A Year

In Discourse

Getting Comfortable with Uncertainty

Editor’s Note: We provoked our co-founder to get introspective about 2024. Unsurprisingly, he turned it back to the discourse. We think it’s a good reflection of the sentiments we keep hearing in our events.

It’s hard for me to fully take stock of the year we’ve just had. You probably feel the same. For me, 2024 was about being in a constant state of interrogation.

Together with my team and with Matt Chmiel at my side, I’ve hosted summits for Fortune 100 brands, countless group chats, in-person roundtable discussions, podcast conversations and I’ve personally interviewed hundreds of business executives, startup entrepreneurs, technology experts and investors. I’ve listened, transcribed, distilled and synthesized. We’ve published multiple reports and over 100 articles.

During all of this I have attempted to embody the values we established when we first started ON_Discourse: Provoke, Listen, and Change. It’s not always easy. Group think is the antithesis of these values. People are so sure of themselves. They are also mostly wrong. We all are. Especially about the future, and almost certainly when it comes to AI.

What I have learned—and what I am certain of, and what I believe we must carry forward into 2025—is this: the ability to provoke new ways of thinking and adapt to ambiguity is no longer optional. It is the foundation of modern leadership.

Toby Daniels

Toby Daniels

Founder, ON_Discourse

AI: The Mirror We Didn’t Expect

When we asked our members earlier in the year if they would implant a neurochip to eliminate mistakes, the responses revealed far more about humanity than technology. One CEO’s words resonated with me so much: “What if our mistakes are what make us human?"

Throughout 2024, AI forced us to question everything—creativity, empathy, work itself. SaaS companies watched traditional models erode as AI introduced per-seat chaos. Meanwhile, leaders marveled at AI tools that seemed to wield emotional intelligence, leaving us both amazed and unsettled.

One member shared a provocation I can’t shake: “AI can make us more emotionally intelligent—if we allow it.” Yet this year made me less certain than ever. Should we let AI shape our humanity, or must we shape it first?

Spatial Computing: The Future or Another Hype Cycle?

When my cofounder Dan Gardner shared the provocation, “Spatial is not the new smartphone; it’s the next internet,” during a summit we held for a Fortune 100 brand, it sparked such a visceral reaction in people, it was fascinating. During the course of the summit we debated whether spatial computing’s promise was transformative or just pattern-matching old narratives onto new tech. Remember, at the start of the year, we wrote about Vision Pro and by November, Apple had announced it was winding down manufacturing of the device. But Meta also announced Orion, its mixed-reality glasses, which was almost universally well received. In one year we’ve gone from thinking we understood the future, to having serious doubts, to feeling almost certain again. We’re basically wrong, most of the time.

This is the tension we love. The difference between defining and exploring is always palpable. Spatial computing isn’t just a technology; it’s a challenge to how we see and name our future. What if the struggle to define it is the point?

Discover more discourse directly in your inbox.

Sign up for the ON_Discourse Newsletter.

SUBSCRIBE

The Content Paradox

At the start of the year, I made the claim that content had been commoditized by AI. But something deeper emerged: a yearning not for content, but for connection. In our closed group chats, we noticed a trend toward trusting tastemakers over algorithmic discovery. One of our members admitted that they sometimes just want to turn on a fast channel and watch whatever is playing. Algorithmically driven recommendations and decision fatigue are both real.

“If content is endless, what we seek is not more of it but something we can trust—a human touch amidst the firehose.”

Technology Meets Emotion

This year, technology blurred the line between utility and intimacy. At another one of our enterprise summits that explored AI and the connected home, an attendee shared how empathic AI and digital twins could transform our homes into emotional ecosystems. But these developments also begged harder questions: Should tech meet emotional needs? Or are some things better left untouched?

One leader put it plainly: “Tech has historically failed to serve emotional needs. That is changing.” Whether we are ready for this shift remains uncertain.

2024’s True Gift: Uncertainty

As the year ends, I find myself drawn less to the answers and more to the spaces where questions thrive. ON_Discourse has become a community not of solutions but of shared exploration.

One member described it perfectly: “This is where curiosity meets rigor.” Another offered a simpler truth: “This is where we admit what we don’t know.”

I don’t know what 2025 will bring, but I know this: Wrestling with uncertainty is where we grow. Together, we will keep asking, keep listening, and keep discovering. Because the questions themselves are the point.

We run events every week. If you want to participate, inquire about membership here. If you want to keep up with the perspectives that we hear, you can subscribe to our weekly newsletter.

