# The Real Reason Your Contractors Keep Failing

Page: https://stenobird.com/podcast/freelance-to-founder-55033/the-real-reason-your-contractors-keep-failing
Text version: https://stenobird.com/podcast/freelance-to-founder-55033/the-real-reason-your-contractors-keep-failing.md
Podcast: [Freelance to Founder](https://stenobird.com/podcast/freelance-to-founder-55033)
Published: 2026-08-17T10:00:00+00:00
Episode link: https://pdst.fm/e/tracking.swap.fm/track/tcQd6Q6C0RUUlOHq1Ytj/mgln.ai/e/51/pscrb.fm/rss/p/traffic.megaphone.fm/TPG8714670874.mp3
Audio file: https://pdst.fm/e/tracking.swap.fm/track/tcQd6Q6C0RUUlOHq1Ytj/mgln.ai/e/51/pscrb.fm/rss/p/traffic.megaphone.fm/TPG8714670874.mp3
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JSON: https://stenobird.com/v1/public/podcasts/freelance-to-founder-55033/episodes/the-real-reason-your-contractors-keep-failing
Duration seconds: 1114

## Resource

Emily has hired contractors before, and it blew up on her—badly enough that she's not sure she can trust the process again. Preston and Kevin Rice, who scaled a business from two people to two hundred, break down why bad hires happen, how to rebuild systems (not just confidence) after getting burned, and why the real fix often has less to do with the contractor and more to do with how you communicate, onboard, and follow through. 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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