Becky Brown and Morgan Holmes, partners at Stride, were honored to join Roman Polnar on the Pillar6 Podcast to discuss essential strategies for smarter bookkeeping, tax planning, and advisory services for small to midsized businesses.
During the conversation, Becky and Morgan shared actionable insights on streamlining financial operations, improving cash flow, and preparing for future tax changes—all while reducing friction for business owners.
For a few key takeaways from their insightful discussion, read on. And to dive deeper, click here to listen to the full interview.
1. The Benefits of Combining Bookkeeping, Accounting, and Tax Services
Becky and Morgan highlighted the numerous advantages of consolidating financial services under one roof. Unlike the traditional model, where bookkeeping, accounting, and tax services are handled by separate providers, Stride’s integrated approach streamlines financial management for small and midsized businesses.
They explained how this holistic model eliminates the need for business owners to act as intermediaries, juggling multiple advisors and coordinating their schedules—a task that often results in delays, miscommunications, or even missed opportunities. At Stride, the bookkeeping and tax teams work together seamlessly, ensuring all aspects of a client’s financial management are in sync. This allows the team to address challenges proactively, such as calculating accurate quarterly estimated taxes or aligning tax strategies with the client’s operational goals.
Becky shared how Stride’s hands-on approach takes the burden off business owners, actively managing tasks like invoicing, payroll, and vendor payments in real-time. This ensures accurate record-keeping and allows clients to focus on their business rather than day-to-day financial administration. Morgan added that having bookkeeping, accounting, and tax advisory under one umbrella also enables Stride to deliver better tax outcomes by minimizing errors and ensuring tax returns are prepared with clean, up-to-date data.
Key takeaway: By integrating these services, Stride not only reduces friction for business owners but also provides a cohesive financial strategy that supports long-term growth and profitability.
2. Why Monthly Financial Reviews Are Essential
Becky emphasized the critical importance of closing your books every month rather than waiting until the end of the quarter or year. She explained that monthly financial reviews are not just a bookkeeping best practice—they are a vital tool for business owners to maintain control over their finances and make informed, strategic decisions.
By reviewing your financial statements monthly, you gain access to accurate, up-to-date insights that highlight your business’s true financial health. This proactive approach helps identify trends, such as cash flow fluctuations or unexpected expenses, before they escalate into larger issues. Becky noted that these timely reviews also allow business owners to uncover potential opportunities for tax savings, such as optimizing deductions or adjusting estimated tax payments throughout the year, rather than scrambling to address these concerns during tax season.
Becky pointed out that waiting until the end of the quarter or year to review your books often leads to errors, missed deductions, or financial surprises that could have been avoided with regular oversight. Monthly closes enable businesses to operate with clarity, reduce inefficiencies, and ensure financial records are always audit-ready.
Key takeaway: By prioritizing monthly financial reviews, business owners can better manage their resources, avoid costly mistakes, and make decisions with confidence—ultimately setting the stage for sustainable growth and profitability.
3. Proactive Tax Planning Makes a Difference
Morgan delved into the significant benefits of proactive tax planning, emphasizing the role of calculating quarterly estimated taxes in maintaining healthy cash flow and avoiding unexpected financial surprises at year-end. He explained that many business owners fall into the trap of consulting their CPA only once a year, often during tax season, when opportunities for meaningful tax-saving strategies have already passed.
By working with a financial advisor or tax expert on a quarterly basis, business owners can stay ahead of their tax obligations, ensuring they’re neither overpaying nor underpaying estimated taxes. Morgan highlighted how this approach provides a clearer picture of a business’s cash flow throughout the year, helping owners understand exactly how much cash is truly available to reinvest in the business, pay themselves, or save for other goals.
Morgan also shared an example of a common scenario where business owners unknowingly sit on large sums of cash in their accounts, not realizing that a portion of it is earmarked for tax obligations. Without proactive planning, this can lead to financial stress when it’s time to pay taxes. In contrast, regular check-ins with a CPA or tax advisor help ensure that tax liabilities are accurately calculated and factored into financial planning, leaving no unpleasant surprises.
Key takeaway: Proactive tax planning isn’t just about compliance—it’s a strategic tool for optimizing cash flow, minimizing liabilities, and enabling smarter financial decisions throughout the year. Regular engagement with your financial team ensures you’re always prepared and positioned for growth.
