
Health Coverage Decisions for Solopreneurs Start Earlier Than you Think
One deadline wraps up last year’s taxes, the next sets your 2027 health coverage. This week's newsletter covers…
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Nikita is the Content Lead for Collective, focused on organic educational content. She has lead financial education for various digital platforms for over a decade. She enjoys taking complex, sometimes confusing subjects, and explaining them in clear, relatable ways. Nikita earned a bachelor’s degree in journalism and mass communications from Florida International University.

Newsletter |
One deadline wraps up last year’s taxes, the next sets your 2027 health coverage. This week's newsletter covers what solos need on their radar for both.

One deadline wraps up last year’s taxes, the next sets your 2027 health coverage. This week's newsletter covers…
Sep 30, 2026 · 4 min read
Ad revenue from one platform counts as income. So does a brand deal paid through PayPal. Affiliate commissions…
Sep 29, 2026 · 8 min read
How to convert an LLC to S Corp status: the 5 steps, whether you need a new EIN,…
Sep 25, 2026 · 10 min read
What's due October 15 and what isn't. Extension deadlines, penalties for filing late, and the retirement contribution date…
Sep 24, 2026 · 5 min read
Collective vs. QuickBooks Solopreneur compared- see why Solopreneur works for Schedule C freelancers but can't support an S…
Sep 17, 2026 · 4 min read
Q3 estimated taxes and extended S Corp returns are due today. Here’s what a reversed IRS reporting rule…
Sep 16, 2026 · 4 min read
Collective vs. Lettuce compared on pricing, bookkeeping, payroll, and support. See which back office fits your business-of-one, backed…
Sep 16, 2026 · 5 min read
If your S Corp pays for your health insurance, the IRS won’t let you treat it like a…
Sep 14, 2026 · 3 min read
Is an S Corp worth it at your income? See the full breakeven table from $40K to $300K+,…
Sep 11, 2026 · 3 min read
Have a W-2 job and 1099 income? Here's how self-employment tax, quarterly payments, and W-4 withholding actually work…
Sep 10, 2026 · 4 min read
From reasonable salary to quarterly taxes, we're answering the S Corp questions solopreneurs ask most.
Sep 9, 2026 · 13 min read
You elected S Corp status to save on taxes, but now you’re staring at your business bank account…
Sep 4, 2026 · 10 min read