📲 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

Most luxury STR owners write that electric bill every month without ever knowing what's causing it. David VanWert did the same thing — until he built a platform to fix it.

In this episode, E and Chris sit down with David VanWert, founder of Umbra and owner of seven STR cabins in the Smoky Mountains and Mammoth Lakes. David built Umbra after spending years watching energy costs silently destroy the profitability of high-end vacation rentals — and after realizing no existing solution was built for the STR world.

In this episode David covers:

- What Umbra does: smart power monitoring and automation built specifically for large luxury STRs

- How Umbra integrates with your PMS to automatically cut power when guests check out

- Real results: 45% reduction in electricity cost per night, $620 saved in one month on one property, 30% lower bill YoY

- How silent system failures — clogged AC units, water leaks, tripped breakers — get caught before they become emergencies

- Why electricity costs in the Smoky Mountains regularly hit $2,000-$3,000 per cabin in winter — and how to stop that

- How David scaled to seven properties in under five years using second home loans, cost segregation studies, and the STR tax loophole

- Why the STR tax play — not cash flow — is the real opportunity for high-income earners buying right now

- David's full AI workflow: how he rebuilt his entire business from the ground up using Claude

- How he cut a 100-hour design project down to under 20 hours with AI

- Why he believes operators have a 4-6 year window to get ahead of AI before things get "weird"

- The time study method: how to audit every 15-minute block of your day and identify what AI can automate

- What happens to property managers and co-hosts when AI agents handle all communications, scheduling, and pricing

- David's #1 secret to STR success: tenacity

This is a rare conversation — equal parts operations, tech, and honest truth about where this industry is headed.

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About David VanWert:

David VanWert is the founder of Umbra, a power-monitoring and automation platform built specifically for large luxury short-term rentals. He owns seven cabins — six in the Smoky Mountains and one in Mammoth Lakes — and built Umbra after experiencing firsthand how much energy waste and property risk goes undetected in high-end vacation rentals. His background is in technology and design, and he now splits his time between operating his own portfolio and helping other owners and property managers answer one simple question: what's running right now, and should it be?

Connect with David and Umbra:

Website: umbra-energy.com

Instagram: @umbraenergy

Facebook: Umbra Energy

Timestamps:

0:00 - Intro

1:22 - Introducing David VanWert and Umbra

5:28 - E's Michelin Restaurant Story: Service Is Black and White, Hospitality Is Color

9:06 - What Is Umbra and Why Did David Build It?

10:58 - The Real Cost of Running a Luxury STR: $2,000-$3,000 Electric Bills in the Smokies

12:49 - How Umbra Works: Smart Power Automation Tied to Your PMS

14:34 - Real Results: 45% Reduction, $620 Saved in One Month

16:37 - How Umbra Catches Silent Failures Before They Become Emergencies

18:34 - David's Background: From High-End Home Automation to STR Investor

20:26 - How David Scaled to Seven Properties in Under Five Years

21:58 - The STR Tax Play: Why High-Income Earners Should Be Buying Right Now

24:30 - Is the STR Market Still Worth It? What David Is Seeing Today

27:46 - How David Rebuilt His Entire Workflow Using Claude and AI

33:25 - From 100 Hours to 20: How AI Changed His Design Business

40:13 - The 4-6 Year Window: Why You Need to Get Ahead of AI Right Now

43:11 - What Happens to Property Managers When AI Handles Everything?

45:00 - Where to Start With AI If You Have No Tech Background

47:26 - David's #1 Secret to STR Success: Tenacity

If you haven't updated your pricing yet — your next booking will pay you less than you expect.

Btw you can grab the spreadsheet from here : https://www.strsecrets.com/airbnbfee

Also, if you want to talk to us directly: http://strsecrets.com/implement

In this training Mike covers:

- What the Airbnb fee change actually means: 15.5% host-only fee applies to nightly rate, cleaning fee, resort fee, pet fee — everything

- Why the split fee showing back up in your account is a bug — not a reversal

- The exact price increase you need to make: 18.34% minimum for direct owners

- How co-hosts and property managers need to handle this differently — and why checking the listing owner's account first matters

- The fee change spreadsheet walkthrough — how to model the right scenario for your business (comment FEE CHANGE to get it)

- How to split the channel fee with your homeowner so nobody loses

- How to track your Airbnb algorithm ranking after raising prices using Rank Breeze

- Why five-star properties make 18% more in RevPAR than 4.7-star properties — and how that matters more right now

- How Mike's portfolio is pacing 130% of June goals and 120% of July goals — and why

- Why now is the time to get on Vrbo — Mike is seeing 10% more bookings YoY from Vrbo this year

- How to retarget past guests with text messages and automated campaigns to offset any Airbnb drop

- Listing optimization basics: why your first five photos, your copy, and your reviews are your most valuable assets right now

This is the most important training for STR operators this month.

