Client Success Story: How a Tech Professional and Business Owner Transformed Uncertainty into Strategic Clarity

Before Truly Aligned: High Compensation, High Complexity, and Big Questions

Tim, a senior software engineer at a top tech company, and his wife Nicole, a medical practice business owner, were in a strong financial position when they first came to Truly Aligned. Tim had accumulated significant equity compensation—millions in RSUs, ESPPs, and ISOs—while Nicole was expanding her private practice from a sole proprietorship to a full-fledged corporation. On paper, they were doing everything right.

But behind the scenes, they were asking themselves some hard questions:

• Am I really optimizing for tax efficiency, or just deferring a giant bill I’ll regret later?
• I know I need to diversify—but how do I know when, how much, or what to diversify into? What if I get hit with AMT?
• I want to retire early and stay retired—how do we make sure that’s possible?

They weren’t just seeking a bigger number in the bank—they wanted proof. Could they retire early and still provide for their kids no matter what the market or the company did? What would it actually look like to model that?

Like many high-performing couples juggling demanding careers and family responsibilities, they didn’t have the time or mental bandwidth to sort through complex planning decisions. They’d met with other financial advisors before, but no one had addressed their full financial picture—until Truly Aligned.

Challenges and Goals

When Tim and Nicole first came to Truly Aligned, they weren’t looking for surface-level investment advice. They were looking for clarity.

• Equity overload. Tim had accumulated multiple millions in company stock—but with it came tax exposure, AMT risk, and decision paralysis around when and how much to sell. Vesting cliffs, ESPP timing, and ISO strategy added even more complexity.
  • What many engineers find surprising is the emotional weight of holding concentrated stock. You’ve put years of effort, loyalty, and belief into building something — and when the stakes are this high, selling, even for smart diversification, can feel more challenging than expected. The fear of making the wrong decision can create hesitation, even when you know it’s time to act.

• Business Expansion without Strategy: Nicole was transitioning her medical practice from a sole proprietorship to a corporation and hiring employees. She needed strategic, proactive financial guidance—not reactive bookkeeping.
• Tax Inefficiencies: Their compensation structures created a messy, high-stakes tax situation. They were unsure how to minimize what they owed or whether they were missing opportunities.
• Lack of Integration: Retirement accounts, business income, equity, cash flow—it all felt disjointed. They wanted a cohesive, long-term strategy that gave them control and confidence.
• Uncertainty around retirement. They wanted to buy back their time and retire early, but weren’t sure if they were on track—or how to know for sure. They needed to see the numbers, modeled across different scenarios, to feel confident they could walk away without looking back.

What many engineers find surprising is the emotional weight of holding concentrated stock. You’ve put years of effort, loyalty, and belief into building something. That’s why letting go, even for smart diversification, can feel harder than expected.

The Turning Point: A Comprehensive, Personalized Plan

Tim and Nicole didn’t need more spreadsheets or sales pitches. They needed a financial plan that was intelligent, integrated, and aligned with how they wanted to live—now and in the future.

After working with Truly Aligned, they:

• Dramatically reduced their tax burden. Through charitable stock contributions, entity structuring, and strategic equity planning, we helped them stop overpaying and start keeping more of what they earned.
• Created a long-term strategy for stock diversification. We analyzed when and how much equity to sell, modeled AMT exposure, and helped them rebalance their portfolio away from overexposure to a single company—protecting their wealth without compromising growth. Using detailed projections and scenario planning, we helped them make confident, rational decisions—so the choice to diversify wasn’t driven by fear or guesswork, but by smart strategy aligned with their long-term goals.
• Helped Nicole scale her practice with intention. We evaluated the tax and growth implications of transitioning her business to an S Corp, then guided her through the setup and strategy shift. From choosing the right entity to setting up a retirement plan, we provided a clear roadmap that supported her expansion, unlocked significant tax savings, and created greater long-term flexibility for their family’s financial future.
• Built a plan to reach early retirement. Instead of guessing, they now have a defined timeline, target number, and strategy to reach financial independence—without sacrificing their lifestyle today. We ran different economic, tax, and market scenarios to give them confidence they could walk away—on their terms.
• Clarified their legacy goals. We facilitated estate planning conversations so their growing wealth is structured to support future generations and reflect their values.
• Gained a proactive financial partner. They no longer wonder if they’re missing something. We anticipate future challenges and bring new ideas before they have to ask—so they can focus on life, not logistics.

Implementation and Onboarding

From the very first step, the process felt focused and clear. Through our Financial Alignment Experience and Wealth Alignment Process, we helped them define what matters most—and built a strategy to match.

We consolidated their entire financial life into one clear plan, combining equity comp strategy, retirement planning, business advisory, and tax optimization under one roof.

The result? Less mental load. More clarity. Smarter decisions.

Results and Achievements

Today, Tim and Nicole feel clear and in control. They’re no longer reacting to financial decisions—they’re driving them.

Together, we’ve:

• Lowered their annual tax bill through equity, business and charitable strategy
• Diversified their investments beyond their employer to reduce risk
• Turned surplus cash into an intentional asset allocation strategy
• Aligned their business growth with their lifestyle and retirement goals
• Built a roadmap to early retirement—without sacrificing financial flexibility
• Established a plan for passing down wealth in a meaningful way

 

“The Financial Alignment Experience and onboarding process were key to understanding our current standing, future goals, and an overall plan to achieve them,” said Tim. “For potential clients considering Truly Aligned, we emphasize the clarity that comes from working with the company throughout the entire planning process. We are now much more confident that we’re executing on a plan that will help us reach early retirement while setting my wife’s business structure up for success.” 

 

Why This Matters for Other Tech Professionals and Business Owners

Many high-income professionals face the same questions Tim and Nicole did:

• Are you sitting on equity you don’t know how to handle?
• Are you building wealth—or just accumulating assets?
• Could a few strategic changes save you tens of thousands in taxes each year?
• Do you have a plan that aligns with your goals—or just a bunch of disconnected accounts?

We’ve worked with many tech professionals navigating concentrated equity and big life questions. If you’ve ever wondered whether you’re making the most of your success, it might be time for a different kind of conversation.

What Makes Truly Aligned Different?

At Truly Aligned, we do things differently.

Co-founder Erin began her career as an engineer, so she doesn’t just understand the mindset of high-performing tech professionals—she shares it. She knows the pressure, the analysis paralysis, and the complexity that come with equity compensation. She lives for the analysis. She gets the “what if” questions. And she loves turning scattered data into confident direction.

We don’t just talk about stock options—we model them, plan for them, and integrate them into your broader financial life. We’ve helped clients manage millions in equity, reduce unnecessary taxes, and build wealth that actually supports their lives.

Most financial advisors stick to the basics. We go deeper—into your taxes, your business, your values, and your future. Because real wealth isn’t just about what you earn—it’s about what you keep, how you grow it, and how aligned it is with your life.

If you’re a tech professional or business owner wondering if you’re truly maximizing your financial potential, let’s talk.

 

There is no guarantee that a diversified portfolio will enhance overall returns or outperform a non-diversified portfolio. Diversification does not protect against market risk. Rebalancing a portfolio may cause investors to incur tax liabilities and/or transaction costs and does not assure a profit or protect against a loss. Asset allocation does not ensure a profit or protect against a loss. This is a hypothetical situation based on real life examples. Names and circumstances have been changed. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. To determine which investments or strategies may be appropriate for you, consult your advisor prior to investing. This information is not intended to be a substitute for specific individualized tax or legal advice. We suggest that you discuss your specific situation with a qualified tax or legal advisor. The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual. All performance referenced is historical and is no guarantee of future results.