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6 Lessons I Wish I’d Known as a First-Time Founder

Jonathan Woahn
Startup Grind
Published in
13 min readSep 17, 2020

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“Failure is a great teacher, and, if you are open to it, every mistake has a lesson to offer.” — Oprah

It’s been over a year since I left my role as CEO of my first startup. Things were fine, but it wasn’t growing as quickly as I’d hoped. After 5 stressful years of 80+ hour weeks, I lacked the physical, mental, and emotional zeal to keep going. So instead of forcing myself into year #6, I chose to step down and leave the job to better, fresher minds.

Enough time has passed now that the scars from my emotional wounds don’t feel quite as fresh and I’m ready to share a few thoughts from that experience.

I had the original idea for the company in January of 2014, while working as a McKinsey consultant. Though I personally had never started a business, all of my friends were entrepreneurs, my dad was a serial entrepreneur, and I figured I was an expert by osmosis.

Turns out there’s a huge difference to being surrounded by entrepreneurs, and being one.

Although I spent an entire year putting together the business plan and convincing my wife it was a good idea, there were a lot of things as a first-time founder that I frankly didn’t know, and didn’t know I didn’t know. Lots of unknowns.

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Jonathan Woahn
Startup Grind

Founder Coach & Startup Advisor. Husband. Father. 4X startups. Entrepreneurship, web3, leadership, and self-actualization enthusiast.