
Retirement Roadmap Success Stories
At Pleasant Street Wealth Advisors, we take pride in helping our clients feel confident and clear about their financial lives. Read the success stories to learn more about how we help our clients Experience Their Wealth's possibilities.

Robert & Rebecca
Age: 56 and 52
Occupation: Biotech Executive and Professor
Primary Goals:
- Consolidate and organize their financial life.
- Create a tax-efficient income stream they will not outlive.
- Plan for healthcare expenses.
The Situation
Robert and Rebecca have enjoyed fulfilling careers, and they are looking forward to a retirement that is just as fulfilling. Robert has accumulated wealth throughout his career in biotech. He holds a variety of accounts, including 401ks from various employers, stock options, an ESPP, and multiple brokerage accounts. Rebecca is a tenured professor with a 403b and pension.
Robert has been handling their household finances throughout their working years, he feels good about the savings base they have built, but he is worried about their tax exposure when they start taking 401k distributions, pension income, and social security. Rebecca is concerned about healthcare costs if they retire before Medicare eligibility.
They admit they don’t know what they don’t know.
When it comes to retirement, Robert and Rebecca have more questions than answers.
The Approach
Robert and Rebecca are looking for an expert to advise them on the technical aspects of retirement, Social Security, Medicare strategy, and tax planning. They want to ensure their retirement plan enables them to live the retirement life they envision without worrying about running out of money.
The Results
Robert and Rebecca found working with the Pleasant Street Wealth team and following their Roadmap to Retirement TM Planning process was easy, enjoyable, and stress-free. They appreciated PSWA’s “team first approach” collaborating with their CPA, Bob, to ensure the tax planning and financial planning were coordinated. Their retirement plan included the following:
- Tax planning strategy that reduced their lifetime tax bill.
- Added elements for spending flexibility they didn’t know existed.
- A software-based client experience helping them track their key financial data and investments in one place.
- A plan to pay for healthcare costs in retirement before Medicare eligibility.
- Retirement withdrawal strategy built for reliability and longevity.
Today Robert and Rebecca are living the retirement of their dreams. They retired in their late 50s, spending the first years of retirement checking off bucket list trips around the globe. Now they split time between New England and Florida, spending time with their grandchildren every chance they get.
They have confidence knowing that they have a reliable income stream, allowing them to not worry about finances and enjoy their retirement.
They love being able to meet with their advisory team virtually, no matter where they are. The timely reviews help them make sense of the ever-changing tax laws, and the Pleasant Street team is always proactive, staying on top of any new opportunities for them.
Note: The above case study is hypothetical and does not involve an actual Pleasant Street Wealth client. No portion of the content should be construed by a client or prospective client as a guarantee that he/she will experience the same or a certain level of results or satisfaction if Pleasant Street Wealth Advisors is engaged in providing investment advisory services.

