Micha Kaufman, CEO of Fiverr, just announced he is laying off 250 people and going back to startup mode. His post was long, transparent, and unapologetically focused on turning Fiverr into an AI-first company. He acknowledged the pain of the decision, thanked those leaving, and doubled down on his vision for a leaner, faster organization.
And he is getting absolutely slaughtered online.
If this post came out of nowhere, the backlash might make more sense. But it did not. Back in May, I highlighted Micha as one of the rare leaders who speaks with urgency and adaptability about the changing AI landscape and the world of work. He told employees that AI would impact everyone, from programmers to designers to salespeople and even his own role. He encouraged people to master prompt engineering and warned that those who failed to adapt would lose value in the market. The honesty was refreshing. It did not sound like it came from a communications team. He was giving everyone a heads up for what was to come with radical transparency. If you missed that post, check it out here:
My criticism at the time was that he didn’t have a plan. Well now he does! And that is what makes this moment so interesting. The backlash he’s receiving on his post includes:
– Name calling: “What a trash statement from a trash human being. I hope you go out of business”
– Jeers: “CEO is a douchebag.”
– And utter denial: “I’m betting on AI to implode and ruin America’s financial foundation.”
Micha has become the face of what fear looks like for the American worker. But AI isn’t the villain, fear is. Fear of change. Fear of irrelevance. Fear of losing control. These are very real, very human reactions. But when fear drives the narrative, we stop listening, stop learning, and stop adapting.
What I see in Micha’s post is not cruelty—it’s clarity. He’s choosing to face disruption head-on rather than pretend it isn’t happening. That doesn’t make the layoffs less painful. But it does make his leadership more honest than most. He’s offering them support and acknowledging the pain, but he’s not doing anything that hundreds of other CEOs haven’t already done.
What is the alternative? Bury your head in the sand and wait for disruption to overtake you? Then everyone at Fiverr will be unemployed. Is that better?
This will be a difficult road. Fiverr is an online marketplace for freelancers, and their future depends on smarter matching between talent and clients. AI can help with that — but it’s not a magic switch. It’s messy, experimental, and harder than the hype suggests.
Just last week I was discussing AI’s ability to run logic models with Eric Fraser, the CTO of Dr. Lisa AI. I asked Eric how leaders are actually using AI. His answer was not the doom and gloom story most people expect. In my conversations with him and numerous other consultants in this space, I’ve learned that very few entire jobs have been eliminated because of AI. What’s really happening is that tasks are being automated, teams are being streamlined, and companies are reallocating resources to explore AI’s potential.
Eric explained that logic work is particularly tricky for AI. AI models are very good at pattern recognition and language generation, but they struggle with reasoning, multi-step logic, and applying common sense consistently. When you type the word “dog” into ChatGPT, it doesn’t just see the word. It represents “dog” as a position in a huge mathematical space that captures all the shades of meaning: the animal, the slang, even metaphorical uses. Then it predicts what words should come next based on those patterns. That’s powerful for language, but it’s not the same as structured reasoning.
Which means Fiverr’s journey to becoming AI-first won’t be simple. It’s a bet on experimentation, not instant replacement. But when people hear “AI-first,” they don’t hear “innovation.” They hear “my job is gone.” Fear drives the outrage — and then fear takes over the comments section.
This reminds me of when Johnny C. Taylor got heat for his I&D announcement. He was vilified online but joined our podcast to talk about the decision. Will Micha back down? The pink slips have already been distributed. The real test now is whether Micha can withstand the storm of fear and keep leading with clarity. Micha, this is your invitation: come on the Culture Leaders podcast and let’s talk it out.
Elsewhere In Culture
Dell’s “Project Maverick” is the other side of the AI coin we talked about in the Fiverr story. Where Fiverr reacted with urgency and panic, Dell is trying to engineer a system-wide reset. It is not just about sprinkling AI on top of old processes, they are overhauling infrastructure to be AI-first from the ground up. That level of planning signals something Fiverr missed: urgency without structure breeds fear, but urgency with a roadmap builds alignment. Dell’s bet is that if they rewire their systems now, they can control the narrative and stay ahead of disruption rather than react to it.
The real question is whether this kind of bold overhaul will translate into results or become another case of tech theater. AI is not a magic wand, it is a lever that only works if people, culture, and execution are aligned. If Dell uses Project Maverick to create clarity and direction, they will avoid the pitfall we saw with Fiverr. If they use it as a shiny announcement without embedding accountability and purpose, they will face the same uncertainty that is now unsettling freelance marketplaces. The lesson is simple: survival in the AI era will not be about who yells “change” the loudest, but about who builds the systems and culture that make change stick.
The wave of firings after Charlie Kirk’s assassination has reignited a familiar myth that free speech is a shield for employment. It is not. I said this on CNN earlier this week and I will say it again. The First Amendment protects you from the government, not from your boss. Most people in this country are at will employees, which means you can be fired for almost anything, from the wrong post online to simply being seen as misaligned with the company’s purpose. That is the legal backdrop. But the real story here is not about constitutional rights. It is about culture.
Leaders today are under immense pressure to act fast when outrage spreads online. Fire the person, issue a statement, distance the brand. That is not leadership, that is panic. The stronger move is slower and harder. It means asking whether the behavior aligns with your stated values, whether it erodes trust, whether it reflects the experience you want for employees and customers alike. American Airlines gave a telling example. Their purpose is to care for people on life’s journeys, and when an employee’s comments clashed with that purpose, they acted in alignment. That is not censorship, that is culture in action. At the end of the day, free speech will not save your job. Culture will decide if you keep it.