7 AI Tools To Help You Buy and Operate Hotels (With No Staff and No Time) | Jake Heller E60

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Dec 2, 2025

Join Jake Heller, founder of the AI for CRE Collective, as he unveils groundbreaking AI tools tailored for boutique hotel investors. Discover how to swiftly research new markets and streamline processes with innovative tech. Jake shares insights on automating administrative tasks, generating professional investor decks, and reducing legal costs through AI-assisted reviews. Expect to learn practical tips on using AI for effective underwriting and asset management, all aimed at giving small operators a competitive edge without increasing staff.

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ADVICE

Start Research Multi-Model And Use RTCF

Start market research with analytical LLMs like Perplexity, then cross-check with generative models for nuance.
Use the RTCF prompt framework (Role, Task, Context, Format) and save prompts to build a reusable prompt library.

INSIGHT

Reverse Engineer Outputs Into Prompts

Reverse-engineer AI outputs to extract high-quality prompts and iterate faster.
Save those prompts into a prompt library so less-experienced team members can produce consistent results.

ADVICE

Underwrite In Excel With AI Agents

Use Excel-native AI plugins like Shortcut and Index to underwrite deals without abandoning your models.
Map OMs into your models and iterate scenarios quickly to underwrite many more deals per week.

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Click here to start your free 7-day trial of the AI for CRE Collective.

Most boutique hotel investors are running lean. No analyst team. No data department. No six-figure tech budget. Yet the demands of buying and operating hotels keep getting heavier.

In this episode, I sit down with Jake Heller, founder of the AI for CRE Collective, to break down the most effective AI tools that give small operators the firepower of a full investment team without hiring more staff or burning more hours.

We workshop real tools you can start using today to:

Research any hotel market in minutes
Underwrite deals 5 to 10 times faster
Build pro-grade investor decks and OMs
Create renovation concepts and renderings
Cut legal costs with AI-assisted contract review
Streamline asset management and portfolio reporting
Automate day-to-day admin and communication

The 7 AI Tools We Cover in This Episode

Claude (Deep Research) – Market feasibility, multi-source synthesis
Perplexity (Market Intel) – Accurate analytical research with citations
Shortcut AI (Underwriting) – Flexible financial modeling inside Excel
Google Gemini (Nano Banana Image & Video Generation) – Property renderings, façade upgrades, interior redesigns, branding, teaser videos
Wilson AI (Legal & Due Diligence) – Contract review, redlines, title exceptions
Gamma (Decks & OMs) – Investor decks, offering memorandums, pitch materials
Wspr Flow (Voice-to-Text & Admin) – Ultra-fast transcription, notes, emails, and communication

Whether you’re trying to scale your hospitality business, underwrite more deals, or operate your hotel with fewer people, these tools will change the way you work.

If you want to buy and operate hotels without a big team or a ton of time, this episode is your new playbook.

Get One Week Free Membership to Jake’s AI for CRE Collective

If you want help implementing everything we discuss in this episode - the prompts, the workflows, the tools, the systems - Jake’s community is the best place to start.

Listeners of The Hotel Investor Playbook can get full access for FREE.

Click here to start your free 7-day trial of the AI for CRE Collective.

About Jake

Jake Heller is a third-generation homebuilder and entrepreneur who co-founded the AI for CRE Collective, a central hub where AI and technology meet real estate. As an expert focused on practical, implementation-oriented solutions in AI in Commercial Real Estate, he built this 400+ member community to provide battle-tested workflows, automation templates, and a database of 300+ vetted AI tools for professionals. Drawing on his experience in development and consulting, including cofounding JDJ Consulting Group, Jake specializes in helping CRE firms and individuals scale and streamline processes to accelerate deal speed across critical tasks such as underwriting and deal analysis.

Learn how to use AI to underwrite faster, streamline operations, automate the busy work, and make better decisions. Start your 7-day free trial of the AI for CRE Collective here.

Connect with Michael:

Invest with Malama Capital: malama-capital.com/invest
Submit a deal: https://www.malama-capital.com/deal-submission
Instagram: @the_hotel_investor_playbook
Contact Us: info@hotelinvestorplaybook.com