The Tax Mistake That Cost Me $30K episode artwork

EPISODE · Sep 9, 2026 · 18 MIN

The Tax Mistake That Cost Me $30K

from Freelance to Founder · host Millo

Lena is staring down her first tax season as a freelancer and wants to know whether she should hire an accountant right away or figure it out herself. Preston and Austin Church share the expensive lessons they each learned the hard way — including a mistake that cost Preston tens of thousands of dollars — and lay out exactly when it makes sense to bring in a CPA versus when you can DIY. They dig into S-corp elections, bookkeeping systems, and the book that finally made cash flow click for both of them. Support our show sponsors -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/sponsors⁠⁠⁠⁠⁠ Submit your own question -> ⁠⁠⁠⁠⁠https://freelancetofounder.com/ask⁠⁠⁠ Learn more about your ad choices. Visit megaphone.fm/adchoices

Episode metadata supplied by the publisher feed · Published Sep 9, 2026

Embed this episode

Ready to play

The Tax Mistake That Cost Me $30K

0:00 18:49

No transcript for this episode yet

We transcribe on demand. Request one and we'll notify you when it's ready — usually under 10 minutes.

No similar episodes found.

Frequently Asked Questions

How long is this episode of Freelance to Founder?

This episode is 18 minutes long.

When was this Freelance to Founder episode published?

This episode was published on September 9, 2026.

Can I download this Freelance to Founder episode?

Yes. Use the download control on the episode player to save the publisher-provided media file.
URL copied to clipboard!