EPISODE · May 5, 2025 · 28 MIN
W-2 vs 1099: How Companies Are Quietly Transitioning from Employees to Contractors
from Everything Entrepreneurship With Kyle Jerome Carter · host Kyle Jerome Carter
They taught you how to clock in, but not how to cash out on your terms. In this episode, Kyle Jerome Carter breaks down the real difference between W-2 employment and 1099 freelancing—and why freelancing might be the most strategic bridge between your 9-5 and full ownership. You’ll learn how to flip job insecurity into opportunity, use your current role as leverage, and structure a freelance offer that gives you both flexibility and real income potential.Whether you're an ambitious employee, a working entrepreneur, or somewhere in between, this is the blueprint for building freedom without recklessly quitting your job.
What this episode covers
They taught you how to clock in, but not how to cash out on your terms. In this episode, Kyle Jerome Carter breaks down the real difference between W-2 employment and 1099 freelancing—and why freelancing might be the most strategic bridge between your 9-5 and full ownership. You’ll learn how to flip job insecurity into opportunity, use your current role as leverage, and structure a freelance offer that gives you both flexibility and real income potential. Whether you're an ambitious employee,...
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W-2 vs 1099: How Companies Are Quietly Transitioning from Employees to Contractors
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