Kyle Bamboo · July 20, 2026
If you’re doing delivery or rideshare work, mileage tracking for delivery drivers is the single biggest tax deduction most people just… leave sitting on the table. I did it for six months before I realized I’d been eating hundreds of dollars in write-offs. The reason? It felt like annoying bookkeeping, so I kept telling myself … Read more
Kyle Bamboo · June 8, 2026
Health insurance for freelancers isn’t optional, but it’s rarely explained in a way that doesn’t make your eyes glaze over. The truth is simple: when you leave a 9-to-5 job, the coverage your employer subsidized just vanishes. Nobody hands you a guide. Nobody tells you what to do next. You’re left to figure it out … Read more
Kyle Bamboo · May 18, 2026
Freelance quarterly taxes are payments you send to the IRS four times a year to cover the income tax and self-employment tax you’ll owe on your freelance income—basically, the government’s way of not waiting until April to collect what you can’t pay in one lump sum. If you’re expecting to owe $1,000 or more in … Read more