The

Internet

Sucks

This is what happens when you play it safe.

Editor’s Note: This essay is a based on a keynote presentation Dan gave at Web Summit in Lisbon.

The internet used to be an idea. That’s how it launched. It manifested the promise of infinite knowledge, connection, and invention. It was going to free up our time, make things easier and faster, and it was going to give us flying cars.

We turned the magic of the internet into the mundanity of office space. Instead of a fantasy zone, the world wide web is the mechanism that facilitates nearly all of our day-to-day activity. It is the DMV of our life. You pay your water bill there while you scroll through boxy reruns of Seinfeld. If you squint hard enough, it even looks like a DMV: beige walls underneath flickering lights with cardboard boxes everywhere, storing everything.

We used to surf the web;

now we're the fish

Dan Gardner

Dan Gardner

Founder & Exec Chair of Code and Theory & Founder, ON_Discourse

Dan Gardner

Dan Gardner

Founder & Exec Chair of Code and Theory & Founder, ON_Discourse

Discover more discourse directly in your inbox.

Sign up for the ON_Discourse Newsletter.

SUBSCRIBE

This is the first problem: its omnipresence is draining the web of intimacy, personalization, and emotional connection. The internet that tracks every single click of my mouse is the same internet that thinks that one visit to a website thinks I need to be reminded about it forever. Despite all of this data, the internet is just a gigantic spreadsheet that is stubbornly uninterested in who we are or what we truly need. Ubiquity is killing wonder.

The second problem is that the internet is obsessed with optimization. We keep trying to tweak our way to another dollar. AI has accelerated this trend, emphasizing future-proofing over original thinking. Vast industries have distilled the wave of energy and enthusiasm of the early web into homogeneous experiences. Everything looks and feels and works the same way. Marketing, and more recently entertainment, have reduced down to optimization and automation. It may feel safe but it stifles creativity and risks irrelevance.

If this is the primary focus, we will see a race to the bottom for many businesses, Look no further to the media landscape as an example, which is crumbling in front of our eyes. This is just the first example of a long decline of an industry where we lost creativity with the wrong focus. This wave will continue unless we change our focus.

How To Fix It

There is hope. The internet is still young, unfinished, and teeming with potential. In order to reach it, we have to go from future-proofing and efficiency to forward-thinking.

Instead of refining the past, we must design for tomorrow’s opportunities. To do so, we must shift our focus from information technology to emotional technology—tools and experiences that foster meaningful relationships, evoke wonder, and embrace the right kind of friction.

Here are

three core principles

that will

bring back the wonder.

1.

Embrace Friction

Friction isn’t a flaw; it’s a feature. While efficiency clears the path, friction creates memories. Think about the tactile joy of flipping a vinyl record or the anticipation of opening a handwritten letter. Digital experiences today are so frictionless they’ve become forgettable.

By designing intentional moments of friction, brands can create meaningful engagement. For instance, music streaming services could reintroduce elements of discovery—like liner notes or curated album experiences—to recapture the magic of analog listening.

I was reminded the other day about the ephemeral nature of everything. I remember eagerly anticipating the release of a Vogue magazine in the 90’s. My endless wait for the release would make me obsess over the issue. When it finally arrived, I would read it front to back several times over. Do you remember that?

People don’t have these feelings anymore, but they can come back. This does not require a regression in our music streaming interfaces by forcing gated monthly content. I just want you to focus on the feeling and then think about modern experiences that can bring that feeling back.

2.

Design for Wonder

Utility fulfills a need, but wonder creates desire. Digital experiences should spark curiosity, evoke emotion, and invite exploration. Travel platforms, for example, should shift from a transactional approach to one that allows users to envision their adventures, inspiring a sense of excitement and possibility. With gen-ai, why can’t I have a sense of memory before I travel that can mimic the memories I have after I travel. (Photo galleries just don’t cut it.)

3.

Build for Relationships

The internet excels at creating connections, but relationships require depth. Relationships are ongoing, personalized, and rooted in trust. Consider the luxury shopping experience—it's not just about purchasing a product but about feeling a sense of belonging. E-commerce platforms must find ways to replicate the intimacy of in-store interactions. Social networking became social media. We went from the promise of actually being connected to another consumption platform. It seems like there is a gap to be connected when in a post-Covid world it’s obvious we seek these human needs.

A Final Vision

The internet doesn’t just need to be used; it needs to be loved. Not the same love we may feel for crack, but more by the way we love a great bottle of wine - enriched, not addicted. By leveraging AI and emerging technologies, we can create customer experiences that are not only functional but emotionally resonant. This shift from transactional to transformational digital experiences can drive engagement, retention, and loyalty.