Barbara
Age: 75
Occupation: Retired
Primary Goals:
- Her husband passed recently, leaving her to manage her finances on her own for the first time in her life.
- She needs to update her estate plan.
- She is nervous about all of the financial news she sees on TV.
The Situation
Barbara and her husband have lived a life filled with joy. They were high school sweethearts and raised three beautiful children. She was a teacher until they started a family. Her husband worked in finance, retiring as an executive at a local bank. While Barbara feels well-informed about her financial life and the world at large, she reads the newspaper and keeps up with the news, which lately has been leaving her very concerned and feeling uncertain. Her husband always made sure she knew what was going on in their financial life, but he was the one making all of the decisions.
Now that he is gone, she isn’t confident she can handle the financial responsibilities on her own. She recently discovered that she is paying more for Medicare now that she is a widow, and she knows she needs to update her estate plan to ensure her estate doesn’t pay too much in taxes, but their estate attorney is no longer practicing, and she doesn’t know where to start.
The Approach
It was important for Barbara to meet with someone who would listen first and ask questions to understand her concerns. She wanted to be heard, not sold to. She wanted someone who could simplify the complexity of taxes and estate planning. She wanted a steady voice of reason in a world filled with financial media clamoring for her attention with a new crisis every day.
The Results
Barbara felt that the team at Pleasant Street Wealth Advisors took the time to listen. They were empathetic to her concerns and helped her remain steady in a volatile world. She appreciated that they understood her goals to create a legacy for future generations and also a memorial to her beloved husband. Through working with the Pleasant Street Wealth team, she was able to:
- Build a relationship with her advisory team built on trust, mutual respect, and understanding. Helping her to understand which news was actionable and what was just noise.
- Connect with a new estate attorney referred to her by the Pleasant Street team. They first helped her identify which strategies to incorporate into her plan and then introduced a few attorneys they had worked with on similar cases before. Barbara chose the person whom she connected with best.
- File an appeal with the Social Security Administration to eliminate her Medicare surcharge.
- Embark on a strategic gifting campaign to start reducing her estate, help her grandkids with college, and establish a permanent memorial bench for her husband in their favorite park.
Barbara now feels safe and secure in her financial life. She gets great joy from seeing her family benefit from the gifts she and her late husband are able to give. She has peace of mind knowing that she is part of the Pleasant Street Wealth family and that their team is working hard so that she can worry less.
Her favorite time of year is the early spring when all of the flowers bloom around her husband’s bench.
Note: The above case study is hypothetical and does not involve an actual Pleasant Street Wealth client. No portion of the content should be construed by a client or prospective client as a guarantee that he/she will experience the same or a certain level of results or satisfaction if Pleasant Street Wealth Advisors is engaged in providing investment advisory services.

Rick and Leanne
Age: 67 and 66
Occupation: Architect and Retired
Primary Goals:
- Improve investment investments..
- Reduce taxes.
- More holistic advice and guidance.
The Situation
Leanne retired from a fulfilling career as a Real Estate agent. She loved connecting with people and helping them find the right home for their families. It’s also how she met her husband, Rick. He is an architect who continues to work with a select group of clients. He isn’t sure that he wants to retire yet. He loves the work he does and the clients he works with.
The challenge isn’t overcoming any financial mistakes or limitations. They have been doing all of the right things and could certainly retire right away with well-funded retirement accounts and ample savings.
They have had a long-time relationship with their broker at a big institution. He only seems to call them with a hot new investment idea. They have asked about withdrawal strategies and taxes, but their broker never really has answers. He is just focused on the next investment idea.
Rick and Leanne wanted to see what other advisor options were out there.
The Approach
Rick and Leanne wanted a true financial planner. They were concerned with more than just their investments. They wanted help with the entire financial picture, especially taxes. Rick wanted specific guidance on financial planning opportunities for people who only partially retired and continued working on their own terms into their 70s.
The Results
Rick and Leanne found the team at Pleasant Street Wealth Advisors to be exactly what they were looking for.
- The advisory team listens to their questions and provides detailed answers. Helping Rick and Leanne understand the recommendations the team makes.
- The investment team built a tax-efficient portfolio that reduced their risk while improving return.
- Their lifetime income strategy is designed to lower their lifetime taxes while improving income longevity.
- They love receiving monthly client newsletters, which are packed with timely financial planning content and clear, concise market views.
- They always look forward to their quarterly meetings to get updates on how they are doing but also pick up great information to share with their friends and family.
Rick and Leanne love working with Pleasant Street Wealth Advisors. The client experience is so personal and high touch, yet the team has the resources and depth of experts of a large institution.
This year Rick finally retired after working into his 70s. His last project was building their retirement dream house, with enough room for all of their kids and grandchildren.
Note: The above case study is hypothetical and does not involve an actual Pleasant Street Wealth client. No portion of the content should be construed by a client or prospective client as a guarantee that he/she will experience the same or a certain level of results or satisfaction if Pleasant Street Wealth Advisors is engaged in providing investment advisory services.