'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)
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
Head of Discourse
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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 The role of the manager as we know it is obsolete.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.
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