About 11 years ago I (52M) met a successful entrepreneur that convinced me to leave my comfy corporate leadership job (CMO) and go to work for one of his struggling start-ups being running by his son.

He used the pitch, “do you want to work for a salary the rest of your life or take a chance on doing something that will financially change your life?”

14 months later, after turning the business around and making it profitable, his son had a nervous breakdown after his wife cheated on him and he basically shuttered the business.

Despite the way it ended, I enjoyed the pace and flexibility so I jumped to another start-up where I had great success. I was there nearly 4 years and grew MRR significantly. Unfortunately, they chose to move the HQ to Austin Texas and my wife/kids refused to go. This was before COVID so full remote was not an option.

I went to another start-up and despite great initial success, they experienced significant cash flow issues and couldn’t make payroll so nearly 60% of the company was laid off unexpectedly, myself included.

I was able to find a new leadership role at a start-up very quickly and had great success over the next 4 years, despite COVID essentially resulting in a year of flat growth in 2020.

I was recruited to another start-up with a huge salary, a sizable starting bonus, and a performance plan that would enable me to make $500k+ a year, and a large amount of equity (4.5%). After discussing it with my wife, I left my very secure role to take on the new challenge.

It was a year of hell. A story much too long to tell here, except that I outperformed my plan and made significant money ($650k) between Jul 2021 and Sep 2022. I quit in Sep because the money simply wasn’t worth the anxiety of working with the President they hired a couple months after I started, a drinking buddy of the founder that hired me.

I immediately began a role at a new start-up , based in Berlin, that I believed with all my heart would be a huge success. I’ve never been so excited about a new opportunity and thought it would be life changing. 10 months later (Jul 2022) they experienced a monumental product issue. The impact was so significant that within days their investors revolted and demanded their money back. They laid off the entire NA team, including myself and the team I had built.

Shortly after I was offered a CRO role with a $6M 3-year old start-up. I was hired, and in turn hired a team, in advance of a large investment they were expecting. Two weeks ago those investors informed us they would be unable to make that investment due to issues with the macro environment in the industry. The company has burned through all of its cash reserves and does not have the cash flow to support their growth or the people they hired. I will most likely be laid off for the 2nd time in 6 months and looking for a new job for the 3rd time in 14 months.

With three short-term roles my resume is a wreck. My confidence in start-up founders is non-existent and my network has to be wondering what the hell is wrong with me to be looking for another role again. For these reasons I’m worried I’ll be facing an extended period of unemployment heading into the holiday season.

Can I even find a job with three short three short term roles on my resume over the past 2 years?

Is it time for me to get out of start-ups? Are there any good founders still out there?

I’m wandering lost in the wilderness and would appreciate the perspective of others in the start-up world.

TLDR: 3 start-up failures in the last 18 months, 5 in 10 years, my resume is a wreck, should I get out of start-ups?