Blake wasn’t burned out. He wasn’t frustrated. He was ready.
After nearly two decades as a senior executive, Blake had built a reputation—and an income—to match. He was earning over $500,000 a year, managing teams, driving strategy, and sitting in rooms where decisions shaped industries. But after years of helping other firms grow, he wanted to do it differently. On his terms. With more freedom, more flexibility, and more alignment with the way he saw the world.
So, he walked away. Not to slow down—but to start something new: a boutique consulting and investment advisory firm designed around the relationships he valued most.
Blake didn’t come to me to figure out if he could afford the move—he could. He came because he understood that success in this next chapter wasn’t just about ambition. It was about structure. He wanted to get it right. And he wanted a team who had walked this road before.
I knew where he was coming from. When I left the firm where I’d spent more than a decade, I didn’t just change companies—I redefined how I work, who I serve, and how I wanted to grow. It meant moving from certainty to possibility. From familiarity to vision. That’s the kind of transition Blake was facing.
To bring order to the uncertainty, we used our RITE Framework—Risk, Investments, Tax, and Estate—a structure that high-performing clients like Blake use to make thoughtful decisions with real confidence.
Risk: Solid Ground Before Scaling Up
Blake’s first priority was keeping his financial life stable while his business gained traction. Though he had savings and a strong network, he wasn’t interested in white-knuckling through the early months.
We separated personal and business finances, funding a six-month reserve for each. We reviewed entity structures and landed on an S-Corp for flexibility and tax efficiency. Professional liability and umbrella insurance were added to match his new exposure as a founder.
These were moves you’d expect from a seasoned executive—strategic, measured, and designed to reduce stress. Planning gave him the ability to focus on building, not reacting.
Investments: Reframing the Portfolio Post-Corporate Life
In his corporate role, Blake’s investments were largely handled through payroll—401(k), deferred comp, and stock options. Now, with income patterns shifting, we needed to rethink his strategy through the lens of liquidity, tax planning, and opportunity.
We opened a Solo 401(k), initially favoring Roth contributions given his temporarily lower income. He also funded a taxable brokerage account to give him optionality—whether for investing back into the business or capturing future opportunities in the market.
We reviewed his legacy holdings, including employer stock and concentrated equity positions. They’d served him well, but in this next phase, diversification and flexibility were more valuable than nostalgia.
Even for a seasoned investor, the transition from executive to entrepreneur requires a fresh look at how capital supports both lifestyle and long-term goals. Blake embraced the shift.
Tax: Planning Forward, Not Just Filing Backward
When you leave behind a $500,000 paycheck, your tax picture doesn’t get simpler—it gets more nuanced.
From the outset, we included Blake’s CPA in our planning conversations. Together, we modeled income projections, structured distributions from his new business, and calculated quarterly estimates to avoid surprises. We built in tax-efficient retirement contributions and implemented an accountable plan for his new home office and business travel.
We also looked ahead: how would future income interact with QBI deductions, Medicare IRMAA thresholds, or Roth conversion windows? What would tax strategy look like once the business took off?
The answer wasn’t a single tactic. It was an ecosystem. With his CPA and our planning team aligned, Blake could focus on his clients, knowing the details behind the scenes were working in sync.
Estate: Rewriting a 15-Year-Old Plan for a 2025 Life
When we asked Blake for his estate documents, he sent over a binder from 15 years ago.
It was last updated when his kids were in elementary school. Today, they’re in their 20s. His assets had grown. His career had evolved. His goals had matured. The documents hadn’t kept up.
We brought in Marie Feindt, JD—our in-house estate planning strategist—to do a full review. Together, we updated his will, powers of attorney, healthcare directives, and trust structure. We discussed how ownership of the business should be handled, both during his lifetime and after. Would shares transfer to a trust? Would his spouse or children play a role in the future?
Marie helped simplify the complexity and make sure the documents reflected today’s values—not outdated assumptions from a past chapter.
For someone like Blake, who’s spent a career making smart decisions, it wasn’t about reinventing the wheel. It was about making sure the plan kept pace with the person.
