The Challenge

When Karen came to Plancorp, she was overwhelmed. She suddenly found herself responsible for a complex estate and trust structure she’d never been involved in:  

• A SLAT her husband had created where she was beneficiary but not trustee  

• A fully funded Generation-Skipping Trust (GST) earmarked for children and grandchildren  

• Multiple taxable and retirement accounts titled across several entities  

• Inconsistent income distributions and unclear tax obligations  

Her biggest concerns were:  

• What can I spend?  

• How do these trusts work now that he’s gone?  

• Am I making mistakes I don’t even know exist?  

This wasn’t basic advice—it demanded a holistic strategy to protect her lifestyle, simplify complexity, and honor her family’s legacy. 

What We Found

Our review uncovered several complex issues that needed immediate attention: 

1. SLAT Distribution Rules Were Misaligned with Her Cash Flow Needs

The SLAT had strict provisions restricting when and how Karen could access funds.  

Her husband had always coordinated distributions manually with the trustee — a process that died with him.  

Without intervention, Karen would either:  

• Take too little and under-fund her lifestyle, or  

• Take too much and violate trust terms with unintended tax consequences 

2. The GST Trust’s Allocation Schedule Was Not Coordinated with Her Own Estate Plan

The GST Trust had a highly technical distribution structure that:  

• Benefited her children and grandchildren  

• Avoided estate tax across generations  

• But required precise long-term planning to avoid over-distributing or collapsing the trust prematurely  

Coordinating her estate plan with a trust that bypasses her future estate added a layer of estate tax and legacy complexity that required expert modeling. 

Our Approach

We focused deeply on solving these two issues — no fluff, no surface-level fixes. 

1. Built a Dynamic Cash-Flow Plan Coordinated with SLAT Provisions

We:  

• Untangled trust rules and mapped a clear distribution plan so Karen could spend confidently without risking tax penalties. 

• Modeled her ideal lifestyle spending through a financial independence analysis (FIA) 

• Structured tax-efficient distributions aligned with legal requirements  

• Created a trustee communication protocol so distributions were automated, consistent, and compliant  

This ensured she could live comfortably without jeopardizing the trust’s integrity or tax status. 

2. Integrated Her Personal Estate Plan with the GST Trust’s Multi-Generational Design

To avoid future estate tax issues or conflicts among heirs, we:  

• Coordinated her personal estate plan with the GST trust’s long-term distribution plan  

• Modeled the impact of different timing and amounts of distributions  

• Updated her beneficiary designations, powers of attorney, and titling  

• Built a 30-year projection showing how the GST trust supports her legacy goals without reducing her lifetime flexibility  

We transformed scattered documents into a cohesive legacy strategy—giving Karen confidence her wealth will support her life and her family for decades.

3. InspireHer Support

Beyond the technical work, we guided Karen through education sessions, workshops, and peer discussions through Plancorp’s InspireHer community.  

She went from hesitant and overwhelmed to confident and engaged — understanding, for the first time, how her family’s wealth truly works. 

The Outcome

• Created a clear, compliant cash-flow plan coordinated with the SLAT’s legal provisions  

• Integrated her estate plan with the GST trust’s multi-generational structure  

• Eliminated risk of misdistribution, IRS scrutiny, and unintended estate tax exposure  

• Fully clarified her long-term financial independence through FIA  

• Helped her gain confidence and clarity through InspireHer’s education and support  

She moved from quietly anxious to deservedly carefree—knowing her plan was solid and her future secure. 

The Challenge

Even though they had accumulated wealth, like many self-directed investors, Tom and Rachel’s portfolio reflected years of reactionary decisions—what they’d heard from friends, read online, or chased during market highs.  

Their challenges included:  

• No cohesive investment strategy or clear asset allocation  

• Overlapping and redundant holdings across multiple accounts  

• Tax inefficiencies caused by short-term trades and emotional buying/selling  

• Anxiety about market volatility and “missing out” on trends  

Tom and Rachel’s portfolio was a patchwork of reactionary decisions—creating risk, inefficiency, and stress. 

