Tax planning that founders are proud to use.

Stop the last‑minute scrambles and turn taxes into a strategic advantage. You don’t need a binder of rules—you need proactive planning that fits your model, your cash, and your goals. We build a year‑round rhythm on top of your Xero books, forecast your tax position before it hurts, and explain what changed and why in plain English. If you’re searching for startup tax planning, S‑Corp strategy, or multi‑state guidance in Chicago or nationwide, this page is for you.

We take the guesswork out of your tax year.

Tax planning should feel calm and coordinated. We start with a discovery session and a fast review of entity structure, state footprint, and your last return, then map a planning calendar that fits your revenue cycles. Within the first month we produce a baseline projection, identify moves with the biggest impact—reasonable compensation, retirement plan design, Section 179 versus bonus depreciation, R&D credit potential, and estimated tax schedules—and align them with cash flow. If you’re coming from a prior firm, we reconcile carryforwards and elections so nothing gets lost in translation. From there, we meet on a steady cadence to update projections, adjust estimates, and document decisions so year‑end is just execution. When it’s time to file, your records, workpapers, and support are already in place. That’s tax planning the founder‑friendly way: structured, transparent, and built to move at startup speed.

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ProConnect

Professional Preparation & E‑File

ProConnect is our preparation engine for complex and multi‑state returns. It handles business and individual filings, supports K‑1s, and streamlines electronic filing so compliance stays predictable. We use it to translate your planning into clean returns, tie back to books and workpapers, and produce the final forms lenders and investors expect. With ProConnect powering the filing, planning ideas don’t die at year end—they become accurate, timely returns.

Stanford Tax

Technical Research & Guidance

Stanford Tax is our research backbone for thorny questions. We use it to confirm positions with primary sources, monitor legislative changes, and keep nuanced items—like §174 amortization, nexus thresholds, and shareholder benefit rules—on solid footing. The goal isn’t to bury you in citations; it’s to give you confidence that strategies we recommend are grounded in current, authoritative guidance and documented for future diligence.

Remitian

Secure Intake & E‑Signature

Remitian keeps sensitive tax data and signatures moving without email chains. Organizers, document requests, and e‑signatures live in one secure portal, and status is visible at a glance so nothing stalls close to a deadline. Founders get a clean checklist, the team gets streamlined approvals, and we get defensible audit trails that tie directly to the workpapers behind your return.

TaxPlan IQ

Strategy Modeling & Accountability

TaxPlan IQ turns planning ideas into a concrete roadmap with projected savings, step‑by‑step tasks, and due dates. We use it to model the ROI of strategies—S‑Corp elections, retirement plans, accountable plan reimbursements, 179 or bonus timing—and then track implementation so savings don’t get lost in the shuffle. Each review we update status, adjust targets, and keep everyone focused on the moves that matter most.

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FAQs

  • What’s the difference between tax planning and tax preparation?

    Tax preparation is the act of completing and filing last year’s return accurately and on time. Tax planning happens in advance and changes the numbers you eventually report. Planning sets reasonable compensation for S‑Corp owners, schedules equipment purchases, picks between Section 179 and bonus depreciation, designs retirement contributions, times grant income and credits, and calibrates quarterly estimates so cash is ready when taxes are due. Preparation without planning leads to surprises and missed opportunities. Planning paired with strong preparation means year‑end is mostly execution and your return reflects the decisions you already made on purpose.

  • When should I elect S‑Corp status and how does reasonable compensation factor in?


    How do R&D credits and §174 amortization affect cash this year?


    Can tax planning help with multi‑state and remote teams?


    Should I use Section 179 or bonus depreciation for new equipment?

Reporting Pack

Pricing and Getting Started

What’s included (every month):

  • Rolling tax projection with federal, state, and local views
  • Quarterly estimate planning with cash set‑aside targets
  • Entity and election review, including S‑Corp timing and reasonable comp
  • Depreciation strategy, 179 versus bonus, and CAPEX timing
  • Credit opportunities assessment (R&D, retirement, HSA, and more)
  • Implementation roadmap and accountability tracked in TaxPlan IQ
  • Workpapers, support, and e‑sign packages organized for filing in ProConnect