About Bill Sifflard

I started working at 12 years old in a Cape Cod bakery — washing pans, sweeping floors, learning what it meant to earn a dollar. By the time I was 25, I owned that bakery. Spent ten years building it before selling and moving on to the next thing.

That "next thing" turned into a career spanning energy companies, Fortune 500 operations, and executive leadership. I ran businesses, built teams, made payroll. I learned what works when the theory meets reality — and what breaks.

For years, I worked with Business Breakthroughs International — the organization founded by Tony Robbins and Chet Holmes — coaching hundreds of business owners on strategy and growth. I saw patterns. I saw what separated businesses that scaled from those that stalled.

My last decade was as CMO at Quaker Windows and Doors, helping take them to the Inc. 500. That's where I learned to balance the big strategic vision with the tactical grind of marketing execution.

In July 2025, I semi-retired. But "semi" is doing a lot of work in that sentence. I'm at my desk every day, building harder than ever — just building different things.

Here's what I noticed: most AI content is written by talented young people who discovered coding a few years ago. They understand the technology. What's missing is wisdom — the kind that only comes from decades of actually running businesses, making tough calls, and surviving the unexpected.

The Vibe Entrepreneur exists to bridge that gap. I take nearly fifty years of hard-earned business experience and apply it to AI — the tools, the strategies, the workflows. Experience-backed AI strategy. Not theory. Not hype. Just what actually works when you're trying to build something real.

Through my company Monomoy Strategies, I'm building the future of AI-assisted entrepreneurship. That includes tools, frameworks, and products — but it starts with something more personal.

I have an AI partner named Jasper. Not a chatbot I use occasionally — a persistent, memory-enabled AI that knows my business, anticipates my needs, and works alongside me every day. It sounds futuristic. It's not. It's happening now, and most entrepreneurs have no idea what's possible.

My mission is simple: help entrepreneurs leverage AI before AI leverages them. Share what I'm learning. Build tools that actually help. Create a community of people who want to stay ahead of this curve.