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.
If you don’t know what’s coming, you’re already behind.
Start with the founder resources below to see what matters, when, and why.
The First Questions Founders Run Into.
A quick set of explanations for the early decisions that usually raise the most uncertainty.
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Founder tax obligations don’t show up evenly throughout the year — estimated payments, payroll filings, information returns, and planning cutoffs all cluster around specific dates. The Founder Tax Calendar lays out the key federal deadlines founders actually run into, so you can see what’s coming, avoid surprises, and make better decisions ahead of time. You can reference it as a checklist or add the dates directly to your own calendar.
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Startup finance roles aren’t interchangeable, and hiring them out of order creates real friction. This guide explains what accountants, controllers, and CFOs actually do for startups, how those responsibilities change as a company grows, and how clean accounting keeps tax, credits, and decision-making aligned over time.
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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. Try out the “Do We Qualify” quick evaluation tool, or explore further using the R&D Tax Credit Guide below.
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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)
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 intakes in any area:
If you prefer strategy first, start here:
What Founders Find When They First Look for Tax Help
Most tax options founders find first end up being some combination of the following:
Proficient, but low in startup experience (key blind spots)
Ambiguous “All things handled” financial solutions (no clear ownership)
Tech-first, people buried (if you can find them at all)
All these setups lead to the same unfortunate outcomes — overpayments and underpayments, startup-specific deadlines missed, and decisions being made without a clear understanding of the downstream tax consequences.
We lead with experienced judgement, supported by modern systems.
Steady, founder-specific guidance across your full tax picture
Clear expectations and upfront communication
Modern tools that streamline work without replacing human expertise
Workflows designed to remove surprises, so you always know what’s happening and when
We’ve seen how these issues play out — and how to prevent them early.