Caleb Crabtree Rand

Retirement Planning is what we do best. We develop custom strategies for retirement income planning, investment management, and tax planning opportunities to support your retirement. We started North Haven Financial because we see a great need to help people in achieve financial security so they can live a life that supports their values and their goals in retirement. If you are approaching retirement or have recently retired, we want to simplify the important decisions you need to make so you can feel confident in a plan that focuses on the priorities and values that are most important to you. We do not sell products or make commissions. We offer retirement planning, tax planning, and investment management, with a focus on retirement income. - Tax Planning - Health Insurance Planning (Medicare, ACA) - Social Security Claiming Strategies - Proactive Aging & Long-Term Care Planning - Estate Planning - Withdrawal Strategies / Pension Payout Options - Guaranteed Income Strategies - Charitable Giving Take a look at our services page for more details on how we can help you.

Mary Rodrigue is a PFS™ credentialed financial advisor with 31 years of industry experience. She has been with Kirkwood Private, LLC since 2006, where she is the firm's sole advisor. Kirkwood Private serves a limited number of high-net-worth individuals, families, related trusts, and private charitable foundations, providing comprehensive wealth management that integrates investment oversight with tax, estate, retirement, and trust planning. The firm operates primarily on a non-discretionary basis, emphasizing asset-class diversification and coordinating third-party managers to implement investment decisions.

Thomas Repeta is the sole advisor at Harbor Investment Advisors in Portland, ME, holding the CFA® designation along with Series 63 and Series 65 licenses. He has 22 years of industry experience and has been with Harbor Investment Advisors since 1998. Harbor Investment Advisors provides discretionary portfolio management primarily for individuals, trusts, and retirement plans, focusing on mutual funds, exchange-traded funds, and balanced allocations. The firm typically serves larger account sizes and combines top-down and bottom-up analysis using third-party research, managing accounts on a discretionary basis with regular reviews and detailed performance reporting.

James Kelly is a Series 65-licensed financial advisor at Northwater Capital with one year of industry experience. Prior to founding Northwater Capital, he worked for 17 years at Stein Mitchell Beato & Missner LLP. Northwater Capital provides investment management primarily to pooled investment vehicles and institutional-style clients, employing a tactical allocation strategy supported by proprietary algorithmic, machine learning, and AI models. The firm combines asset-based management for private funds with project-based hourly consulting services.

Michael Perna is a CFA® charterholder and holds a Series 66 license, with eight years of industry experience. He is the Managing Member of Flying Point Advisors and provides business consulting, accounting, and tax planning services alongside investment management. Prior to founding Flying Point Advisors, he worked at The Wanderlust Group for seven years. Flying Point Advisors offers financial planning and discretionary portfolio management primarily to individual and high-net-worth clients. The firm uses long-term, tax-aware investment strategies centered on broad diversification and low-cost index funds and ETFs, and uniquely combines advisory services with accounting and tax planning.

Bradley Mccurtain is a financial advisor at Maine Securities Corporation with 48 years of industry experience. He has been with Maine Securities Corporation since 1985. Outside of his advisory role, he is the sole owner of a coffee importing business that sells green and roasted coffee in the United States. Maine Securities Corporation provides investment advisory and portfolio management services primarily to individual clients, with a focus on quantitative value investing and the use of listed options for income and hedging. The firm operates a combined RIA and affiliated broker-dealer structure, offering discounted commission rates and occasional underwriting roles, along with an affiliated life and health insurance agency.