Insights

Thoughts on strategy, efficiency, and the practical application of AI in the enterprise.

Newsletter
Jun 29, 2026

Token Efficiency Is a P&L Issue. Most Finance Leaders Don’t Know It Yet.

At Semafor’s World Economy Summit this past April, Reid Hoffman was asked how companies should think about AI adoption.

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Newsletter
Jun 29, 2026

Microsoft Has 20 Million Copilot Seats. The Agents Inside Them Are Ungoverned.

The scaling problem is not technical. It is operational. And most organizations are not ready.

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Newsletter
Jun 16, 2026

The Rocking Chair Is Rocking on Thin Ice: How AI Can Save Cracker Barrel (and Restaurants Like It)

Cracker Barrel has a problem that no amount of biscuits can fix.

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Newsletter
Jun 16, 2026

Anthropic Measured the Token Problem. The Number Is 134,000.

An AI influencer declared it this week: MCP servers are dead.

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Newsletter
Jun 12, 2026

Stop Prompting. Start Building Loops.

The operators winning with AI aren’t the ones with the best prompts. They’re the ones who stopped prompting altogether.

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Newsletter
Jun 12, 2026

Stop Uploading PDFs to Claude (There’s a Better Way)

How converting documents to Markdown before sending them to an LLM can cut your AI costs by 30–60% — and why it matters for operators building at scale.

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Newsletter
Jun 12, 2026

The SBA Just Doubled Its Loan Limit to $10 Million. Most Small Business Owners Will Wait for Their Banker to Tell Them. That’s a Mistake.

If you have ever said “I want to buy a competitor” or “I need a bigger facility” but the financing never quite made sense, this is worth five minutes of your ti...

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Newsletter
Jun 12, 2026

Meta Just Became a Trade School. Small Business Owners Should Pay Attention.

Meta announced America’s Workforce Academy this week.

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Newsletter
Jun 3, 2026

The Guardrails Are Gone. Now What?

The Financial Times, working with AI safety group Alice, ran an experiment last month.

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Newsletter
Jun 2, 2026

NVIDIA GTC 2026: The AI Economy Just Went Operational — What Operators Need to Do Before the Window Closes

Jensen Huang didn’t announce a product. He announced a business model. Here is what operators and investors need to know.

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Newsletter
Jun 2, 2026

Greg Abel’s First Big Move: What Berkshire’s $8.5 Billion Housing Bet Tells Every Operator About Timing, Capital, and Platform Thinking

Warren Buffett spent 60 years building Berkshire Hathaway into the world’s most admired conglomerate.

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Newsletter
May 20, 2026

The 30-Year Treasury at 5.2%: What CFOs and Operators Need to Do This Week

At 11:55 AM EDT today, the U.S.

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Newsletter
May 17, 2026

ChatGPT Just Entered Personal Finance. Here’s Why That’s Good News for AI Strategy.

On May 15, 2026, OpenAI launched a personal finance experience inside ChatGPT that lets Pro subscribers connect their bank accounts, credit cards, and investmen...

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Newsletter
May 14, 2026

The World May Be Shifting. Here’s What It Means for Your Business.

Two events landed within 24 hours of each other this week.

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Newsletter
May 14, 2026

Anthropic Just Gave Small Business Owners a Real AI Operator

For years, small business owners heard the same promise: AI will change everything.

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Newsletter
May 12, 2026

3.8%. Rate Cuts Unlikely. What Do You Do Tuesday Morning?

Your suppliers are not waiting for the Fed.

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Newsletter
May 12, 2026

OpenAI Just Validated the Hardest Problem in AI. Here’s What That Means for Your Business.

OpenAI did not launch a new model this week.

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Newsletter
May 11, 2026

Jane Street Made $16.1 Billion in 90 Days. Here Is What Founders Should Steal.

Jane Street posted $16.1 billion in Q1 2026 trading revenue.

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Newsletter
May 8, 2026

Anthropic Is Building a Services Company. Here Is What It Means for the Mid-Market.

Anthropic just announced one of the most significant deals in enterprise AI this year.

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Newsletter
May 6, 2026

AI Is Not a Tool. It’s the Operating System Your Business Runs On.

The most important shift happening in business right now is not about which AI tools you are using.

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Operations & Finance

2 Cents from six50: The $3,200/Month Mistake Hiding in Manual Invoicing

Businesses lose $2,500–$4,000 per month not because customers won’t pay — but because invoices are sent late. Fixing this takes less than 7 days.

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Strategy & AI

2 Cents from six50: Why 70% of “AI Projects” Never Pay Off

Most AI initiatives fail because they automate activity, not outcomes. Projects tied to a measurable metric are 3× more likely to deliver ROI within 90 days.

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Operations & Efficiency

2 Cents from six50: One Automation That Saves 12 Hours a Week

Automating internal approvals (quotes, discounts, invoices, POs) saves 8–15 hours/week and reduces delays by 30–50% — with minimal tech changes.

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Automation Strategy

2 Cents from six50: The 3-Tool Rule That Keeps Automation from Failing

Automation stacks with more than 3 core tools see adoption drop by 40%. Fewer tools = higher usage, lower failure rates.

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Process Optimization

2 Cents from six50: Why Faster Automation Isn’t Always Better

Automating a broken process can make things worse. Teams that stabilize workflows first see 2× faster ROI and fewer rework cycles.

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