What We Found

Through Plancorp’s portfolio analysis, we discovered:  

• Over 130 individual positions across taxable and retirement accounts  

• Heavy overlap in U.S. large-cap stocks, with minimal international or fixed-income exposure  

• Nearly $80,000 in avoidable capital gains taxes triggered over the previous three years due to unnecessary trading  

• No consistent rebalancing or tax-loss harvesting to maintain alignment  

Our Approach

We educated them on our evidence-based approach—simplifying complexity and restoring confidence.  

Then, we:  

• Transitioned their portfolio into one of three Plancorp investment models, tailored to their risk tolerance and personal values.  

• Strategically reallocated their assets to reduce overlap and improve tax efficiency.  

• Implemented systematic rebalancing and tax-loss harvesting to capture opportunities and maintain discipline during market swings.  

• Provided ongoing education so they understood the why behind every move—building trust and alignment.  

Our advisors also coordinated with their CPA to ensure all investment moves aligned with their tax picture.  

The Outcome

Within a year, Tom and Rachel’s portfolio shifted from chaotic to cohesive. Their strategy was clear, their tax drag was reduced, and—most importantly—they stopped reacting emotionally to the markets.  

When market volatility hit the following year, Tom said, “This is the first time I haven’t felt the urge to sell. I finally get it.”  

• Reduced taxable turnover by 40%, minimizing capital gains  

• Improved portfolio diversification and expected risk-adjusted returns  

• Lowered total investment costs by consolidating redundant funds  

• Emotional peace during market downturns  

• Trust that their portfolio is optimized and constantly monitored  

Now, when asked what they’d do differently, both Tom and Rachel give the same answer:  

“I wish we’d started with Plancorp sooner.” 

The Challenge

Mark and Ellen were ready for more time together—but had two core anxieties about early retirement: 

1. The emotional hurdle of drawing down their portfolio after decades of building it up.  
2. The complexity of managing multiple retirement accounts, tax buckets, and investment allocations without a clear strategy.  

They were ready for more time together—but not ready to take a financial leap without proof they’d be okay not just tomorrow, but for the long run.  

What We Found

Through onboarding, we collected every piece of their financial landscape: 401(k)s, IRAs, taxable investments, pension, and spending goals. We ran their Financial Independence Analysis (FIA) using over 1,000 simulated market outcomes to test the sustainability of retiring earlier than planned.  

Results showed:  

• 93% probability of success if Mark retired immediately instead of at 67.  

• A sustainable annual spending level of $200,000, with projected assets still exceeding $3 million at age 95.  

• An opportunity to reduce long-term taxes by beginning IRA withdrawals earlier, before Required Minimum Distributions (RMDs) kick in.  

Our Approach

We built a two-part proactive roadmap—balancing risk, taxes, and timing—so they could retire with confidence: 

1. Transition Planning:  
   1. Adjusted their asset allocation to lower risk as they moved from accumulation to drawdown.  
   2. Knowing the situation and their preferences, built a withdrawal strategy to fund the first five years of retirement from lower-volatility assets, reducing exposure to early market swings.  
2. Tax Optimization:  
   1. Balanced pre-tax and post-tax withdrawals to minimize future RMDs. 
   2. Created a plan for early IRA distributions to smooth out their lifetime tax liability.  

We also used the FIA to model “what if” scenarios: retiring now, waiting one more year, or increasing annual spending. The numbers gave Mark and Ellen clarity to make decisions confidently, not fearfully.   

The Outcome

Mark retired two years earlier than planned to focus on time with Ellen—without sacrificing their long-term financial security. They moved from uncertainty to strategic clarity—retiring two years early without fear of running out of money. 

• 93%+ probability of success confirmed for early retirement  

• Tax-efficient drawdown plan projected to save $250,000+ in lifetime taxes  

• Portfolio allocation optimized to reduce downside risk during early retirement years  

• Confidence to retire earlier without fear of running out of money  

• Clarity around how and when to draw from accounts 

The Challenge

When John and Brenda came to Plancorp, they already had estate documents—but they hadn’t been reviewed in over a decade. Their plan didn’t reflect their current wishes or protect their family’s long-term interests.

What We Found

• Their named executor had passed away.
• Assets were set to be distributed outright, leaving them vulnerable to lawsuits, creditors, or divorce.
• No provisions were made to fund their grandchildren’s education, despite that being one of their stated goals.

