7 AI Tools To Help You Buy and Operate Hotels (With No Staff and No Time) | Jake Heller E60
The Hotel Investor Playbook
When to Rely on AI in Legal Work
Jake cautions where human judgment remains essential and recommends combining AI first-passes with attorneys.
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.
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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
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