Blog & Resources
Insights
Thoughts on operations, AI, leadership, and building things that last. From someone who's done it across every industry.
The Optimist and the Doomer
Clare Hawthorne and Max Tuchman compare notes on AI: one thinks it ends badly, one is still optimistic with caveats. Part I of a three-part series.
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The Stack You Don't Own
Clare Hawthorne and Max Tuchman on heavy bags, portability and continuity when the AI stack underneath you belongs to someone else. Part II of a three-part series.
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Harvest, Maintain, or Grow
Clare Hawthorne and Max Tuchman on the decision hiding inside "AI gave us time back," and why harvest wins by default. Part III of a three-part series.
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Happy Birthday, Caribu
The odds were against Caribu surviving. Here's the exact recipe of people and community that made it, and why it still exists ten years later.
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The Honest Timeline: The Weekend Was Real. So Were the Five Months After.
The weekend rebuild was real. So were the five months of tweaking after it. The honest ledger: monthly subscriptions under $500, mistakes made, and why paying someone to skip the middle is the worst move you can make.
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The Most Expensive Problem With Your Most Expensive Hire
Recruiters keep seeing the same thing: CAIO job descriptions written by CEOs with no working knowledge of AI. The wrong person gets hired, the systems never get built, and the bill lands a year later.
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The door is open
The AI window is wider than it has ever been for the people who got shut out of the last few tech waves. It will not stay open, so here is why waiting is the expensive choice.
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I teach you to fish
Leaders kept catching me in the hallway after AI trainings to quietly admit they were lost. Why I tutor the person at the top instead of handing anyone a fish.
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The expensive problem
We built Caribu for traveling parents. The data said grandma. Product-market fit is not a nice idea, it is a specific person with a problem expensive enough to pay to fix.
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If only investors are giving you money, quit
Everyone says never quit. The better rule: if customers pay you, keep going; if only investors do, you have not found product-market fit, and grit will not manufacture it.
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Selling your company
It is traumatic, even the clean deals. Find your doppelganger inside the buyer, guard both your financial and emotional runway, and know the assertive-woman tax is in the room.
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Luck is preparation meeting opportunity
On March 14, 2020, Caribu grew tenfold overnight. It was not luck, it was preparation. And the trust we refused to trade for growth was the real moat.
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The Boring Work I Never Think About Anymore
The real payoff of building an agent team is not the flashy stuff. It is the boring recurring work that now runs itself, like the invoice chase, so you never think about it.
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How I Actually Trust AI: The Guardrails I Put on Everything
I do not trust AI blindly, and neither should you. The system I built around it: restrict the sources, demand citations, read every link, and make the models argue.
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The Weirdest Ways I Have Used AI
From a 1965 Impala's dead taillights to ranking quantum physics books I will probably never finish, the strangest and most useful ways I put AI to work.
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The One Place Women Cannot Hand Over the Keys: Our Own Health
Agentic AI is going to shape women's health whether we participate or not. Here is how to give it real jobs, from perimenopause meal plans to a personal trainer that travels with you.
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Meet My Cabinet: How I Run Dark Horse Ops With a Team of AI Agents
I built a team of AI agents to run Dark Horse Ops, each named after a woman and trained to own one job. Here is who works for me, and how they hand work to each other.
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Why I Named My Entire AI Cabinet After Women
The names were not an accident. Here is the real reason I put eight women to work, and why women cannot afford to sit this build out.
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AI Literate Is Not AI Fluent. Executives Keep Confusing The Two.
There is a quiet conversation happening inside boardrooms right now: "We have AI covered. The team is using ChatGPT." That is not AI coverage. That is AI literacy. And literacy is no longer the finish line.
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The Jumpable Chasm: From Chatting With AI To Building With Agents
Seventy-nine percent of enterprises say they use AI agents. Only eleven percent run them in production. The chasm between chatting with AI and building with agents, and how to jump it.
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I Rebuilt My Business With AI in a Weekend
A small business website built by an agency takes six to ten weeks and runs five to twenty-five thousand dollars. I rebuilt mine in a weekend with AI. What worked, what broke, and what every executive should learn from it.
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Why You Cannot Let Your Team Find Out How Behind You Actually Are.
Korn Ferry's research found that 71 percent of US CEOs experience impostor syndrome. AI is the loudest voice in the room making it worse. Most senior executives are quietly behind, and they cannot let their teams find out.
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I Love AI. But It Just Told Me Taylor Swift Doesn't Exist.
I am a believer. But last week, AI scared me. And I have spent the days since trying to articulate exactly why. Here is the moment that changed my read on hallucinations and what it means for executives shipping AI work.
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Moore's Law, But Make It Faster
Moore's Law says transistor density doubles every 24 months. METR data shows AI capability is doubling every 4 to 7 months. If your three-year strategy was built on the old cadence, your planning windows are between three and six times too long.
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Stop Watching AI Videos. Start Breaking Things.
There is a popular learning framework that says people retain 90 percent of what they do, 10 percent of what they read. The exact percentages are not real. The principle is. Why most AI demos fail executives, and what 10 minutes a day of hands-on actually changes.
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Last Month's Coolest AI Company Is This Month's LLM Feature
Last quarter, AI startups absorbed 81 percent of all venture funding in the world. The standalone AI tool you signed a contract with is becoming a feature inside something larger. Three procurement habits that protect you from paying twice.
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Conference ROI Was Always Terrible. AI Made My Last Conference Profitable.
Up to 80 percent of leads collected at conferences never get any follow-up. CEIR estimates the waste at $5.4 billion a year. This year my conference was different. Here is the math, and what AI agents actually did during and after.
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Knowledge Workers Are The First Wave. Trades Are The Second.
Most plans for AI displacement assume a single wave. There are two: knowledge work first, physical trades second, on different timelines. If your three-year strategic plan does not name both, it is not actually a plan.
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First Time In History Non-Technical People Can Compete At The Top.
By the end of 2026, eighty percent of technology products will be built by non-IT professionals. Citizen developers will outnumber professional developers four to one. For non-technical operators, the door is unusually wide. For now.
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