If your short-term rental revenue still lives and dies on Airbnb, this episode is the clearest roadmap to changing that. Rafa Loza sits down with Mark Simpson — founder of Boostly, creator of a WordPress direct booking framework that converts at 5x the industry average, and the force behind Boostly Connect — to break down exactly how STR hosts are using AI and PMS integration to build their own marketing machines. Direct bookings, vacation rental automation, and the tools that make it all work w...
Jun 05, 2026•1 hr 11 min•Season 3Ep. 1
Giving you all a end of year Short Term Rental market update. Also, big news. I'm taking the podcast solo!
Nov 27, 2025•24 min
In this episode, we sit down with Gil, the founder and CEO of CraftedStays, as he shares his inspiring journey from a tech career to the short-term rental industry. Gil talks about his transition from a secure W2 job to building a thriving hospitality business with properties in The Great Smoky Mountains and Branson. He dives into the importance of diversifying beyond Airbnb, the creation of his direct booking platform, and how CraftedStays empowers hosts to succeed with direct bookings. Gil als...
Nov 20, 2024•50 min•Season 2Ep. 17
Josh Dixon shares his journey from growing up in a construction family to becoming a successful real estate investor. He discusses the importance of setting goals, balancing family life with business, and the value of mastermind groups in maintaining focus. Josh emphasizes the significance of building strong relationships with subcontractors and the role of administration in scaling his construction business. He aims to grow his portfolio to 500 doors while ensuring a healthy work-life balance. ...
Nov 13, 2024•59 min•Season 2Ep. 16
Whit McCarthy, one of the co-founders of The Helm, joins us on the show to chat about the world of real estate lending. We dive into topics like hard money lending, business purpose lending, and the key differences between conventional and investor loans. He breaks down how loans get originated, funded, and sold to institutional buyers, while emphasizing how crucial local expertise is in lending. We also touch on residential properties, especially one to four unit construction projects and build...
Nov 06, 2024•43 min•Season 2Ep. 15
In this episode, we talk about our journey from non-investors to buying businesses, and how finding the right mentors and communities made all the difference. We dive into the challenges of online courses and influencers, break down the importance of understanding business metrics, and share what we look for when evaluating potential acquisitions. We also touch on the power of networking, how ad backs factor into business valuations, and why having a long-term vision is key. We wrap up by encour...
Oct 30, 2024•30 min•Season 2Ep. 14
In this episode, Hayden Albert shares his journey from the Navy to diving into real estate and entrepreneurship. He talks about starting a window company, navigating partnerships, and finding success in a unique niche of real estate. He talks about his current focus on a new niche in real estate that offers market share and profitability without the need for a large operation. The conversation focuses on the strategy of using hard money loans to purchase properties with extra acreage, then subdi...
Oct 23, 2024•1 hr 8 min•Season 2Ep. 13
In this episode of The Big Break Show, we dive into a recent quadruplex deal we checked out in Topsail Beach, North Carolina. We talk about what we learned through the process and how teaching and learning go hand-in-hand in real estate. We break down everything from the renovation standards and underwriting to how we analyzed the market. We also chat about what was driving the seller and how important it is to build relationships in the industry. By the end, we reflect on whether the deal was w...
Oct 16, 2024•19 min•Season 2Ep. 12
Dan Rivers and Mike Savage discuss their backgrounds in real estate and their journey to becoming successful investors. They share their experiences in property management, short-term rentals, and the challenges they faced along the way. They also highlight the importance of mindset and the power of networking and building relationships in the industry. The conversation emphasizes the creative ways they financed their investments, including taking out loans against their assets. Overall, the con...
Oct 09, 2024•1 hr 8 min•Season 2Ep. 11
In this episode of the Big Break Show, we would answer some of your questions and share our real estate experiences, focusing on the ins and outs of raising capital through debt and equity. We talk about tips on structuring deals and highlight the importance of knowing your audience and building strong partnerships. We also discuss different investment strategies, preferred returns, and why clear communication is key when working with partners. New episode every Wednesday! #TheBigBreakShow #Q&am...
Oct 02, 2024•30 min•Season 2Ep. 10
In this episode, Kelli Garrett dives into how sports have shaped their business mindset and skills. Kelli shares insights on teamwork, quick decision-making, and learning from setbacks. They discuss the value of masterminds and surrounding yourself with supportive peers, as well as the mindset shift needed for scaling a business. Kelli also highlights the importance of determination, discipline, and leadership, and talks about living life fully and without regrets. From hosting local meetups to ...