The Next Phase Is More Than a Pivot—It’s a Philosophy
Blake’s story isn’t unique—but it is rare. Many people stay where they are because it’s comfortable. Blake chose to step into uncertainty, not recklessly, but with clarity and purpose.
Helping Blake reminded me why I love working with successful people in transition. They’re not trying to start over—they’re trying to do more with what they’ve built.
If that sounds like you—if you’re leaving behind a high-income role to build something more aligned, more intentional—here’s my advice:
First, give structure to your vision. The RITE Framework is how we help clients keep momentum without missing key steps.
Second, invest in the mindset required to lead this next chapter. Some of the books I recommend to clients in Blake’s position—and that shaped my own thinking—include:
The next phase isn’t about repeating the past. It’s about building something that reflects who you’ve become—and who you want to be next.
If that’s where you are, I’d love to help you think it through and structure it right.
Let’s talk before momentum becomes complexity. Let’s get ahead of it.
The strategies described above are complex legal structures that must be tailored to each family’s circumstances. Always consult with your own estate planning attorney and tax advisor before implementing any trust, gifting, or insurance strategy. Members’ Wealth does not draft legal documents and works alongside your legal counsel to support and coordinate your estate planning efforts.
These examples are for illustrative purposes only and do not represent actual client experiences. Individual results will vary based on personal financial circumstances and tax laws.
Stu Caplan is Senior Wealth Strategist at Members’ Wealth, a boutique wealth management firm that offers a comprehensive approach to serving individuals, families, business owners, and institutions.
The firm’s goal is to preserve and grow its clients’ wealth to endure over time, while thoughtfully evolving its strategy to suit an ever-changing world. With over 20 years of industry experience, Stu and the Members' Wealth team thrive on bringing clarity and confidence to clients' unique situations.
Stu received his MBA from The Robert H. Smith School of Business at the University of Maryland and his bachelor’s degree from the Eller College of Management at the University of Arizona. Stu resides in Bucks County, PA with his wife and two sons. He’s an avid golfer and is thrilled that his boys have embraced the game. He also volunteers his time as a board member of the PKD Foundation and Abrams Hebrew Academy.
To get in touch with the Members’ Wealth team today, I invite you to email info@memberswealthllc.com or call (267) 367-5453.
You can learn more about how we serve our clients by tapping the button below.
Investment strategies, including rebalancing, do not guarantee improved performance and involve risk, including potential loss of principal. Past performance does not guarantee future results.
The information provided is for educational and informational purposes only and does not constitute investment advice and it should not be relied on as such. It should not be considered a solicitation to buy or an offer to sell a security. It does not take into account any investor's particular investment objectives, strategies, tax status or investment horizon.
All information has been obtained from sources believed to be reliable, but its accuracy is not guaranteed. There is no representation or warranty as to the current accuracy, reliability or completeness of, nor liability for, decisions based on such information and it should not be relied on as such.
Investment advisory services are offered through Members’ Wealth, LLC., a Registered Investment Advisory Firm.
Registration with the SEC does not imply a certain level of skill or training. We are an independent advisory firm helping individuals achieve their financial needs and goals
Members’ Wealth does not provide legal, accounting or tax advice. Please consult your tax or legal advisors before taking any action that may have tax consequences.
This commentary reflects the personal opinions, viewpoints and analyses of the Members’ Wealth, LLC employees providing such comments, and should not be regarded as a description of advisory services provided by Members’ Wealth, LLC or performance returns of any Members’ Wealth, LLC client. The views reflected in the commentary are subject to change at any time without notice. Nothing in this commentary constitutes investment advice, performance data or any recommendation that any particular security, portfolio of securities, transaction or investment strategy is suitable for any specific person. Any mention of a particular security and related performance data is not a recommendation to buy or sell that security. Members’ Wealth, LLC manages its clients’ accounts using a variety of investment techniques and strategies, which are not necessarily discussed in the commentary. Investments in securities involve the risk of loss. Past performance is no guarantee of future results
Copyright © 2023 Members' Wealth LLC