Strategic Small Business Planning, Featuring Jason "Drew" Webster Financial Planner Q & A

At Employers Advantage, we’re committed to supporting small businesses not just with HR guidance, but with the broader strategies that fuel growth, sustainability, and long-term success.

That’s why we love connecting our clients with trusted partners who share that same mission.

In this Q&A, we sat down with Jason “Drew” Webster, a seasoned Wealth Management Advisor with Thrive Financial Partners, to explore how small business owners can strengthen their financial foundations, avoid costly pitfalls, and plan smarter throughout the year. From tax strategies to employee benefits and succession planning, Drew shares practical insights that can help business owners stay ahead — one quarter at a time.

Q: Can you tell us a bit about your background and how you help businesses as a consultant?

A: I’m a Financial Planner who offers business planning, coaching and consulting services, with a focus on helping small businesses and entrepreneurs optimize their financial strategies. My work involves a blend of consulting, strategy development, and long-term planning. I focus on areas like entity structure review, employee benefits implementation, cash flow management, and tax mitigation strategies, all of which are crucial for the health and growth of any business.

I tailor each strategy to the unique needs of the business, ensuring that they are not only tax-efficient and legally compliant, but also designed for sustainable growth. Whether it’s refining the business’s structure or guiding them through succession planning, my goal is to create a clear financial roadmap that helps owners make informed decisions.

Q: How do you structure your consulting services throughout the year?

A: I’ve structured my consulting services into four quarters, each focusing on key areas that help businesses thrive throughout the year. Here's an overview:

• Quarter 1 focuses on strategies designed to set the business up for success in the new year. We review the profit and loss, identify target revenue and income numbers, evaluate entity structure, and plan for succession. It's also the time to review business risks, especially key business partnerships, and look at merchant services and cash position.

• Quarter 2 is about refining the business’s financial health. We do another profit and loss review, evaluate compensation structures, and discuss tax mitigation strategies. Additionally, we assess partnership and legal agreements*, liabilities, assets, and business cash flow. I also review credit card usage and lines of credit to ensure the business has the appropriate financial tools in place.

• Quarter 3 centers around employee benefits and how businesses can improve their offerings to retain and attract top talent. In addition to reviewing benefits such as health, life, and 401(k) options, we look at profit and loss, debt management strategies**, and potential buyout conversations. This quarter is key for businesses planning to scale or transition.

• Quarter 4 is all about wrapping up the year with strategic financial planning. We focus on end-of-year mitigation strategies, review your income statement, outstanding invoices, and cash flow for subsequent years. This is also the time to consider purchases and ensure margins are optimized for the next year.
  

Q: Why is it important to review the entity structure of a business, especially in Quarter 1?

A: The entity structure review is a key part of Quarter 1 because it sets the foundation for everything that comes next. Whether a business is an LLC, S-Corp, or C-Corp, the structure has significant tax, liability, and operational implications. In Quarter 1, I evaluate whether the current structure is optimized for tax savings and growth. If not, I make recommendations to help the business owner make adjustments before the year progresses. This early check is designed to help ensure that the business can operate efficiently and with appropriate protections in place.

Q: What’s the importance of tax mitigation strategies, especially in Quarter 2?

A: Tax mitigation is a crucial part of any business's financial strategy, particularly as the year progresses. In Quarter 2, I work closely with business owners to review their tax strategy and identify opportunities for mitigation. This can include evaluating current deductions, credits, and the business structure, to ensure they are taking full advantage of tax laws and minimizing liability. Implementing these strategies early in the year can have a lasting impact on the business’s bottom line, saving money and optimizing cash flow.

Q: What are some of the key conversations you have with business owners during Quarter 3?

A: In Quarter 3, we dive into the company’s benefits packages, focusing on areas like health insurance, retirement plans, and other employee benefits. This is often a time when business owners realize the importance of offering competitive benefits to attract and retain top talent. Additionally, we review the business’s profit and loss, assess debt, and start conversations about potential buyouts. For businesses that are looking at growth, this is also the time to begin planning for transitions or exits, ensuring they’re prepared for whatever comes next.

Q: Quarter 4 seems focused on preparing for the future. What kind of steps do you take to close out the year?

A: Quarter 4 is all about wrapping up the year with a clear strategy for the future. We review the financial health of the business, focusing on profit and loss, outstanding invoices, and ensuring that cash flow is optimized. It’s also a time for businesses to make end-of-year purchases that can benefit them tax-wise, while also planning for the next year’s margins and targets. In addition, we discuss any last-minute tax mitigation opportunities and review strategies to ensure that the business enters the new year in a strong position.

Q: What advice would you give to business owners who are just starting to think about consulting and planning services?

A: Generally, the earlier you bring in a business planner, the better. Many business owners try to manage everything themselves, but having a professional consultant in your corner helps you navigate complexities, avoid costly mistakes, and plan for the future. Whether it's structuring your business for growth or optimizing employee benefits, there’s always room for improvement. My advice is to take a holistic approach to your business finances and regularly review your strategies to ensure you’re on track. Planning isn’t just for big corporations—it’s essential for small businesses too.

*Neither MML Investors Services, LLC nor any of its subsidiaries, employees or representatives are authorized to give legal or tax advice.  Consult your own personal attorney legal or tax counsel for advice on specific legal and tax matters.

**We do not offer formal debt management programs.

Jason (Drew) Webster is a registered representative of and offers securities, investment advisory, and financial planning services through MML Investors Services, LLC, Member SIPC, 100 Sterling Parkway, Suite 307, Mechanicsburg, PA 17050, Tel: 717-791-3300. CRN202801-7577277