Meet Jake — owner of Cobscook Financial

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