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#162 Why Human Creativity Still Wins in an AI-Driven World with Catherine Holt and Dr. Michael Orkin

Today we’re speaking with Dr. Michael Orkin and Cat Holt. Dr. Orkin is a professor, researcher, and author of The Story of Chance – Beyond the Margin of Error, bringing expertise in mathematics and statistics to help make sense of complex data. Cat Holt is a marketing strategist and entrepreneur who has shaped iconic campaigns like Progressive Insurance’s Dr. Rick and now leads Coologee, Inc., a one-team marketing model that drives measurable business impact. She also co-founded Lion + Owl, a kids’ apparel brand that combines innovative design with a mission to promote creativity and inclusion. In this episode, we explore how data, strategy, and storytelling come together to create smarter decisions and stronger brands.
“Don’t forget your humanity when you’re having a conversation… treat it with respect, because that’s what it deserves.” — Catherine Holt
“If I could characterize my book in one or two words, it’s a book about randomness in everyday life.” — Dr. Orkin

About the Episode

Welcome to another deep dive into the world of marketing, strategy, and AI innovation! Today we’re exploring the engaging conversations from Episode 162 of the NTM Growth Marketing Podcast, hosted by Andrew. We had the pleasure of hosting Catherine Holt, founder of Coologee and brand strategy expert, followed by Dr. Michael Orkin, statistician, author, and educator. Together, their stories shape a broad, lively, and absolutely relevant snapshot of what it means to build brands, adapt to new technologies, and navigate an increasingly AI-driven world.

If you’re a marketer, entrepreneur, educator, or just curious about how chance, randomness, and technology impact your life and work, this post is for you. Grab a coffee, settle in, and let’s break it all down — from the human side of brand building to the creative chaos of AI and statistical thinking.

Who is Catherine Holt?

Catherine Holt is a brand strategist, veteran marketer, and founder of Coologee. With over 25 years in the industry, Catherine’s journey is a patchwork of agency life, in-house transformation at giant corporations like Progressive Insurance, and entrepreneurial ventures. Driven by change, curiosity, and creativity, Catherine refers to herself as a “beast horse of a different color” — an apt description for someone who never stops asking, “what’s next?”

  • Career Highlights:
    • 25+ years across branding and digital agencies
    • Led marketing strategy for Progressive Insurance (yes, that Progressive)
    • Founded Coologee, a brand-first marketing consultancy
    • Embraces fast change, experimentation, and a “free spirit” attitude

“I like change and I like it to happen fast… I’m really well suited for coming in and helping organizations do something they’ve never done before.”

If you’ve ever felt boxed in by routine or corporate inertia, Catherine’s story is a breath of fresh air. Her drive is all about moving quickly, experimenting boldly, and always putting humanity back into the business equation.

Coologee’s Mission: Making Brand Matter

At Coologee, Catherine and her team believe brand is misunderstood. It’s not just a logo or campaign — it’s a massive business asset that’s often managed with less strategy than it deserves.

What sets Coologee apart:

  • Treating brand as the core of business strategy
  • Services spanning reputation management, rebranding, positioning, campaign launches, reorganizations, and fractional CMO
  • Bold stance: Brand IS business

Coologee works with clients to “prove that brand is business and to show in what way and how.” Their methodology: start from core values, human touch, and authentic stories. From there, build everything else — campaigns, digital platforms, and growth strategies.

Agency vs. Corporate: The Speed of Change

Transitioning from agency to in-house at Progressive was a pivotal moment for Catherine. She led a wave of change inside a Fortune 500 environment. The biggest lesson? Corporate structure can slow the pace of innovation:

  • Agencies (or your own consultancy) = fast adaptation
  • Corporations = slower cycles, longer time to integrate ideas

Catherine reflects on her time at Progressive:

“I had accomplished a lot of change, but… the idea of just continuing to do the same thing felt like I was missing something.”

That hunger for novelty led Catherine back to entrepreneurship, where she could pilot new strategies quickly — and help clients leapfrog the competition without slogging through unnecessary bureaucracy.

Marketing Strategies for 2025: Humanizing Insurance

Insurance marketing has a reputation problem. Many people picture the “mobster guy” pitching fear — the classic, “You never know what could happen…” To stand out, Catherine’s client needed a total reinvention.

