Ep 272 - How AI Will Replace Most STR Ops Work (And What Operators Should Do) with Shahar Goldboim

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Dec 15, 2025

Shahar Goldboim, Co-founder and CEO of Boom, shares insights from his journey in real estate and technology. He explains how AI is revolutionizing short-term rental operations and suggests that fragmented software is hindering growth. Shahar discusses the importance of focusing on operational data, which lets AI handle 80% of guest communications. He emphasizes that businesses must evolve or risk falling behind. Additionally, he highlights that building relationships is key to success in the industry.

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ANECDOTE

From One Airbnb To $150M Management

Shahar scaled from designing one Airbnb to running a tech-enabled management business that reached $150M in assets.
He spun out separate companies (fund, construction, design, management) after learning each needs its own DNA.

ADVICE

Don’t Combine All Services Under One Roof

Split businesses into focused entities instead of forcing one company to do funds, brokerage, construction, design and management.
Give each unit a separate commercial purpose so it can develop proper DNA and scale independently.

INSIGHT

AI Needs Full Operational Data To Work

Fragmented PMS stacks cause manual work, mistakes, hidden costs, and block AI's effectiveness.
True AI value requires a fully connected lifecycle so decisions use complete operational data.

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AI isn’t a tool anymore — it’s infrastructure.

In this episode, Chris and E sit down with Shahar Goldboim, founder of BOOM, to break down how AI is fundamentally changing short-term rental operations, exits, and scale.

From selling a property management company to building tech that replaces broken workflows, this conversation dives deep into why fragmented tools are failing and why operators who don’t adapt will fall behind.

Inside this episode:

Why “tech-enabled” STR businesses still fail
The biggest mistakes operators make when exiting
Why one company can’t do funds, PM, design, and tech well
How AI eliminates 80% of guest communication (without killing hospitality)
Why fragmented STR software stacks are breaking ops
How AI becomes the new infrastructure for scale

00:00 – Why Solving Everything Breaks Most Tech-Enabled STR Companies

03:05 – “Business as a Service” vs Traditional STR Software Stacks

06:20 – From Operator to Platform Builder: Shahar’s Real Estate Path

10:10 – Why Tech-Enabled PMs Fail Without Focus

14:30 – The Hidden Cost of Fragmented PMS + Tools

18:05 – Why AI Fails Without Full Operational Data

22:40 – How AI Can Eliminate 80% of Guest Communication

27:15 – The Real Bottleneck: Scaling Ops, Not Software

32:10 – Why All-in-One STR Platforms Are the Future

38:20 – The Direction of AI, Automation, and STR Businesses

Guest Bio:

Shahar Goldboim is the Co-Founder and CEO of Boom, the world’s first Autonomous Property Management System (AiPMS)—a platform redefining how real estate assets are operated through AI. Before founding Boom, he built DesignedVR, a hospitality management company overseeing more than $150 million in assets. This extensive experience gave him a firsthand understanding of the intricate, day-to-day challenges property operators face.

Throughout his career, Goldboim has been involved in hundreds of millions of dollars in real estate transactions as an investor and broker, and has deployed over $50 million in syndication funds. That deep operational and financial experience shaped his belief that the future of property management lies in automation, intelligence, and human-centered design.

Today, Boom merges hospitality, real estate, and AI to help operators around the world manage smarter, scale faster, and unlock the full potential of their assets.

Guest Link:

https://www.linkedin.com/in/shahar-goldboim-80820b95?utm_source=share&utm_campaign=share_via&utm_content=profile&utm_medium=ios_app

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