Bill Sifflard
Entrepreneur · CEO · CMO · CSO · Inc. 500 Board Advisor
Hudson, NH · Monomoy Strategies
There's no shortage of AI content. Most of it is written by talented people who discovered entrepreneurship around the same time they discovered AI. What's missing is the other side of the equation: the wisdom that only comes from decades of actually running things.
I've been building and running businesses for nearly half a century — across food service, energy, financial services, and building supplies manufacturing. I've served as CEO, CMO, and CSO. I've recreated complete branding strategies for $300 million companies and built sales organizations that achieved unprecedented growth. As an Inc. 500 Board Advisor, I've had a front-row seat to what separates companies that scale from companies that stall.
For years I worked with one of the world's leading business coaching organizations, where I consulted and coached hundreds of organizations, from early-stage startups to established companies facing their next inflection point.
The Framework That's Defined My Career
Every business I've ever worked with goes through the same three phases:
You start by launching — figuring out who you are and what you do. You move into leveling — building systems, finding rhythm. Then comes the critical moment: leap or decline. Companies that refuse to leap don't stand still — they fall behind, because the market, the customers, and the competition keep moving.
For growth companies, every major revenue milestone demands a new transformation:
Each threshold requires a different organization, a different strategy, different people, different systems. Skip the transformation and you don't plateau — you decline.
Now — The AI Moment
I've watched a lot of technology waves come and go. I've seen businesses that rode them to new heights and businesses that dismissed them and disappeared. What's happening with AI is the biggest paradigm shift I've seen in nearly half a century of business — and it maps perfectly to the framework I've spent my career teaching.
Right now, every business is in the forming phase of AI. The ones that move through norming and into transformation will build capabilities their competitors can't match. The ones that wait will find themselves in the same position as companies that ignored the internet in the late '90s.
That's not theory. That's the pattern I've watched play out across industries for five decades. And it's exactly why I built The Vibe Entrepreneur.
My mission is to take everything I've learned — about building businesses, leading organizations, and navigating transformational change — and apply it to AI in a way that actually helps real entrepreneurs and business owners. Not the twenty-five-year-olds who grew up with technology. The people who built things the hard way, and now want to build them smarter.
I'm based in Southern New Hampshire — and loving every bit of it. New England is home: the Cape, Boston, and the beauty of New Hampshire. When I'm not working with businesses to transform their organizations, I'm with family, enjoying the region I've always loved. The work never really stops — but neither does the life around it.