The Big Break Show Podcast

You think you keep a customer by being likeable and good. You make the effort from the first 100 days..

Full Episode is out now on Youtube, Spotify, Apple Podcast!

Most people have never heard of the business Jason runs, and that is exactly why it works sowell. He takes old, dead buildings, empty offices, dead retail, whatever is sitting there, and turns them into salon suites that he rents out to hairstylists and beauty pros. It cash flows,it scales, and almost nobody is competing for it.

Here is what got me. His tenants are business owners who do not want to give 40 to 60 percent of their money to a salon owner, so they happily pay him for their own space. He buys these buildings around 1.1 million and sells them for over 2 million, and keeps the cash flow the whole way. Then he runs a system on the back end that keeps those tenants for years, so the income does not churn.

I have spent my whole career in short-term rentals and this conversation still made me rethink what a scalable real estate business can look like. If you have ever wanted cash-flowing real estate that is not another Airbnb, this is the model to study.

TIMESTAMPS

0:00 - Who Jason is and the business nobody knows about

3:45 - From a college painting franchise into real estate

7:16 - What salon suites actually are

8:15 - How he stumbled into the model

10:15 - Why marketing makes or breaks any business model

12:35 - Why beauty pros pay for their own suite

16:22 - How this is arbitrage for commercial buildings

18:24 - Why it scales faster than buying rentals

19:16 - How he raises capital for each deal

20:39 - Buy for $1.1M, sell for $2.1M: the spread

31:19 - The first 100 days system that keeps tenants for years

40:29 - The exact market he looks for

42:28 - How he uses local partners as boots on the ground

1:00:11 - Where to find Jason

CONNECT WITH JASON

Instagram: @jasoncousineau

The Big Break Show with Rafa Loza every Thursday.

Real operators. Real numbers. No fluff.

Instagram: @itsrafaloza | STR specialist.

Wondering how and where to start your STR journey?

Join the community: https://www.skool.com/the-airbnb-blueprint-rafaloza/about

New episodes every week! subscribe so you don't miss them.

I have made just about every business partnership mistake there is. Some of my partners became people I now call family. Others cost me hundreds of thousands of dollars and a lawsuit I am still cleaning up. In this solo episode I break down everything nine and a half years of both taught me.

I walk through how I structure the deal end to end: how I split equity, how I vet who I let in, active versus money partners, partnering with friends and family, and how to catch a partnership that is drifting before it ends up in court. The thread through all of it, and I say it flat out at the end, is that almost every problem traces back to roles. Clear roles, in writing, with people who give as much as they take.

CHAPTERS

0:00 Why I'm doing a whole episode on partnerships

2:24 Every partnership problem traces back to one thing

3:37 The 3 things a partner must bring: time, money, or experience

6:23 The principle that keeps a partnership from breaking

10:15 Define the roles before anyone does anything

12:36 The deal I did with no contract, and what it cost me

13:02 How to structure equity splits fairly

15:00 Why aligned goals matter more than the money

21:40 The partner who wanted 70 percent, and why I walked

26:53 The partnership that turned into a lawsuit

31:16 The red flags I ignored

38:05 What to actually put in your contract

42:49 The clauses that protect everyone

45:02 Why I always pay my investors back

47:12 It all comes back to roles

Join my community: https://www.skool.com/the-airbnb-blueprint-rafaloza/about

Follow me on Instagram: @itsrafaloza

The Big Break Show drops new episodes every week. Follow the show so you never miss one.

Episode 12 Releasing tomorrow!

A mistake from a business partnership you can do once is to pick the wrong person, this is the exact topic i will share from the full episode, and this is just a tiny bit of what i had to share, I walk through how I structure the deal end to end: how I split equity, how I vet who I

let in, active versus money partners, partnering with friends and family, and how to catch a partnership that is drifting before it ends up in court. The thread through all of it, and I say it flat out at the end, is that almost every problem traces back to roles. Clear roles, in writing, with people who give as much as they take.

Stay Tuned!

Guest messages never stop. Check-in times, the wifi password, is there a blow dryer, the door code, something is broken, and it all lands on you at the worst possible hour. That was my life for years, and it is the exact problem Annie set out to kill.

Annie is the co-founder of HelloHost, and before she built it she answered more than 10,000 guest messages herself while running a 16-unit retreat in Ontario. So this is not a founder guessing at what hosts need. She lived it. HelloHost is a team of AI agents that answer your guests in your own voice, around the clock, and quietly pull the maintenance tasks out of those conversations so

nothing slips through.