📲 Connect with STR Secrets:

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 - What Just Happened: Airbnb's Fee Change Explained

1:16 - The Split Fee Is Not Back — It Was a Bug

2:23 - What 15.5% Host-Only Fee Actually Means for Your Payout

3:04 - Step 1: Increase Your Airbnb Pricing by 18.34% Right Now

4:27 - Step 2: Track Your Algorithm Ranking After Raising Prices

5:44 - How to Check and Confirm Your Fee Setting in Airbnb

8:21 - The Fee Change Spreadsheet Walkthrough

12:30 - How to Split the Channel Fee With Your Homeowner

14:26 - What Co-Hosts and Property Managers Need to Do Differently

15:12 - How to Make Pricing Changes Inside Your PMS

16:03 - Testing Price Increases: 15% vs 18% vs 25% — What We've Seen

18:01 - The Airbnb Algorithm: What Actually Moves Your Ranking

18:25 - Five-Star Properties Make 18% More in RevPAR

19:48 - Virtual Stays, Friends and Family Reviews and Algorithm Boosts

20:15 - Mike's Portfolio Is Pacing 130% of June Goals — Here's Why

21:03 - Get on Vrbo: Mike Is Up 10% YoY From Vrbo This Year

22:15 - Retarget Past Guests With Text Campaigns Right Now

23:45 - Listing Optimization Basics: Photos, Copy and Reviews

24:07 - Action Steps and Where to Get the Spreadsheet

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

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

E just got back from the Unreasonable Hospitality Summit in Nashville — and this solo episode is his full recap.

Will Guidara wrote Unreasonable Hospitality during COVID. He took Eleven Madison Park from a nice restaurant to the #1 restaurant in the world — the only restaurant to ever go from one Michelin star to three in a single year.

His philosophy: service is what you do for people. Hospitality is how you make them feel.

In this episode E breaks down the biggest lessons from the summit — how to systematize hospitality so your team delivers it consistently, why hiring the person over the resume matters more than you think, how to build a culture of praise and feedback that makes teams want to grow, and why the magic moments your guests remember are never accidental.

He also tackles the AI question head on: the answer is not cutting your team — it is repurposing them to create more human moments in a world where genuine connection is becoming a scarce resource.

The episode closes with the question Will Guidara asked the room that E says called him to greatness: "What would you attempt to do if you knew you couldn't fail?"

Get the book: Unreasonable Hospitality by Will Guidara

New book: Unreasonable Hospitality Field Guide (released April 28, 2026)

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

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

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

If you want to join our weekly free training:

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

Most property managers and co-hosts pitch homeowners on management fees.

Mike Reilly pitches them on $100,000 in tax savings. And it closes more deals than anything else.

In this Portfolio Clinic training, Mike breaks down the STR tax loophole — why it works, who qualifies, and exactly how to use it to attract high-income homeowners and win management contracts.

This is not investment or tax advice. But it is the most powerful conversation you can have with a prospective homeowner — and most co-hosts and property managers are never having it.

In this training Mike covers:

- Why taxes are the #1 expense for every high-income W2 earner and business owner

- How a doctor making $375K in California goes from a $145K tax bill to a $47K tax bill — with one STR

- What a cost segregation study is and how it accelerates depreciation in year one

- The two requirements to qualify for the STR loophole: 7-day average stay and 100+ hours of material participation

- Why 90% of CPAs don't know this loophole exists — and how to help your homeowner educate theirs

- The exact conversation flow to have with prospective and new homeowners

- How Mike charges a $20-25K consulting and design fee upfront — then takes over management in year two

- Real results: one homeowner got $80K back this year, another got $60K last year

- How to structure the deal so the homeowner qualifies AND you get the management contract

- What to do with a cost segregation study if the homeowner wants to be fully passive

- How to handle depreciation recapture and when to recommend a 1031 exchange

This is one of the highest-leverage strategies a co-host or property manager can learn right now.

