Cliff Westberg's Pinehills Story
I had the privilege of growing up in Plymouth but dealt with long commutes to work in the corporate world of investments, consisting of dark suits, white shirts, and mahogany boardrooms. When I first read about the vision for The Pinehills—a walkable, nature-filled community with winding roads without street lights, lit walking trails, and a vibrant Village Green—it struck a chord. It felt like me.
After hearing more from Tony Green, John Judge, and Mike Babini of what they believed the dirt roads of The Pinehills would become, I was sold.
Tony had one condition for me: "This is not really going to be a suit and tie kind of place, professional and well done, yes, but warmer."
Inspired, I reached out to my clients and said, "I'm thinking of opening my own office in this place that doesn't even exist yet. Will you come along the journey with me?"
Fortunately, they said yes, because they trusted that I'd always do right by them—with integrity. That's where the name With Integrity Wealth Management came from.
Starting out wasn't easy. Construction delays meant we opened in 2003, a year later than planned, and it caused some nervous conversations. In the early days, Bob Hollis and I saw fewer than 10 cars pass our window each day, but Donna Tefft (The Pinehills original Marketing Director) told us "just you wait," and boy was she right! But also, back then I knew every road, every neighbor and even acted in a couple Pinehills Cabana Room Players plays—way outside my comfort zone.
More than 20 years later, we've grown alongside this amazing community—from 82 homes (office opening day) to thousands, dirt paths to thriving streets, jazz festivals to beer gardens. We weathered challenging times together, such as the Great Recession, which cost us a national hotel chain, but gave us Mirbeau Inn & Spa.
Today, I get to work in my hometown, in a beautiful and active community—not a concrete jungle. And best of all? I don't have to wear a suit anymore. Pretty great!
