Redwood Case Study:
Building for Retirement
Meet Mark & Jennifer
In their mid-50s, Mark and Jennifer weren’t asking, “Can we afford to retire?” Rather, they wanted to understand how (and more importantly, when) to retire the right way.
At 57 and 53, Mark and Jennifer spent decades building successful careers. Mark was an engineering director and Jennifer owned a thriving small business. While retirement wasn’t imminent, they still wanted the freedom to make work optional.
The pair knew they were in good financial shape, and they didn’t come to us looking for a complete overhaul. Instead, they wanted to find a seasoned guide and a structured framework to make informed decisions that would support their plans.
Clarify their long-term plan to provide flexibility in retirement
Manage portfolio risk as retirement neared
Keep taxes in check, both now and in the future
Balance their desire to save for their children’s college with their other more immediate financial needs
Mark & Jennifer’s 4 Key Questions
Should we keep all of Mark’s company stock? If not, how can we offload it in a tax-effective way?
How do we smartly draw from the Inherited IRA from Jennifer’s parents, and what will the tax ramifications be?
How can we prioritize college costs, a remodel, and future retirement without derailing our plan?
We don’t need to retire yet, but how do we prepare to make work optional in the next 5–10 years?
How We Helped
After getting a sense of Mark and Jennifer’s immediate priorities and longer-term plans, we hit the ground running to bring all components of their finances into one integrated plan.
We modeled several retirement timelines, each of which was stress-tested for key factors including longevity, tax impact, and flexibility. Mark and Jennifer appreciated how these models made them feel more informed and confident in their decisions moving forward.
College Tuition & Renovations (Spend Bucket):
We used ETF and stock proceeds to cover some of those major upcoming expenses, including college and a home renovation project. In addition, we set up a securities-based lending solution, which provides Mark and Jennifer with some optional liquidity they can access during periods of market volatility. This liquidity also enables them to sell and draw down taxable assets more strategically throughout retirement.Company Stock & Portfolio (Grow Bucket):
Working with their CPA, we developed a tax-focused strategy for selling off some of Mark’s concentrated stock positions in phases. Selling some of his employer stock gave Mark and Jennifer access to greater cash flow, reduced risk in their portfolio, and eased their concerns about feeling overexposed to one stock. We also transitioned from passive ETFs to a more customized portfolio to enhance their tax efficiency and flexibility.Retirement Income & Legacy Goals (Secure Bucket):
We adjusted their investment portfolio to pursue long-term growth with a focus on producing income in retirement.
Since Mark and Jennifer didn’t need their retirement funds immediately, we recommended investing Jennifer’s inheritance for aggressive growth and deferring distributions for later, providing them longer lasting income throughout retirement.
The Outcome
- Mark & Jennifer feel more confident having their assets now align with their life goals
- No longer are they overexposed to Mark’s company stock, which brings a great sense of relief
- They’re confidently covering more immediate expenses, like the home renovation, without disrupting their portfolio’s long-term growth
- Jennifer has leveraged her Inherited IRA into a future income source for retirement
By optimizing their existing resources and addressing their biggest concerns head on, Mark and Jennifer now have a clear path to and through retirement. More importantly, they have what they wanted all along—options, flexibility, and reassurance.