Want help implementing this in your business?

Go to: https://strsecrets.com/implement

📲 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 - Why Taxes Are Your Homeowner's Biggest Expense

3:20 - The Math: How a Doctor Paying $145K in Taxes Can Change Everything With One STR

6:00 - What Is a Cost Segregation Study and Why Every Homeowner Needs One

8:30 - How Much Can You Depreciate in Year One? (The 25% Rule)

10:00 - The Two Tests to Qualify for the STR Loophole

12:00 - Running the Numbers: From $145K Tax Bill to $47K With One Property

14:30 - The Exact Conversation to Have With Every Prospective Homeowner

16:30 - How to Charge a Consulting Fee and Design Fee Upfront

18:00 - Real Results: $80K Back This Year, $60K Last Year

19:30 - What If the Homeowner Wants to Be Fully Passive?

21:00 - Depreciation Recapture and When to Recommend a 1031 Exchange

22:00 - Q&A: Cost Seg on an Existing Property, Passive Losses and More

In 2016, Cara and Mark Truckey lost their 14-month-old son. He never woke up at daycare.

Most couples don't survive a loss like that. Instead, it became the moment that changed everything.

In this episode, E and Chris sit down with Cara and Mark Truckey — two STR Secrets boardroom alumni who have built a real estate portfolio of 65+ units across Wisconsin and Florida while raising three kids and running multiple businesses.

This is one of the most honest and human conversations we have had on this show.

In this episode Cara and Mark cover:

- How losing their son reshaped their entire perspective on time, work, and money

- How Cara quit her hospital job in 2020 and Mark quit his plumbing W-2 in 2021

- How they went from a few house flips to 65+ rental units across two states

- Their first STR — a lake property in Wisconsin they bought by accident

- Why Mark struggled with delegation for years — and the 80/20 rule that broke the pattern

- How to find the right people for the right seats — and why belief in the vision matters more than skills

- How Cara transitioned into Savvy Realty as a top agent in the Tampa Clearwater market

- What actually keeps a husband and wife business partnership aligned

- The daily habit that is their real superpower — and has nothing to do with business

- How to change your identity before the results show up

- Mark's upcoming $130 million capital campaign for a K-12 school in Wisconsin

- Cara's goal: 40 STRs under management in Florida by end of 2027

- Their #1 secrets to success: courage and fighting past limiting beliefs

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

Connect with Cara:

Instagram: www.instagram.com/caratruckey

Facebook: www.facebook.com/caratruckey

Savvy Realty: www.savvy.realty/cara

Timestamps:

0:00 - Highlights

1:00 - Introducing Cara and Mark Truckey

5:05 - Their Story: Growing Up in Wisconsin and Losing Their Son in 2016

7:32 - How Grief Changed Their Relationship With Time and Money

9:03 - How They Built the Portfolio: Flips, BRRRs and Their First Accidental STR

10:21 - How They Split the Business: Cara on Sales, Mark on Construction

11:56 - Building the Team: Florida and Wisconsin Operations

14:11 - Mark's Delegation Journey: The 80/20 Rule That Changed Everything

16:48 - Right People in the Right Seats: Why Belief in the Vision Matters Most

18:24 - Identity First: You Have to Become the Person Before the Results Show Up

21:33 - How to Actually Change Your Identity — Not Just Understand It

24:28 - Why Being Part of a Mastermind Has Always Been Their Edge

25:25 - Running a Business With Your Spouse — What Actually Works

26:47 - Spiritual Alignment: The Foundation That Kept Them Together Through Tragedy

27:23 - The Matthew McConaughey Analogy: You Won't Always Walk Side by Side

32:21 - How Cara Made the Decision to Join Savvy Realty

35:00 - Their Real Superpower: Health, Accountability and Alignment

38:27 - What's Next: Mark's $130M School Campaign and Cara's Management Goals

42:23 - Their #1 Secrets to STR Success

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

Every time a past guest books your property again through Airbnb — Airbnb takes the fee. Again. Repeat guests generate over $1 billion in revenue for Airbnb annually. And most STR operators are doing nothing to capture that themselves.

