Michael Kaleikini
About
Michael Kaleikini is a dynamic force in modern marketing, known for his ability to bring clarity to chaos and drive measurable growth through strategic thinking, systems development, and authentic connection. With over 20 years of experience across digital marketing, sales leadership, and experiential brand strategy, Michael’s work is where vision meets execution.
As a Fractional CMO and the founder of Coffee With Mike™, Michael advises founders, CEOs, and leadership teams on how to align marketing with business goals, optimize performance across channels, and build brands that last. Whether he’s guiding a SaaS startup toward scale, reengineering a local business’ customer journey, or helping a creative agency fine-tune their revenue operations, Michael brings a proven, repeatable framework for success rooted in clarity, empathy, and systems thinking.
Michael currently serves as Chief Operating Officer for Activate Entertainment, LLC, a nationally recognized experiential marketing firm where he has led activations at San Diego Comic-Con, New York Comic Con, CES, and other high-traffic cultural events. His work spans everything from brand partnerships and consumer engagement to immersive booth design, always with a focus on lead generation, conversion, and emotional resonance.
In addition, Michael is CMOx for Sierra Solutions, LLC, a full-service marketing, advertising, and PR agency. At Sierra Solutions, he helps businesses in the financial services, legal, and professional services industries build authority, increase exposure, and generate leads through proven systems and strategies.
A graduate of the Sonoran Desert Institute, Michael earned his degree with honors in Firearms Technology and brings a surprising duality of precision craftsmanship and creative marketing to his worldview. He’s passionate about elevating people and ideas—and he does it with a deep love for coffee, strategic storytelling, and building scalable systems that free entrepreneurs to lead more impactful lives.
Michael is also the host of the Java Chat Podcast, a relaxed-yet-informative show where entrepreneurs, creatives, and change-makers share their journeys, wins, and wisdom over a metaphorical cup of coffee. Whether he’s behind the mic or on stage, Michael brings a grounded yet energizing presence to every conversation.
Podcast/Show
Java Chat Podcast
Startups, coffee, whiskey, business, health & wellness, Crypto, AI...they're all relative.
Inspiration over coffee is a must!
Get your CAFFEINE ON!
CMOx
Sierra Solutions LLC
Sierra Solutions, LLC is a full service Marketing, Advertising and PR agency. We use systems and strategies that help build authority, increase exposure and generate leads for businesses in the financial services, legal, and professional services industries.
Activate Entertainment
Nationally recognized experiential marketing firm where he has led activations at San Diego Comic-Con, New York Comic Con, CES, and other high-traffic cultural events.
Speaking Topics
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Modern Marketing Strategy & Systems for Sustainable Growth
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How to Market Like a CMO (Even If You Don’t Have One)
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Building a Business That Brews Loyalty Like a Good Cup of Coffee
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Scaling Brand Presence Through Experiential Marketing
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Leadership Lessons from the Frontlines of Strategy & Sales
In The Media
Questions for the Media
- What do most businesses get wrong about marketing strategy—and how do you help them find clarity over chaos?
- How do you balance creativity with data when building a strategy that actually drives growth?
- What role does storytelling play in brand strategy today?
- How do you approach scaling a business with limited resources or budget?
- What’s one marketing system or principle you wish every business owner understood?
- Your brand 'Coffee with Mike' and your podcast 'Java Chat' both tie coffee to conversation—why coffee, and how does it inspire your approach to business?
- What parallels do you see between brewing a great cup of coffee and brewing a winning marketing strategy?
- How does 'Java Chat' let you explore both business and personal growth topics in ways that traditional interviews don’t?
- If you could share one cup of coffee with any business leader, past or present, who would it be and why?
- What lessons from firearms training carry over into your approach to marketing and business strategy?
- How do you balance the seriousness of teaching people how to protect themselves with making it approachable?
- What does success look like for you beyond business metrics?
Investment Verticals
Investors Seeking Marketing Expertise for Portfolio Companies
Michael partners with investors and private equity firms to unlock growth potential across their portfolio companies. His expertise helps businesses:
Align marketing with business objectives for sustainable ROI
Design scalable marketing systems that replace ad-hoc efforts
Navigate brand repositioning, market entry, or go-to-market pivots
Optimize revenue operations to increase enterprise value
With over 20 years driving real-world results, Michael brings strategic insights that bridge vision and execution—helping investors maximize the performance and valuation of their investments.
Startups Looking for Fractional Leadership to Accelerate Scale
Early- and growth-stage startups often lack the in-house expertise to transform strong products into scalable brands. As a Fractional CMO, Michael helps startups:
Develop marketing strategies that prioritize impact over noise
Build foundational systems for lead generation, nurturing, and conversion
Avoid costly missteps in messaging, positioning, and market fit
Scale operations efficiently while preserving brand authenticity
From SaaS to experiential brands, Michael’s fractional leadership provides startups with senior-level guidance without the overhead of a full-time executive, ensuring smarter scaling and market success.
Businesses Exploring Joint Ventures in Experiential Marketing or Digital Strategy
Michael’s extensive background in experiential marketing and digital strategy makes him a valuable partner for businesses exploring joint ventures. He collaborates with organizations to:
Create high-impact brand experiences that drive engagement and loyalty
Integrate digital strategy into live events for measurable results
Develop unique offerings that blend creative storytelling with systems thinking
Co-create products, services, or platforms that capitalize on emerging market trends
Whether it’s launching an immersive activation, co-developing a new platform, or partnering on innovative digital experiences, Michael brings both creativity and operational rigor to joint venture opportunities.