Case Study: Can Do Insurance & Can Do Financial

  • Legacy agency sold their name, lost brand equity
  • Wanted independence from major financial partners
  • Coologee named them “Can Do Insurance/Financial” — channeling their optimistic, proactive mindset

With Catherine’s help, they designed a fully integrated lead aggregator platform that reduces lead cost, prioritizes human connection, and uses digital tools the smart way.

Industry challenge:

  • Big insurance firms pay upwards of $2,000 per lead
  • Small, independent agents are priced out
  • Old aggregator systems don’t work — needed something radically new

Coologee’s solution:

  1. Built a holistic platform: digital, campaign, brand positioning, measurement
  2. Put brand story and humanity FIRST
  3. Lowered lead cost so small agents can compete

“By putting the brand first, telling a story that feels more human, we’re able to make a difference. We’re breaking through and we’re getting leads.”

Catherine’s approach flips the script — proving you don’t have to be the biggest player to win. The key? Make it easy, make it real, and actually care about your customer’s story.

The Power of Simplicity and Emotional Connection

How do you sell complex products like insurance (or finance, tech, or healthcare) when most people feel out of their depth?

Common customer challenges:

  • Insurance jargon is intimidating
  • Customers fear they’ll get tricked or “played by the system”
  • Feels like companies aren’t on your side

Catherine stresses a radically simple approach:

  • Strip away complicated language
  • Start with people’s emotions and needs
  • Build bridges — guide customers, don’t overwhelm them

Quick List: Human-Centered Marketing Channels

  • In-person meetings
  • Digital touchpoints (text, apps, articles)
  • Useful phone outreach
  • Respectful follow-up, not pushy sales tactics

“Don’t forget your humanity when you’re having a conversation with a prospect or a customer and treat it with respect, because that’s what it deserves.”

Forget aggressive tactics; real marketing builds trust, clarity, and long-run relationships.

AI and the Modern Marketer: Opportunity & Oversight

Catherine is refreshingly candid about her experience with ADHD:

“ADHD loves AI… I feel like we were uniquely created for this crazy world that we’re navigating.”

AI has become a power tool for marketers willing to experiment. It lets you:

  • Speed up ideation and creation
  • Perform rapid research and analysis
  • Develop new tools (like policy advocacy products)

But — as Catherine highlights — it’s not all magic. Human oversight is critical. You need to:

  • Train AI systems to your standards
  • Maintain rigorous quality control
  • Never let tech sideline your own strategy

“AI can help us get to a destination faster… but it’s not without some kind of oversight.”

Coologee’s AI Innovations

  • Developed a policy advocacy product for a major PNC (Property & Casualty) organization
  • Used AI to safeguard knowledge, protect competitive advantages, and keep human experts central

A major takeaway: AI disrupts knowledge-driven businesses fastest. The organizations that thrive will combine digital speed with human accountability, not replace real people with machines.

Crossing the Chasm: Bringing Teams Along for the Ride

It’s easy to geek out on AI if you’re an innovator — but not everyone is on board. Catherine references Geoffrey Moore’s classic framework, “Crossing the Chasm,” to explain adoption waves:

  • Innovators: Love playing with new tech
  • Early Adopters: Willing to try, but need guidance
  • Early Majority/Late Majority: Need clear value, workflow integration, and support

“The things I love about AI are probably still scary for a lot of people. So we’re applying change management, psychology, and training to make it accessible.”

Coologee now focuses on change management — designing products and training environments that help users cross the adoption gap. True organizational change comes when people stop dabbling and start using AI to shift real workflows.

AI wins when it’s not just cool — but mandatory and deeply embedded in your processes.

Fun Fact

Second and third movers—not the first—often become market leaders in new tech. Steady, thoughtful implementation beats rushing in and burning out.

AI, Remote Work, and Mentoring the Next Generation

The podcast dives into a tricky double whammy: remote work and AI adoption.

  • Remote work = less face-to-face mentorship, casual learning (“watching you walk the hallways or the casual coffee”)
  • AI = automates junior roles, the ones where newbies traditionally learn foundational skills

Catherine urges companies to actively plan how to nurture young talent:

  • Create new methods for mentorship (virtual shadowing, intentional coaching)
  • Protect experiential knowledge even as digital tools transform workflows

“With AI adoption, it’s going to put the onus on companies to bring the next generation along… So that’s going to be a really interesting management challenge.”

