Ryan McCoy

"Where can AI create compounding impact in my business?" That's the question every builder, operator and executive should be asking themselves. Here’s our answer at Elevate: 1) Coding We build with Claude Code and Cursor, though we’re moving fully to Claude Code (seems to be the trend). AI coding dramatically speeds iteration. I can’t imagine building a startup without it. 2) Data transformations We use OpenAI API calls for aggregation, cleaning, and enrichment of messy data (e.g., customer deduplication, revenue stream categorization, smart cleanup). This is the unglamorous work most platforms avoid, and historically required headcount. We improve our models as our context grows. 3) Analytics agent On top of clean data, we run a Gemini-based analytical agent that does a first layer of QA and lets operators ask questions conversationally and get answers they can use. We tightly scope what the agent can access and how it reasons to protect accuracy. A few observations: We use all three major model providers (Google, OpenAI, Anthropic). For our use cases, they’re close enough to interchangeable, but we’re constantly testing that hypothesis. We are not using AI for sales outreach. The work is too contextual, relationships matter, and our ACVs are too high. We do use AI for GTM research. The landscape is changing fast, so we share learnings every week in our All Hands to stay current, e.g., yesterday, Steve Mazzari shared his latest Claude skills stack. What else should we be doing?

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One thing I’ve learned leading growth at Casiola vacation homes: Scaling isn’t about doing more things, it’s about doing fewer things exceptionally well. Our growth playbook is built around a few non-negotiables: • We obsess over the right homeowners, not just more leads • Sales and marketing are designed together, not handed off • Systems exist to support people, not slow them down • Culture is treated as a growth lever, not a buzzword None of this is flashy. And that’s the point. Sustainable growth comes from repeatable fundamentals, clear ownership, and leadership that protects focus and prioritizes what truly matters. I’ll be sharing pieces of what’s worked for us, what we’ve refined, what we’ve learned the hard way, and what I believe actually scales in this industry. If you’re building for the long term, you already know: the real playbook isn’t public, it’s practiced. #Casiola #GrowthLeadership #GoToMarket #ScalingTeams #SalesLeadership #ServantLeadership #ShortTermRentals #HospitalityLeadership

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We invest at Pre-VC and Pre-Seed, and then help our founders find a Seed round when they're ready. Here are 27 Seed investors that we *know* are active right now. Blue Moon Bonfire Ventures Chingona Ventures Flying Fish Partners Foothill Ventures Great North Ventures ground game HealthX Ventures InsurTech Venture Partners KCRise Fund Las Olas Venture Capital Leva Capital Maven Ventures Monte Carlo Capital Moonshots Capital OneSixOne Ventures Oval Park Capital Pixel Perfect Ventures Range Ventures Revolution SNAK Venture Partners Startup Capital Ventures Supernode Global Susa Ventures Trilogy Equity Partners True Ventures True Wealth Ventures

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Ira Rosenbloom thinks having staff get a bonus for identifying scope creep is a good thing ... do you agree? If the client signs off on the additional fee, some % of the margin goes back to the staff. At our AI summit, Jason Staats, CPA, talked about incentivizing staff in a similar way as it pertains to AI-driven efficiency. Greg O'Brien, CPA and the folks at PASBA: Professional Association of Small Business Accountants talk about using production based scheduling to build out staff variable compensation. Do you agree? Have you tried these methods??

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