The W-9 Lesson: How One Business Owner Learned the Hard Way

A Guide for Business Owners Facing Serious Tax Debt

You may have heard the buzz about some changes taking place in the United States Postal Service. On December 24, 2025, adjustments were implemented that could affect whether time sensitive items are considered to be mailed “on time”.

Have you ever said, or thought, “I will deal with the books at tax time”?

Are you so glad the year is over? Are you completely burnt out, and you don’t even want to look at your P&L? If you don’t want the coming year to mirror this last year, if you want to end next year feeling revived and excited instead of being worn out and generally disinterested then let’s go through this year end checklist together. Let’s start a new habit.

I’m going to tell you a story about a business owner I’ll call Mark . He had built a small but stable company, employed a handful of people, and, for most of his career, did exactly what the IRS expects—filed his returns, made his deposits, and treated payroll taxes as a priority rather than an afterthought. Then a serious medical issue intervened.

Every January Mike’s Bistro went quiet. During the Holiday season there was barely time to breathe. Lines out the door, catering orders piling up, and staff pulling double shifts. He assumed the income from the holiday rush would be enough to carry him through the slow season. But, by the third week of January the rush was gone and his bank balance told a harsh truth: Mike had no cushion and no plan. The bills started stacking up and he had to dip into his personal savings to keep the doors open.

Social media is flooded with sensational claims about “the path to zero tax.” Influencers and so-called experts are eager to share tax loopholes or hacks to avoid paying taxes altogether. But what’s real, and what’s just hype? Let’s separate myth from reality, so you can make informed, responsible decisions and avoid costly mistakes.

A Candid Conversation That Revealed a Deeper Problem Just last week, I met with a restaurant owner whose operation appeared—at least externally—to be thriving. His dining room was consistently active, yet beneath that surface of apparent success was a financial trajectory that had been quietly deteriorating for months. Despite steady revenue, he was withdrawing money from his savings every single month to cover operating expenses. He admitted he had been reluctant to raise prices, relying instead on what surrounding restaurants were charging rather than on his own cost structure. His hesitation was rooted in fear—fear of guest backlash, fear of making things worse. But the numbers were unequivocal: If he continued operating under the same assumptions, he would exhaust his resources and have to close the doors within 18 months. The Crucial Question: “When Did You Last Cost Your Menu?” When I asked when he had last conducted a comprehensive plate-costing analysis, he paused, then confessed he couldn’t remember. He had a general sense of which items were “profitable,” but that belief was based more on intuition than on data. To establish a baseline, we chose one of his higher-priced, supposedly high-margin entrées and examined it in meticulous detail. Together, we itemized every cost associated with that dish: the ingredients, the small plastic containers for butter and cream, the complimentary rolls, and even the to-go packaging that roughly one-third of guests utilized. What emerged from that analysis was sobering. A plate he believed was generating strong profit was, in reality, carrying a 40% cost—a level that left little room for labor, overhead, or debt service. And if this was true for one flagship menu item, we both understood it was likely symptomatic of the entire menu. Menu Costing is Essential I reminded him of a truth we see repeatedly: restaurant owners often assume that their best-selling items are also their most profitable, even though these two metrics rarely align without deliberate cost control and menu strategy. You cannot manage what you have not measured. Menu costing provides more than clarity; it provides a structured method for transforming a menu from a passive list of offerings into an intentional, revenue-driving instrument. A Clearer Path Forward 1. Establish Data Integrity - Calculate plate costs with accuracy, capturing all expenses that typically slip through the cracks. 2. Identify Profit Leaders and Margin Eaters - Identify which dishes are supporting the business and which ones are quietly eroding margins. 3. Implement Strategic, Evidence-Based Pricing - Armed with reliable numbers, adjust prices—not reactively or fearfully, but with rational confidence. 4. Reposition the Frontline Team as Sales Professionals - Inform the staff which items truly contribute to financial stability, enabling them to guide customers intentionally Most owners are overwhelmed by the idea of auditing an entire menu, but the process truly begins with a single plate. Analyze one thoroughly, and you may uncover insights that fundamentally reshape how you view your business. Accurate, consistent plate costing is the cornerstone of profitability. Once you have it, even incremental adjustments can yield meaningful improvements. Your Menu Holds Untapped Value — Let’s Reveal It Countless restaurants operate with hidden vulnerabilities simply because their menu has not been designed to support the business strategically. Menu costing is not merely a financial exercise; it is a lifeline for owners who want their restaurants to thrive rather than survive month-to-month. If you’re ready to understand the true profitability of your menu and create a pricing structure that sustains your business, we can guide you through the process—and help you write a success story rooted not in guesswork, but in clarity and control. Schedule a free advisory session now.

