I have a confession to make.
I just hosted the 2025 edition of The Uprising, my annual marketing retreat. During this event, I became so intensely focused on the content and the conversations that I forgot to take notes. Happens every year. So, it’s quite a struggle writing a blog post without notes!
This is a great opportunity to ask for an AI assist, and the combination of resources that went into this write-up is impressive.
First, Daniel Nestle and Brian Piper used a recording technology called Plaude to instantly transcribe the live sessions. Brian then took these transcripts and the session slides to build a Custom GPT based on the event. I could then query the AI to help me fill in the blanks and present a representative sample of what happened at this electric event!
First, let’s set the stage …
What is an Uprising?
I don’t like big marketing events. They’re crowded, overwhelming, and generally boring. They are iterative — how to make slight improvements on our Facebook ads or improve our SEO — while the field of marketing is going through a cataclysmic transition right in front of our eyes.
The Uprising solves four problems in marketing events today:
- It’s limited to 30 people. You have real conversations and make lifetime friends.
- The focus is the future. What is coming next, and how do we get ready?
- It’s safe and honest. My proudest moment was when people said, “I want to push back on that.” When do you see THAT happen at a marketing event?
- It’s co-created. Everyone has an opportunity to participate at their comfort level. So we use the brains in the room! And … it’s a lot of fun! It is a retreat, after all.
Almost everyone who attends will tell you the same thing: It’s difficult to describe. This combination of a wooded lodge, generous people, great food, big brains, and relaxing fun ignites people and takes them to a new level of competence and confidence.
The Uprising has always been about digging beneath the surface, about meaningful connections and bold ideas. But this year, it felt different. More urgent. More human. More audacious. It was the best one ever.
By the way, The Uprising was inspired by my call-to-action in Marketing Rebellion to bring people together. You can’t have a rebellion without an uprising!
Now … what happened this year? Here are the voices, the visions, and the visceral truths that made this gathering unforgettable.
How AI is changing our customers
I kicked things off with a two-part presentation: 1) data on how AI is changing humanity (our customers!), and 2) how humans fit in this new AI-dominant ecosystem. It became a community-driven revelation of what it means to be a marketer in the age of synthetic intelligence.
This was a rallying cry. As AI seeps into every pore of our professional lives, I challenged the group to zoom out—to don’t obsess over AI’s creepy parts. Look at how we must evolve as marketers and serve these changing customers.
Drawing on my research for Belonging to the Brand and the newer Audacious, I painted a stark picture of the near future. We are stepping into a world where content is infinite, synthetic, and indistinguishable. AI won’t just change how we work. It will change who our customers are. Their expectations. Their behaviors. Even their identities, which I covered in this blog post.
Throughout the event, we discussed eight seismic shifts AI will bring to humanity: cognitive decline, emotional intelligence, a search for truth, moral judgment, human agency, creativity, meaning, and critical thinking.
And yet, there is hope. If we understand what makes us irreplaceable — our ability to form community, to inspire, to provide comfort, safety, and hope — we can thrive.
We live in a world where people may not care if the content is human or AI. My urgent plea was to MAKE THEM CARE. That phrase echoed through every session, becoming the unofficial motto of the event. It’s not about resisting the machines and more about embracing what is going to keep us relevant, including the personal brand, brand communities, and content that transcends this pandemic of dull.
Decoding Authenticity by Generations
Dr. Mara Singer revealed some new, original research on how emotional needs shift by generation. With her six pillars of authenticity—accuracy, connectedness, originality, legitimacy, expertise, and integrity—she deconstructed the most overused word in marketing.
She didn’t just talk about the importance of authenticity; she showed us how different generations construct it. For Gen Z, legitimacy and consistency matter more than you’d expect. For Boomers, expertise and accuracy still rule.
In a time when AI can mimic tone, replicate imagery, and fake just about everything, authenticity becomes your only real differentiator. Mara’s message was clear: authenticity is not a style. It’s a strategy.
One jaw-dropping reality is how children as young as six or seven are becoming TikTok influencers as they swarm Sephora stores to try skin care products. Another counter-intuitive fact is that older people place little value on originality in brands and marketing.
The Joy of Prompt Engineering
Andy Crestodina, Lindsey Bowshier and Shannon Yost at The Uprising
The brilliant Andy Crestodina of Orbit Media delivered an exquisitely practical talk. His rapid-fire breakdown of the seven levels of AI proficiency was like a map through the AI jungle. Starting from basic prompt writing to full-on multi-step automations, Andy gave us the tools to turn AI into a creative ally.
One of his themes: “Every prompt is a draft. Iterate. Improve. Reuse.”
He reminded us that AI doesn’t diminish creativity—it redefines it. And with the right mindset, we can all become architects of reusable, scalable, and deeply impactful content systems. Andy’s generosity in sharing his prompt playbook turned his session into an instant classic.
Navigating the Infinite Content Abyss
Brian Piper, with a futurist’s eye and a practitioner’s rigor, pulled back the curtain on what’s coming next in content.
