From Winning to Losing

Welcome to this week's edition of The Weekly Trail Report, where we share,

1 Story, where real stories of architects and engineers meet tailored financial strategies,

1 Actionable Tip, to provide actionable insights and guide you towards financial success,

1 Financial Term, to demystify key concepts and empower your decisions.

Whenever you’re ready, there are 2 ways I can help you:

1. Want to Experience Financial Abundance? Download the Guide!

The Wealth Blueprint: The Architect's and Engineer's Guide to Financial Peace, Confidence, and Abundance

This guide serves as a roadmap, helping you lay the financial foundation that supports not only your business success but also the life of freedom and fulfillment you deserve.

Download The Wealth Blueprint

2. Ready to Transform Your Financial Future? 

Schedule a complimentary consultation to unlock your financial potential. 

During our call, we will explore personalized strategies to help you overcome your financial challenges and achieve your goals. 

Your path to financial freedom starts with a deliberate choice today.

Schedule Your Free Consultation

1. Story: From Winning to Losing

Cory, a 45-year-old engineer and firm owner, had always prided himself on being financially savvy. Years ago, he picked a handful of individual stocks that performed exceptionally well; one in tech, one in energy, and another in a booming consumer brand. Over time, those positions exploded in value and grew to represent a huge part of his portfolio.

What started as a few thousand dollars had quietly turned into several hundred thousand, a significant portion of his net worth.

“I knew I was overweight,” Cory admitted in our first call. “But those stocks had done so well for me. Selling felt like admitting I didn’t trust my own judgment.”

The problem wasn’t picking winners, it was holding them without a plan.

Cory wasn’t watching the companies closely anymore. He didn’t have exit criteria or a strategy to protect gains. And as market volatility returned earlier this year, one of those stocks, his biggest winner, dropped over 40% in just a few months.

“That one drop wiped out two years of gains,” he said. “It felt like a punch in the gut. I kept thinking, why didn’t I sell some when I had the chance?”

That experience forced him to step back. 

He realized he didn’t want his financial future hinging on a few companies he no longer actively followed. What he needed wasn’t another “hot pick”, he needed a system.

We started by mapping out his entire financial picture: business income, personal cash flow, retirement goals, and risk tolerance. Then we broke down each stock:

• What role did it play in his portfolio?

• How much risk was it adding?

• What was the worst-case scenario if it dropped further?

Together, we created a structured drawdown plan. Instead of dumping everything at once, which could trigger taxes and emotional whiplash, we set thresholds for selling in stages. We trimmed the biggest positions and reallocated into a diversified portfolio built around his long-term goals.

“I didn’t want to completely abandon my picks,” Cory said. “But now I know exactly how much I’m willing to risk. And when it’s time to take chips off the table, I don’t hesitate.”

We also built rules for the future. Any new stock positions would have pre-defined sell triggers, automatic rebalancing, and clear limits so emotion would no longer drive his decisions.

Now, instead of watching a single ticker dominate his mood, Cory feels calm. His portfolio is balanced, his business is thriving, and his investments are finally aligned with the life he’s building.

“My money finally feels like it’s working for me, not the other way around.”

2. Actionable Tip: Don’t Let Winners Turn Into Anchors

It’s a great feeling when a stock you picked takes off. You watched it climb. You told your friends. You might’ve even felt like a genius.

But that winner, the one that tripled, quadrupled, or more, can become a hidden liability if it starts to dominate your portfolio.

What starts as a smart investment can quickly morph into a concentrated risk. You may feel emotionally attached or fearful of paying taxes, so you avoid selling. But doing nothing can be more dangerous than locking in a gain.

The bigger your position gets, the more damage it can do in a downturn. And if that money is meant to fund your retirement, your freedom, or your family’s future, why leave it exposed?

A good financial strategy protects what you’ve built. That often means taking chips off the table and redeploying them more strategically.

Celebrate your gains. 

But don’t let your winners turn into anchors.

3. Financial Term: Concentration Risk

Concentration risk is what happens when too much of your wealth is tied up in a single stock, sector, or asset. It’s like walking a tightrope without a safety net. When things are going well, it feels great. But a stumble can wipe out years of growth in a matter of days.

Many firm owners accumulate concentrated positions over time, maybe from years of working at the same company, investing in what they know, or simply not knowing when to sell. The risk builds slowly and often goes unnoticed until volatility hits.

Managing concentration risk doesn’t mean abandoning your winners. It means developing a strategy to reduce exposure in a thoughtful, tax-efficient way. That might include gradual rebalancing, setting price targets, or using charitable giving strategies.

The goal isn’t to kill growth, it’s to protect what you’ve built and ensure your future isn’t riding on the performance of just one asset.

Happy Trails,

Ryan

Disclaimer: We employ fictional characters to illustrate financial concepts faced by individuals in the architecture and engineering industry. Any resemblance to real persons, living or dead, is coincidental. While the stories are inspired by our experiences, the specific details, circumstances, and outcomes mentioned are entirely fictional and created for educational purposes only. Real client information is strictly confidential and never disclosed without explicit consent. Our aim is to provide relatable examples for educational purposes, respecting the privacy and confidentiality of our clients. This information is presented for educational purposes only and is not to be considered financial, tax, legal, or investment advice.