It Writes Itself performing at 2026's SXSW, featuring a live, AI-driven variety show and creative workshop.

Veronica Zin

Imagine you’re the head of an enterprise organization that just dropped hundreds of thousands of dollars on AI consultants. Racing to introduce artificial intelligence into your workflows, you also bought the latest pricey tools and invested in time-consuming workshops to get your people ready.

It’s all worth it, you think, to own the AI revolution.

Then something beyond annoying happens. You notice your people aren’t using these resources in any meaningful way. This dovetails with findings from the front lines of corporate America. An MIT NANDA report, The GenAI Divide: State of AI in Business 2025, found a pronounced split between the tiny number of organizations that achieve value from AI and the rest that stay mired in doomed AI initiatives that fail to launch.

“What we’ve found is that access isn’t the problem with this technology. Adoption is holding companies back,” said Mike Jacobson, one half of the husband and wife AI performance company, It Writes Itself. A Grand Effie-winning strategist and Forbes 30 Under 30 honoree, Mike is a leading brand and content strategist. Sami Kriegstein Jacobson, his partner, is an award-winning creative director and voiceover actor.

Neither set out to become technologists. Instead, in 2022, when ChatGPT hit the mainstream, they felt compelled to understand it. As a professional magician and mentalist who performs for corporate events, Mike was used to acting out his thoughts and ideas. So was Sami, especially from all her creative and voice acting work. This led them to ask the question that corporate leaders reeling from staff resistance, should ponder, “What if learning this new tool could be … fun?”

Building on the trend of PowerPoint parties where friends gather to deliver presentations on topics of their choice, the duo hosted a night out starring the burgeoning AI technology. They expected only a small group to attend the New York bar where they hosted an interactive show. Instead, 60 showed up. “We realized we had tapped into something,” Sami said. “There was this huge curiosity around AI, but people didn’t know where to start.”

Their first slogan captured people’s emerging feelings about this tech: “Smart people. Dumb AI.” Building on their improvisational chops, they invited attendees to partake in what may have been the first AI-powered variety show. From the start, it unfolded with the kind of energy you might find at The Moth where people swap tales on stage or StorySLAM, open-mic nights at bars and small venues that encourage audience participation and speaker vulnerability.

The concept scaled from there, leapfrogging from NYC pubs to corporate stages, including at companies like Meta, Unilever, and Disney. They also performed at SXSW this March, where I met them while moderating a panel on the future of creativity in the AI Age sponsored by Superhuman. With guest appearances by Nick Rutherford, Eric Andre and Maylee Todd, they put on a live comedy variety hour involving sketches, music, storytelling and games.

It was yet another example of the playful impulse characterizing how they present AI to businesses struggling with group adoption. “We always say we’re not AI experts. We’re AI explorers,” Sami told me. “That’s key because exploration can unlock something that instruction cannot: ownership.”

Zooming out, the idea that using improvisational comedy and roleplaying to acclimate businesses to AI might seem silly, bordering on the nonsensical. But there’s precedent for this type of instruction. Second City Works offers something similar along the lines of interpersonal development. As The Hollywood Reporter explains: “the venerable Chicago-based improvisational comedy institution, has quietly built out a surprising side-hustle: Using the fundamentals and tactics of improv to teach corporate executives and professional athletes how to be better communicators.”

Its creative director, Tyler Kempf, describes the importance of play, especially silliness, to achieve breakthroughs in team dynamics and media training. That makes sense for the current business climate. For years, educational pundits pushed for developing expertise in left-brain fields like STEM (science, technology, engineering, and math.) Now that AI can code and increasingly excels at math and science, so-called “soft skills” are making a comeback, a subject I recently covered for Forbes.

Back in the late 20^th century, Johan Roos and Bart Victor at the International Institute for Management Development, developed something similar, LEGO Serious Play (LSP). SI Labs describes it as “a facilitated workshop method in which participants build three-dimensional models from LEGO bricks to explore complex questions, develop strategies, and understand systems.” The same site explains its participatory approach for success. “In a traditional workshop, quiet participants can remain silent while dominant personalities steer the discussion. In LSP, every participant builds their own model and must explain it to the group. There is no hiding behind silence or behind someone else’s slides.”

The often stuffy, stifling nature of business has long encouraged this kind of disengagement across organizations. Stepping out of the corporate line could provoke deleterious repercussions from criticism to outright job loss. As a result, office teams tend to keep their heads down and do the work. But as LSP, Second City Works and It Writes Itself reveal, there’s real utility in adults behaving in the less guarded, spontaneous ways children act. When adults lean into the act of play, allowing themselves to be swept up in the fun, their guard comes down and their minds open up. Especially to new possibilities and new technologies.

Sami and Mike told me that one of the most surprising outcomes of their work with corporate teams appears when they work with highly technical audiences, including the very engineers building AI systems. “We expected skepticism,” said Mike. “Instead, developers are often invigorated by the fact that they finally got to play with the tools they are wrestling with daily. Suddenly, they are out of ‘productivity mode’ and onto ‘possibility mode.’”

It’s no secret this type of experimentation is rare in corporate cultures where the lion’s share of personnel wants the AI craze to just blow over. All those executives who have spent so much time and resources to foster adoption would do well to promote an explorer mindset over an avoider one. Because while training is essential, it’s not enough. What It Writes Itself shows is that adoption comes when people let down their barriers and play. Children show us this reality daily.

Want AI buy-in for your team? Make it fun first. Adoption tends to follow.