About The Broke Boss
I’m Kyle Bamboo. I spent eleven years running engineering teams — steady paycheck, health insurance, a boss who wasn’t me. Then a layoff and one very bad quarter made me my own boss overnight, and it turned out nobody tells you the real stuff about working for yourself: how lonely it gets, how confusing the taxes are, how one client ghosting can wreck a whole month.
So this site is where I write it down. Not as a guru looking down from a beach with a laptop, but as someone about one week ahead of you on the same road, waving back to say “here’s what I wish someone had told me.”
What I Write About
Freelancing, gig work, and side hustles that are trying to become main hustles. Pricing, invoicing, taxes at 11pm, the emotional whiplash of being broke and booked out in the same month. I’ve been both, and I’m not embarrassed by either.
I also write about the other side of it — hiring a first employee, putting off a firing for three months, running performance reviews for a team of two — because going solo often turns into managing people faster than anyone warns you.
My Standards
- Radical honesty over polish. Real numbers, real failures, real timelines — not highlight-reel success stories. Where I use illustrative figures rather than my own, I say so on the page.
- Competence without condescension. I know this stuff — pricing, invoicing, contracts — but I’m not talking down to you.
- Something actionable, every time. A script, a number, a template, a step — not just vibes.
- I’m not your accountant. I write from my own experience going self-employed, not as a CPA, financial advisor or attorney. Where a post touches tax, insurance or contracts I link the primary source and tell you to confirm anything consequential with a professional.
Get In Touch
Got a question, a correction, or a topic you want covered? Contact me here.