Blog
City of LA Freelance and Business Tax FAQs (updated for 2026)
The City of Los Angeles imposes a gross receipts tax on freelancers and businesses. You must file by the end of February annually, even if you’re not profitable or made no money.
Who needs a 1099? (FAQs + examples)
Who needs a 1099? The decision tree you use (based on W-9 info, payment method, and contractor status) has changed.
Who needs a W-2? (overview + examples)
Who needs a W-2? How has the OBBBA changed W-2 requirements? Are there penalties? Here’s what you need to know.
Five things about 2026 health insurance
Health insurance is getting more expensive in 2026—and more complicated. Jill James breaks down what’s changing, what small business owners need to do before December 15, and how to find the best option for your team or yourself. Plus, join a free expert Q&A session on October 28.
Is your team entitled to paid time off?
Confused about whether you need to provide paid leave? Our updated state-by-state guide for paid sick leave, family leave, and holiday requirements
2026 Health Insurance Guide for Self-Employed & Small Business Owners
Choose your 2025 self-employed or small business health insurance with confidence
Celebrating women entrepreneurs
AI, YouTube, public reading parties, and why Mark Cuban finally agrees with me: four fall trends I’m watching that could shape how we grow, market, and lead our businesses in 2026.
Four trends and how to use them now
AI, YouTube, public reading parties, and why Mark Cuban finally agrees with me: four fall trends I’m watching that could shape how we grow, market, and lead our businesses in 2026.
Can you outrun the bear?
In choppy markets, your competition isn’t BigCo—it’s the other small business trying not to be the slowest human. Here’s a calm, practical playbook: monitor policy shifts without doom-scrolling, move cash-flow reviews monthly, invest where inaction creates permanent gaps, and prioritize profitability over tax perks. Plus: key 2026 health insurance resources and dates.
My big take on economic things
It’s not just politics or headlines—growth has slowed, uncertainty is creeping in, and spending behavior is shifting. If you run a business, now is the time to plan carefully. In this post: hiring your kids, high-value marketing ideas, must-know deadlines, and what to watch in the economy for the next 18 months.
City of LA Freelance and Business Tax FAQs (updated for 2026)
The City of Los Angeles imposes a gross receipts tax on freelancers and businesses. You must file by the end of February annually, even if you’re not profitable or made no money.
Who needs a 1099? (FAQs + examples)
Who needs a 1099? The decision tree you use (based on W-9 info, payment method, and contractor status) has changed.
Who needs a W-2? (overview + examples)
Who needs a W-2? How has the OBBBA changed W-2 requirements? Are there penalties? Here’s what you need to know.
Five things about 2026 health insurance
Health insurance is getting more expensive in 2026—and more complicated. Jill James breaks down what’s changing, what small business owners need to do before December 15, and how to find the best option for your team or yourself. Plus, join a free expert Q&A session on October 28.
Is your team entitled to paid time off?
Confused about whether you need to provide paid leave? Our updated state-by-state guide for paid sick leave, family leave, and holiday requirements
2026 Health Insurance Guide for Self-Employed & Small Business Owners
Choose your 2025 self-employed or small business health insurance with confidence
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