4. Choosing the Right Entity Structure
Becky and Morgan highlighted the critical role that selecting the right business entity—whether it’s an LLC, S Corporation, or sole proprietorship—plays in shaping tax liabilities and long-term financial health. They explained that an entity structure isn’t a “set-it-and-forget-it” decision. As businesses evolve, their needs and financial goals may change, making periodic reassessments of the entity type essential for maintaining tax efficiency and asset protection.
Morgan detailed how S Corporations are a common choice for many small to mid-sized businesses due to their ability to minimize payroll taxes. He walked through scenarios where clients transitioned from sole proprietorships or single-member LLCs to S Corporations, reducing their tax burdens by leveraging strategies like reasonable compensation. This approach allows business owners to pay themselves a salary that meets IRS guidelines while taking additional distributions that are not subject to payroll taxes.
Becky provided insight into how they evaluate entity structures based on each client’s unique situation. She shared examples of clients who initially opted for sole proprietorships to keep things simple but later discovered that their growing revenues made an S Corporation a more advantageous option. Becky emphasized that entity choice affects not only tax obligations but also how owners compensate themselves, handle liability protections, and plan for long-term goals like retirement or business succession.
They also touched on the importance of seeking expert guidance when considering a change in entity structure. For example, while LLCs provide flexibility and liability protection, electing to be taxed as an S Corporation can often unlock additional benefits—but only when executed with careful planning and compliance with IRS regulations.
Key takeaway: The right business entity is a foundational aspect of a business’s financial strategy. Regularly reassessing your structure with knowledgeable advisors like Becky and Morgan ensures that it aligns with your growth, protects your assets, and optimizes your tax efficiency. Making the switch at the right time can lead to significant financial benefits and long-term stability.
5. Looking Ahead: Preparing for Tax Law Changes
With potential tax law changes looming in 2025, Morgan stressed the importance of staying proactive and informed to navigate these updates effectively. He explained that major legislation, like the potential extension of provisions from the Tax Cuts and Jobs Act (TCJA), could significantly impact business owners’ financial strategies. For example, deductions such as the Qualified Business Income (QBI) deduction or changes to state and local tax (SALT) caps could remain in place or undergo adjustments, directly affecting how businesses plan for the future.
Morgan highlighted that the uncertainty surrounding upcoming tax law changes makes it crucial for business owners to maintain a forward-thinking approach. By working closely with financial professionals who monitor legislative developments, businesses can adapt their strategies in real time, ensuring compliance while also taking advantage of any emerging tax-saving opportunities.
He also shared how Stride approaches this challenge with clients. Their quarterly advisory sessions allow them to anticipate potential changes, model different scenarios, and advise on actions that could mitigate risk or capitalize on opportunities. For instance, if certain deductions are likely to sunset, businesses may need to rethink their current expense strategies or adjust their cash flow planning to avoid surprises.
Morgan pointed out that navigating these complexities alone can be overwhelming for business owners already wearing multiple hats. By partnering with a financial team that takes a proactive, advisory-led approach, business owners gain peace of mind and confidence that they are prepared for whatever legislative changes come their way.
Key takeaway: With potential tax law updates on the horizon, staying informed and agile is critical. Regularly consulting with knowledgeable financial professionals like Morgan ensures that your strategies are optimized for the evolving tax landscape, allowing you to stay ahead of changes and maintain financial stability.
Final Thoughts: Start With Clean Books
Throughout the discussion, Becky and Morgan stressed a recurring theme: keeping your books accurate and up-to-date is the foundation for all financial success. Whether it’s tax compliance, forecasting, or long-term planning, clean books allow for better decision-making and fewer headaches.
For more insights and practical tips, listen to the full Pillar6 Podcast episode.
About Stride
Stride provides comprehensive financial solutions, specializing in bookkeeping, accounting, tax, and advisory services for Managed Service Providers, digital agencies, and professional service firms. Our proactive approach helps businesses improve cash flow, profitability, and decision-making.
Have questions or need help with your financial management? Contact us at hello@stride.services or visit stride.services to schedule a consultation today.
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Show Notes + Transcript:Â
Becky Brown: LinkedIn
Morgan Holmes: LinkedIn
Roman Polnar: LinkedIn
