Never look in your rear view mirror

How a life of taking risks teaches you to have a short memory

I always knew I wanted to start a business, probably mostly because I don’t like taking orders from others.

Life’s funny.

Instead of having one boss to report to, a pursuit of my dreams has resulted in collective control by customers, investors, industries, and establishments who’s single, coordinated goal is to drain me of every drop of energy before they drop me like yesterday's news...from my perspective of course. ;p

Over that past 10 years of my journey towards feeling comfortable calling myself an entrepreneur, I’ve learned a few life changing lessons. Whether these are obvious to most or simply things one can only spot with perspective is beyond me, but they are things I wasn’t able to truly understand until I experienced them.

I obviously think I’m amazing, but when others agree?, that’s a head trip.

I often find myself asking myself “If I had to do it again, would I?” The honest answer is “I’m not sure.” Starting a business is the most difficult mental pursuit I have ever undertaken. You can watch a million YouTube videos talking about the loneliness or the seeming lack of support or understanding from close friends & family, but until you’re in it for an extended period of time, it's difficult to comprehend.

On the flip side, the highs are incredible but also incredibly fleeting. A day to celebrate accomplishments would feel like a lifetime. Moments of epiphany are followed by years of hard work in the pursuit of capturing that next high.

Those feelings and emotions seem to attract an almost cult like following that can be addictive when you’re in it, empty when you’re away from it, and scary when you reflect on it. I obviously think I’m amazing, but when others agree?, that’s a head trip.

Ultimately, I am where I am and I can’t go back. As I reflect at this point in my life (I’m 37), I can’t help but be proud at what I’ve accomplished but also confident that life would have been far easier if I had just stuck with my corporate gig. While I am unsure if I would follow the same path if I had to do it again, where I sit today I can’t envision a different path forward. This ambitious pursuit has turned me into a person I am proud to be today and excited to see where it takes me in the future.

I’m still working to change the world…well, maybe…


Matt Zimmer is a serial entrepreneur most known for his first company Stacked Wines.  He now runs Novvum Inc, a modern software production agency based in Irvine, CA.

This article was originally written in 2019 and has been republished here. Some information may be out of date.