The Big Break Show Podcast

Rafa Loza
  • 4.8 (24)
  • Entrepreneurship
  • Updated Weekly

Your go-to podcast for real estate investing, business acquisitions, mindset, and lifestyle. Get expert tips, actionable strategies, and inspiring stories every week.

  1. 6d ago

    Annie of HelloHost: AI Guest Messaging That Answers Your Airbnb Guests 24/7

    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.

  2. Season 3, Episode 11 Trailer

    Why A Fast Reply Won't Save Your Airbnb Reviews | HelloHost

    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.

  3. Aug 6

    How Airbnb Revenue Management Really Works with Dan Rivers (Synergy Stays)

    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

  4. Season 3, Episode 10 Trailer

    Dan Rivers: Why Doing Seven Things Made Him Fail At All Of 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.

  5. Jul 30

    How To Get Into Real Estate When You're Starting With Nothing | Carl Dumesle

    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

  6. Jul 23

    Patryk Swietek: How To Run 150 Airbnbs Without Owning A Single One

    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.

  7. Jul 16

    The HR Expert Behind Tim Bratz: Why Your Top Performers Leave | Scott Hanis

    Most operators do not lose their business to the market. They lose it to a team that was never set up to win. In this episode Rafa sits down with Scott Hanis, co-founder of Fortitude HR Solutions and the man Tim Bratz brought in to build the structure behind his company. Scott has scaled organizations, run HR for over a thousand employees, and spent years fixing the exact team problems that quietly stall real estate operators. Rafa gets honest about blowing up his entire virtual team, and Scott breaks down why that almost always traces back to the leader, not the people. They get into the first hire you should actually make, how to know when you can afford it, why culture and values are worthless until you live them out loud, and the two lines from this episode that will stick with you. People live up or down to your expectations. What you permit is what you promote. If you are trying to grow past doing everything yourself, this is the conversation that shows you where it really breaks and how to fix it. TIMESTAMPS 0:00 - Intro 0:50 - Who Scott is and what Fortitude HR does 5:06 - How Tim Bratz convinced him to go all in 9:03 - Why he walked away from a corporate HR salary 11:52 - The first hire every operator should actually make 15:04 - When you can really afford to hire full time 19:29 - Rafa: why I blew up my entire team 21:41 - What culture and values really mean 27:03 - Mission and vision, and why most people skip it 29:51 - The three solutions rule 33:38 - People live up or down to your expectations 39:10 - Setting expectations in your personal life 47:05 - How faith shapes hiring and firing 51:25 - How to actually become a better leader 54:52 - What you permit is what you promote 56:34 - How AI is changing HR and where it gets dangerous 1:01:43 - Where to find Scott CONNECT WITH SCOTT Fortitude HR Solutions: https://fortitudehrsolutions.com 🎙 The Big Break Show with Rafa Loza every Thursday. Real operators. Real numbers. No fluff. 📲 Instagram: @itsrafaloza | STR specialist. just a note please add this tmoving forward for podcast description: Tools I use to run my rentals: Hospitable: hospitable.com/partners/rafael - 15% OFF in your first 3 months! HelloHost: hellohost.com/partners/rafael 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.

  8. Jul 9

    AI Agents That Runs Your Entire Airbnb Business with Jan Sahagun (Trellis, Y Combinator)

    Most people think running an Airbnb is passive. You list it, go to the beach, and the money shows up. Anyone who actually does it knows the real job is the coordination. The messages that never stop, the maintenance that has to get scheduled, the vendor who has to be found and called, and the ten different tools that somehow have to talk to each other. In this episode Rafa sits down with Jan Sahagun, co-founder of Trellis, a Y Combinator company building autonomous AI agents for short-term rentals. Trellis is not another chatbot. It sits on top of the tools you already use, pulls all your operations into one place, and runs AI agents that actually do the work. The agent talks to your guest, figures out the problem, and if nobody on your team can fix it, it picks up the phone, calls an outside contractor, and gets it scheduled. You just approve it. Jan went from professional ice hockey in Europe to building one of the most talked about AI companies in the short-term rental space. He and Rafa get into how you keep an AI agent from going rogue, how much work it really takes to train it on your business, the first thing smart operators should automate, and why you cannot just vibe code a real software business. If you own or manage rentals, this is the conversation that shows you where the next few years are going. CHAPTERS 0:00 - Intro 2:06 - Meet Jan and what Trellis actually is 3:20 - From pro hockey to short-term rentals 5:51 - Why he built an AI that runs the business itself 8:03 - What happens when you plug your rentals in 15:39 - The agent that actually calls your vendors and staff 17:14 - How they keep the AI from going rogue 19:37 - How much work it takes to train it 22:44 - The first thing smart operators automate 23:38 - Zero to 3,000 listings in under three months 38:12 - What AI will replace and what it won't 50:40 - Why you cannot vibe code a real software business 56:09 - Jan's story: a broken ankle that changed everything 59:26 - Where to find Jan and try Trellis TRY TRELLIS Website: https://trellistech.com Connect with Jan on LinkedIn: Jan Sahagun Apps that i use for my Airbnb Business: Hospitable: https://hospitable.com/partners/rafael HelloHost: https://hellohost.com/partners/rafael If you want to apply AI in your business to save time and earn more.. Join the community: https://www.skool.com/the-airbnb-blueprint-rafaloza/about Follow Rafa on Instagram: @itsrafaloza The Big Break Show drops new episodes every Thursday. Follow the show so you never miss one.

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4.8
out of 5
24 Ratings

About

Your go-to podcast for real estate investing, business acquisitions, mindset, and lifestyle. Get expert tips, actionable strategies, and inspiring stories every week.

Information

  • Creator
    Rafa Loza
  • Years Active
    2021 - 2026
  • Episodes
    111
  • Rating
    Explicit
  • Copyright
    © 2025 Rafa Loza
  • Show Website
    The Big Break Show Podcast

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