Leaders who embrace this challenge will attract talent, win clients, and build organizations that thrive in an era of constant disruption. The question isn’t whether the internet can evolve—it’s whether we have the imagination to shape its future.

So, where do you live? In a world of mundane digital tasks—or one full of wonder, connection, and possibility?

We run events every week. If you want to participate, inquire about membership here. If you want to keep up with the perspectives that we hear, you can subscribe to our weekly newsletter.

Evaluating AI

Effectiveness

Do what you love and let AI do the rest.

Matt Chmiel

Toby Daniels

Co-Founder, ON_Discourse

Editor’s Note: This is a dispatch Toby wrote from his recent trip to Web Summit in Lisbon.

“When you deploy AI in your business, you have two fundamental paths: you can either enhance the things people love doing or eliminate the things they hate doing. This distinction might sound basic, but it’s crucial.”

This is what Nicholas Durkin, the CTO of Harness, an AI-delivery platform said during a roundtable discussion that Dell and NVIDIA hosted during Web Summit in Lisbon.

Take AI code generation, for example. Developers generally love writing code—it’s their craft and their passion. But when AI tools like code generators were introduced, there was pushback. In fact, recent DORA metrics showed that developers using AI code generation tools were less efficient than they were before adopting them. Why? Because these tools inadvertently disrupted the part of their job they enjoy most—writing code.

Durkin went on to say “It’s like telling a chef, we’ll handle the cooking for you,” but leaving them with all the prep and cleaning instead. Chefs thrive on the act of cooking; they don’t want to lose that joy. Conversely, if you use AI to handle the worst parts of the job—like prep work or cleanup—you empower the chef to focus on what they love. This approach doesn’t just maintain their passion; it enhances their ability to excel.

Discover more discourse directly in your inbox.

Sign up for the ON_Discourse Newsletter.

SUBSCRIBE

It’s like telling a chef, we’ll handle the cooking for you, but leaving them with all the prep and cleaning instead.

I spent time with Nick after the roundtable and went much deeper into this topic with him, he went on to outline a model that he uses with his clients. He considers these three metrics when evaluating AI effectiveness:

  1. Efficiency – Does it make processes faster?
  2. Reliability – Is the output consistent and of high quality?
  3. User Experience – Does it make people feel good about their work?

But the most critical factor is alignment with people’s passions. If your AI diminishes the best parts of someone’s job, you’ll face resistance. If it tackles the worst parts, people will embrace it. Focus on “love” and “hate.” Build AI for things people love to do but can’t due to limitations, or for things they can do but don’t want to because it’s boring or repetitive. That’s where AI can make the biggest impact.

We run events every week. If you want to participate, inquire about membership here. If you want to keep up with the perspectives that we hear, you can subscribe to our weekly newsletter.

Twelve Provocations

About 2025

We do provocations, not predictions.

Matt Chmiel

Matt Chmiel

Head of Discourse

Editor’s Note: On the last Friday before Thanksgiving, we assembled members and guests for our second annual End of Year provocations call.

Predictions are boring. None of us knows the future and therefore no one cares what you think is going to happen. Your prophecy is as valuable as mine because you're as stupid about the future as me.

Another problem with predictions is that they are designed to benefit the prophet. The end result is either credit or performative humility; either way you win.

Provocations are different. There is no right or wrong, just boring or stimulating. As a result, they can take many more forms: a meaningful question, a firm statement, or ambiguous feeling.

For the second year in a row, ON_Discourse asked members to prepare a provocation - not a prediction - about the year ahead. In 60 minutes, we tackled the following 12 provocations. We hope at least one of these items stirs up a reaction in you, because this call was full of them.

Discover more discourse directly in your inbox.

Sign up for the ON_Discourse Newsletter.

SUBSCRIBE

1.
Content is dead. Experience is king.

No one reads. Social posts vanish into the algorithmic void. AI has not democratized quality. It has democratized quantity. Too many creators are stuck in the old paradigm of making more, but more isn't better. Better is better, and the real magic I believe, exists in crafting immersive, adaptive experiences that matter.

This provocation did not go unchecked. It was immediately hit with pushback. "Participation in media requires a seismic change in habits, and most people are too passive for that shift."

2.
Why don’t brands do drugs?

There are no mainstream brands that talk about recreational drugs in any kind of a interesting or fun way. There are all these kind of legal psychedelic things coming up, but they're all medical, and they're really, really boring.

