Financial Planning Case Studies

Current State of Finances

Richard Whitman is in his early 60s, officially retired after the recent sale of his privately held company. The liquidity event pushed his net worth to over $57 million—most of it now held in cash and real estate. He and his wife have adult children in their 30s and several young grandchildren. With work behind him, Richard is turning his attention toward what comes next—not just for himself, but for his entire family.

Despite his wealth, his current portfolio is relatively simple. He’s been paying for traditional AUM services but recently realized…

Current State of Finances

Margo Sinclair has spent the past 30 years quietly building a sizable real estate portfolio. A former civil engineer turned full-time investor, she now owns more than a dozen residential properties—mostly single-family homes and duplexes—spread across four states. Her net worth is around $19 million, but nearly all of it is tied up in real estate. Rental income comes in reliably, but managing the portfolio has become increasingly demanding. Now in her early 60s, Margo is ready to retire. She wants less stress, more time with her grandchildren, and a plan that doesn’t depend on staying hands-on with every tenant and every tax bill.

Current State of Finances

Richard Whitman is in his early 60s, officially retired after the recent sale of his privately held company. The liquidity event pushed his net worth to over $57 million—most of it now held in cash and real estate. He and his wife have adult children in their 30s and several young grandchildren. With work behind him, Richard is turning his attention toward what comes next—not just for himself, but for his entire family.

Despite his wealth, his current portfolio is relatively simple. He’s been paying for traditional AUM services but recently realized…

Current State of Finances

Ethan and Claire Mitchell, a married couple in their mid-40s, have reached a pivotal financial moment. Ethan works for a rapidly growing tech company and recently experienced a substantial equity event tied to an early grant of stock options and RSUs. Between his and Claire’s salaries, their annual household income sits above $750,000. The couple currently rents their primary residence but owns undeveloped land in a more rural region where they plan to build a long-term home. They also have a modest seasonal property abroad for family getaways.

Current State of Finances

Ellen Parker, a successful executive in her early 60s, was preparing to retire after a long career with a publicly traded company. Her investment portfolio totaled just under $12 million, but more than $7.5 million of that was held in her 401(k)—with the majority concentrated in her company’s stock. The position had grown steadily over the years, and while it reflected years of loyalty and success, it now posed a serious risk to her retirement plan.

Current State of Finances

Mr. and Mrs. Carter, recent retirees, have stepped away from high-powered executive careers and are now focused on crafting a retirement life that aligns with their values. Mrs. Carter recently retired as CEO of a major national chain, while Mr. Carter built his career in finance. The couple has amassed a considerable portfolio, including approximately $20 million in cash savings and $15 million in invested assets. Much of Mrs. Carter’s current holdings are tied up in individual company stock from her former employer.

Current State of Finances

The Wagners have spent decades building a successful construction business, generating substantial wealth through ownership in the company, related ventures, rental properties, and land acquisitions. Their business is in the midst of a potential succession plan involving current partners, though it remains unclear whether those partners can afford to buy them out. The Wagners are navigating how to structure the exit in a way that is financially viable for everyone involved.

Current State of Finances

Daniel and Rachel Harper, a couple in their late 40s, have spent years building a successful law practice in Chicago. Their income has always been strong, ranging from $500,000 to $1.5 million annually depending on firm performance. But everything changed when they won a landmark case, resulting in a $5 million windfall.

That case dramatically shifted their financial picture. Their invested assets grew to $8 million almost overnight. With the new wealth came new questions: Should one of them retire? Both? Is now the time to invest aggressively or cautiously? Could they finally buy the home they’ve always wanted?

Current State of Finances

The Jim and Lisa Thompson, both in their late 60s, have recently retired and are now focusing on managing their significant wealth and enjoying their golden years. They have successfully paid off all their debts and have accumulated a wealth of $9 million, primarily in retirement accounts, stocks, and real estate. They spend about $180,000/year plus $60,000 on travel.

Current State of Finances

Jane and Keith Martin are in their early 60s and find themselves at a financial crossroads as they contemplate retirement. Jane is a Vice President at a Fortune 50 company, with a significant portion of her seven figure compensation coming from bonuses, deferred compensation, and a schedule of Restricted Stock Units (RSUs). The RSUs and deferred comp will vest and require payout in the 3 years following retirement. Keith has been managing their family’s many rental properties, which have been a steady source of income but also a point of uncertainty regarding their future financial strategy.