Meet Jake — founder & owner of Cobscook Financial

Jake Vanidestine founded Cobscook Financial to raise the standard for insurance in Maine — delivering tailored strategies, decisive guidance, and a deep understanding of Maine communities to deliver meaningful service.

He began in the industry in 2017 while still in college, building a strong book of business in life insurance, mortgage protection, and retirement coverage — long before launching a firm. Before Cobscook Financial, Jake was the Financial Manager for a $2+ billion credit union, leading statewide development across Maine. Jake’s time as a business analyst in New York City gave him firsthand experience with national markets and high-level financial infrastructure — insight he brings home to strengthen local service and strategy in Maine.

With family roots in Lubec, Jake built Cobscook Financial on the values he grew up with: trust, clarity, and follow-through. Now based in the heart of Portland, he stays active in the business community as a board member for PROPEL Portland and serves as an adjunct faculty member in the business school at Thomas College. He holds a BA, MSEd, and MBA — all from Thomas — and ensures insurance planning feels simple, honest, and grounded in real life.