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Management Team

Tom_PTom Penland
Founder | CEO

Tom grew up in Cleveland, Ohio as the second oldest of five boys, raised by a loving, single Mother and Grandmother. He learned the value of family and pitching in. He began working 32 hours per week in the kitchen of the local hospital during his high school years and helped care for his youngest brother while his Mother worked. His financial career began in the early 80’s as a fully registered rep/stock broker, working in the offices of Shearson Lehman Brothers, overlooking Lake Erie. He did very well, achieving the “Rookie of the Year” award his 1st year. His career and client list grew quickly until October 1987 when he experienced his first market crash, as an advisor. He says, “I was naïve. I thought the highly paid analysts really knew something when they told me what to ‘sell’ each morning. My confidence was shaken and over time it all seemed more like a game of chance. I became less comfortable asking people to ‘risk’ their hard earned money.” He made a change, educated himself in ‘safe money’ strategies and principal preservation and moved to California.

Tom moved to the Southbay in 1989, where he has been an active member of the community since day one. Tom became a single father when his two sons Canaan and Easton were 3 and 6. Easton is now a cryptologic linguist in the Air Force and Canaan, having graduated summa cum laude with a degree in Business and Finance is following his father into a financial career. Tom says, “it is the biggest and most rewarding accomplishment of my life… being a Father. But, I wouldn’t want to start over.” He currently lives in Rancho Palos Verdes. He spends time volunteering to educate Wartime Veterans about little known benefits and he volunteers time at the Beach Cities Health District. Having been in the financial industry almost 30 years, Tom says, “By applying simple, safe, financial strategies clients have stopped losing money. It has been a pleasure helping them out pace others that are invested ‘in the market’. We all sleep better that way too.” He has come to advocate and follow the two rules of investing as stated by Warren Buffet; Rule #1-Never lose money, Rule #2- Never forget rule #1. Tom Penland has handed down his “Safety First” philosophy to his staff at Greenline Associates, believing that in the current economic climate most of us cannot afford to lose our hard earned money and very likely do not have the time to earn it back, once lost.

Tom said he owes his success to always treating others the way I would want to be treated. He says, “The best things I can give to my clients are the benefit of my knowledge, honesty, simplicity and the understanding that we all deserve to make our own choices. We are all different and we don’t all want or do the same things.” He is committed to helping the people that are worried about outliving their money and those that want to know the best ways to pass on their hard earned savings and investments to the people they love and care about the most.


canaanCanaan Penland
Retirement Planning Advisor¹

One of the most successful pioneers of global investing said that the four most dangerous words of investing are “this time it’s different.” No truer statement has ever been made about Wall Street. The only thing that you can consistently rely on in the financial markets is inconsistency. As a financial advisor, Canaan has repeatedly witnessed individuals make the exact same mistakes, especially those nearing retirement. Originally from Virginia, he graduated summa cum laude with honors from Roanoke College with a BBA and concentration in finance. His interests in the financial markets and portfolio design began well before becoming an advisor, with years of experience in complex market research and the development of investment analysis software. Now residing in Southern California, he educates investors and retirees on how to maximize the value and security of their portfolios and retirement plans. “Being a financial advisor is not a matter of telling people what to invest in, but listening to their concerns and circumstances and educating them on the best available options. There must be a great deal of understanding and confidence between the advisor and the client. It is a partnership…” says Mr. Penland. “The long-standing theory of ‘buy and hold’ has become ‘buy and hope’ with little understanding of the risks involved. Hope should never be part of an investment strategy and certainly not a retirement plan.” As an insurance-licensed Investment Advisor Representative with Brookstone Capital Management, he designs portfolios and retirement plans that meet the very specific needs and goals of each of his clients. Through COFE, he greatly enjoys educating individuals, couples, and business owners on the best options available, adding superior value and security to their financial future.


 Rosa Martin
Administrative Director

Rosa Martin has over 25 years of experience as an office administrator and program manager. As the highly valued Administrative Director at Greenline Associates, she is responsible for making certain everything operates effectively and smoothly in our busy work environment. She is a major team player and loves making our visitors and clients feel welcomed, as she genuinely likes people and wants to help. It goes without saying, “Rosa is a problem solver and self-starter”. She is a very fast learner, starting part-time as a receptionist and quickly advancing to her current role as a full-time and indispensable member of our team. We are grateful to have her at Greenline Associates!

Prior to her joining the Greenline, Rosa worked as a program director for the YWCA, a non-profit organization providing multiple resources to low income families. She ran her own programs and was highly active in all fundraising events. Rosa is a proud mother of a 17-year-old son and enjoys spending time with family. When time allows, she also enjoys crafting.


¹  Investment advisory services offered through Brookstone Capital Management, LLC (BCM), a registered investment advisor.  BCM and Greenline Associates are independent of each other.   Insurance products and services are not offered through BCM but are offered and sold through individually licensed and appointed agents.