How we can help


Name: William and Janette
Age: 64 and 61, respectively
Occupation: Executive at a Pharmaceutical Bio-Tech Company
Current Net Worth: $3M (80% in company stock)
Projected Net Worth Post-Retirement: $7M

William and Janette have been married for 30 years and have two grown children - one child is financially self-sufficient, and the other is capable but needs guidance.

William and Janette are active philanthropically. Bob is a trustee on the Endowment Executive Committee at his alma mater; Mary is a founding member of a local community organization.

Janette has a complex benefits package that includes stock options, restricted stock grants and outright shares, as well as both qualified and non-qualified retirement plans.


Janette’s corporate and their joint philanthropic responsibilities leave little time to focus on their own financial situation. They are concerned about having the guidance, resources and support they need to make the right decisions about Janette’s complex benefit package.

Specific areas of concern include heavy concentration in company stock, stock option restrictions and the income tax implications of both stock sales and taxable lump-sum distributions.

Additionally, William and Janette are concerned about how to treat their two children compassionately and fairly.


Carolina Wealth can develop models and plans to help William and Janette have more clarity and feel more confident in their financial decisions. Our resources, guidance and support allow us to help them:

  • Build and implement a plan that allows William and Janette to manage their post-retirement cash flows and minimize income taxes with respect to both lump-sum retirement distributions and the exercise of stock options. 
  • Design a step by step plan to diversify out of Janette’s company stock by setting target prices to sell based on the cost basis of the various tranches. 
  • Establish appropriate portfolio models for their investments, retirement income and gifting plans, based on their unique risk tolerance, as well as their time horizon.
  • Design and implement an estate plan, in coordination with their estate-planning attorney and CPA, to meet their unique family dynamics and charitable goals


Name: Dr. Joshua
Age: 62
Occupation: Doctor and Co-Owner of the medical practice
Current Net Worth: $1.5M (exclusive of business)
Business Worth: $15M

The majority of Josh’s wealth is locked up in his practice. He is ready to retire, but doesn’t know if the sale of the practice will provide a stream of income to replace the salary and bonus that he has been receiving.

His goal is to monetize his interest in the practice. Josh would entertain an offer from a third-party buyer, but his partners will remain in the practice and will not entertain offers from parties outside of the business. Since there is no controlling shareholder, decisions regarding the sale need to be made jointly with his partners, who will be the buyer of Josh’s interest.


The original buy-sell agreement includes a valuation formula which does not fully address the fair market value of the business. The agreement was drafted early in the business’ life and was never revised when the company found success. Josh’s partners maintained that the formula in the original buy/sell agreement was adequate. However, Josh disagreed; he wanted to obtain full and fair market value for his interest but wasn’t sure how to determine what the business was worth.

Not only is Josh uncertain of the true value of the business, he doesn’t know how much he needs to sell the business for to provide a continuing stream of income into retirement.


Carolina Wealth can develop plans to help Dr. Josh have more clarity and feel more confident in his financial decisions. Our resources, guidance and support allows us to help him:

  • Identify and lead a team that includes specialist attorneys (contract, litigation and tax), a CPA and valuation experts.
  • Review proposals and appraisals from various valuation firms to assess the methodologies and valuations that best fit his privately-traded company.
  • Deliver an easy-to-understand analysis of the various valuation options to Josh.
  • Coach Josh to prepare for his emotionally-charged conversations with his partners, in which Josh has the relevant data required to communicate with his partner about updating the formula from the original Buy-Sell agreement.
  • Customize an asset allocation plan designed to provide a stream of income to replace his salary and bonus and help Josh to maintain his lifestyle through his retirement.


Name: Mrs. Jennifer
Age: 65
Occupation: Retired
Current Net Worth: $7M

Less than a year after his retirement, Jennifer’s husband, Donald, died suddenly.

Jennifer had been involved in all the financial and investment meetings, but deferred primary decision-making authority to her husband. Don took the lead in developing and implementing their estate and investment plans.

Educated as an attorney, Jennifer practiced law for several years after graduation, but left her firm to focus on her family and community interests after becoming a mother. Now, Jennifer’s three children and seven grandchildren all live out of state.


Jennifer involuntarily inherited sole responsibility for all financial decisions. Following Don’s death, Jennifer was charged with understanding and optimizing a complex group of entities including partnership interests, trusts, a private family foundation, a complex stock portfolio and a taxable estate.

Emotionally, she felt alone and needed guidance and support.


Carolina Wealth Stewardship Group can develop models and plans to help Jennifer have more clarity and feel more confident in her financial decisions. Our resources, guidance and support allow us to help her:

  • Facilitate a Family Plan to engage her adult children in all of the family’s financial affairs.
  • Create a single-page snapshot summary of the current estate structure to align Jennifer as grantor with her trustees and beneficiaries.
  • Update the estate plan, in coordination with her estate planning attorney and CPA, to further minimize estate taxes and address some of Jennifer’s personal philanthropic pursuits.
  • Model various scenarios to help Jennifer decide which assets to keep/sell and identify appropriate sources for a targeted income stream.