Back to Monomoy Strategies

The Blog

Practical insights on AI, business strategy, and smart operations — from someone who's been building businesses for forty years.

April 15, 2026·8 min readleadershipAI strategyentrepreneurshipThe Vibe Entrepreneur

What Forty Years of Building Businesses Taught Me That AI Can't Replace

By Bill Sifflard · Founder, Monomoy Strategies

I use AI every day. It's already better than I am at a dozen things. But forty years in the arena made something else clear — the part the machines can't carry for you, and why that's exactly where the work is now.

Read More
March 9, 2026·10 min readAI agentsentrepreneurshipThe Vibe EntrepreneurleadershipAI strategy

I Built a Team of 5 AI Employees. Here's What I Learned in the First 30 Days.

By Bill Sifflard · Founder, Monomoy Strategies

Thirty days ago, I hired five new employees. They don't take lunch breaks. They don't call in sick. And at least two of them were working while I slept last night. Here's what I've learned — and why the entrepreneur's role isn't diminished by AI. It's amplified.

Read More
February 20, 2026·12 min readAI strategyentrepreneurshipAI agentsleadershipinnovation

I Built an AI Board of Directors. Here's What Happened.

By Bill Sifflard · Founder, Monomoy Strategies

Four frontier AI models. Three rounds of debate. One strategic recommendation. After forty years running businesses, I finally found the thinking partner I've been looking for — and it doesn't charge by the hour.

Read More
February 18, 2026·6 min readproductivityorganizationAI

Stop Losing Documents: The 10-Second Naming Convention Every Business Owner Needs

By Bill Sifflard · Founder, Monomoy Strategies

You scanned the receipt. You filed it somewhere. Three months later, you need it — and it's buried in a folder called "New Folder (3)." After forty years in business, I've watched this problem get worse, not better. Here's the simple formula that fixes it permanently.

Read More

Free Resources

Grab our free downloads — practical guides and tools built from decades of real-world business experience.