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?
I have a similar situation, although I am not from the United States, I worked in a startup in 2020, then the startup changed the model and was sold, however I had very good savings so I spent them to move to San Francisco, I managed to get hooked on another startup until February of this year, supposedly we were going to wait for the series A to achieve a stable salary and earn a lot of money, my boss was betting on the sass market, however I wanted to change to retail to relieve some pain, the deadline arrived and the investment, I returned to my country without savings, I have not been able to get hooked on tech again, so I took a teaching position at a university, worse it seems that I disconnect from startups
Frankly, most of these are not your issues. If you underperformed and were fired due to that in all 3 roles, it’s a different story. That’s not the case here. You’ve had a series of bad luck.
Startups do have a high failure rate. I was involved in a leadership role in a Startup where I worked 80+ hours and it was mentally and emotionally exhausting. I had to quit for my own mental health.
It happens.
Your resume is not a red flag. It’s how you tell your story. If you’ve been laid off because of issues outside of your control, it’s not on you to worry.
Don’t internalize this. