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Episode #21 – Chance Favors the Prepared: Small Business Edition

In this episode, Rusty Dripedge and Bobby Downspout explore how preparation drives real growth in small business. From hiring before you need to, to buying your next truck or upgrading your space ahead of demand, being ready is often the difference between thriving and stalling out.

Dennis introduces his Business Growth Chart—a tool that helps business owners forecast needs, avoid self-imposed ceilings, and build for the future. They share real stories from Cape Cod Gutter Monkeys and other businesses that hit roadblocks because they didn’t plan ahead—and those that broke through by thinking one step ahead.

Whether you're in your garage or your growth phase, this episode shows why smart, strategic planning is one of the best investments you can make. Because chance favors the prepared.

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Nicole Spencer has built a life around movement—not just as a runner, but as a nonprofit leader, coach, and now founder of Apex Strategy Partners. In this episode, she shares how a simple love of running became a tool for healing, leadership, and impact.

From organizing a 275-mile relay from Ground Zero to Cape Cod, to raising hundreds of thousands for veterans, to helping small organizations find their footing—Nicole shows us what it means to lead with heart. Her story is a reminder that in a noisy, complex world, purpose doesn’t have to be complicated.

Sometimes it just starts with putting on your shoes and walking out the door.

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Most small businesses never look beyond the day-to-day—or maybe a year out at best. But if you want to build real value, you need a plan that reaches further.

In this episode, Chris and Dennis walk through what a true five-year business plan looks like: how to set short-term goals, when to reassess and pivot, and why defining what business you’re actually in is a critical early milestone. (Hint: Dennis thought he was in the ski business. He wasn’t.)

Whether you're starting fresh or already in year two, this episode lays out a clear, practical path to growth—how to set real goals, track your progress, make smart adjustments, and stay focused on building a business that lasts.