standards?

3:57 - Why Time Feels Like It's Running Away (The Science of Memory Markers)

6:13 - Stop Just Learning — Start Experimenting

7:13 - Tony Robbins' 3 S's: State, Story, and Systems

9:23 - Why Mindset Work Alone Keeps Failing You

9:47 - The 5 Core Wounds Behind Every Self-Sabotage Pattern

11:23 - How Your Brain's 3 Layers Are Keeping You Stuck

13:38 - Self-Centered vs. Self-Aware: The Shift That Changes Everything

15:37 - The Belief Thermostat: Why You Keep Reducing Yourself

17:05 - Your Honest Q1 Review: Facts Only, No Stories

18:38 - 3 Questions to Ask Yourself Before Q2 Starts

20:33 - Nobody Is Coming to Save You

22:56 - "Is This the Final Version of You?"

If you want to increase your revenue, automate your day to day operations and spend more time with your kids: http://strsecrets.com/apply

Check out our free 6 step course: https://level.strsecrets.com/pc-book

If you want to join these live trainings:

https://www.facebook.com/groups/STRentalsecrets

If your listings aren't getting booked right now — don't panic and drop your prices.

In this week's Thursday training, Mike Reilly sits down with Maryann Wahhab, revenue management expert and STR operator across 6 states, to break down exactly what's working right now to get booked at the rates you want.

Maryann went from college basketball coach to full-time STR revenue manager — and now helps operators stop leaving money on the table in soft markets.

In this episode, Mike and Maryann cover:

- Why your slow bookings are probably a listing problem — not a pricing problem

- The booking window zones every operator needs to understand (and how to price each one)

- How Mike went 30% up year over year on Vrbo with one simple OTA trick

- The "booking velocity" metric Maryann tracks at 7, 15, and 30-day marks

- How a listing went from page 6 to page 2 on Airbnb in one week

- Why virtual stays are a game changer for dead listings

- The full listing re-optimization playbook for properties with no bookings in 30+ days

- How to use Airbnb's rule sets and length-of-stay discounts to capture more revenue in slow season

This is the training your listings need right now.

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🎙️ About Maryann Wahhab:

Maryann is a revenue management expert and STR operator managing properties across 6 states. A former Division I basketball coach, she left the game in 2023 to manage properties full-time — and now helps STR operators maximize revenue in any market condition.

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Timecodes:

0:00 - Why Your Listings Aren't Getting Booked Right Now

2:30 - Meet Maryann Wahhab: From Basketball Coach to STR Expert

6:00 - How to Read Your Market Before You Touch Your Prices

10:00 - Booking Window Zones Explained (And How to Price Each One)

15:30 - Booking Velocity: The Metric That Tells You When to Act

20:00 - How to Play the Airbnb and Vrbo Algorithm Game

25:30 - The OTA Trick That Got Mike 30% Up Year Over Year on Vrbo

30:00 - Virtual Stays and How to Reinvigorate a Dead Listing

36:00 - The Full Re-Optimization Playbook for Struggling Listings

41:30 - Length-of-Stay Discounts and Airbnb Rule Sets in Slow Season

46:00 - How to Differentiate Your Listing So You're Never in a Price War

Connect with Sean:

Instagram: https://www.instagram.com/sean_bakhtiari/

Check out Seacoast 2 Summit: https://www.seacoast2summit.com

Check out our free 6-step course for scaling STR operators: https://level.strsecrets.com/pc-book

STR Secrets FB group: https://www.facebook.com/groups/STRentalsecrets

What happens when a corporate finance guy from Boston decides he's done working for someone else — and bets on short-term rentals?

Sean Bakhtiari is the co-founder of Seacoast 2 Summit Vacation Rentals and The Bakhtiari Group, a top-performing real estate sales team across Massachusetts, New Hampshire, and Maine. As an active STR investor, his work sits at the intersection of real estate, hospitality, and investment strategy throughout New England.

After 9 years in Boston's financial district, Sean bought his first STR. Then a second. Then started building a management company.

At 12 properties, he hit a wall. He was good at business development and client relationships. But systems, operations, and scale? Not his strengths. That's when a serendipitous call from Chris changed everything.

Today, Sean and Chris co-run Seacoast to Summit Vacation Rentals — managing 120+ properties across the New Hampshire seacoast, lakes and mountains region, and North Shore of Massachusetts. Almost entirely on referrals, with virtually no paid marketing.

In this episode, Sean and Chris pull back the curtain on:

- How they identified each other as the right partner (and what 3 things you need to align on before you sign anything)

- Sean's "help first, never sell" philosophy — and why it's responsible for most of their growth

- Why they've said no to 10+ deals in the last 3 months (and why that's the right call)

- The two fears they stay up at night thinking about as they scale

- How to delegate without feeling like you're losing control

- What it takes to keep your team culture intact as you grow

- Why boutique hotels might be the next frontier for this business

This is a rare episode — a founder bringing on his business partner and pulling off the veil on how a real, values-driven STR company actually works at scale.

