This Mistake Cost Me $30,000 episode artwork

EPISODE · Feb 23, 2026 · 18 MIN

This Mistake Cost Me $30,000

from Freelance to Founder · host Millo

Lena is a new freelancer staring down one of the most universally dreaded moments in self-employment: tax season. She knows taxes are confusing, but she's not sure whether to invest in an accountant from the start or try to handle it herself. Preston and Austin Church—both of whom learned the hard way—share what they wish someone had told them earlier, including the costly mistake that set Preston back $20,000 to $30,000, and the simple mindset shift that makes all the difference. Support our show sponsors -> ⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠ Submit your own question -> ⁠⁠⁠https://freelancetofounder.com/ask⁠⁠ Join Austin's Community for Advanced Freelancers -> ⁠Freelance Cake Community Learn more about your ad choices. Visit megaphone.fm/adchoices

Episode metadata supplied by the publisher feed · Published Feb 23, 2026

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This Mistake Cost Me $30,000

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