While Return on Investment tells you whether past investments paid off, forecasting it ahead of time can help you choose the right opportunities and avoid costly mistakes. Restaurants have such slim profit margins that ROI isn’t optional. It’s survival. This is a lesson one restaurant owner learned the hard way. Meet David. David is a typical small restaurant owner. He is passionate about food and creating the best possible experience for his customers. But, like many independent restaurant owners, when it comes to big decisions, David trusted his gut. And it nearly sank his business. In late winter, David decided to invest $25,000 to expand with an outdoor seating area. He believed it would bring in more customers during the spring months, which would boost revenue and set him apart from the competition. But David never sat down to do the math. He didn’t ask any questions. How many new customers would this expansion really bring in? How long would it take to recoup the investment? Do current customers even want this change? Passion is essential in business. But numbers keep the doors open. At first, the buzz was exciting. Photos of the upgrade went up on social media and looked amazing. The marketing campaign brought in a small burst of interest, but few repeat customers. But, by the middle of summer, the numbers told a different story. Total revenue increase from outdoor dining: only $7,000 Unexpected costs: $3,000 in permits, $2,000 in maintenance Weather delays: Lost 4 peak weekends due to rain Net profit? Basically zero Worse, the investment delayed upgrades to his kitchen, which caused longer wait times and affected customer satisfaction. David had sunk $25K into something that felt right—but didn’t pay off. How ROI-Based Decision Making Could Have Helped If David had used a simple ROI based decision-making process , things could have turned out very differently. Here are what those steps would have looked like. 1. Understand ROI Basics Projected net profit is calculated by subtracting the projected costs from the expected revenue over a specific period of time. For example, if you want your project to produce a return on investment over three years, you would project your net profit over three years. Then, to find the percentage of ROI, divide the projected net profit over time by the estimated cost of the project (investment), then multiply the result by 100. ROI = ((net profit – investment) / investment) x 100 2. Identify Decision Area For restaurants there are many areas that could be analyzed for return on investment. Things to consider would be new equipment, menu changes, or investments in technology, such as an updated POS System. David should have asked: “Will outdoor seating bring in more profit than other things I could invest in?” This would have given him more insight into the best area to focus his capital. 3. Estimate All Costs As we all know, most investments end up costing more than we originally expected. Think about legal fees, market research and insurance. Instead of assuming $25,000 was the final price, if David had done some more research he would have realized he needed to include costs for permits and licensing and extra maintenance costs. 4. Forecast the Returns How can you forecast realistic return on investment? Use historical data or industry benchmarks when possible. Also, look at average foot traffic and sales from previous years. David didn’t factor in the extra time for table turnover in an outdoor space. Research shows that people may stay longer for a meal when seated outside. After considering all the factors David might have decided to invest his money in an endeavor that had the potential of a much better ROI. 5. Calculate ROI After completing all of the research, now is the time to calculate the projected return on investment. After plugging your forecasted numbers into the ROI formula, it is important to ask questions about the results. How long will it take to break even? Is the ROI positive, and over what period of time? Is there a better place to invest that capital? For David, he would have come up with a negative ROI in year one. This would have given him the opportunity to do more research or refocus his goals. 6. Compare Alternatives If you’re choosing between options (e.g., a new fryer vs. a marketing campaign), calculate forecasted ROI for each and compare. Then you can choose the one with the best ROI and strategic fit . (Use our free ROI comparison calculator to compare options.) What if, instead of outdoor seating, David spent $8,000 on a new kitchen line to speed up service? If that option showed an ROI by end of year 4, it would be a better option. Here is an example: