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Bob Dockendorff

Personal Finance, Retirement, Investing
“As Vice President at Claro Advisors in Boston, Massachusetts, Bob Dockendorff provides cash flow based financial planning and investment management services, with a strong emphasis on maximizing tax efficiency and employee benefits.”

Claro Advisors

Job Title:

Vice President


Bob Dockendorff is a financial planner with Claro Advisors, a fee-based Registered Investment Advisor in Boston, MA. Bob started his career as a tax attorney with Ernst & Young in 2010 and then moved to The Colony Group, a large private wealth management firm based in Boston, MA. At The Colony Group, Bob built and serviced financial and investment plans for high-net worth individuals and families, and also provided tax planning and preparation services, as well as estate planning strategies. Additionally, his focused on the implementation of investment, estate, and tax planning tailored to the specific goals of diverse clients.

At Claro, Bob focuses on delivering comprehensive financial planning and investment services to young families and individuals planning for retirement. He is a big believer in low cost index funds, closing the behavior gap, and achieving large financial goals by taking small, manageable steps in the right direction. He helps his clients achieve their financial goals through careful analysis and the development of long term plans that encourage consistent, achievable actions.

Bob graduated from the University of Vermont in 2006 with a degree in Philosophy, and has also obtained a law degree from Suffolk University Law School, as well as an LL.M. in Taxation from Boston University Law School. He holds a Series 65 licenses, and the Life and Health.

Outside of work, Bob enjoys golf and going to the beach with his wife, Caitlin, and two sons, Charlie and Tommy.


BA, Philosophy, University of Vermont

Assets Under Management:

$300 million

Fee Structure:

Assets Under Management, Retainer

CRD Number:


Insurance License:



Investment advisory services offered through Claro Advisors, LLC, a Registered Investment Advisor with the U.S. Securities and Exchange Commission ("SEC"). Claro does not provide tax, accounting, or legal advice to clients. Custody services and other brokerage services provided to clients of Claro Advisors, LLC are offered by Fidelity Brokerage Services LLC, Member NYSE/SIPC.

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July 2017
    Financial Planning, Retirement, Retirement Plans, Retirement Savings
October 2018
    Insurance, Financial Planning, Retirement Savings
August 2016
    Investing, Lifestage Based Planning, Retirement Plans, Starting Out
November 2017
    Career / Compensation, Investing, Stocks
April 2018
    Long-Term Care Insurance, Insurance

All Answers
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    Estate Planning, Investing
Is it a good idea to have a brokerage manage my investments, and if so, how do I find a firm to do it for me?
100% of people found this answer helpful

It sounds like you have a lot going on even with this new inheritance, so you should seek a full service firm. This is a firm that will:

  1. Start with a big conversation about your financial life, where it is, and where you want it to go
  2. Provide advice and accountabilty on things like your household cash flow, savings rates, work benefits, and any other area of finance that you have questions
  3. Provide guidance at each financial transition of your life (new jobs, lost jobs, college, marriage, retirement, medicare, social security, estate planning)
  4. Invest your capital to give you the best chance of meeting those goals

Stay away from "investment only" shops that claim to have the latest and greatest market-beating investments. The best firms in the industry use a disciplined, standardized investment approach to seek superior risk adjusted returns over the long term. For that service, along with all the financial planning I described above, will charge an annual fee of about 1% of your account size. 

Plenty of firms out there will be happy to help you, and they don't necessairly need to be in your geographical area. If you find someone online, give them a call because many good advisors work remotely with clients outside of an occasional face to face meeting. 

October 2018
    Financial Planning, Retirement, Asset Allocation, IRAs, Mutual Funds
What is the best way to simplify my portfolio and avoid a high tax bill on short- and long-term capital gains?
100% of people found this answer helpful
January 2019
    Debt, Estate Planning, Investing, Real Estate
Should I pay off a commercial loan principal monthly or invest the extra capital?
100% of people found this answer helpful
January 2019
    IRAs, Taxes
Do I have to make quarterly tax payments when performing a Roth conversion?
100% of people found this answer helpful
January 2019
    Real Estate, Taxes
Can my spouse and I claim expenditures for rehabbing our rental property when we file our tax return if the property did not sell in the year we paid for the expenses?
100% of people found this answer helpful
January 2019