At best you see tangential associations with recreational drug use - see: Snoop Dog at the Olympics - but no brands seem willing to commit to this direct messaging, yet.

Someone noted: "Will Coca-Cola return to its roots?"

3.
AI won’t take jobs; it will take tasks.

AI won't eliminate jobs. That's what most people are afraid of. Still. It will just redefine them, and it's already starting to redefine them by taking over mundane tasks.

This is an optimistic expression that was not shared by some. This reaction says it all: "AI has already started taking jobs. I am seeing it. The first hits are in marketing functions, especially here in the Bay Area, where these big tech companies need to hire more AI tech talent, which is extremely expensive. They're doing that by cutting back on their marketing teams, quite simply, laying off a whole bunch of marketers and having the rest of the folks that are left in those marketing departments use their own AI tools."

4.
Streaming platforms are the new Facebook.

Streaming platforms are doing to Hollywood what Facebook did to publishers. What's happening to the studios is what happened when Facebook did with their famous pivot to video, forcing all these publishers to change their models and bend to the whims of Facebook's massive algorithm. I think the difference here is that there's more than one streaming platform.

Nobody pushed back on this one, so I won't invent an argument. I'll just build on the provocation by emphasizing the cascading effect of this system. The commodification of content is diminishing the operational model in Hollywood.

5.
I want the AI bubble to burst.

Right now, AI equals LLMs and Gen AI, but we will not revolutionize the world by generating words and fake videos. AI is much more than that.

As always, I can't tell you who said this, but I can tell you that this person is a founder in AI technology and the emphasis of looking beyond the LLM version of AI got a lot of people excited by this provocation.

6.
Sam Altman is the new Elizabeth Holmes.

The house that Sam Altman built is actually going to create a lot of mini Elizabeth Holmes; we're entering this unregulated environment where there's just going to be more fraud because general AI literacy is still low.

People in the room wanted to edit this take; the underlying theme landed in the room, but the reference was wrong. "I think FTX and SBF in particular are a better parallel because there is a technology at the foundation has real utility but no regulation yet."

7.
Google will win the search wars.

It's very easy for them to flip the switch from being a search dominant metaphor to a chat based one with ads, in the way that perplexity is trying to get towards. I think Google is going to keep winning, and it's very hard for anyone to compete with them.

This provocation had some pushback, but the most effective reaction came from another participant who agreed. This particular member run an AI service provider and has decades of experience in ML, saying: "Google has the best training data by a billion miles with every single click that everybody's done for every Google search and how long they spent on a page and where they went and what they saw when they were there. That's why their current version of search, with AI summaries, has less hallucinations. It's very rare to get hallucination in their AI search summaries. I think they will continue to crush search just because the data."

8.
AI will break the Gartner Hype Cycles.

I am sick and tired of hearing about people talking about Gartner's hype cycle, and I think that, like hype cycles aren't real. Things do not happen linearly, and I think we need a better framework to talk about what's happening right now.

Most people in the group saw some value in the hype cycle. Others gave Gartner credit with turning a banal observation about technical adoption into an evergreen marketing funnel.

9.
The Trump bump will not return for news companies.

The spectacle that inflated the value of some of the news platforms in the first term is being met with a total exhaustion of interest in news. And so now they have to come up with a way to sort of engage audiences on things outside of that.

News is entertainment and people are switching the channel. What are newsrooms to do in this environment? The bro podcast network came up; so did Jon Stewart and The Daily Show. Nobody knows what happens next.

Are the tired of the content or the outrage? The notion of fatigue kept coming up. Someone summed it up like this: "Outrage fatigue is temporary, but trust, once broken, is permanent."

10.
AI will kill the resume.

Every resume looks perfect, looks the same, every candidate feels the same kind of thing.

Everyone is having a hard time finding talent and reporting back from friends who are having a hard time finding work. The outdated notion of CVs feels like they are starting to break conventions.

11.
LLMs are the NFTs of AI.

I think that the LLM bubble bursting. I think people are realizing that LLMs can take you some of the way there or but then they hit a wall. But the AI bubble is not bursting. People are applying different AI techniques to make AI work properly, so you can use it at scale and trust it.


We have heard this notion repeated in several events. AI is bigger than LLMs and maybe 2025 will be the year we move beyond that aspect of it.

12.
We're all cowards.

I think we're afraid to disagree. I count myself in this by the way. We're afraid to call things out and put ourselves out there.

