Sole Prop, S-Corp, or C-Corp? Demystifying Early Tax Strategy for Founders
I sit down with Dave Wanis, Tax Principal at Weaver, for the first episode in a series we’re doing together on tax strategy for entrepreneurs.
đź’ˇ This episode is titled:
“Sole Prop, S-Corp, or C-Corp? Demystifying Early Tax Strategy for Founders”
🎙️ Dave put it best: “The most tax-efficient thing you can do is talk to an advisor early and often.”
🔑 Key Takeaways:
- Plan Early, Review Often: The biggest founder mistake? Setting up an entity on Day One and never revisiting it. Your structure should evolve with your business.
- Flexibility of LLCs: LLCs aren’t just one thing — they can be taxed as a Sole Proprietorship, Partnership, S-Corp, or C-Corp. Choices will vary depending on many moving pieces including current and future profitability, salary needs and exit horizon
- Self-Employment Tax Surprises: Sole proprietors often miss that 100% of income is subject to self-employment tax — a costly mistake if you’re not prepared.
- S-Corp Advantages: With S-Corps, founders must pay themselves a salary, but profits above that can avoid employment tax — creating real tax savings.
- State Nexus Risks: Expanding across states? Watch out for state income, payroll, and sales taxes. Ignoring “nexus” is one of the biggest red flags Dave sees in diligence.
- Investor Readiness: Entity choice today impacts investor interest tomorrow. Acceptance of S-Corps is increasing although recent regulatory changes are making C-Corps more attractive.
This is just the start — we’ll be diving into more advanced topics with Dave in upcoming episodes (think asset vs. stock sales and Section 1202).
Madhur Duggar is a Senior M&A Advisor at Excendio Advisors and focuses on IT Services
Reach out to Madhur at Madhur@excendio.com or 212.731.4230
Book an Appointment with him on his LinkedIn.
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