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The Hotel Investor Playbook
Welcome to The Hotel Investor Playbook, hosted by real estate investors and hospitality experts Michael Russell and Nathan St Cyr. As the founders of Malama Capital and Howzit Hostels, Michael and Nathan have a wealth of experience in owning and operating boutique hotels, hostels, and other experiential lodging properties. With over $30 million in real estate investments, including short-term rentals, long-term rentals, commercial retail, and hospitality properties, they bring a unique perspective on how to turn passion-driven investments into financial freedom.
In this podcast, they share their roadmap for transitioning from traditional real estate investments to boutique hotels, offering listeners the insights and strategies needed to succeed in this niche market. Whether you're looking to learn about identifying the right property, managing operations, or understanding the financial complexities of boutique hotel ownership, The Hotel Investor Playbook has you covered.
Join Michael and Nathan each week as they document their journey towards building a $400 million real estate-based business and bring you along for the ride. Subscribe now and start turning your real estate investment dreams into reality.
The Hotel Investor Playbook
7 AI Tools To Help You Buy and Operate Hotels (With No Staff and No Time) | Jake Heller E60
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.
Connect with Jake
Website: https://a
Connect with Michael on Instagram or LinkedIn.
Email Us at info@hotelinvestorplaybook.com
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