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When you're pre-revenue, hiring full-time W2 staff is a massive risk. 1099 lets us test talent without committing to long-term overhead.
Examines hiring strategy from a founder's perspective, highlighting risk mitigation, cash flow management, and rapid scaling.
Forming an LLC taxed as an S-Corp was a game-changer for my 1099 income. Saved me thousands in self-employment taxes last year.
Practical strategies on establishing legal entities to protect personal assets and optimize deductions as an independent contractor.
Taking two weeks off stings more when you realize you aren't just taking time away—you're directly losing billable revenue.
Weighs the guaranteed comfort of paid leave against the freedom of taking unlimited—though unpaid—vacation as a contractor.
If I have to work set hours, join daily standups, and report to a manager, I shouldn't be getting a 1099 at the end of the year.
Discusses worker classification laws and whether startups frequently treat independent contractors like full-time employees without offering perks.
People look at a $100/hr 1099 rate and think you're rich. After covering my own health plan, equipment, and self-employment taxes, it feels closer to $55.
Breaks down out-of-pocket expenses—like self-employment tax, private health insurance, and software licenses—that new contractors often overlook.
I stayed W2 for years because of health insurance, but once my side projects matched my salary, the tax write-offs of a 1099 made total sense.
Explores the mental and financial tipping point where professionals decide to leave traditional employment for independent contracting, or vice versa.