# The Tax Mistake That Cost Me $30K

Page: https://stenobird.com/podcast/freelance-to-founder-55033/the-tax-mistake-that-cost-me-30k
Text version: https://stenobird.com/podcast/freelance-to-founder-55033/the-tax-mistake-that-cost-me-30k.md
Podcast: [Freelance to Founder](https://stenobird.com/podcast/freelance-to-founder-55033)
Published: 2026-09-09T10:00:00+00:00
Episode link: https://pdst.fm/e/tracking.swap.fm/track/tcQd6Q6C0RUUlOHq1Ytj/mgln.ai/e/51/pscrb.fm/rss/p/traffic.megaphone.fm/TPG8382445156.mp3
Audio file: https://pdst.fm/e/tracking.swap.fm/track/tcQd6Q6C0RUUlOHq1Ytj/mgln.ai/e/51/pscrb.fm/rss/p/traffic.megaphone.fm/TPG8382445156.mp3
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JSON: https://stenobird.com/v1/public/podcasts/freelance-to-founder-55033/episodes/the-tax-mistake-that-cost-me-30k
Duration seconds: 1129

## Resource

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

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## Transcript

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