About this episode
This episode is a live mini-workshop recorded with members of the Escapee Collective (and released here because it was too useful to keep inside the community).My guest Diane Kennedy (CPA) breaks down what most new escapees get wrong about taxes and business structure — and why the real first question isn’t “LLC or S-Corp?”It’s: Are you building a business… or replacing a paycheck?From there, we get into the most common setup for solopreneurs (LLC + S-Corp election), how to think about deductions without getting cute, and why “keeping it small and keeping it all” is the solopreneur cheat code.We also bring in Lisa Dini from Lettuce, who explains how they help solos run the S-Corp model without turning you into an accountant.Heads up: This is educational, not legal/tax advice. Talk to your pro for your situation.What you’ll learnThe real first question for escapees: build a business vs replace a paycheckWhy “LLC vs S-Corp” is usually the wrong framing (and what Diane recommends instead)Why Diane believes you should set up an LLC early (asset protection + flexibility)The 3 “buckets” of income for solopreneurs: Earned, Leveraged, & Passive (the holy grail)A simple way to think about deductions: ordinary + necessary (and how to find write-offs you already have)How S-Corps can help you keep more of what you earn (salary vs distributions, plus other benefits discussed)Real-world Q&A on: partners, joint ventures, and multi-state setups, California “special rules” , Schedule C vs S-Corp timing, Solo 401(k) and related retirement ideasResources Mentioned:Lettuce.co: https://hubs.ly/Q03Yz8KX0Tax Calc: https://hubs.ly/Q03Yz8Rf0Tax Prep: https://hubs.ly/Q03Yz8JY0GuestsDiane KennedyCPA and long-time solopreneu
