AI-Driven Vacation Rentals: Shahar Goldboim on Automating Property Management 2026

(0:01) Hi everyone, welcome back to the AI Interconnect podcast. I'm your host Lauren. On this show, I speak with (0:09) founders, operators, and investors. We are building and shaping the next generation of technology across prop (0:18) tech, fintech, and AI. AI interconnect is designed as a platform for real conversation with the people building (0:27) the infrastructure of tomorrow. No pictures, no re narrative, just honest insights from people we are in the area. (0:38) Okay. Today I'm joined by Shahar Goldwin, (0:43) founder and CEO of Boom. And Boom is an AIdriven property management platform designed (0:51) to help short-term rental operator and hospitality companies automate operation (0:58) and move toward autonomous business system. Jahar, thanks for being here. Very happy to have you [clears throat] (1:06) on the show. (1:07) Lauren, really happy to be over here and thanks for inviting me. Chapter 2: Shahar’s Journey Across Industries (1:12) Very nice. can't wait with this conversation and (1:18) I let me start you have a fascinating background across multiple (1:26) industries retail operation across the US e-commerce real estate investment (1:35) and eventual building a large short-term rental operation before (1:40) starting boom Um Shahar, how how did your journey across those industries lead you to eventually build boom? (1:54) That's a good question. I guess it's being curious being entrepreneur. (2:02) Coming to United States in a young age started like to work in retail understanding I can do it by myself. Chapter 3: Identifying Opportunities in Real Estate and Vacation Rentals (2:11) building location across 20 states then getting into real estate as an investor as a broker (2:19) did hundreds of million dollar transactions then understanding like I did a startup (2:28) to real estate to find return in the market meaning like every time I went as an investor to find a property (2:36) I would look okay what's the return I can make on it so what's a property that sold all around it, what's the rentals that was around it and then how much I (2:44) can get for it and understand what's the return I can make on my money. I said why there isn't like a software that doing it automatically. So we build a (2:52) software like that. During that time a friend came to me and told me hey remember the house that we got to my parents in Eastern Shore which is a fancy community in Miami. (3:04) They decided not to move into it and I want to do it Airbnb. I told him, "It's great that you want to do it in Airbnb, (3:11) but what's the connection to me?" So he told me, "Everything that you do, you do good." (3:16) So he told him, "You know what? Let me think about it." And I found a company in Australia that can implement interior design on top of empty (3:22) pictures. So I took that pictures and we implemented the furniture on it. And we created a fake listing on Airbnb (3:31) with the address of the house, the picture of the house, but with fake furniture in it. And we started receiving a lot of reservations. (3:40) And then my wife, she's an interior designer. So I asked her, do you want to design a home? (3:43) We got like I think we have like a really good business over here. So she said, hell yeah. (3:51) And then we wrote everybody that we are sorry that the house got flooded, but we put new furniture and from here to there we started to operate it. (4:02) It was really successful business. (4:06) And then I had an investment like I had a flip that we got stuck with. So we changed it also to an Airbnb. Chapter 4: Building Tech-Enabled Property Management Tools (4:14) A friend asked me like we bought for him a multifamily on the ocean. (4:19) So we also changed that to vacation rental and all of a sudden he has a property management company. (4:27) And then using the tools I decided hey you know what it's not good enough let's build on top of those tools and we built a tech enabled company that grew up to be a (4:34) company that manages $150 million under portfolio. (4:41) So I guess it's moving from opportunity to opportunity and rolling with it and understanding the business concept into it and understanding the suffering. (4:54) I had a lot of suffering as a businessman right like you're using software that not necessarily working for you. Chapter 5: What Is Boom and How It Transforms Property Management (6:13) your operation needs to be really good but also the technology and the ability to control everything must be good as (6:21) you scale. So this is how I created boom. Okay. I just love it. Bravo. (6:31) [laughter and gasps] (6:32) This sounds great. Chapter 6: Boom as a Business Operating System and ERP (6:41) Let's go on to Boom. Boom is not just another property management software. Your vision seems to be (6:50) building a platform that moves from traditional SaaS toward something you describe as business as a software. (7:01) When you explain Boom to someone outside the proptech and hospitality industry, how do you describe what the company actually does and who it helps? Chapter 7: AI and Automation in Vacation Rental Operations (8:49) Somebody is asking for an early checkin. If I want to give him an early check-in it means I (8:56) need to check my task management to see if there is a toilet that needs to be fixed (9:04) and then I need to see if somebody did a late checkout and then I need to see if cleaning was done. Chapter 8: Who Benefits Most from Boom’s Platform (10:59) Right now our major clients are property managers in the vacation rental sector that have above 80 properties normally that they manage. (11:11) These are our clients but in the end of the day our clients also have clients. Chapter 9: Scaling Boom and Overcoming Implementation Challenges (12:09) What feels like the hardest part of running or scaling boom? (12:18) Implementation. To come to a company and change all of their tech stack is hard. Chapter 10: Operational Frictions and How to Overcome Them (13:14) Operational friction. Can you explain it better? Chapter 11: Market Education and Internal Challenges (14:00) It's also implementation it's taking their whole team and moving them to work on different software. Chapter 12: Technological Shifts in Hospitality and PropTech (14:40) The point is that you will be able to talk to the system rather than click it. Chapter 13: Underestimated Impact of AI in Professions (16:39) From your vantage point in proptech and hospitality technology, what major shift is happening that people underestimate? Chapter 14: Trust in AI and System Improvement (17:01) I had a conversation with my accountant around a year ago. Chapter 15: Future Vision for Boom and AI in Hospitality (20:02) Elon opened the opportunity to do auto drive. Chapter 16: Goals for Growth and Impact (21:16) Systems we build today need to get better and better as models improve. Chapter 17: Scaling Technology and Infrastructure (21:44) Data collection is getting better. Chapter 18: Lessons for Founders in PropTech (23:15) To be a property manager is really hard because you need to be 24/7. Chapter 19: Mindset and Family Business Dynamics (29:18) Born to the right family like both of my brothers build with me boom. Chapter 20: Advice to Younger Self and PropTech Entrepreneurs (30:26) Advice to your younger self. Chapter 21: Final Advice for PropTech Founders (31:33) Proximity is power. Chapter 22: Closing Remarks and Contact Information (32:27) Shahar thank you so much for joining. (32:46) Thank you it was great being here. (33:02) You can find me on LinkedIn and boomnow.com. (33:39) That's it for today's episode of AI Interconnect. (33:56) See you next time.