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If you’re a small business owner in Orlando, Florida , chances are you’ve worked with freelancers, contractors, or consultants this year. That leads to one of the most common tax questions we hear from local business owners: If you’re a small business owner in Orlando or Central Florida , issuing 1099s correctly  isn’t optional — it’s required to stay compliant with the IRS. If you paid a contractor, freelancer, or consultant $600 or more  for services this year, you may be r

As a small business owner, you’ve likely had that sinking feeling when tax season rolls around: “Why does it feel like I’m paying too much?” If that sounds familiar, you’re not alone. Most business owners don’t need another tax preparer — they need a tax strategist . At Watchmen Consulting, we help entrepreneurs proactively plan their taxes, not just file them. Here are seven signs it’s time to start building your tax strategy plan. 1. You Feel Like You’re Overpaying in Taxes

Running a business today is no small feat. Whether you’re managing a law firm, an e-commerce store, or a small to medium enterprise, the financial landscape is constantly shifting. You need more than just basic bookkeeping or tax filing. You need customized financial planning that fits your unique business needs and helps you grow with confidence. That’s where I come in, sharing insights on how tailored financial strategies can empower your business to thrive. Why Customized

Running a business is no small feat. Between managing operations, serving customers, and growing your brand, the last thing you want is to be caught off guard by tax season. But what if I told you that with the right approach, taxes don’t have to be a headache? In fact, strategic tax planning can become one of your most powerful tools to save money and boost your business’s financial health. Today, I’m going to walk you through practical tax optimization strategies that can m

By Watchmen Consulting Growing a business is no small feat. It takes more than just hard work and passion. You need smart, tailored...

By Watchmen Consulting Growing your business financially is not just about making more money. It’s about making smart decisions that...

Running a small business means wearing many hats—sales, marketing, operations, and everything in between. But one hat you can’t afford to...

When it comes to managing your business finances, not all bookkeeping is created equal. Many business owners hire a standard bookkeeper to track transactions and keep the books in order—but is that enough to help you grow, stay compliant, and plan for the future? The truth is, while basic bookkeeping is useful, CPA-led bookkeeping takes things to a whole new level. It doesn’t just record the past—it equips you with insight, strategy, and confidence for what’s ahead.

When it comes to running a successful law practice, most attorneys don’t enter the field with dreams of managing financial ledgers or reconciling bank accounts. But bookkeeping is a foundational part of building a sustainable and compliant law firm. If ignored or mishandled, it can lead to major headaches—from tax penalties to ethical violations.

By Carlton, CPA & Founder of Watchmen Consulting 📣 Law Firm Owners: Don’t Miss These Tax Breaks! Running a successful law firm means...

Carlton went from Big 4 to building small businesses—and now he’s sharing what he’s learned. Free advice from a CPA who gets it. Not Just...

Running a small business is no small feat. Between managing sales, operations, customer relationships, and growth strategies, it's easy for your finances to become an afterthought—until tax season rolls around or cash flow problems arise. That’s where a professional bookkeeper steps in—not just as a number-cruncher, but as a strategic partner in your business.