Our Approach

We updated their executor, introduced lifetime trusts for their children to protect inherited wealth, and added education funding clauses for their grandchildren.

The Outcome

With a few strategic updates, we helped John and Brenda:

• Protect nearly $5 million in family wealth from potential loss.
• Ensure tax-efficient wealth transfer to the next generation.
• Fund higher education for all five grandchildren.
• Gain the confidence that their wishes will be honored and their legacy preserved.

For John and Brenda, the value wasn’t just in tax savings or legal documents—it was in peace of mind. They now know their family will be cared for exactly as they envisioned, with less risk, less complexity, and no lingering uncertainty.

The Challenge

When John and Brenda came to Plancorp, they had an estate plan—just not one that reflected who they were today. Their documents were more than 10 years old and no longer aligned with their wishes or their family’s needs. 

Like many families, they were also hesitant to discuss money openly with their children. They wanted clarity and family alignment—but didn’t know how to start the conversation. 

What We Found

Our review uncovered several gaps that could have created significant stress and financial risk for their family: 

• Their named executor had passed away. 

• Assets were set to be distributed outright, leaving them vulnerable to lawsuits, creditors, or divorce. 

• No provisions existed to support their grandchildren’s future education—even though that was one of their top priorities. 

We also reminded them that estate planning isn’t just for families above the federal estate tax exemption. Every family needs clarity on decision-making roles, asset protection, minor/education planning, and efficient wealth transfer—regardless of net worth.  

Our Approach

We updated the foundational components of their plan to ensure accuracy, security, and alignment with their wishes: 

• Updated their executor to their oldest child, ensuring the right person was in charge. 

• Introduced lifetime trusts for their children to protect inherited wealth from outside risks. 

• Added education provisions to fund college for each grandchild. 

But the most meaningful part of this plan came next: 

We didn’t just update documents—we led a family education session that turned confusion into confidence. During the meeting, we walked their children through the structure of the estate plan, explaining why changes were made, and aligning everyone around John and Brenda’s goals. 

The Outcome

With a few strategic updates and guided conversations, we helped John and Brenda: 

• Protect nearly $5 million in family wealth from unnecessary risk 

• Ensure tax-efficient and protected transfer of assets to their children 

• Fund higher education for all five grandchildren 

• Create family alignment through a structured, advisor-led education session 

• Gain complete peace of mind that their wishes will be honored 

For John and Brenda, the value wasn’t just in updated documents. It was in knowing their family understands the plan, supports the vision, and will be cared for exactly as they intended—with less risk, less confusion, and no uncertainty. 

The Challenge

James’ income supports nearly all of the family’s financial goals and lifestyle — including their mortgage, tuition, and annual savings toward retirement. Like many high-earning professionals, James believed his employer coverage was enough—until we uncovered a $4.2M lifetime income gap. 

During a review of his overall risk management plan, we discovered that his employer policy only covered 60% of base salary with a $15,000/month cap — less than half his true after-tax spending needs. Bonuses, profit-sharing, and retirement contributions weren’t covered at all.  

If an injury or illness prevented him from performing surgery again, the family’s financial independence could be compromised overnight. James wanted to ensure his family’s future wasn’t dependent on his ability to work in a physically demanding specialty.  

What We Found

We ran a disability needs analysis that accounted for the family’s spending, income sources, and existing assets.  

Even with strong savings and investment accounts, the projection showed that a permanent disability would create a $4.2 million shortfall in lifetime income through James’ planned retirement age of 60.  

His employer plan would replace only about 35% of total income after taxes, leaving a significant gap in coverage.  

Our Approach

We built a plan to fortify their financial foundation—so their family’s future wasn’t left to chance: 

• Adding a supplemental disability policy tailored to James’ specialty, ensuring benefits would continue even if he could work in another capacity outside of surgery.  

• Structuring combined employer and personal coverage to replace up to 85% of their after-tax income, covering all fixed and discretionary expenses.  

• Coordinating policy design with their CPA to ensure premium payments were structured efficiently for tax purposes.  

• Incorporating disability coverage into the broader financial plan, updating projections annually as income and goals evolve.  

