5 Issues That Keep Business Owners Up At Night

November 04, 2016

By: Paul K. Loyacono Jr. and John P. Henson Jr.


You’re laying in bed, about to go to sleep after a long day. Despite your exhaustion, you start thinking about work, the meeting you had with your CPA last week, and the big project you’re bidding on this week. As if on cue, the myriad of questions and challenges that come with being a business owner start up, and the hope of drifting off to sleep easily starts to fade.


Insurance options. Retirement planning. Taking your business to the next level. The concerns of a business owner are multifaceted and never ending. Stepping out from the corporate umbrella and starting your own business can be one of the most rewarding experiences, but it comes with a lot of risks. In a world of no guarantees, a successful business owner must be vigilant at all times.


We know this well because we are in the same boat. As business partners who started our own company, we understand the unique burdens you bear from first-hand experience. Knowing that you aren’t alone in making decisions can alleviate some of the burdens, but having team of professionals to help you create and execute a strategy to address these concerns is invaluable.


Sometimes the act of naming the things that keep us up at night is the first step to finding a solution. Below are some of the major categories of concerns we see business owners facing and how a team of financial advisors might be able to help.

1.  How do I make sure my family is taken care of?


  • What happens if I die prematurely?


  • What happens if I become disabled and can no longer work?


  • How do I balance time at work and spending more time with my family?


  • How do I best prepare for my children's future education?


Perhaps one of the biggest concerns for business owners is how to best provide for their loved ones. If the worst should happen, will my family be okay? Many spouses are not involved in the day to day operations of a business, so having a plan in place to secure their well being is of utmost importance. We can help create an estate plan that helps preserve wealth and protect families in a tax-efficient manner. With our help managing your finances, your time and energy can be spent investing in the people you care about.

2.  How do I take care of my employees?


  • What sort of retirement plan can I offer and afford to provide?


  • How do I attract high-quality employees?


  • How do I retain my best employees?


  • What happens if I lose a key employee?


Successful companies are made up of quality people who are passionate about what they are doing. You want to ensure that you have the right people on your team and that they are well taken care of. Between insurance options, benefits packages, and retirement plans, there’s a lot to consider. Which plan works best for you and your employees? It’s difficult to know whether to choose a SIMPLE IRA or a 401(k) plan. Discussing your options with a financial advisor can help make the decision-making process more straightforward.

3.  How do I plan for my own retirement?


  • Does it make sense to keep investing in my own business?


  • Should I consider diversifying my net worth instead of having 70-90% tied up in my company?


  • Will my current retirement plan be enough?


  • How much income will I need at retirement?


As a business owner, you are most likely a visionary, always looking ahead. However, planning for retirement can feel like trying to hit a target blindfolded. There are so many variables to consider and no way to predict the future. Planning early and adjusting often is the best strategy, especially for business owners who might have a lot of their net worth tied up in their companies. At WealthPoint, we can help you look at all the aspects that go into a sound retirement plan with the goal to help you retire with a steady and reliable source of income.


4.  What Is My Succession Plan and/or Exit Strategy?


  • How will I create liquidity to provide the cash to retire?


  • How do I keep a family business intact and treat all my family members equally?


  • When is the optimal time to sell my business?


  • How do I prepare to sell my business to get top dollar?


Preparing for the long-term plan takes lots of insight and strategy. Business owners have a lot to lose if they attempt to sell their company without proper planning. Many business owners are blinded by a subjective view of their company. Without an objective game plan to appeal to prospective buyers and help a company thrive after they leave, they fall short of their goal. This is easily avoidable.

5.  How Can I Lessen My Tax Burden?


  • How much will I pay in capital gains if I sell my company? What are the most tax efficient options?


  • Are there tax deductions that I’m overlooking?


  • How do I minimize my own taxes now and during retirement and still draw a healthy income?


  • How do I plan my estate to maximize what my family receives and diminish what I’m giving to the IRS?


You are an expert in your field and passionate about the company you started. Chances are you aren’t as passionate about the nuances of tax law or an expert in how to best leverage those taxes to lessen what you owe each year. That lack of knowledge could be costing you more than you know. Most business owners don’t know about simple ways to make cut taxes and leverage investing strategies to save the most possible. Let us use our area of expertise to help you and your business thrive!




Starting and maintaining a successful business isn’t easy. The issues that keep you up at night are valid concerns that need to be addressed. Rather than shouldering the burden on your own, why not invest in a team of people that can help speak into some of the specific challenges you are facing? As a small business ourselves, we are passionate about empowering people like you to make the best financial decisions.


About Paul

Paul Loyacono is the founder and managing director of WealthPoint Investment Management, a boutique investment and financial planning firm, with more than a decade of experience in the financial service industry. He works with a variety of clients in Mississippi as well as throughout the South. Many of his clients are business owners as well as individuals in need of retirement and financial planning.

Paul started his career in the insurance industry, working with Citigroup. He quickly realized that many of his clients also needed assistance with their finances and investments. To assist them with all of their financial strategy needs, he became a financial advisor. Over the course of several years, he worked with large, national firms, including Wells Fargo and Merrill Lynch, and a private firm, Stephens, Inc. With a desire to focus more on his clients’ needs and serve them objectively, he founded WealthPoint Investment Management and joined independent broker-dealer LPL Financial, one of the leading financial services companies and the largest independent broker/dealer in the nation.*

Paul holds FINRA Series 7 and 63 registrations through LPL Financial, and holds FINRA Series 66 registration through IFG Advisory, LLC and LPL Financial. He also holds life and variable annuity insurance licenses. Born and raised in Vicksburg, he enjoys working with the good people in Mississippi, as well as throughout the South. He enjoys spending time with his wife, Kati, and their three daughters. When he isn’t working with clients, he spends much of his time outdoors, whether he’s golfing, playing tennis, or duck hunting.

*As reported in Financial Planning magazine 1996-2018, based on total revenues.

About John

John is a Wealth Management Advisor at Wealthpoint Investment Management. Through an in-depth understanding of every client’s specific needs and objectives, he is driven by a passion to help individuals, families and business owners develop plans and strategies to RETIRE with confidence, PROTECT their assets, and leave a LEGACY.


Prior to joining WealthPoint Investment Management, John spent 24 successful years with a leading wealth management company, helping clients work towards their financial goals and building a lifetime of impactful relationships. He served as the Business and Estate Planning Specialist, for their Mississippi agency, and served several years in management positions recruiting, developing and training Financial Advisors. John is a former president of Jackson Association of Insurance and Financial Advisors.


John is a graduate of the University of Mississippi with a Bachelor’s degree in Business Administration. He holds Life and Health licenses as well as the FINRA Series 6, Series 7 and Series 63 with LPL Financial and holds FINRA Series 66 registration through IFG Advisory, LLC.


John, a Greenwood, MS native, lives in Madison, MS with his wife Alison. They have two children, John and Ally. Away from the office, John enjoys spending time outdoors playing golf and boating with his family.