You’re in marketing for one reason: Grow. Grow your company, reputation, customers, impact, profits. Grow yourself. This is a community that will help. It will stretch your mind, connect you to fascinating people, and provide some fun along the way. I am so glad you’re here. -Mark Schaefer
On every post I’ve written for at least two years, I’ve included a badge that states: “100% Human Content.” And this is, too (as you’ll see) but I used AI to compose most of it. I’d like to use this as a teachable moment on a smart way to use AI.
This post is about my annual Uprising Retreat. Nearly everyone there noted that this event is impossible to describe unless you’re there, but I’ll try. It’s a gathering of curious and brilliant people who openly share and teach one another, creating a bond that fosters career relevance. We also have a lot of fun in a breathtakingly beautiful place.
Now, during this event, I am psychologically and emotionally immersed. There is no way I can capture all the great highlights. This is where AI comes in.
Many of the attendees used the Plaud voice recorder to record and transcribe the talks. Dr. Matt Wilkinson uploaded these transcripts to Notebook LM, where we could all slice and dice the commentary. I used this to create a first draft of a highlight post and then used Claude to massage it a bit and put it in my voice.
So … what you are about to read is fully human content, parsed and assembled by AI.
The gift of uncertainty
Before each event, I send out a survey to let attendees prioritize the agenda. This year, one word kept popping up as they wrote about their careers: Uncertainty. So, I set the tone for the event with a brand new talk called “The Gift of Uncertainty.”
We are living in a “poly crisis.” Not just a hard moment. A genuinely disorienting one, where the norms and traditions and even laws that used to orient us feel like they’re shifting in real time. We are in a world of malignant uncertainty.
I opened the Uprising by saying this isn’t a flaw in the system — it’s our fuel, especially if you’re in marketing. I encouraged everyone to explore the “courage dividends” that come from overcoming fear and acting on opportunity, even when the outcome is uncertain.
We live in chaos. But that sets the stage for hope. And leaders who can genuinely dispense hope — not spin, not optimism theater, but real grounded possibility — are going to matter enormously in the years ahead.
The agentic economy is here, and most people aren’t ready
Dan Nestle, Dr. Matt Wilkinson, and Brian Piper built the technical foundation for the event with a live demonstration of what an AI-orchestrated workflow actually looks like end-to-end. They showed how they used Gemini, Claude, and other tools in parallel to explore every angle of a new product launch.
They laid out the technical reality clearly: We are moving from B2B and B2C toward an agent-to-agent economy. Your customers will soon have personal AI agents filtering what they see. You will have agents producing content. The question is whether there’s anything human left in the middle.
Brian introduced what he called the “human-in-the-loop sandwich” — and the image stuck with me. Your unique expertise and stories form the foundation. AI synthesizes and organizes. But human judgment sits at the top, as the final filter. Strip that out and you get what everyone is starting to call AI slop.
Dan made a point I think is genuinely underappreciated: keep your intellectual property separate from your tools. Your brand missions, your frameworks, your SOPs — those belong in a tool-agnostic library you can plug into whatever model is performing best this month. Claude, Gemini, ChatGPT. The models change. Your thinking shouldn’t have to change with them.
Matt demonstrated a system that turns static buyer personas into interactive AI simulations. Impressive. But he noted something that grounded the whole presentation: the real reason people show up to an event is still the humans in the room. No simulation replaces that.
The scariest AI risk isn’t replacement. It’s surrender.
Dr. Jasmine Gruia-Gray named something I think we all feel but don’t say out loud. She opened with a line that landed hard: “One day I couldn’t tell which parts of my thinking were mine.”
She cited a Wharton study where roughly 73% of participants followed faulty AI advice — not because they couldn’t tell it was wrong, but because the model was confident, and they stopped checking. That’s cognitive surrender. AI doesn’t replace your thinking. It keeps you from noticing you’ve already stopped thinking.