---

Timestamps:

0:00 - Introducing Sean Bakhtiari: Chris's Business Partner

2:45 - How Sean Went From Corporate Finance to STR Management

6:30 - Building Seacoast to Summit: From 12 to 120 Properties

10:15 - How Sean and Chris Found Each Other (The Serendipitous Call)

15:00 - The 3 Things You Must Align On Before Partnering

18:30 - The "Help First" Sales Mindset That Built the Business

23:00 - Why They Said No to 10 Deals in 3 Months

27:00 - The Two Fears They Have About Growing Too Fast

32:30 - How to Delegate Without Losing Control

37:00 - Keeping Team Culture Intact at Scale

42:00 - What the Future Looks Like: Boutique Hotels and Brand Building

46:00 - Sean's #1 Secret to STR Success

Connect with Jeremiah:

Instagram: @jeremiahkwatson

Business: www.affluentvacays.com

Check out our free 6 step course: https://level.strsecrets.com/pc-book

STR Secrets FB group https://www.facebook.com/groups/STRentalsecrets

He did everything people told him to do.

Got clean. Went to college. Got a good job. Made good money.

And he was still unhappy.

In this episode, we talk with Jeremiah Watson. Jeremiah just quit his corporate job. He now runs an 18-property cohosting business in Los Angeles. He is the 73rd person to leave their job through STR Secrets.

Here's what you'll learn:

→ How Jeremiah went from addiction and jail to building a real business

→ Why he lost $50K his first year — and what he changed

→ How he got his first cohosting deal with one cold call

→ The small team that runs his business today

→ His goal: 66 properties by the end of 2026

This is what actually doing the work looks like.

Timestamps:

00:00 - Who Is Jeremiah Watson?

03:12 - From Addiction and Jail to Turning His Life Around

08:11 - Why He Chased the Corporate Dream

11:36 - He Tried STRs and Lost $50K in Year One

13:16 - How He Found Cohosting and Got His First Deal

16:36 - How He Grew From 1 to 18 Properties

19:11 - His Team and How the Business Runs Today

21:27 - His Big Goal: 66 Properties by End of 2026

22:45 - What to Do If You Have a Job and No Time

27:06 - How to Balance Drive With Gratitude

31:57 - Why This Business Is About More Than Money

Scaling a short-term rental company isn’t just about getting more properties.

It’s about building the team that can support the growth.

In this episode, Chris and E sit down with Alex Hall — talent advisor and leadership strategist — to break down the real challenges STR operators face when building teams.

From job clarity and org structure to burnout, hiring, and leadership development, Alex shares the frameworks that help operators scale from a handful of listings to a real company.

If you're trying to grow beyond the stage where you do everything yourself, this episode is a masterclass in leadership and people management.

Inside this episode:

• Why most STR companies don’t actually know who reports to who

• The biggest hiring mistake operators make while scaling

• How to structure a team from 10 to 100+ listings

• Why burnout happens during fast growth

• The leadership habits that retain great talent

• When to introduce equity or long-term incentives

If you want a real business — not just a portfolio of properties — it starts with leadership.

Guest Bio:

Alex Hall is the founder of Valinor Talent Solutions, where he serves as a fractional HR executive helping growing companies build strong people strategies, leadership development, and scalable teams. With over a decade of experience in talent and organizational development, he partners with businesses to create high-performing workplaces. Alex works with short-term rentals to develop their talent strategy so they can focus on delivering exceptional guest experiences through thoughtful design, strong systems, and hospitality-driven service.

Guest Contacts:

alex@valinortalent.com

www.valinortalent.com

Get FREE Access to our 6 STEP course:

https://www.strsecrets.com/podcast

Timestamps:

00:00 – Why Most Teams Don’t Know Their Role

02:00 – Success, Identity, and Leadership Growth

04:30 – Introducing Alex Hall: Talent Advisor for STR Operators

07:25 – When STR Businesses Actually Need HR Support

09:20 – The 3 Levels of Team Structure as You Scale

12:40 – The Most Common Hiring Problems in STR Companies

14:00 – Why Job Clarity and Accountability Are Missing

17:10 – The 33% Rule: When Leaders Outgrow Their Team

20:05 – Burnout Signals Every Operator Should Watch

23:20 – Building Org Structures for 10–100 Listings

26:00 – Why Systems Matter More Than Org Charts

27:00 – How Great Leaders Reward and Motivate Teams

30:00 – Equity vs Performance Bonuses for Key Employees

33:00 – The 3 Rules of Leadership: Clear, Kind, Respectful

36:10 – Leadership Lessons for First-Time Founders

39:50 – AI’s Role in Future STR Operations

42:40 – Final Advice for Building a Great STR Team