CASE STUDY: THE HIGH EARNER
Creating Flexibility and Optionality.
Dave (51) moved up the ranks quickly at his publicly-traded Fortune 100 company and is now VP of Business Development. He manages a team of five directors and 31 high-performing sales representatives. Dave earns a very healthy base salary, has a bonus structure based on revenue targets, and receives equity compensation. Dave approached Pillar to help him stabilize and maximize his variable cash flow.
*For privacy reasons, these case studies do not include real client details.
The Challenge
Dave was referred to Pillar by a fellow business owner who recognized that his financial situation had become too complex to manage with his current advisors. As a high-level executive, Dave excels in his role and finds real purpose in his work, but the demands are relentless. His schedule often bleeds into evenings, weekends, and vacations, leaving little room for rest or time with his family. The pace is unsustainable, and he knows it and feels it.
Stepping away doesn’t feel like a realistic option. Dave earns a substantial income, has excellent benefits, and holds a significant amount of unvested restricted stock. While these financial incentives have rewarded his hard work, they’ve also made him feel chained to a role he can no longer see himself maintaining for much longer. He needed someone to help him understand what’s possible, evaluate the financial implications of leaving early, and create a strategy to protect what he’s built - without burning out in the process.
Pillar stepped in to help Dave build a roadmap that supports both his professional exit and his personal well-being.
The Pillar Effect
Stabilize the Foundation
Pillar built a plan to protect Dave’s equity compensation by taking advantage of stock discounts, tax-advantaged holding periods, and creating a liquidation plan. Pillar set up a more efficient taxable brokerage account to create flexibility and liquidity should Dave choose to retire before age 59½.
Maximize Assets
The team helped Dave optimize his 401(k) by maxing out pre-tax deferrals to reduce income and by funding up to the maximum profit-sharing limits via Mega Backdoor Roth Conversions.
Strategically Build
Pillar introduced Dave to a health insurance broker and helped him determine which policy would be most appropriate when he loses his company benefits and before Medicare begins at age 65. The team discussed Net Unrealized Appreciation and the Rule of 55 ahead of Dave’s retirement.
The Results
A Plan that Inspires
Clarity & Confidence
With Pillar’s help, Dave is organized and fully understands his options. He no longer feels overwhelmed by the complexity of his financial life.
A Secure Future
for His Family
Dave now knows that switching from his sales role to his own consulting practice in five years will allow him to provide for his family, use his assets wisely, and reduce tax burdens along the way.
A Steady Guide
Through the Journey
He has a trusted partner in Pillar Wealth to help navigate every step, decision, and life change alongside him and his family.
Are You Ready to
Rest on Pillar?
Our group of clients is affectionately referred to as “The 111.” We only work with 111 families at a time so that we can give each client the attention and high-level strategy they need.
Find out if you’re a good fit by contacting us using this form, or let us help evaluate your situation by answering questions to see where you land on our “Financial Complexity Scale."