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
What this episode covers
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
NOW PLAYING
This Mistake Cost Me $30,000
No transcript for this episode yet
Similar Episodes
Mar 26, 2026 ·1m
Mar 19, 2026 ·34m
Feb 18, 2026 ·11m
Feb 11, 2026 ·45m