Founder Files

#22 - Tax Problems Start Before Tax Season | Entity Structure, Planning & Year-End Mistakes (Part 1)


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Tax season doesn’t create problems, but it reveals them.


In Part 1 of this conversation, I sit down with Bayaan Oluyadi, CPA and founder of KTB Services, to talk through the questions founders and CEOs ask every year right before tax season and usually too late.


We cover:

• How to think about entity structure and why “I’m an LLC” isn’t an answer

• The tax mistakes that happen when finance is reactive instead of planned

• R&D credits and Section 174 and where companies get tripped up

• Sales tax, nexus, and why this becomes a problem during diligence

• What year-end planning should actually look like for growth-stage companies


Part 2 goes deeper into the role of the CFO, fractional finance teams, and how to build the right finance function as you scale.


Want a copy of the Year-End Financial Checklist?


Email [email protected] and we’ll share it with you.


(02:13) Entity structure confusion

(03:17) Why a CPA alone isn’t enough

(05:18) QSBS and planning from day one

(06:52) R&D and Section 174 pitfalls

(09:38) Why sales tax breaks deals

(11:58) When an LLC should consider S-Corp status

(17:17) What year-end planning should look like


We’re the outsourced finance function for SaaS, tech, AI, and e-commerce companies that want clarity, scalability, and an embedded partner, not just bookkeeping.


If you’re ready to move from chaos to clean books, visit cypherfin.com or ⁠book a call⁠.


💡 New episodes drop every Tuesday at 7 AM EST.


⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠Talk to Cypher⁠⁠


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Tech-Enabled Accounting & Finance. Built for Growth.

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Founder FilesBy Cypher