Sep 25, 2024•1 hr•Season 2Ep. 9
Joe Prillaman shares his journey from selling industrial equipment to building a portfolio of 32 short-term rental properties. He emphasizes the importance of being in the right room with the right people and joining mastermind groups like GoBundance. Joe discusses the challenges he faced in the early stages, including working full-time jobs and renovating properties at night. He highlights the benefits of short-term rentals, such as higher income potential and the ability to live beneath your m...
Sep 18, 2024•58 min•Season 2Ep. 8
Tyson Cobb is a retired orthopedic surgeon turned successful real estate investor. With a diverse background that includes professional rodeo experience before entering medical school, Tyson has trained at the Mayo Clinic and practiced for over two decades. Currently focused on real estate syndications and various asset classes, he brings a unique perspective to the investment world. In this latest episode, we discuss Tyson's journey from orthopedic surgery to real estate investing. The episode ...
Sep 11, 2024•1 hr 11 min•Season 2Ep. 7
Cassie Tollens is the Operations Master of multiple hotels in Carolina Beach. She oversees the day-to-day operations, ensuring the smooth functioning of the establishments. With a keen eye for detail and a passion for hospitality, Cassie is dedicated to providing exceptional guest experiences and maintaining high standards in the hospitality industry. In this latest episode, Cassie discusses the successful operations of the hotels in Carolina Beach. From managing bookings to implementing new sys...
Sep 04, 2024•1 hr 1 min•Season 2Ep. 6
Juan Huizar is the president of SAGE Real Estate, a boutique multifamily commercial company situated in Long Beach, California. With a CCIM certification, Juan stands out as an expert in the real estate industry, providing invaluable insights and knowledge to his clients and followers. His dedication to educating others on building wealth through real estate investment is evident in his popular YouTube channel, where he shares practical advice and strategies to help individuals enter the realm o...
Aug 28, 2024•1 hr 12 min•Season 2Ep. 5
Tim Vitale is a commercial real estate investor and owner of multiple apartment complexes in the affordable housing space. With over 1,600 units across several states, Tim specializes in buying commercial apartment complexes in the LITECH and Section 8 sectors. He has a background in finance and accounting and made the transition to real estate after realizing the limitations of his W-2 job. Tim is passionate about providing quality affordable housing and helping investors achieve financial succ...
Aug 21, 2024•58 min•Season 2Ep. 4
Erica James is a two-time national CrossFit champion, real estate agent, and entrepreneur based in Greenville, South Carolina. She is the owner of the fitness studio, The Booty Shop, and is passionate about empowering women through fitness and community-building. In this episode, Erica shares her journey from being a cheerleader in college to finding her passion in fitness and entrepreneurship. She discusses how she transitioned from being a full-time employee to becoming a business owner and re...
Aug 14, 2024•59 min•Season 2Ep. 3
Dan Tollens started his career in fix and flipping houses before transitioning into the hotel business. He currently owns and operates multiple boutique hotels in North Carolina, with a focus on providing unique and memorable experiences for guests. In this episode, Dan shares their process of hotel acquisitions and the ins and outs of running a successful boutique hotel business. He shares his expertise and provides valuable insights into finding deals, underwriting, financing, and managing hot...
Aug 07, 2024•39 min•Season 2Ep. 2
Welcome to season 2 of The Big Break Show! We have some exciting news for this new season. Unfortunately, Jesse Vasquez will no longer be part of the show, but we introduce a new co-host and discuss some upcoming fire plans for the future of this podcast. As always, we will continue to provide valuable insights into investment strategies, lifestyle, mindset, and more. So the new co-host will be Dan Tollens! Dan Tollens is a real estate investor and entrepreneur with a background in sports. After...
Aug 02, 2024•31 min•Season 2Ep. 1
In this episode, we sit down with Matt Krueger. He is a full-time real estate investor based in Des Moines, Iowa. He started his real estate journey with a low income and has since built a substantial portfolio of properties. Matt and his wife have been able to achieve financial freedom through creative financing strategies and by house-hacking multiple properties. Matt shares his journey from being a cell phone sales rep to building a substantial real estate portfolio. He started by buying a pr...
Jan 10, 2024•52 min•Season 1Ep. 80
In this episode, we sit down with Blake Anthony Carter. He is a real estate agent and entrepreneur based in Austin, Texas. He has a background in property management and has built a successful business in the short-term rental industry. Blake is known for his expertise in co-living and short-term rentals, and he also runs a real estate brokerage and design team. He has experienced both the highs and lows of the real estate industry, from growing up in a family involved in real estate to facing h...
