# The Real Side of Entrepreneurship with Jake Karls from Midday Squares

Page: https://stenobird.com/podcast/if-you-know-you-know-7380237/the-real-side-of-entrepreneurship-with-jake-karls-from-midday-squares
Text version: https://stenobird.com/podcast/if-you-know-you-know-7380237/the-real-side-of-entrepreneurship-with-jake-karls-from-midday-squares.md
Podcast: [If You Know You Know](https://stenobird.com/podcast/if-you-know-you-know-7380237)
Published: 2026-04-08T11:51:38+00:00
Episode link: https://rss.com/podcasts/if-you-know-you-know/2708022
Audio file: https://content.rss.com/episodes/334783/2708022/if-you-know-you-know/2026_04_30_17_37_56_2a474241-2633-40c3-b9f9-166d577891a9.mp3
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Duration seconds: 2299

## Resource

In this episode of If You Know You Know , we sit down with Jake Karls to talk about the real side of entrepreneurship, beyond the highlight reels. From building Mid-Day Squares from the ground up to navigating the pressures that come with growth, Jake opens up about the mindset it takes to keep going when things get tough. We dive into personal growth, the importance of therapy, and how to handle criticism and hate while putting yourself out there. Jake also shares what it’s really like working with family, the challenges that come with it, and how it’s shaped both the business and his personal life. This episode is honest, unfiltered, and packed with insight for anyone building something, feeling the pressure, or trying to stay focused through the noise. If you’re into entrepreneurship, mindset, and real conversations about what it actually takes, this one’s for you.

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## Transcript

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