1. EachPod

Our Biggest Business Mistakes (and Why We’re Weirdly Grateful for Them)

Author
Audrina & Sydney
Published
Wed 16 Jul 2025
Episode Link
None

Ever made a mistake so cringey it kept you up at night for years? Good, that means you’re doing it right.

In this episode, Audrina and Sydney get real about the mess-ups that shaped them... the kind that felt like disasters in the moment but ended up being the exact lessons they needed. These aren't just "oops" moments. We're talking business partner drama, pricing flops that nearly tanked whole businesses, and the hard lessons that come with mixing friendship and hiring.

But here’s the twist: they wouldn’t undo any of it. Because every painful misstep helped them build the profitable, rock-solid agency they run today.

In this conversation, you’ll hear:

  • Why the old saying “hire slow, fire fast” hits extra hard when you’ve learned it the hard way

  • How to hire someone close to you (without setting fire to the relationship)

  • Sydney’s boat analogy that’ll change how you think about delegating in your business

  • Why it’s so important to remind your clients the impact you’re making — even if it feels obvious to you

  • A peek at how Sydney got herself out of the day-to-day at The Hive so she could focus on CEO-level growth

  • Why the lowest-paying clients often demand the most (and how to protect your energy)

  • And the hot take: business mistakes might be more valuable than an MBA

If you’re dreaming of starting something of your own (or knee-deep in figuring it out), this one’s for you. Mistakes aren’t proof that you’re failing, they’re signs you’re in the game, learning, adjusting, and getting sharper every step of the way.

Connect with us:
Instagram: https://www.instagram.com/swearingbyitpod/

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LinkedIn:
Audrina: https://www.linkedin.com/in/audrinablackburn/
Sydney: https://www.linkedin.com/in/sydneymsherman/ 

Referenced: 

Carrying On When It Feels Like Everything’s Falling Apart


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