AI Startup Playbook: Do’s, Dont’s, and Beyond
AI Startup Playbook: Do’s, Don’ts, and Beyond
Moving beyond the AI hype to build, scale, and compete.
Featuring Moderator Dave Cotter of Kelsor Ventures, alongside panelists Kevin Bolger, John McIntyre, and Florian Engel.
AI is reshaping how companies develop products, allocate resources, and build competitive advantage. For founders and investors, the challenge is no longer simply understanding what AI can do—it’s knowing where it creates meaningful value, how to implement it effectively, and when it makes strategic business sense.
Join Chimera Community for AI Startup Playbook: Do’s, Don’ts, and Beyond, a virtual conversation moderated by Dave Cotter of Kelsor Ventures, featuring industry experts Kevin Bolger and John McIntyre. Together, they’ll explore the practical realities of building, scaling, and competing in an increasingly AI-driven market.
From identifying high-value use cases to avoiding costly implementation mistakes, this discussion will examine the strategic decisions that separate meaningful AI adoption from experimentation without a clear business case.
Discussion Topics
Where AI Creates a Competitive Advantage — Explore how AI can drive product differentiation, operational efficiency, faster execution, and more effective customer acquisition.
The Pitfalls of Building with AI — Unpack common technical, operational, and strategic mistakes, from over-engineering to pursuing solutions without a clear customer need.
When AI Makes Business Sense — Learn how to evaluate AI opportunities based on customer value, implementation costs, measurable ROI, and alignment with business objectives.
The Next Phase of AI and Startups — Discuss emerging technologies, evolving business models, and what continued AI adoption means for startup strategy, scalability, and investment opportunities.
Why This Conversation Matters
For founders, AI presents an opportunity to build more efficiently, make smarter product decisions, and uncover new sources of competitive advantage. For investors, understanding how AI translates into sustainable growth, operating leverage, and differentiated business models is increasingly critical to evaluating opportunities.
This conversation will go beyond the technology itself to address the questions that matter most:
Where is real value being created? What separates lasting opportunities from temporary hype? And how can founders leverage AI to build businesses positioned for long-term growth and VC-backable models?
Join moderator Dave Cotter and panelists Kevin Bolger and John McIntyre for a practical, candid discussion on the opportunities, trade-offs, and strategic decisions shaping the next generation of AI-enabled companies.
Event Details
Date: October 29
Time: 10:00 AM PST
Format: Virtual
Moderator: Dave Cotter
Panelists: John McIntyre, Kevin Bolger
Featured Moderator & Panelists
Dave Cotter — Moderator, Kelsor Ventures
Dave Cotter helps health-tech companies make their funding go further, from closing a raise to preparing for the next round. Dave is the founder of Kelsor Ventures, where he provides fractional CFO and COO services. As a former founder, ex-PwC professional, Dave brings financial and operational expertise to help companies navigate growth, manage resources strategically, and build toward their next milestone.
John McIntyre — Panelist, CEO of Caltana
John McIntyre is the CEO of Caltana, a serial entrepreneur, a Harvard Business School MBA. John is building the pioneering industry-recognized AI platform for commercial real estate operations. Backed by JLL Spark (the strategic arm of JLL) and REACH (National Association of Realtors), Techstars and more.
Kevin Bolger — Panelist, Founding Partner of Shannon Alliance
Kevin Bolger is a Founding Partner at Shannon Alliance, focused on AI and machine learning operational excellence. Passionate about biotechnology and edge AI applications, Kevin brings an interest in translating advanced AI and ML capabilities into practical, real-world applications that drive innovation, improve operational performance, and unlock new opportunities across industries.
Florian (Senior) Engel — Panelist, CEO of NLEVEL
Florian Engel is the CEO of NLEVEL, specializing in Layer 0 energy architecture, AI, and deep-tech due diligence. His work sits at the intersection of advanced technology and foundational infrastructure, with a focus on evaluating complex technical systems and the underlying architecture that enables next-generation AI and deep-tech innovation.
Hosted by Chimera Community, a network of 1,000+ founders, ecosystem partners, and service providers connecting entrepreneurs with the expertise and resources they need to grow.