As one can imagine; people were not ready to embrace this one. A few reactions to it: "I thought that provocation sucked."

We run events every week. If you want to participate, inquire about membership here. If you want to keep up with the perspectives that we hear, you can subscribe to our weekly newsletter.

Group Chat Recap
11 • 08 • 24

Your eCommerce site isn't ready for an agent

eCommerce needs to focus on the plumbing first

Matt Chmiel

Matt Chmiel

Head of Discourse

Editor’s Note: We invited an AI expert to talk about the future of eCommerce in the agentic era.

Are AI agents coming to eCommerce platforms? Not if you believe the takeaways from this Group Chat. It features a bonafide AI expert with academic credentials and multiple successful ventures (including a new one that we cannot mention now, that is serving eCommerce sites).

This session paired AI optimists with eCommerce realists. It was a good one. Here are some takeaways.

Discover more discourse directly in your inbox.

Sign up for the ON_Discourse Newsletter.

SUBSCRIBE

Personalization is a mirage

I think the promise of personalization that we have today on our platforms is not there. There's a lot of personalization that's happening on these sites, but it's not real, and it's certainly not a value to most of us. It's why there's so many rails that are run across a PDP or a PLP because they're like shit, maybe they’ll click on this one for no reason.

The future is better search results, not agents

The conversation was practical; before we let agentics magically interpret our mood and behavior with perfect recommendations, we should maybe focus on search results that properly understand customer intent.

One on hand this feels obvious, on the other hand, as one of our guests admitted, this is not always the case.

So getting customers to feel after getting better search results: ‘Oh yeah, that heard me.’ Like, that's amazing. We have a lot of those insights during gifting moments, whether it's holiday, Mother's Day, Father's Day, Valentine's Day, finding. But all we do right now in gift seasons, the lowest common denominator…

eCommerce tech stack is outdated

The most pervasive issue, and blocking a lot of eCommerce companies from being able to take advantage of this technology is their tech is stuck in 2010. So far what they've done now is build wrappers around this so they've put lipstick on it to make it kind of look pretty but it doesn't function.

We run a Group Chat every week. If you want to participate, inquire about membership here. If you want to keep up with the perspectives that we hear, you can subscribe to our weekly newsletter.

Group Chat Recap
11 • 15 • 24

AI and the Law

Finding the line between government and governance

Matt Chmiel

Matt Chmiel

Head of Discourse

Editor’s Note: We invited a legal expert on AI and copyright law to talk about the ethical and legal landscape for an AI-powered internet. We can’t tell you who was there but we can tell you what was said.

AI is the ultimate blackbox. Does that mean entrepreneurs are shielded from liability? We hosted a Group Chat that dug into this question. Here are 3 takeaways:

Discover more discourse directly in your inbox.

Sign up for the ON_Discourse Newsletter.

SUBSCRIBE

Section 230 and AI

Liability remains murky when it comes to AI-generated content. The legal shield of Section 230, which protects platforms from user-generated content liability, extends ambiguously into the AI realm.

Questions of liability scatter across the tech stack. The platform that hosts the agent; the brand that sponsors it; and the software developer that launched it all play a role in this equation.

If you are creating an agent that goes out and makes false claims about a product, the developer could claim immunity under Section 230… but this is not a certainty.

Good Governance

You have to understand what your AI does and then you have to rigorously test it against every bad-case scenario. And then you have to keep records of what you're doing.

Red teaming—stress testing AI systems to expose vulnerabilities—is emerging as a critical practice for ethical and functional deployment.

One of the interesting takeaways we heard was a distinction between communication and reporting tools.

You have to make the decision on whether you are a communication tool or a reporting tool. Then we had to make a decision about how our AI responds to extreme scenarios like suicide threats or violence.

Colorado and the States

The federal government is probably not going to set any standards for AI. The real action is happening in the states.

Emerging regulations like the Colorado AI Act reflect a trend toward greater oversight of AI's societal impacts.

If you don't know about it now, you should read up on the Colorado AI Act.

If you don't know what data is training your model by February of 26 and you know you're going to be deploying your tool in Colorado or to consumers or businesses in Colorado, you're going to be out of compliance. So you know you really need to be thinking about that.

We run a Group Chat every week. If you want to participate, inquire about membership here. If you want to keep up with the perspectives that we hear, you can subscribe to our weekly newsletter.

Breakfast Recap
10 • 10 • 24

Inevitable AI

The unavoidable future of generative content?

