The Wrong Advice Newsletter — Issue #63 — Entrepreneur Life

John Picciuto
3 min readJun 22, 2022


So You Want to be an Entrepreneur?

Let’s talk about being a band of one

Is it easier to be a solo artist or the backup singer in a huge band?

In March of 2019 after close to 5 years working in the crane industry I decided to branch off and start my own company and thus New Jersey Crane was born. For 1-year I was my own man band and it was great!

I was lucky enough to make a fair bit of money brokering cranes for sale from March of 2019 to about December of 2019. That first year flew by in a flash for sure. The only downside to the one man band scenario was an unexpected desire to work with more people.

You see, for the entirety of my working life I was part of a team, a cog in the wheel. When you’re a solo entrepreneur there is nobody to work with at first, no team…There are no teammates to rely on, no other departments to generate needed help etc. It was me, myself, and I. If you measure that first year in terms of finances it was a wild success.

But I was lonely and wanted more.

In March of 2020 I took a job with a growing company in a field I had never worked in before. I have detailed pretty extensively how that failure impacted me so I’ll save you the details here. That being said, 6-months after joining a team, I found myself as a solo artist yet again.

Something funny happened after my failure to join another team, I started to branch out in multiple ways. First, I started The Crane Exchange, an online marketing platform for people in the construction industry to sell their used and new equipment. Then I started my photography business which has been one of the greatest joys of my life. Shortly after going full time in photography I launched The Wrong Advice Podcast ! To say the podcast has changed my life would be underselling it completely.

Since the launch of the podcast I’ve started this newsletter and am even in the process of launching another digital marketing agency. So after all of that do I enjoy the life of an entrepreneur? (btw I hate the word entrepreneur) There are equal parts yes and equal parts no.

At times, there is still the solo artist in me that longs to be part of a team. I often times find myself wanting to collaborate with people as to break up the monotony of being a single contributor. Financially can be a whole other conversation in itself. The life of a single provider can often be unpredictable. The fluctuations in money can be infuriating but also incredible. Jury is out on the long term in that regard.

When I started this post I wanted to dive deep into the concept of being a solo artist versus someone in a proverbial band and my experiences with both.

But the truth is that I don’t have the answer just yet!

Although I am 3 years into a solo journey (with a 6-month detour) I find myself going back and forth with what the pros and cons are. Ultimately I know that my life will figure itself out and for that I’m extremely happy that I am able to be content along this path. However, there is one great lesson I’ve learned throughout this entire journey:

Taking risks is tantamount to living a fulfilling life.

Of course failure is an option, but so is success. If you don’t take chances in life you’ll constantly be playing a regretful game of what if. The best advice I can give to you if you’re thinking about going solo, is to do your research and make a concrete plan. Being on your own is a constant battle of juggling 1-million things and almost always evolving. So far I’m happy and extremely lucky! Things do change so we shall see where things take us in the future but for the time being I’m happy being a solo act!



John Picciuto

Storyteller, Photographer, and host of The Wrong Advice Podcast. You can find more of my work at