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Jake Karls

Jake Karls

Entrepreneur

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I Wrote a Letter to My Past Self — Here’s What I Wish I Knew Before Becoming an Entrepreneur

What I wish I knew before starting my entrepreneurial journey about how to handle slow progress, uncertainty and emotional swings while staying in...

19.06.2026 8

Entrepreneur

Jake Karls

Why Great Products Still Fail — What I Learned After Building a Multi-Million-Dollar Brand

Attention isn’t something you get by building a great product — it’s something you earn by consistently showing up and making your story...

12.06.2026 10

Entrepreneur

Jake Karls

This Business Strategy Made No Sense On Paper — But Drove Most of Our Customer Loyalty

What started as handwritten notes in our earliest orders became a lasting lesson in why the most “inefficient” moments are often the ones...

18.05.2026 20

Entrepreneur

Jake Karls

How Successful Founders Stay Grounded Through the Emotional Whiplash of Entrepreneurship

Entrepreneurship rarely feels like a straight line, but learning to separate short-term volatility from long-term progress can help founders make...

15.05.2026 10

Entrepreneur

Jake Karls

Why We Invest in Therapy Every 7 to 10 Days as a Business

What scared me most about building Mid-Day Squares with family wasn’t the risk or uncertainty, but the possibility of damaging the relationships...

06.05.2026 10

Entrepreneur

Jake Karls

I Sucked as CMO. Here's Why I Gave Up My 'Chief' Title to Do What I'm Actually Great At

I stopped chasing a title and built a role that truly fit me.

05.08.2025 20

Entrepreneur

Jake Karls