Question 1

When does tax planning pay back?

Accepted Answer

For most self-employed and S-corp owners, the first year of quarterly planning recovers more in reduced estimated-tax penalties and retirement deductions than the annual fee. The payback is clearer when you have been filing without planning: a prior-year return with a large April balance is the clearest indicator.

Question 2

What if I just need filing, not planning?

Accepted Answer

Starter is the right tier. It covers a straightforward 1040 with year-round async CPA email and one annual tax-snapshot call. Planning touchpoints are not included at Starter, which keeps the quarterly fee lower for clients who do not need them.

Question 3

Do you do bookkeeping?

Accepted Answer

No. We work from organized records you or your bookkeeper provide. If you need bookkeeping, we can refer you to a service that connects to our document portal so the handoff is clean.

Question 4

How often do we actually talk?

Accepted Answer

Growth includes two 30-minute planning calls per year (Q2 and Q4) plus year-round async CPA email with a 2-business-day response. Professional adds monthly 30-minute check-in calls (12 per year) and a 24-hour priority response.

Question 5

What is the S-corp reasonable-comp analysis?

Accepted Answer

IRS requires S-corp shareholders who work in the business to pay themselves a reasonable salary. The analysis compares your role to market data, sets a defensible compensation figure, and documents the rationale. Getting this wrong is one of the most common S-corp audit triggers.

Question 6

Can you advise on retirement plans (SEP-IRA, Solo 401(k))?

Accepted Answer

Yes. We compare the contribution limits and tax treatment of each account type relative to your income structure, recommend one, and confirm the contribution amount before the annual deadline. We do not open accounts or manage investments, but we coordinate the timing and amounts with your custodian.

Question 7

Do you handle multi-state planning?

Accepted Answer

Yes. Growth covers up to two state returns and Professional covers up to three. Multi-state income allocation, resident versus non-resident filing determinations, and credit-for-taxes-paid calculations are all included within those limits.

Question 8

What if I am not an S-corp yet?

Accepted Answer

The S-corp election analysis is the first step. We model whether the election makes sense for your revenue and cost structure. If it does, we prepare Form 2553 and file it before the deadline. If it does not, we document why and revisit it each year.

Question 9

Is this a fit for someone with W-2 plus side income?

Accepted Answer

Yes, if the side income creates a meaningful estimated-tax obligation. Growth covers this with quarterly estimated-tax calculation and two planning calls per year. If the side income is small and the 1040 is otherwise simple, Starter may be the right starting point.

Question 10

What is NOT included in tax planning?

Accepted Answer

Bookkeeping, payroll processing, audit representation, R&D or ERTC studies, FBAR and 8938 foreign reporting, and entity formation or dissolution are outside scope at every tier. The add-on price list at /pricing shows what each of these costs when needed.

Question 11

How do self-employed people avoid the April tax surprise?

Accepted Answer

Three habits handle most April surprises: (1) recalculate quarterly estimated taxes from actual income each quarter instead of using last year's number, (2) max out the deductible retirement contribution (SEP-IRA or Solo 401(k)) before its deadline, and (3) for S-corp owners, set a defensible reasonable salary so the IRC §6654 underpayment trap does not fire. Growth tier ($449/quarter) covers all three. The April number becomes a known quantity by Q3.

Question 12

Should a freelancer earning $150k convert to an S-corp?

Accepted Answer

Usually yes, but the math matters. At $150k of net self-employment income, a reasonable S-corp salary in the $90k–$100k range typically saves several thousand per year in self-employment tax (the 15.3% Medicare + Social Security combined rate applies to the salary, not the distributions). The savings need to clear payroll-processing costs (~$500–$1,200/year) and your CPA fee. We run the break-even analysis as part of onboarding and file Form 2553 if the numbers work.

Question 13

What does year-round tax planning actually involve?

Accepted Answer

It is the work that happens between filings: quarterly estimated-tax recalculation in March, June, September, and January; a mid-year S-corp salary review; SEP-IRA / Solo 401(k) sizing before the contribution deadline; multi-state allocation if you cross state lines; and a Q4 year-end optimization pass covering charitable timing, capital-gains harvesting, and S-corp distribution decisions. None of it happens during a one-time tax-prep engagement — which is why filing alone leaves money on the table.

Question 14

How do quarterly estimated taxes work and who calculates them?

Accepted Answer

If you are self-employed or have non-W-2 income, you owe estimated payments to the IRS four times per year — April 15, June 16, September 15, and January 15 — under IRC §6654. Underpaying triggers an underpayment penalty even if your final return shows a refund. Most CPAs hand you safe-harbor numbers based on last year's tax. We recalculate from current-year actuals each quarter and send you the payment amount and due date by email before the IRS deadline.

Tax planning, not just tax filing.

Find out if year-round planning fits your situation

Four quarters. No April surprises.

What we plan, not just file.

How a year of planning works.

If you are one of these three, planning pays back fast.

Consultant or freelancer earning $150k or more

S-corp owner running a 1 to 3 person agency or studio

Two-income household with side income, rentals, or RSUs

Frequently asked questions

Plan ahead. Pay less. Stop dreading April.