Editor’s Note: 18 Industry leaders in NYC joined us for breakfast to talk about the future of content. The word inevitability was uttered many times, generating a lot of pushback.

We hosted our breakfast in the back room at Gemma Italian Trattoria at the Bowery Hotel in New York City.

The discourse centered on this prediction about AI:

The future of content will be generative, ephemeral, and prompted by your needs, wants, and desires.

This future will come in 3 distinct phases
(we are currently in phase 1)

Phase 1

AI tools for professionals to produce more content more efficiently.

Phase 2

AI tools for non-professionals to produce professional-looking content (similar to blogs and print)

Phase 3

Brands generating consumer content based on targeted user data.

This theory does not predict a total takeover of the content supply chain; cinema will still exist; live sports will still exist; but the majority of content consumption will be generative.

Why it matters

As AI moves from assisting creators to generating personalized content in real time, we’re on the brink of a media transformation that could either revolutionize how we consume or isolate us further into echo chambers.

Matt Chmiel

Matt Chmiel

Head of Discourse

Discover more discourse directly in your inbox.

Sign up for the ON_Discourse Newsletter.

SUBSCRIBE

The table had several key reactions:

The Dystopian Risk

Some attendees warned this will create tribal bubbles, reinforcing personal biases and isolating communities. One participant pointed to political radicalization, noting AI’s role in amplifying divisive content.

"We’ll end up in a civil war before we reach this inevitability."

The Loss of Choice

Concerns were raised about algorithms controlling our consumption:

“We’re just TikTok zombies at this point.”

The fear is that AI will strip away free will, reducing us to passive consumers.

Hope for Personal Content

Others embraced the potential for wildly creative, personalized experiences, like one attendee’s dream of blending Darth Vader with Rocky in a custom AI-generated adventure.

Interactive, participatory content could reshape entertainment into a collaborative experience—where viewers not only watch but star in their own creations.

Too Much?

What happens to shared experiences? If everyone gets a different ending to the same movie, are we losing cultural touchstones? Some worried this could fragment society further, erasing the moments that bring us together.

We run closed-door events every week. If you want to participate, inquire about membership here. If you want to keep up with the perspectives that we hear, you can subscribe to our weekly newsletter.

Group Chat Recap
10 • 03 • 24

Escaping Data Jail

AI is very quickly changing the SaaS business model

Matt Chmiel

Matt Chmiel

Head of Discourse

Editor’s Note: How much are you paying your SaaS vendor? Do you think AI - whatever that means to you - can change that cost burden and redefine your relationship? This recap is for you.

We invited 2 SaaS founders into a Zoom call with 3 other executives. I can’t tell you who was there, but you can preview some of the discourse.

The takeaways on this list might drive the next conversation you have with your SaaS vendor.

Discover more discourse directly in your inbox.

Sign up for the ON_Discourse Newsletter.

SUBSCRIBE

AI Won’t Replace SaaS

SaaS is not going anywhere, but the way it has traditionally operated is about to change dramatically. One of the founders put it this way, “AI stitches together smaller, bespoke solutions,” allowing businesses to create customized workflows that fit their needs. The days of relying on one-size-fits-all platforms are over. Those on the cutting edge are using AI to personalize and streamline their SaaS stacks. If you’re not exploring how AI can take your tools to the next level, you’re already falling behind.

SaaS companies are under more financial strain than ever before.

The Golden Age of High Margins Is Fading

The pressure on SaaS margins is mounting. As interest rates rise and customer demands shift, the once-lucrative model of massive upfront spending with guaranteed long-term revenue is fading. One CEO cautioned, “SaaS companies are under more financial strain than ever before.” The key takeaway? Profitability now hinges on constant innovation and real-time value creation. SaaS clients are already eyeing exists from long-term contracts. Why is that?

AI Can Break Out of Data Jail

AI is demolishing the barriers that once made switching SaaS platforms difficult. “Data jail” is becoming a relic, with AI-driven solutions making it easier to move from one system to another. This shift has empowered businesses to pivot quickly and ditch legacy systems without the massive headaches of the past. Is your SaaS provider evolving fast enough? If not, expect to see churn rates rise as switching costs plummet.

You Still Need SaaS

The buzz around AI-generated rapid prototyping is real, but don’t be fooled. While AI makes it easier than ever to build flashy demos, turning these prototypes into robust, scalable solutions is still a major challenge. As one respected executive observed, “Prototypes are about 2% of the work.” The real value lies in operational excellence, something that can’t be replaced by a few lines of code. The smartest leaders are focusing on building sustainable, scalable systems with nimble SaaS solutions.

