Zachary Winning, CFA®

Real estate creates opportunity — but it also creates complexity: uneven cash flow, taxes, timing, leverage decisions, and concentration risk.

I help real estate investors and real estate professionals coordinate a clear plan for liquidity, investing, cash flow, and long-term wealth. Whether your wealth is tied to transactions, rental income, development, brokerage, lending, ownership, or property acquisitions, the goal is to help ensure each financial decision fits into a broader strategy.

Real estate decisions rarely happen in isolation. Buying, selling, refinancing, scaling, distributing cash, reinvesting in the business, or preparing for retirement can all affect the rest of your financial life.

A physician's financial life is different from most professionals.

The career path often starts with years of training, delayed earnings, significant student debt, and limited time. Then income rises quickly, and the financial decisions become more complex: how much to save, how to invest, whether to pay down debt faster, how to evaluate employer benefits, how to protect income, when to buy into a practice, and how to plan for long-term wealth.

I help physicians and medical professionals coordinate these decisions into a clear plan. My focus is especially well-suited for physician practice owners, physician partners, high-income specialists, and established medical professionals who need planning that connects investments, benefits, taxes, risk management, practice ownership, and long-term family goals.

For Physicians Building Wealth After Training
Physicians often begin serious wealth-building later than peers in other fields. That can create a compressed planning timeline where savings rate, investment strategy, tax coordination, and retirement planning matter early.

Common Planning Issues:

• Transitioning from residency or fellowship to attending income
• Prioritizing student loans, savings, investing, and lifestyle goals
• Understanding employer benefits and retirement plans
• Building liquidity and emergency reserves
• Avoiding lifestyle creep after income increases
• Coordinating Roth, pre-tax, after-tax, and taxable investment accounts
• Protecting future earning power

For Established Physicians and Specialists
As income grows, decisions can become more technical. Higher compensation may create opportunities, but it can also increase tax exposure, investment complexity, insurance needs, and planning tradeoffs.

Common Planning Issues:

• Investment strategy and portfolio construction
• Retirement readiness and tax-sensitive savings strategies
• Employer benefit review and deferred compensation/supplemental retirement plans
• Education funding, charitable giving, and estate planning coordination
• Insurance and risk management review

For Physician Practice Owners and Partners
Practice ownership adds another layer of complexity. Your financial life may include both personal wealth and business value, and decisions inside the practice can affect your household plan.

Common Planning Issues:

• Practice retirement plan design (profit-sharing or cash balance plans)
• Partnership buy-ins, buy-outs, buy-sell planning, and disability buyout considerations
• Key-person and partner protection
• Practice succession planning
• Business cash flow and personal cash flow coordination
• Retaining associate physicians and key staff

Core Planning Pillars

• Student Debt and Cash Flow: Student loans, home purchases, family goals, retirement contributions, and taxable investing all compete for cash flow. I help physicians evaluate how those decisions fit together instead of treating each one separately.
• Income Protection and Risk Management: For physicians, future income is often one of the largest assets in the financial plan. Disability insurance, life insurance, malpractice considerations, and business-owner protections should be reviewed as part of the broader plan. (AAFP physician resources specifically highlight disability, malpractice, and life insurance as critical planning considerations.)
• Investment-Informed Planning: As a CFA charterholder, I bring an analytical perspective to portfolio design, risk management, diversification, and long-term investment decisions. For physicians with limited time and complex choices, the goal is to create a planning framework that is both rigorous and practical.

A thoughtful workplace wealth strategy can help business owners compete for talent, retain key employees, and reward the people who help drive the business forward.

For many companies, the right question is not simply, "Do we have a retirement plan?" The better question is, "Is our benefits strategy helping us achieve the goals of the business?"

That may include attracting stronger candidates, improving retention, rewarding leadership, creating owner and executive planning opportunities, and helping employees make more confident financial decisions.

Core Areas of Workplace Wealth Strategy

1. Retirement Plan StrategyYour company's retirement plan should be evaluated in the context of business goals, employee needs, owner objectives, and plan design opportunities.

This is especially important when business owners are considering whether their current plan is enough — or whether additional strategies may better align with their goals.

Areas of Focus:

• 401(k) plan evaluation
• Profit-sharing considerations
• Cash balance plan opportunities
• Safe harbor plan design
• Plan competitiveness and contribution strategy
• Investment menu review and participant education
• Provider and fee review
• Owner and executive retirement savings opportunities

2. Multiple Plan Evaluation

As businesses grow, leadership teams often need to evaluate more than one benefits strategy at a time.

A 401(k) plan may be the foundation, but it may not be the full answer. Depending on the business, ownership structure, employee demographics, cash flow, and retention goals, additional plan design conversations may be appropriate.

Areas of Focus:

• Whether the current 401(k) design is still competitive
• Whether profit sharing could support owner and employee goals
• Whether a cash balance plan may be worth evaluating
• Whether executive benefit strategies could help retain key people
• Whether deferred compensation planning should be considered
• Whether an ESOP or ownership transition strategy belongs in the conversation
• How multiple plans may work together as part of a broader workplace wealth strategy

3. Executive Benefits

For owners, executives, and key people, standard employee benefits may not fully address retention, retirement savings, or leadership continuity goals.

Executive benefits can be part of a broader conversation about how the business rewards leadership, retains important people, and aligns compensation with long-term priorities.

Areas of Focus:

• Nonqualified deferred compensation considerations
• Supplemental executive retirement strategies
• Executive-level benefit coordination
• Key-person retention planning
• Long-term incentive planning conversations
• Coordination with tax, legal, and plan professionals

4. Owner & Executive Planning Opportunities

Business owners and executives often have financial planning needs that go beyond the company retirement plan.

The right workplace wealth strategy should consider both sides of the equation: what the company is trying to accomplish and what the owners and executives are trying to accomplish personally.

Areas of Focus:

• Retirement savings strategy & deferred compensation planning
• Concentrated wealth considerations
• Business cash flow and personal cash flow coordination
• Tax-sensitive planning coordination & liquidity planning
• Succession, transition considerations, and estate/legacy planning coordination

Additional Leadership & Fiduciary Considerations

• Investment-Informed Plan Review: As a CFA^® charterholder, I bring a disciplined investment lens to workplace wealth conversations. That perspective can be especially valuable when reviewing how a plan's investment structure, participant experience, and executive planning needs fit into the larger financial picture (menu structure, diversification, risk/return tradeoffs, participant behavior, and plan-level oversight).
• Plan Sponsor & Fiduciary Awareness: Business owners do not need to handle every retirement plan detail alone, but they should understand that sponsoring a plan involves ongoing responsibilities. A thoughtful review process helps leadership teams ask better questions regarding plan design, fees, provider relationships, investment menu structure, employee education, and documentation.
• ESOP & Ownership Transition Conversations: For some business owners, employee ownership or an ESOP may be part of a broader succession, liquidity, retention, or legacy strategy. This planning area involves aligning business transition goals, owner liquidity needs, employee ownership considerations, leadership continuity, valuation, and financing.