Her solution is a Socratic framework she calls BRACED — boundary testing, reversal from stakeholder, assumption surfacing, counter-hypothesis, disconfirming evidence, decision with tradeoffs. The specifics matter less than the principle. She ran it as a live game called Prompt Arena, where the goal wasn’t to get a better AI output. It was to build better thinking habits. That distinction is the whole ballgame right now.
The body knows things the brain ignores
Nicole Donnelly, the founder of Hello Moxie, gave what I thought was the most unexpected talk of the event. She’s been studying the intersection of trauma, workaholism, and leadership — and her argument is that most of our professional systems reward us for managing our bodies like machines. We optimize for output. We suppress the signals that slow us down. And we pay for it in creativity, in empathy, in the quality of our decisions.
We don’t need to move faster. We need to stop long enough to think. Embodiment is the last moat.
You can see her TEDx talk here.
Safe marketing compounds irrelevance
Jason Dressel, CEO of The History Factory, pushed back on what he called “confidence porn” — the performance of authority that substitutes for actual expertise. The market is correcting for that. People are hungry for real knowledge delivered through real stories.
His framework is simple: great stories need purposeful characters, a three-act structure built around conflict, and what he calls touchstones — the specific language and images that make a world feel real. Stories are 22 times more memorable than talking points. That’s not a preference. It’s neuroscience.
John Kowalski of BYK-Gardner Instruments said something I want to stitch on a pillow: safe marketing compounds irrelevance. He told the story of a company whose bear-resistant trash can failed spectacularly in a field test — and turned that failure into an unforgettable brand. The gap between what an industry expects and what an audience actually craves is where brand equity gets built. He called it the Awe Gap. I’m going to keep using that term.
Emotion is the experience. Full stop.
Stacy Sherman of CX Done Right made a case that I think is more important than ever. As AI ingests public sentiment at scale, every micro-moment in the customer journey builds or erodes a ledger. The failed QR code. The boring hold music. The email that was obviously a form letter. These small failures accumulate, and AI systems are now reading that accumulated sentiment to rank brands.
Dana Malstaff, CEO of BOSS MOM, added a critical nuance on vulnerability — the kind that actually builds connection versus the kind that undermines authority. Her distinction: share your scars, not your wounds. Processed experiences with a lesson attached. Not active pain that you’re still in the middle of. Amen to that!
Dana also led a session on the future of brand communities, driving home the point that the best communities emerge from a dissatisfaction with the status quo. What do you want to change in the world?
Trust is the only distribution strategy that scales
Sarah Stahl, VP Marketing for Lake.com, shared how a startup resort hit $2 million in revenue on a $30,000 budget by out-trusting rather than out-spending. The mechanism was micro-creators with real proximity to real audiences. Sixty-eight percent of consumers trust a creator over a brand. That number should reorganize your marketing budget.
Chad Parizman of Ader Communications entertained everyone with a brief analysis of predictive markets and the potential dangers of addictive betting markets.
His argument was that prediction markets — platforms where people bet on real-world outcomes rather than company stocks — represent an underutilized seam for brands. 8.5 million monthly users, 25 trades per day. The conversations already happening around these markets are data-rich, audience-specific, and almost entirely untouched by brand strategy. The brands that figure out how to own those conversations are sitting on something.
It was the right mix of mind-blowing information and entertainment to end the day.
The future of content marketing
What an honor it was to sit side by side with the legendary Joe Pulizzi and hold court on the future of content marketing. Over the years, Joe and I have not always agreed but we have always been friends. As always, this was a spicy, energetic, and insightful 90 minutes.
Joe and I talked about what he calls the Trust Portfolio — and I think it’s one of the most practical ideas to come out of the event. Don’t bet everything on a single brand voice. Build a diversified network of employee creators. Give them room to be specific, to be themselves, to be a little weird. The marketing team becomes a media operations hub. The employees become the signal that cuts through the synthetic noise.