He warned that we’ve moved from a world of content scarcity to Content Shock. And AI is making the goal of visibility even more difficult. In this new landscape, human-made content may soon be just 10% of what exists online.
His advice? Build communities. Focus on content that builds trust and emotional connection. Optimize not just for search engines, but for AI discovery systems, voice platforms, and emerging interfaces.
And most critically, become known. Not viral. Not famous. Known. Because in the chaos of AI, trust will be our last currency.
The AI-influenced customer journey
Dr. Matt Wilkinson brought PhD-level clarity to the AI conversation. Once a skeptic, now a strategic believer, he emphasized that AI is not a savior, but the powerful new influence on the customer’s decision process.
What stood out most was his call to reimagine the customer journey. With 80% of it happening before a human contact, AI is already deciding which brands get seen, which stories get heard.
His warning? Don’t get stuck in the past. The “how-to” blog post era is dying. We need to evolve into trusted guides, thought leaders, and distinctive voices that resonate even when we’re not in the room.
The Invisible Labor of Great Content
Ann Handley’s fireside chat with me was a masterclass in emotional resonance. She reminded us that meaningful work requires emotional fortitude. Every sentence you sweat over, every nuance you consider—it all matters.
She spoke of the importance of creating a body of work that endures. Of using ephemeral platforms to build something lasting. And of showing up with your whole heart, not just your content calendar.
Her insight? The journey is the outcome. And in a world chasing outcomes, that’s a radically beautiful stance. Ann and I talked about Phronesis — the ancient Greek concept of practical wisdom gained through hard work. In a world optimized for speed, maybe our greatest rebellion is thoughtfulness.
Ann gave us a glimpse of her upcoming book and captivated everyone wither her bold and honest answers to questions about her career and writing process.
The Future of Social Media
Kami Huyse took us on a journey from 2005 blogging panels to today’s fractured, frenetic social landscape. Through it all, one truth remains: community is the constant.
Her viral quote summed it up: “The first rule of social media is everything changes. What doesn’t change is the community’s desire to connect.”
Kami reminded us to follow the people, not the platforms. And more importantly, to co-create with them. Whether it’s a tweet, a TikTok, or a town hall, if it doesn’t resonate with your community, it’s noise.
Orchestrating Word-of-Mouth in a Scalable World
Valentina Escobar-Gonzalez, Chelsea Stuck, Sarah Neely, and Mark Schaefer at The Uprising
Sarah Neely, at her fourth Uprising, delivered a lesson in modern magic: scaling the unscalable. Word-of-mouth may feel spontaneous, but Sarah showed us it can be engineered.
She started with a deeply personal story of hauling plywood at muddy event sites and rose to architect campaigns that helped brands like Red Bull infiltrate Major League Baseball. Her framework? Activities. Goals. Targets. Story.
In that order. If you want people to talk about your brand, you must understand what they do before they buy and then intersect with those behaviors. Her message: Viral isn’t magic. It’s math. It’s emotion. And it’s a story worth sharing.
A Modern View of Metrics
Kyle Akerman led a session on modern marketing metrics. He identified common measurement problems all marketers face, including having too much data, having data in too many places, and focusing on vanity metrics.
Marketers spend very little time on measurement (one hour or week, or sometimes just one hour a month). So the challenge is, how do we make the most of that time?
Kyle said we should create (and document) a simple measurement plan. It should include the questions you want to answer, the data you need to answer the questions, and the actions you will take based on the data. A good plan also includes the KPIs (with time-based targets), and key user segments (because aggregated data hides the important insights).
Most companies can effectively measure marketing performance using Google’s “Holy Trinity” of free tools: Google Analytics (where data is stored), Google Tag Manager (the measurement implementation), and Looker Studio (visualization tool). Many marketers also benefit from the free heat mapping and session recordings provided by Microsoft Clarity.
A powerful reframe for measurement – it’s how we “listen” to the conversations happening on our websites.
The Audacious Workshop: Wine, Grit, and Bold Storytelling
Alice Ferris leadning a brand activation workshop at The Uprising
The heartbeat of this year’s Uprising was the Audacious Workshop. With a real-world brand (Nicole Hayden’s Indiana Daylily Estates Winery) and a room full of brilliant minds, we put the theories of my book Audacious to the test. With the help of a new Audacious workbook (available here), we twisted her startup brand by having three teams brainstorm ways to disrupt the story, the media, and the storyteller.
From “our wine slept with your beer” to corn mazes ending in wine tastings, this was a ton of fun that resulted in a real marketing framework!
The Human Renaissance
As we wrapped Uprising 2025, one truth emerged above all: we are not just marketers. We are artists, connectors, philosophers, and warriors of relevance in turbulent times.
People described the event as unforgettable, magical, and inspirational. But most of all, I think every person walked away with a new sense that the human connection we all experienced makes all the difference. Even when AI dominates the marketing scene, we can still make them care.
I hope you will join me at the next Uprising event, which will be April 21-24, 2026. Space is extremely limited and registration is open here.
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