Jared Smithson is the COO of RJM Tax Exemption, and we spoke about the hidden traps, costly assumptions, and overlooked opportunities around U.S. sales tax compliance—especially for ecommerce entrepreneurs and those selling across multiple states. What began as an ecommerce side hustle gone wrong turned into a mission: help businesses avoid the legal and financial disasters he once faced. “We were looking for gold and we ended up finding a problem—and started selling the shovels to the solution.” Today, Jared’s team has helped over 5,000 businesses stay compliant, protect profits, and scale without fear of audits or shutdowns. We discussed: Why relying on your regular accountant for sales tax is a dangerous assumption How clicking a single button in your AI tax software can cost you $200,000 What “nexus” really means and how to know if you’ve triggered it How international sellers break into the U.S. legally and smartly Why failing to handle tax issues can derail a business sale—or destroy a thriving company Quotes to remember: 💬 “One mouse slip—$200,000. That’s all it took.” 💬 “You’ve basically got 50 countries in one in the U.S. when it comes to sales tax.” 💬 “The worst thing that I could think would happen is… you start having to let people go because of your oversight when it came to tax in the beginning.” Takeaways: Sales tax ≠ income tax: Most accountants don’t specialize in sales tax, and it varies dramatically by state. Software ≠ solution: Tech tools are helpful, but human expertise is essential to avoid expensive mistakes. Exemptions matter: Paying sales tax twice—on both inventory and customer orders—is a profit killer many don’t even notice. Compliance protects exit value: Non-compliance can cost you your sale—and your dream payout. Early awareness saves pain: Don’t wait for success to start thinking about risk. Prepare before you're audited. Whether you're just launching or eyeing a business sale, this episode is your wake-up call: sales tax is boring—until it breaks your business.