Our main debate centered around the most likely role of humanity in an AI-dominant content world. Joe thinks the window is closing. I think human art will persist. We’ll have to meet again in a few years to see what happens.
The future of your brand
Sarah Neely of Signal Swell has presented several times over the years and always has a fresh and relevant message. This year, she updated her core word-of-mouth marketing wisdom with a spin for the AI Age. She introduced a new framework — the Five C’s of AI Discoverability.
- Clarity
- Conversation
- Current
- Credible
- Composition
Mary Lague of Pilot 44 ran a foresight exercise that’s worth sitting with. If AI agents are mediating $3-5 trillion in commerce by 2036, and culture has fragmented into hyper-niche communities, what signals should we be watching now?
She hosted an interactive exercise that let every attendee create a vision of their own brand emerging from a set of megatrends such as brand communities and virtual humans.
But here’s the best part
These highlights are only the tip of the iceberg. Most attendees will tell you that most of the learning came from questions and answers, small group discussions (led by Valentina Escobar-Gonzalez, Lauren Colbert, Alice Ferris, and Chelsea Rae Stuck), breakout sessions on branding and personal branding, and late-night conversations at the bar.
For example, here are some takeaways from several attendees:
“I learned to not just embrace uncertainty, but to be grounded in it.”
“The biggest shift wasn’t a tactic. It was realizing that staying still long enough to understand what’s happening is often more powerful than reacting quickly to what’s changing.”
“Growth starts to feel heavy when nothing is compounding. That was the moment I realized the issue isn’t effort, it’s what the effort is building toward.”
Sarah Stahl, Founder, Market Movers
“Community creates the space for people to feel safe enough to move toward the future.”
“What do we hold onto and what do we release — that is our wisdom.”
Brian W Piper, Founder of AIreFlow Solutions
Melanie Borden, Author, “Theatre of the Mind” · Founder, The Borden Group
Mike Carr, Cofounder of John13.org & Autism Labs
“When Mary Lague said 44% of Gen Z workers try to sabotage their company’s AI, it reordered my worldview. Leveraging AI is far more than mastering prompts and learning tools. It also involves helping people understand and work through massive change, many fear or don’t understand, so they seek to control it, apparently often to the detriment of their employer.”
“As Mark Schaefer said, leaders dispense hope. And when he exhorted us to create pockets of hope, order, and meaning, it landed as a clarion call to action for me and my business.”
Dan Christ, Owner and founder of Dan Christ Digital Services
“It’s possible not to be completely freaked out and overwhelmed about AI.”
Lisa Kohn, International Speaker, LisaKohn.com
“When you can’t tell if you’ve become part of the AI hive mind, you realize you’ve done it to yourself. Jasmine Gruia-Gray’s session on cognitive surrender was a moment that turned the conversation inward. While every other session was about forces changing the world around us and how to respond, she asked what we might be doing to our own thinking in the process.”
“Mark opened by making the case that uncertainty is the entry point for original thinking, and John Kowalski’s awe gap session reinforced it from a different angle. Safe marketing compounds irrelevance. The seam, the real opportunity, is in the unexpected.”
Elizabeth Humphries, Marketing Strategist, Market Your Marketing
“I was in awe of the people in the room at Uprising! Inspiring and engaging. It reminded me of the importance of presence and being fully present at an event like this will allow you to get the most out of your experience. If you’re distracted and disengaged, you could miss something that could change your life.”
Sid Meadows, President of The Collaborative Network and Host of The Trend Report Podcast
“The jaw-dropping moment for me was when I was encouraged to break through a self-limiting belief about what type of speaking engagements I could get paid for. For the first time in 25 years, I saw a path forward to market myself.”
Mike Garrison, founder of Values Based Mindset and author of Can I Borrow Your Car?
“Leaders dispense hope… giving your team, your customers, and your industry permission to believe something better is possible. When you stop selling features and start offering a vision worth following, you stop being a vendor and become the reason people show up.”
“The sheer volume of knowledge, expertise, and insight in this room was mind-blowing.”