Do You Want to be Klarna Right Now?

They generated cutting out all SaaS contracts, but our SaaS founders were not convinced this is the right long term move.

“Klarna said we just tore out their CRM, etc. I'm really looking forward to the stories from that. I don't know Klarna at all - and no offense to anybody there - but man, that sounds like a really aggressive move. And I have a feeling that we're going to find some people leaving saying some interesting things about operations.”

Usage-Based Pricing is Coming

The era of flat monthly fees is fading, and usage-based pricing is quickly becoming the new norm, particularly in AI-driven SaaS. One of our guests put it this way, “This is going to create friction for finance teams” SaaS leaders need to prepare for a future where billing is based on usage, which means rethinking everything from budget forecasts to financial planning. If you're not ready, this shift could catch you off guard.

SaaS Agents?

The future of SaaS isn’t just about automation—it’s about intelligent, autonomous agents that can seamlessly integrate into your workflows. "SaaS is moving towards agentic architectures” but for how long?. This trend is reshaping how businesses think about software. These agents, often paired with conversational UIs, can handle complex tasks, but there’s a catch: without structured data, their effectiveness plummets. The next wave of SaaS innovation will hinge on balancing flexibility with the structured environments needed to make these agents work reliably. Those who master this dynamic will lead the pack; those who don’t will struggle to keep up.

We run a Group Chat every week. If you want to participate, inquire about membership here. If you want to keep up with the perspectives that we hear, you can subscribe to our weekly newsletter.

Group Chat Recap
09 • 27 • 24

'A Bleeping Nightmare'

Top-down transformation nightmares and 2 other takeaways about integrating AI into enterprises from members and guests

Editor’s Note: It was the last Friday in September and so we assembled all our members, experts and guests for our end of the month virtual event. These events are shaped by the group dynamic; we start with a plan, but the group dictates the discourse.

0:00 / 0:00

We came into this session with a plan: provoke Peter Pawlick, head of experience design at Proto. Pawlick published a 5 part series on our platform about AI simulations and his perspective deserved attention. If you haven’t read it yet, here it is in a nutshell: design thinking is dying and many brands and agencies don’t know it yet.

Design thinking is the engine that drives digital transformation. It is an endless iterative and agile process that is designed to ‘move fast and break shit.’ It is more than a method, it is a culture. And that culture is about to be replaced.

Synthetic data and other generative AI systems make it possible to preview ideas before they are designed or built. This means that an enterprise that wants to chase a north star vision can stress test 10,000 pathways to get there before deploying any capital on design or development.

In other words, move fast and break synthetic shit so the first public launch is a guaranteed success (or so the theory goes).

As I was saying, we came into the session with, dare I say, a good plan. But like all good plans, it fizzled on first contact; the group took over the discourse. I love when that happens.

The group was full of agency leaders, enterprise representatives, and founders in AI startups. In other words, all sides of the digital transformation spectrum were covered.

Here are 2 other takeaways from the group - anonymized in the way we always do:

Matt Chmiel

Matt Chmiel

Head of Discourse

Discover more discourse directly in your inbox.

Sign up for the ON_Discourse Newsletter.

SUBSCRIBE

1. The AI Firewall

We heard perspective from members who have been struggling to sell AI builds and services into corporate clients.

The only groups willing to consider these services are the marketing and customer service departments. The use-case is pretty clear: the content and services can live freely outside of the company firewall; mistakes in this instance are a minor issue rather than a compliance nightmare.

The rest of the organization is dragging its feet, for good reason. As we’ve heard in other events, AI is great at rapid prototyping but not running a product or ensuring compliance. As one insider put it, AI might work for "marketing procurement, but AI within the rest of the organization is going to be pretty slow.”

Top-down AI transformation is a fucking nightmare.

2. Realistic AI

Now let’s drill deeper: what is the conversation like for the few corporations that are willing to integrate AI deeper into the org-chart? We heard a few perspectives that might influence the way you collaborate with partners.

“AI is not a magic button” and “LLMs are not always the answer to the problem.” The real problem is that expectations for how this technology can help is not fully understood. This creates a communication issue that blows up if not addressed the right way.

One of our members put it bluntly: “Top-down AI transformation is a fucking nightmare.” In other words, employees reject it and compliance pushes back. One blocker comes in after another.

Real change is coming from the bottom-up, where employees (or agencies) are hacking together solutions, often without waiting for permission. One group is speeding up brand assets and media buying. Another group uncovered a way to track and deal with disinformation in social media using AI tools. This is opening up new service-offerings that were never before considered.