In this Portfolio Clinic session, Mike Reilly breaks down the direct booking system he uses across his 30-property portfolio — and reviews a real direct booking website live with a community member.

He walks through how to collect guest info from every Airbnb and Vrbo stay, how to build a 12-touch text and email funnel that brings guests back without the OTA in the middle, and how to incentivize your team to close direct bookings on your behalf.

He also covers the occupancy tax process most operators get wrong, why your contact list is a business asset that increases your company's exit value, and what actually makes a direct booking website convert.

If you are still relying 80-100% on Airbnb for bookings — this is the training that changes that.

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

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

Timestamps:

0:00 - Why Airbnb Makes $1 Billion From Your Repeat Guests

2:27 - Why You Can't Build a Business on Someone Else's Land

4:36 - How Airbnb's Fee Change Impacted Revenue (And What to Do)

7:05 - Occupancy Tax: The Mistake That Could Cost You a Six-Figure Bill

9:23 - Live Website Review: Lori's Direct Booking Site

13:43 - What Makes a Direct Booking Website Actually Convert

19:53 - How to Collect Guest Info From Every Airbnb and Vrbo Stay

21:15 - The QR Code Exit Strategy That Drives Direct Bookings

21:35 - The 12-Touch Text and Email Funnel for Repeat Guests

24:34 - Why Mike Pays His Team $50 Per Direct Booking Closed

25:41 - Two Social Posts a Week — Done by Your Team, Not You

27:32 - How a 3,000-Contact CRM Protects You If Airbnb Shuts You Down

31:07 - Why Direct Bookings Increase Your Company's Exit Valuation

33:54 - Action Items and Closing Thoughts

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

Most STR operators don't think about regulation until it's already too late.

Julie pulls back the curtain on what’s really happening in short-term rental regulation and why hosts can’t afford to stay invisible. From local politics to nationwide advocacy, this episode is a wake-up call for operators who think regulation is someone else’s problem.

Here's what we covered:

• How Julie went from accidental host to industry advocate

• Why anti-STR arguments often hide deeper community concerns

• The biggest mistake hosts make when regulations start changing

• Why advocacy is not charity, but a real business investment

• How small hosts can contribute without becoming full-time activists

• What the Right to Rent Collaborative is building for the future of the industry

Guest Bio:

Julie Marks is Executive Director of the Right to Rent Collaborative (R2RC), a national initiative supporting state and local short-term rental associations in building advocacy capacity, legal readiness, and sustainable funding infrastructure. An association founder and industry advocate, Julie works at the intersection of national strategy and local execution, helping communities organize and engage effectively with policymakers.

Julie founded the Vermont Short-Term Rental Alliance (VTSTRA) in 2021 and served on the Vacation Rental Management Association’s Government Affairs Council from 2022 to 2024. She operates Homestead Hospitality in Vermont and manages rental properties in Vermont and Washington.

Connect with Guest:

julie@r2rcollaborative.org

https://www.linkedin.com/in/juliemarksvt/

https://www.instagram.com/vtstra/

https://www.instagram.com/r2rcollaborative/

Timestamps:

0:00 - Intro

8:01 - Introducing Julie Marks

8:28 - How Julie Accidentally Became an STR Advocate

10:00 - From Op-Ed to Statewide Alliance: The Vermont Story

11:26 - Why the Same Fight Is Happening in Every Market

12:23 - What Communities Are Really Upset About (It's Not What You Think)

16:19 - The Hard Truth: What STRs Have Genuinely Changed

18:34 - Why "It Won't Happen in My Market" Is a Dangerous Assumption

21:16 - How to Get Involved Without Going to Every City Hall Meeting

23:35 - What the Right to Rent Collaborative Does and How It Works

26:17 - "I'm Too Small to Matter" — Julie's Response

28:21 - The $2 Per Booking Model: Your Business Insurance Policy

29:08 - Why This Is a Branding Opportunity, Not Just an Obligation

35:52 - How to Start a Local Association From Scratch

38:23 - Where to Find Julie and Get Connected

39:36 - Julie's #1 Secret to STR Success

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