John Kowalski, Disruptive Awe Architect, Disruptive Awe
“Our humanity is being stripped from us. Each talk pointed back to specific actions we can take to be more human, including choosing to be hopeful, more discerning, actively cultivating community by creating spaces where people feel valued, and reframing failure as experimentation. The more we lean into these things, the more we will become the trusted leaders and brands of the future.”
“Nanocommunities of 40 or fewer will be the future! This affirmed our company’s strategy. Scale is not always the answer.”
Nicole Donnelly, Founder, Hello Moxie
“Personal consequence is the real work. The breakout conversations are where ideas become valuable because they become personal. The unique element of The Uprising is that we get to intentionally take the time to unpack it and ask: What does it mean for me now?”
“Malignant Uncertainty” looms over livelihoods. The time needed (and spent) to process this feeling, with other smart folks, became the difference-maker.
“The Uprising had a contagion of bravery and a level of openness that elevated everyone.”
Lauren Colbert, Principal—Strategic Facilitator of Strategy, Innovation, & Collective Intelligence at Filament
“The fireside chat between Mark Schaefer and Joe Pulizzi reframed how I think about trust at scale. Mark mentioned that Cisco had trained more than 10,000 employees to speak on behalf of the brand — certified, equipped, and amplified. Joe called this building a Trust Portfolio. Distributed authorship. Distributed trust. Distributed reach. That changes the marketing job.”
Matt Wilkinson, CEO, Strivenn
“In an era of automation, bots, and synthetic content, care becomes premium. People want guidance, reassurance, belonging, support, and human attention. This made me rethink how I show up online and how I position my own services—not just as a consultant, but as someone who helps people navigate change.”
Valentina Escobar-Gonzalez, MBA, Bilingual Marketing Consultant and Founder of Beyond Engagement
“I’m energized by Mark’s idea of ‘uncertainty as fuel.’ It’s a powerful reframe in a time of so much chaos. ‘Negative capability’ is another reframing that speaks to intentionally and patiently pausing to connect new dots. I learned so much over the two days, and I know that I will continue to learn from this circle of smart humans.”
Sarah Neely, Vice President of Strategy at Fuzz and Founder of SignalSwell
“Each courageous moment rewires you to believe in yourself. This is the courage dividend.”
“I appreciated Sarah Neely’s new perspective on the future of discoverability — the S.H.A.R.E. framework (surprising, helpful, authentic, relevant, experiences).”
Jasmine Gruia-Gray, Managing Partner at Strivenn and co-host of A Splice of Life Science Marketing podcast, Product Marketing Tips newsletter
“Courageous actions rewire who you believe yourself to be.’ —Mark Schaefer. I found this particularly pertinent because every time I have taken a leap professionally or personally, it has paid off, and helped me douse some of that imposter syndrome or lack of confidence you get when you’re in a room that you’re not quite comfortable in.”
Stacey Miller, Vice President, Communications at Auto Care Association
“I need more community in my life! (inspiration, empowerment, safety).”
“Trust = safety. Nurture messaging creates belonging.”
Knox Keith, Author of Validated
“I’m inspired by how domain experts forge and build AI solutions. Just as my agency is building AI to address concerns related to accuracy and contextualization, I was so impressed by Dr. Jasmine Gruia-Gray’s work focused on critical thinking and cognitive decline. Her Socratic method-based BRACED framework was excellent.”
“Joe and Mark’s discussion has me completely re-imagining our leaders and employees as characters of our story, and how we tell that story through both company-owned and employee-owned platforms. This will likely be the biggest actionable takeaway in my strategic and tactical shift.”
Jason Dressel, CEO, History Factory
“We shouldn’t treat AI LIKE an audience. AI IS an audience—multiple audiences, in fact.”
“Negative Capability is the skill we need to cope with chaos. Marinate in an issue before acting under pressure to respond, and that’s how insights will be revealed.”