This perspective is important because it represents an agency offering for recalcitrant enterprises: do not look for the silver bullet; instead, build tools that solve specific problems. Keep adding new tools, solving new problems, eventually developing a suite of services.

We run a Group Chat every week. If you want to participate, inquire about membership here. If you want to keep up with the perspectives that we hear, you can subscribe to our weekly newsletter.

Group Chat Recap
09•19•24

'Holy Bleeping Bleep'

What it feels like to build a functioning CRM in 3 hours, and 4 other takeaways about AI and team management.

Editor’s Note: This Group Chat was a prolific blend of personalities and perspectives spanning a variety of unrelated industries. We provoked this group with practical questions about AI and management. Their respective answers fed into a good discourse. Here’s a public-facing recap)

0:00 / 0:00

People are always asking what happens in our events. We can’t tell you. That’s part of our deal; we have closed-door sessions with real discourse. Our members get to share raw thoughts, compare notes, and develop new connections. And you get this sanitized recap.

This group had 4 members:

  • 2 Founders (1 AI startup and 1 large public company & venture development firm)
  • 1 Chief Digital Officer in prestigious cultural commerce
  • 1 Chief Operating Officer of an agency

They generated 5 takeaways.

Matt Chmiel

Matt Chmiel

Head of Discourse

Discover more discourse directly in your inbox.

Sign up for the ON_Discourse Newsletter.

SUBSCRIBE

1. Middle Management is Ready for an AI Take Over

In private they don’t mince words: “We want to replace the manager, just like Uber replaced the dispatcher. AI can do a better job at managing people than humans. Managers are the most dysfunctional part of an organization, and people leave jobs because of bad managers, not bad companies.” The role of the manager as we know it is obsolete.

Another participant, tired of slow corporate change, took drastic measures within their company, reshuffling the hierarchy to move faster: “We took our chief creative officer, made them Chief AI Officer, and launched initiatives to trim the fat.” The focus here was cutting out inefficiency and embracing AI as a force for operational speed and innovation.

Managers are the most dysfunctional part of an organization, and people leave jobs because of bad managers, not bad companies.

2. AI Prototyping: Faster Than Bureaucracy Can Keep Up

With greater efficiency comes an unexpected issue. As one exec put it: “We spun up an AI-driven CRM prototype in just three hours, and the reaction was ‘holy fucking shit.’” But the challenge surfaced when this quick success bumped into a familiar corporate problem: maintenance. As this leader explained, “Now, I don’t know what to do. If everyone starts using it, it becomes a product, and then I need to support it.”

The prototype worked so well but it was just a proof of concept. Implementing this thing is where it gets sticky again.

This dilemma—building too fast to scale—captures the double-edged sword of today’s AI landscape. It’s faster to build something tangible than to even discuss building it, but as they pointed out, “The challenge comes when you have to support and scale what was meant to be a prototype.”

3. Mediocrity Won’t Survive

Another issue: people. They put it bluntly: mediocrity will not survive in this new AI-driven world. “Being mediocre is just going to be very difficult.” The pace of AI innovation is outstripping human adaptability. The faster the models retrain, the faster the gaps between skill levels grow. In this environment, anyone slow to adapt will be left behind.

The Chief AI Officer that was mentioned earlier is in charge of hiring new resources. All of them have to demonstrate real opinions, experience, and output from various AI platforms if they want to get hired.

4. Donkeycorn Ventures

Forget unicorns. While some chase billion-dollar valuations, a new concept emerged during the discussion—the “donkey-corn.” This represents small, high-performing companies with $2 million in revenue, built by tiny teams grinding hard in niche markets. The future belongs to companies focused on efficiency and scalability without bloating. Someone referred to the Sam Altman question: “Who’s going to be the first billion-dollar brand owned by one person?” That question does not imply a single business. In this executive's mind, it is a network of donkeycorns.

5. AI-First Companies

One consistent theme throughout the chat was the consensus that any new company starting today is an AI-first company. “You have two types of people: those who embrace change and those who fight it. Only one of them wins.” Whether it’s AI managing teams or personalizing brand experiences, the clear takeaway was this: the future is not waiting for anyone. The business leaders in this chat agreed—AI isn’t just a tool; it’s a revolution in how work will be done.

We run a Group Chat every week. If you want to participate, inquire about membership here. If you want to keep up with the perspectives that we hear, you can subscribe to our weekly newsletter.