What sold me was not that it replies fast. It is that it replies well. Her team got the error rate down to 0.01 percent, and when they studied 1,800 guest reviews, almost none of them could even tell an AI was answering. It knows about 80 percent of your property from day one with no training,

and it asks you before it guesses on anything it is unsure of.

If you run rentals and your phone still buzzes at 2am with a guest asking how to get in, this is the conversation that shows you the way out.

TIMESTAMPS

0:00 - Intro and who Annie is

0:41 - From management consultant to Airbnb host

2:25 - What HelloHost actually is

2:40 - The 16-unit retreat and 10,000 guest messages

5:42 - Why she went all in on AI guest communication in 2023

6:51 - What makes the message quality stand out

8:27 - The multi-agent system and the edge cases

9:56 - How it learns and asks before it guesses

17:01 - The 1,800 review study

23:10 - Getting the error rate down to 0.01 percent

26:42 - Setting your own confidence level

33:48 - 80 percent ready on day one, no training

35:25 - The 30 day free trial and 2 day setup

45:10 - Why Rafa calls it a no-brainer

59:07 - Where to find HelloHost and Annie

Tools I use to run my STR business:

Hospitable (Get your 15% Discount on your first 30 Days!): hospitable.com/partners/rafael

HelloHost (AI guest communication): https://www.hellohostai.com/rafa

The Big Break Show with Rafa Loza every Thursday.

Real operators. Real numbers. No fluff.

Instagram: @itsrafaloza | STR specialist.

Wondering how and where to start your STR journey?

Join the community: https://www.skool.com/the-airbnb-blueprint-rafaloza/about

New episodes every week! subscribe so you don't miss them.

Episode 11 Releasing in an HOUR!

On this episode, I said the part nobody wants to hear: speed is not the win. A fast reply that sends the wrong info or does not actually solve the problem just gets you a bad review faster.

I run all my guest messages on HelloHost, and the difference was not just speed. It answers to what the guest actually needs, so they stop second-guessing and just confirm and book.

My response rate went up and my reviews went up right along with it, because guests feel taken care of instead of handled.

Dan Rivers and I are in the same mastermind, and his team runs the pricing on some of my own properties, so this one is personal. He came up blue collar in Brockton, got thrown into managing 600 units with zero experience, and built Synergy Stays into one of the sharpest revenue teams in short term rentals. But the part that stuck with me was not the business.

Most people treat their nightly price like a slow cooker, set it and walk away. Dan makes the case that in 2026 that is exactly how you quietly lose money, because the platforms change the rules every month and an algorithm nobody is watching will happily underprice your best weekends. Then he flipped the whole conversation. He asked what feeling your goal is actually chasing, and once he started building toward calm and presence instead of a number, everything got clearer.

I have hit numbers that meant nothing the day I reached them. Dan put words to why.

CHAPTERS

0:00 Meet Dan Rivers

1:56 His first big break: 600 units, zero experience

3:28 Two open-heart surgeries and his second chapter

11:48 The breakfast meetup that rewired how he thinks

20:03 Thinking 100K a year meant he had made it

22:12 You only learn when you start losing (the 150K lesson)

24:38 Why he killed 6 businesses to focus on one

31:58 What Synergy Stays actually does

35:35 Why set it and forget it pricing is dead

39:47 The client who netted 38K more in a year

43:35 Goals vs feelings: the reframe that made the episode

50:00 Why he will never retire

51:52 Where to find Dan and Synergy Stays

Tools I use to run my rentals that saved me 10 hours a week:

Hospitable: hospitable.com/partners/rafael - 15% OFF your first 30 days!

HelloHost: https://www.hellohostai.com/rafa

Want to learn how I actually use AI in my short-term rental business? Join the community: https://www.skool.com/the-airbnb-blueprint-rafaloza/about

🎙 The Big Break Show with Rafa Loza every Thursday.

Real operators. Real numbers. No fluff.

📲 Instagram: @itsrafaloza | STR specialist.

🔔 New episodes every Thursdays! subscribe so you don't miss them

Dan Rivers was running seven businesses at once and slowly bleeding money. The fix was not working harder. It was cutting six of them and going all in on the one thing he was already great at.

Carl Dumesle survived the 2010 Haiti earthquake at 15, then raised his three younger brothers before he ever touched real estate. I wanted him on because he builds at a level most people call impossible, and he treats it like it is nothing.