Dan Nestle, Founder and CPIO of Lilypath
“Within the first 15 minutes, I had my first ah-ha moment, when Mark said: ‘Every time I feel afraid, I do it!’ I need a poster of this in my office.”
“We are in the eye of the AI storm, but it also presents so many opportunities. I realized that I don’t have all the answers about how businesses will assimilate or adopt AI platforms, but I do know that the most powerful force in business is still human connection. Spending three days with 39 of the most knowledgeable, forward-thinking leaders in AI and new technologies left me feeling inspired and full of hope. The Uprising was an Executive Education course on steroids!”
Anne Deeter Gallaher, Owner/CEO of Deeter Gallaher Group LLC
“In a world that constantly competes for our attention, we need to ‘control the inputs.’ In other words, be deliberate about how much news we consume, which social media we engage with, whose opinions we give weight to, and how much access the outside world gets to our inner peace. Those inputs shape our focus, our fear, our energy, and ultimately, how we show up at work and in life.”
“We’re living in a time of ‘malignant uncertainty,’ where change isn’t only constant, it’s harder to predict. Companies need to let go of overly rigid plans and pay closer attention to what customers and employees are thinking, feeling, and doing in real time. The brands that earn trust will be the ones that build emotional connection when everything else feels uncertain.”
Stacy Sherman, International Keynote Speaker, Influencer & Podcaster: DoingCXRight.com
“AI is evolving and changing how we operate at a personal and work level faster than ever before. There is opportunity in seeing this ‘seam.’ Uncertainty makes room for me for creativity, growth, and progress.”
Debra Feresten, Debra Feresten Homes
I used to believe more content would grow my business, but now I see that trust is the real currency—and content is just the vehicle to earn it. That changes everything: from chasing reach to building a small, intentional audience that actually cares.”
“My AHA moment was realizing we’re not heading toward a world with better ads—we’re heading toward a world without them. When there’s no ‘skip button,’ only brands that create trust, community, and meaning will survive.”
Yevette Lynn, Kingsport Headshot Photographer and Studio Owner, The Journal
“AI tools become personal. They are like the hammer that a carpenter uses every day. They form to his hand and are customized to his needs. There is beauty in the wear of such tools, but if you were to pick one up, it feels foreign. To use them properly, one must interact with these tools and shape them to one’s personal needs.”
“Being raw in our content gives our community permission to share. But that sharing should come from scars, not wounds.”
“The tension between the obligation to react to the world and the value of marinating in uncertainty is the obligation of leadership.”
Atom Freeman, Founder of Prana DM, Host of Comic Industry Insiders podcast
“Building a personal brand is not a project, it’s a LIFESTYLE.”
“The customer journey is the cumulative effect of every interaction, good or bad.” Every micro moment shapes perception, and people are constantly evaluating, even when you are not thinking about it. What they remember is not necessarily the process, it is how it made them feel. “Emotion IS the experience”, and that is ultimately what defines your brand.
Your most powerful, underutilized influencer channel is already on payroll. Employees are a built-in network of credible, motivated nano-influencers, but only if you replace control with trust and give them a clear, supported way to share. If your own people are not advocating for your brand, why would someone else?
Chelsea Rae Stuck, CEO Craeve, and Host of the Curiously Stuck Podcast
And … back to me.
We can’t stay relevant on our own. Everybody who attended The Uprising has a new set of tools and a professional network to help them navigate the future.
The 2026 Uprising was a call to stop trying to be “safe” and instead build a future where our humanity is our most discoverable and durable asset. I hope you will join us May 04-07, 2027. Registration is open.
Some photographs provided by Yevette Lynn Photography
Need a keynote speaker? Mark Schaefer is the most trusted voice in marketing. Your conference guests will buzz about his insights long after your event! Mark is the author of some of the world’s bestselling marketing books, a college educator, and an advisor to many of the world’s largest brands. Contact Mark to have him bring a fun, meaningful, and memorable presentation to your company event or conference.