Jan 03, 2024•1 hr•Season 1Ep. 79
In this episode, we sit down with Derek Sherrell, also known as "That ADU Guy." He is an expert in the field of accessory dwelling units (ADUs) and infill housing. He has been involved in the real estate industry for over 27 years and is passionate about helping people navigate the complexities of ADU development. He believes that ADUs can play a crucial role in addressing the housing crisis and creating more affordable housing options. He shares some valuable insights into the world of accessor...
Dec 27, 2023•1 hr 5 min•Season 1Ep. 78
In this episode, we sit down with Sean Martin. He is a successful entrepreneur and business owner. He grew up in the Bronx during the late 80s and early 90s and faced many challenges and hardships. Now, he is dedicated to giving back and making a positive impact on the lives of young people. Sean is the founder of R.e.a.l. Success Mentors, a program that aims to empower underserved youth, transform 10 million inner-city students into real-life success stories, and provide them with the tools and...
Dec 20, 2023•1 hr 13 min•Season 1Ep. 77
In this episode, we sit down with Fouad Bazzi. He is a real estate investor and entrepreneur based in Detroit, Michigan. He has a background in banking and has built a successful portfolio of short-term rental properties. Fouad is passionate about building relationships and creating awesome experiences for his guests. Fouad shares his journey from the corporate world to short-term rentals. He emphasizes the importance of building relationships and finding the right mastermind groups to grow and ...
Dec 13, 2023•1 hr 4 min•Season 1Ep. 76
Claire Bays is a CrossFit athlete, coach, and nutrition and fitness coach. She overcame her alcohol addiction and now helps others on their wellness journeys. In this episode, Claire shares her journey from growing up in a small town in Oklahoma to overcoming alcohol addiction and finding her passion for fitness. She emphasizes the importance of community and support in her recovery and the transition to a healthier lifestyle. She believes in the power of slow progress and meeting individuals wh...
Dec 06, 2023•1 hr 13 min•Season 1Ep. 75
Aileen Grimesey is a healthcare professional with over 12 years of experience in the industry. She and her husband own and operate residential care facilities for the elderly in the Bay Area. Aileen is passionate about providing compassionate care and helping others start their own facilities. In this episode, Aileen shares her journey in the healthcare industry, her passion for helping others, and how she started to have residential care facilities for the elderly in the Bay Area. She discusses...
Nov 29, 2023•1 hr 9 min•Season 1Ep. 74
Jeff Welgan is an investor strategist at Blueprint Home Loans with 19 years of experience in the mortgage industry. He specializes in helping clients build and scale their real estate businesses, providing guidance and expertise in financing options for real estate investors. In this episode, Jeff shares his expertise in the mortgage industry and provides insights into the current market conditions. He discusses the challenges and complexities of mortgage lending for real estate investors and em...
Nov 22, 2023•1 hr 16 min•Season 1Ep. 73
Fraser Bayley is a strength coach and nutritionist who specializes in helping entrepreneurs and business owners optimize their health to improve their overall well-being and performance. He has a background in nutrition and physiology and has worked with high-profile clients such as musicians and entrepreneurs. In this episode, Fraser shares his personal journey of overcoming mental health issues and transforming his health through nutrition and lifestyle changes. He emphasizes the importance of...
Nov 15, 2023•1 hr 11 min•Season 1Ep. 72
We had the pleasure of speaking with Dan Tollens. He is a real estate investor and entrepreneur based in Charleston, South Carolina. He is the co-founder of several businesses, including a boutique hotel company, a construction company, a property management company, and a roll-off dumpster business. He shared how his journey started with flipping houses and then evolved into managing job sites for a TV show. When that opportunity ran its course, he pivoted to HOA management, which eventually le...
Nov 08, 2023•1 hr 20 min•Season 1Ep. 71
In this episode, we had the pleasure of speaking with Diya Liu. Diya's journey is truly inspiring as she went from being a patent litigation attorney to achieving financial freedom through real estate. Her success includes owning and managing STRs and expanding her ventures to include boutique hotels. She now owns four boutique hotels and a dozen short-term rentals across the USA. She has become a seasoned traveler, actively seeking creative financing options and below-market deals in different ...
Jul 12, 2023•1 hr 5 min•Season 1Ep. 70