This is a human problem, not just a tech one. You can automate tasks — but you can’t automate wisdom.

Dr. Michael Orkin: The Game of Chance, Statistics, and Storytelling

Catherine’s segment transitions into the second guest, Dr. Michael Orkin — a lively statistician, educator, and author. If you ever doubted the power of randomness in everyday life, Dr. Orkin’s story will change your mind.

Dr. Orkin’s backgrounds:

  • Consults for the gaming industry (defining games of skill vs. games of chance)
  • Teaches statistics at Berkeley City College
  • Publishes on Amazon, blogs on Substack (“The Neutral Zone”)

Life isn’t just about data — it’s about finding stories in the numbers.

From Math Classrooms to Substack: Building a Community

Dr. Orkin’s move to Substack was inspired by simplicity and curiosity. Substack is now one of the web’s hubs for tech-forward, early adopter audiences — mirroring the podcast’s own vibe.

He shares insights and fun facts about probability:

  • Do vaccines cause autism? (Nope, but here’s the data.)
  • What are the odds of winning Mega Millions?
  • Was Humpty Dumpty accident prone? (Yes! Or maybe not…)

“If I could characterize my book in one or two words, it’s a book about randomness in everyday life.”

Statistical ideas, told without heavy math, are suddenly inviting for regular readers.

Promoting Books in the Modern Age

Book marketing looks nothing like it did 20 years ago. Forget expensive ads in the New York Times — today’s authors are building presence online:

Dr. Orkin’s toolkit:

  • Podcast guest spots
  • Personal website
  • Substack articles
  • LinkedIn networking

“I’m thinking about trying to get a bigger publisher… But right now I get to do my own types of marketing.”

Self-publishing is empowering, but it also means becoming your own marketing department. It’s a high-energy, DIY world — and tech tools make it possible. Even the book itself started as a textbook and morphed into a regular-people-readable guide to randomness.

Cartoons and Creativity: Using AI to Illustrate Ideas

Dr. Orkin admits he’s “a terrible artist” — but that hasn’t stopped him from illustrating cartoons for his Substack. The secret? AI drawing tools (via ChatGPT 5.0 and prompt engineering).

Step-by-step, he trades text prompts with AI to create unique cartoons that breathe life into his posts. No art degree required.

Why This Matters

AI unlocks creativity for non-artists.

  • More expressive content
  • Opens new channels for engagement
  • Personalized illustrations, faster and cheaper

“I asked [AI] to do a drawing, and it was amazing. It came up with this great cartoon… So now it’s opened this door of creativity for me.”

Readers love visuals. It’s no longer a barrier if you can’t sketch — the prompt is your brush.

AI in Education: Navigating the New Normal

Tech is transforming classrooms and test-taking equally:

  • Students use AI tools to take online tests, sometimes without the teacher’s knowledge
  • Some educators fight this; others (like Dr. Orkin) see it as an evolution

Dr. Orkin’s take?

  • It’s like calculators and computers before: inevitable and useful
  • Tests should be hard for AI, but students will use them in life after graduation
  • The real solution is teaching prompt engineering and critical thinking, not banning progress

“If they learn how to use AI, why not learn now? Nothing you can do to stop them.”

Real-world skills are about knowing the right questions to ask, not just memorizing answers.

Final Thoughts: Finding the Human Touch in a Digital World

Despite all the noise about AI, productivity, and online expansion, both guests circle back to human connection:

  • Catherine: “We have to remember we’re still humans at the end of the day craving human connection.”
  • Dr. Orkin: Draws on spirited campus debates, reminds us that face-to-face learning (even if occasional) drives lasting insights.

The challenge — and opportunity — for marketers, educators, and innovators is keeping human connection at the center of digital transformation. Smart tech should amplify our curiosity, empathy, and creativity, not erase them.

More Episodes

The School for Humanity Archive

Explore our archive of NTM’s original podcast, The School for Humanity, created to discuss the greatest challenges humanity faces and help promote those who are helping to find solutions. 

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