
Episode #34
20-35%: The Pay Bump You Should Demand Before Going 1099
The PA Millionaire Path is out! If you're earning great income but feel like taxes are quietly eating into your ability to build real wealth, this book gives you the framework to make your income work harder for you. Buy it here: https://www.millionairesinmedicine.com/pabook W-2 or 1099? Employee or contractor? For a lot of PAs, NPs, pharmacists, and CRNAs, that decision gets made without ever fully understanding what's actually on the table β in terms of pay, taxes, deductions, and risk. In this episode, Kristin sits down with Jason Watson, CEO and partner of WCG CPAs and Advisors and a tax expert who's spent decades working specifically with medical professionals, to break down what most clinicians get wrong about contractor income, tax strategy, and real estate. Jason and Kristin dig into how much more you should actually be earning to make a 1099 contract worth it, why treating your 1099 income "like a business" unlocks a completely different set of tax tools, when an S-Corp election actually saves you money (and when it backfires), and the short-term rental tax strategy that's become one of the most talked-about tools in medicine right now β including exactly what it takes to qualify for it. Inside, you'll hear: The pay increase Jason and Kristin both recommend before accepting 1099 over W-2 work Why 1099 income unlocks deductions W-2 employees lost back in 2017 The income threshold where an S-Corp election starts to actually make financial sense A common, costly mistake medical professionals make with S-Corp timing when switching mid-year How a recent change to SALT limits is reshaping S-Corp tax strategy in 2026 Why long-term rentals are great for building wealth but do almost nothing for your tax bill The short-term rental loophole, what "material participation" actually requires, and how it can offset W-2 income Other advanced (and much riskier) tax strategies Jason sees medical professionals explore, from car washes to oil and gas Why Jason says roughly half of his strategy calls end with a client deciding to do nothing β and why that's actually a win If you've ever wondered whether you're leaving money on the table with your tax strategy, or you're weighing a 1099 opportunity and don't know what questions to ask, this episode will change how you think about your next conversation with a CPA. Ready for a real plan for your income, debt, and investing? Apply to join the MiM Coaching Program here: https://www.millionairesinmedicine.com/coach Resources / links WCG CPAs & Advisors: https://wcginc.com/tax-center/millionaires-in-medicine The PA Millionaire Path: https://www.millionairesinmedicine.com/pabook Disclaimer The Millionaires in Medicine Show is for educational and informational purposes only. The content shared is not intended as medical, legal, financial, or investment advice and should not be relied upon as such.