That is the thread through this whole conversation. Carl runs his development, architecture, construction, and management all under one roof, and the reason is not ego, it is control. Every piece he brought in-house was a failure point he refused to hand to someone else. If you have ever had a deal die because a contractor vanished or a permit dragged an extra year, this is the mindset that fixes it.

The part that stuck with me was not the buildings. It was how he handles hard things. When you have watched your school fall floor by floor in 50 seconds, a late permit stops feeling like a problem. Most people build a giant mental gap between where they are and where they want to be. Carl came in with no ceiling because he never knew one existed.

We also get into the two F's, feelings versus facts, the cleanest decision filter I have heard on this show, and why owning fewer, higher-quality assets with low leverage beats chasing doors you will spend years wishing you could offload.

CHAPTERS
0:00 Who is Carl Dumesle
2:30 Surviving the 2010 Haiti earthquake at 15
7:00 Becoming head of household for his brothers
9:16 Why he still does not feel successful
11:00 The first thing you have to predict is yourself
14:00 Why business problems are not real problems
16:13 The slingshot, the deeper the low the higher the launch
17:41 You are closer than you think
20:16 From a student-housing startup into development
22:55 The 25 percent margin rule
26:00 What actually makes a deal work
28:23 The two F's, feelings versus facts
31:00 How he flies under the radar on approvals
34:49 Controlling every pillar in-house
44:00 Partnerships, hire slow and fire fast
59:00 Extreme ownership with investors
1:03:47 Own less, hig
her quality, lower leverage
1:07:00 The takeaway

Connect with Carl Dumesle:
https://www.instagram.com/carldumesle/

Tools I use to run my rentals that saved me 10 hours a week:
Hospitable: hospitable.com/partners/rafael - 15% OFF in your first 3 months!
HelloHost: hellohost.com/partners/rafael

Want to learn how I actually use AI in my short-term rental business? Join the community: https://www.skool.com/the-airbnb-blueprint-rafaloza/about

🎙 The Big Break Show with Rafa Loza every Thursday.
Real operators. Real numbers. No fluff.

📲 Instagram: @itsrafaloza | STR specialist.

Wondering how and where to start your STR journey?
🔗 Join the community: https://www.skool.com/the-airbnb-blueprint-rafaloza/about
🔔 New episodes every week! subscribe so you don't miss them

Most investors chase the wrong kind of income. They buy a door, watch a couple hundred

dollars trickle in every month, and wonder why the freedom never shows up. Patryk ran that

math and made a hard pivot.

He walked me through the moment it clicked. He owned a rental he bought for 306 thousand

that was worth 465, with a pile of equity just sitting in it, netting him around a thousand

a month. Then he looked at buying a co-hosting business for 165 thousand that was throwing

off close to fifteen thousand a month. Same money out the door. Completely different life.

He bought the business, kept buying more, and now runs 150 properties he does not own a

single one of.

We get into how he found and bought those companies, why he still works in the business

even though it runs without him, and what he plans to do with the money now. I have built

the operator side of this for years and this conversation still made me rethink where I put

the next dollar.

TIMESTAMPS

0:00 - Intro

0:57 - From corporate tech to short-term rentals

3:46 - Why he could never work for someone else

4:42 - Buying the co-hosting company in Joshua Tree

5:04 - Why passive income was never going to be enough

17:28 - Scaling the company and what happens next

19:15 - Why he still works in the business by choice

24:05 - The math that changed everything

36:44 - The takeaway that stuck with him

58:42 - Why he gave his team equity

1:05:17 - His big break moment

1:12:43 - What he actually wants to do with the money

1:13:32 - Where to find Patryk

CONNECT WITH PATRYK

Patryk Swietek, Owner of The Cohost Company

Instagram: @patryk_swi

Here's my Tool stack i use for my STR Business:

Hospitable (Get your 15% Discount on your first 30 Days!) : hospitable.com/partners/rafael

HelloHost (AI guest communication): HellohostaiHelloHost | Rafa Recommended

The Big Break Show with Rafa Loza every Thursday.

Real operators. Real numbers. No fluff.

Instagram: @itsrafaloza | STR specialist.

Wondering how and where to start your STR journey?

I build and share my STR strategies by implementing AI and test them out for a free trial without spending anything for a week!
Join my community: https://www.skool.com/the-airbnb-blueprint-rafaloza/about

New episodes every week! subscribe so you don't miss them.