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Frequently Asked Questions

Tailored Wealth is a great fit for executives and business owners in their prime earning years who are ready to design the next phase of their career and life. We specialize in helping high achievers plan a hybrid retirement, the intentional transition into more flexible, purposeful work on their own terms. Founded by Dan Pascone, a former corporate executive turned business owner, the firm understands the real pressures you carry and turns complex tax, equity, and income decisions into one clear plan.

Because a custom financial plan is the foundation everything else grows from. Think of a wealth partnership like a tree, with your plan as the roots. To make confident money decisions that fit your goals and your life, you need that clear plan first. We use comprehensive planning software to map your full picture, model what-if scenarios, and weigh tradeoffs, then pair that data with our team's experience. Starting here also lets us work together, deliver real value early, and mutually decide whether a long-term partnership makes sense.

Tailored Wealth is built to be your one-stop financial partner, the quarterback of your financial team, so you coordinate with fewer professionals, not more. We start with your plan, then execute it with precision across cash flow, retirement, risk management, insurance, taxes, and legacy planning. We manage investments and help with equity compensation, trust coordination, and thoughtful giving. For busy leaders, we add practical support like tax preparation, estate planning coordination, compensation and offer review, business exit planning, healthcare and benefits reviews, and family wealth education. Where you already have trusted advisors, we coordinate with them so everything works together toward your goals.

It starts with a custom financial plan, priced below market so you can see real value before making a larger commitment. Our plans risk free and backed by a money back guarantee. From there, ongoing clients choose from two simple pricing models: a flat ongoing fee, or a percentage of assets under management when we manage investments. Every option is net to you, with no hidden trading, product, or platform fees. Ongoing clients receive our full suite of services, from planning and investments to tax strategy, insurance, and coordination, for one transparent cost.

Yes. Tailored Wealth is legally and ethically bound to act in your best interest at all times. We are fee only and compensated solely by the transparent fees clients pay, not by investments, products, or referral kickbacks. Our advice is independent, objective, and aligned with your goals, and we are structured to minimize conflicts of interest as your long term planning and investment partner.

We tie portfolio design directly to your financial plan and the timing of your cash flow needs. Using our proprietary Life Driven Investing framework, we fund near term spending with cash and guaranteed income, then align short term, midterm, and long term buckets to appropriate risk and growth engines to lower sequence risk. Portfolios are diversified across public markets and selectively include private investments for added diversification and upside. We rebalance with discipline, manage taxes, and adjust as your goals evolve.

Yes. We integrate equity decisions into your financial plan so each grant, vest, exercise, and sale serves your goals. We model scenarios to minimize taxes and surprises, including AMT for ISOs, sell-to-cover for NSOs, RSU same day sales, ESPP holding periods, and 10b5-1 trading plans when helpful. We also manage concentration risk and turn company stock into a funding engine for other priorities.

Tailored Wealth helps executives and business owners navigate every kind of career transition, whether you are stepping into a new role, negotiating a promotion, moving toward full retirement, or designing a hybrid retirement. For many leaders, that next phase means shifting from a corporate seat into business ownership. Whatever the move, we align it with your financial plan so each decision supports the income, taxes, equity, and life you want. The result is clarity and confidence at a moment when the stakes are high.

We help founders get exit-ready early and turn valuation into a lasting outcome. We model deal structures and cash vs. rollover decisions, coordinate with your CPA and attorney, and design tax-smart strategies such as QSBS §1202 planning, pre-event charitable giving, and post-sale diversification. We also plan for life after the close by aligning cash flows, investments, and estate goals so the next chapter funds what matters most.

It starts with a Wealth Clarity Chat, one focused conversation where we get to know you, your financial situation, and what you want to accomplish. You also get to know us, how our process works, and what you would gain from a custom life-driven financial plan. The goal is simple: decide together whether there is a mutual fit. We answer every question you have and walk through the process in more depth. If it is a fit, we build your custom plan, a stage that is risk free and backed by a money back guarantee.

Our Process

The 5 P’s of an Effective Wealth Management Partnership

Designing Portfolios Based off of Life Goals

The New Version of Retirement

Tax Diversification