Every May we recognize the people who sign the front of the checks, carry the risk, build the teams, and keep the lights on…our small business owners! 

It’s also a time to pause and consider a few financial questions that often get pushed aside while the business is busy growing.  Below are three that we believe matter most. 

1.  What is your business actually worth? 

Many owners have a number in their head, but few have had that number tested in the real market.  Important questions to consider when exploring the value of your business are: 

• What would a buyer realistically pay today based on current financial and market conditions? 

• How dependent is the business value on you personally? 

• How much of the family’s net worth is tied up in the company? 

• If you planned to sell in 3-5 years, what would increase the value? 

For many owners, the business is their largest asset, making an accurate valuation a critical planning step. 

2.  What happens if you can’t show up tomorrow? 

This question doesn’t hinge simply on you passing away, it’s an operational one that is focused on the what ifs of life…health, retirement, disability, etc.  Every business should be able to withstand an unexpected disruption. 

• Is there a buy-sell agreement in place?  If so, when was the last time it was reviewed? 

• Would your family, partners, or employees be financially protected if something happened to you? 

• Who would make day-to-day decisions or manage client relationships and revenue if you were unavailable? 

Businesses that survive leadership disruption are usually the ones that planned before the disruption happened. 

3. How does your business fit into your personal wealth plan? 

For many owners, the business and personal finances are deeply connected but rarely reviewed together. 

• Is the business your primary retirement asset? 

• Are you building wealth outside the business as the business grows? 

• If the timing of the sale isn’t ideal, what is your Plan B? 

Owners who want to retire on their terms may need to build financial independence outside the business to help manage the wealth gap created between what is needed and what the business can provide. 

If you’re a business owner who hasn’t stepped back to look at these questions recently, it may be time to start the conversation.  The goal isn’t complexity, it’s clarity.  At The Cypress Group, we believe the right planning helps business owners plan well, invest wisely, and live fully. 
 

Tyler Thomas is a Financial Advisor with The Cypress Group Team of RBC Wealth Management located in Wilmington, NC, helping families, professionals, and business owners plan, invest, and live with confidence. Business valuation services provided by RBC Wealth Management Corporate and Executive Services.  

[email protected] 

www.linkedin.com/in/roberttylerthomas 

1055 Military Cutoff road, Suite 200 

Wilmington, NC 28409 

910-509-0832 

Investment and insurance products offered through RBC Wealth Management are not insured by the FDIC or any other federal government agency, are not deposits or other obligations of, or guaranteed by, a bank or any bank affiliate, and are subject to investment risks, including possible loss of the principal amount invested. 

© 2026 RBC Wealth Management, a division of RBC Capital Markets, LLC, registered investment adviser and Member NYSE/FINRA/SIPC. All rights reserved.