Tax Insights
Built for Founders
Curious how key tax decisions impact your year? With The Millennial CPA, you get clear, founder-specific guidance backed by real human judgement—so you can move forward with confidence.
We built this hub to give founders confidence that they’re doing things right.
It reflects years of working with builders who want solid guidance and support that holds up as their companies grow. We believe in providing the full tax picture, not just one piece of the puzzle.
Start With the Questions Every Founder Runs Into.
A quick set of explanations for the early decisions that usually raise the most uncertainty.
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Founders have a different rhythm than traditional employees — filings, quarterly decisions, equity timing, and planning windows all land at specific points in the year. The Founder Tax Calendar gives you a clear view of what matters and when.
→ Founder Tax Calendar (coming soon)
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Exercises, vesting, liquidity plans, or moving states can meaningfully change your tax picture. The Equity & Residency Timing page outlines how these choices interact with federal and state rules so you can make informed calls ahead of time.
→ Equity / Residency Timing (coming soon)
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Early-stage teams often qualify, but the details matter — what you build, how you document it, and how the IRS tests are applied. The R&D Credits page explains the fundamentals and the common patterns we see in software, product, and technical teams.
For the Questions With No Easy Answers.
These guides break down the tax decisions that accountants usually don’t explain, so you can understand what actually matters and why.
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Early choices around structure, accounts, and recordkeeping have real downstream impact. This guide walks through the setup decisions that save founders time, risk, and cleanup cost.
→ Founder Day Zero Guide (coming soon)
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Deadlines, filing points, planning windows, and what happens in each quarter — laid out without jargon. This guide shows the rhythm of the year so nothing blindsides you mid-build.
→ Founder Tax Calendar Deep Guide (coming soon)
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A practical breakdown of the IRS tests with examples from real software and technical teams. Enough detail to understand where you stand — without guesswork.
→ R&D Qualification Deep Guide (coming soon)
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Timing, state rules, income sourcing, and long-term impact — all explained in one place. This guide helps founders understand the tradeoffs before making a move.
→ Equity / Residency Deep Guide (coming soon)
Founders usually manage both sides of their tax picture at once — their personal return and their business filings. Whether it’s equity timing, choosing compensation, or early C-corp or S-corp questions, these decisions stack.
Start with simple guidance in either area:
If you prefer strategy first, start here:
Day Zero Founder’s Guide (coming soon)
The Founder Tax Calendar Deep Guide (coming soon)
Most options end up being either:
Too scattered and reactive (last-minute asks, unclear steps, no timelines), or
Too automated to trust (AI prep, zero understanding of your actual situation).
What Founders Usually Run Into When Looking for Tax Help
We combine the best of both worlds:
Steady guidance for your full tax picture (that means personal taxes, too)
Clear expectations and upfront communication (no guessing what to do next)
Modern systems to streamline work (not replace expert judgment)
Workflows built to remove surprises (so you know what’s happening, when)