How Two Educators Built $2.6M and Retired with Confidence
Key Numbers*
Net Worth
$4M
Invested Assets
with TrueNorth Wealth
$2.6M
* Data as of October 2025.
Subject to change.
The Smart Way to Give
David and Theresa wanted to give $50,000 to their favorite charities.
Instead of donating cash, we helped them donate appreciated stock they’d held for years through a Donor-Advised Fund.
When you donate stock directly to a charity, you get a tax deduction for the full market value and you never pay capital gains tax on the appreciation.
This strategy meant they could actually give more than if they’d sold the stocks and donated the proceeds after paying capital gains.
After donating the stock, they used cash to buy the same stocks back at current prices, thus “resetting” their cost basis to today’s value.
The result is that they were able to give more to the causes they care about, save thousands in taxes, and position their portfolio for better tax treatment in the future.
Over multiple years, this strategy has saved them significant money while allowing them to be even more generous.
David and Theresa spent their careers serving their community — David as a school administrator and Theresa in HR. They saved diligently without the help of a financial advisor, and built a $1.4 million portfolio by age 67.
But as retirement approached, they felt anxious. They weren’t completely confident they could afford to retire. They had no idea how much they could safely spend, and they were worried they were making costly mistakes without realizing it.
They wanted confidence in their entire financial approach as they prepared for this important transition.
The Vision
David and Theresa wanted straightforward answers on important decisions, such as how much they could spend in retirement without worrying, when to take Social Security, and whether their portfolio was appropriately set up for their stage of life.
Most importantly, they wanted to know they weren’t making significant financial mistakes that could hurt them later.
Meet David & Theresa
- David and Theresa are a classic example of “the millionaires next door.” They worked steady jobs in education, lived below their means, and saved consistently.
- By the age of 67, they had saved $1.4 million in their employer retirement plans. David had a pension from the school district, and they would both receive Social Security.
- Despite their success, they had never worked with a financial advisor. As retirement neared, they realized they didn’t want to risk making costly mistakes with money that had taken them a lifetime to build.
- They had questions about taxes, Roth conversions, investment strategy, and Social Security timing. The internet had too many conflicting answers.
- David was also doing some consulting work on a 1099 basis. This created opportunities for additional tax strategies, but they didn’t know what those might be.
TrueNorth Wealth Process
David and Theresa had done the hard part. They’d built real wealth through discipline and smart choices. Our job was to make sure that wealth worked as hard as possible for them in retirement.
We created a comprehensive income and tax plan specifically for their transition into retirement. This included analyzing their tax situation annually and optimizing their investment strategy for retirement income and legacy planning.
Our Strategic Solutions
- Each year, we analyze David and Theresa’s tax return for Roth conversion opportunities. The amounts have varied from $0 to over $100,000 based on their income that year. In total, we’ve converted well over $300,000 to Roth accounts that will never be taxed again.
- When David took on consulting work after “retirement,” we used that 1099 income to fund SEP IRAs. This gave him business-owner tax advantages he wouldn’t have had as a W-2 employee.
- David and Theresa give generously to charity each year. We helped them donate appreciated stock directly to multiple charities instead of cash. This saved them significantly on taxes while supporting causes they care about.
- We also helped them “bunch” their charitable donations across years. By giving larger amounts in some years and smaller amounts in others, they receive bigger tax deductions.
- We analyzed their Social Security options and helped them choose the optimal claiming strategy, maximizing their lifetime benefits given their expected lifespan.
- Because David and Theresa had a propensity for going back to work for stretches of time, we advised them to wait to take their benefits until 67, when they would no longer be penalized for having earned income. Factoring in the growth of their assets and likely lifespans, we determined they were most likely to be the most wealthy at the end of their lives by taking Social Security at 67.
Where They Are Now
David and Theresa’s portfolio has grown from $1.4 million to $2.6 million, nearly doubling in just seven years. They live comfortably off David’s pension and Social Security. Their investments continue to grow for their children’s inheritance.
They no longer worry about money. Their anxiety about making mistakes has been replaced by confidence in their trajectory. They know exactly how much they can spend and still leave a substantial legacy for their children.
Most importantly, they sleep well at night knowing they’re not making any significant financial mistakes that could derail their retirement.
This case study is based on a real client situation with names and certain details changed to protect privacy. Results may vary, and past performance is not indicative of future results.
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