We also stress-tested their financial plan, showing that with the new policy in place, they could continue funding education, maintain their lifestyle, and meet all long-term goals — even under a total disability scenario.  

The Outcome

James and Laura now have the assurance that their family’s future is protected regardless of what life brings. Their updated financial independence analysis shows a 98% probability of success, even if James were unable to practice medicine again.  

When reviewing the plan, James shared,  

“It’s a huge relief knowing we’re protected. For the first time, I feel like I can focus fully on my work and family without worrying about the what-ifs.”  

• Coverage increased from 35% to 85% of their after-tax income 

• Lifetime income shortfall drastically reduced 

• 98% probability of success in their financial plan, even under total disability 

• Peace of mind knowing their family’s lifestyle and goals are protected 

Insurance is an often overlooked portion of any complete financial plan. We find many clients come to us under-insured adding unnecessary risk to the success they’ve built or uniquely over-protected in a way that could cause confusion should they want to file a claim. We help find the balance and keep it updated as your needs change. 

The Challenge

Like many executives, Sarah's wealth had grown faster than her diversification. About 40% of her net worth was concentrated in company stock. While she understood the theoretical risk, she was hesitant to sell shares that had performed well. 

At the same time, she faced complex tax challenges from RSU vesting and upcoming option exercises. Her equity plan hid costly surprises—under-withholding and concentration risk that could derail her goals. As an insider with material non-public information, there was a lot of fear around making the wrong choice. 

What We Found

Through a comprehensive review of her equity compensation plan and financial independence analysis (FIA), we identified:  

• Overconcentration in a single stock (40% of total net worth)  

• Under-withholding on RSU income, creating annual tax shortfalls  

• Expiring non-qualified stock options (NQSOs) that could lose value if left unexercised  

• Lack of a long-term diversification and liquidation strategy  

We modeled multiple outcomes, including a 30% decline in company stock, which would have reduced her retirement success rate from 95% to 82%. That’s a lot of eggs in one basket.  

Our Approach

We built a proactive strategy to diversify, capture value, and eliminate tax shocks—aligning her wealth with her vision:  

• Diversified systematically: Created a structured plan to sell shares as they vested, reducing company stock exposure from 40% to 10% over five years. All within the restrictions of an insider. 

• Planned for taxes: Adjusted withholding and estimated payments to avoid underpayment penalties and surprise tax bills.  

• Captured value: Exercised in-the-money NQSOs before expiration and evaluated ISO opportunities to avoid triggering AMT.  

• Integrated investments: Reinvested proceeds into a globally diversified portfolio aligned with her risk tolerance and long-term goals.  

• Collaborated with CPA: Ensured tax efficiency and compliance across every step of the strategy. 

The Outcome

By taking a proactive, evidence-based approach, our client gained both control and confidence over her equity wealth.  

• Reduced company stock exposure from 40% to 10% of total portfolio 
• Avoided potential six-figure tax liability through strategic planning  

• Captured value from expiring options before loss  

• Improved retirement probability of success from 82% → 96%  

• Peace of mind knowing her wealth is protected regardless of one company’s performance 

The Challenge

When John and Brenda came to Plancorp, they already had estate documents—but they hadn’t been reviewed in over a decade. Their plan didn’t reflect their current wishes or protect their family’s long-term interests.

What We Found

• Their named executor had passed away.
• Assets were set to be distributed outright, leaving them vulnerable to lawsuits, creditors, or divorce.
• No provisions were made to fund their grandchildren’s education, despite that being one of their stated goals.

Our Approach

We updated their executor, introduced lifetime trusts for their children to protect inherited wealth, and added education funding clauses for their grandchildren.

The Outcome

With a few strategic updates, we helped John and Brenda:

• Protect nearly $5 million in family wealth from potential loss.
• Ensure tax-efficient wealth transfer to the next generation.
• Fund higher education for all five grandchildren.
• Gain the confidence that their wishes will be honored and their legacy preserved.

For John and Brenda, the value wasn’t just in tax savings or legal documents—it was in peace of mind. They now know their family will be cared for exactly as they envisioned, with less risk, less complexity, and no lingering uncertainty.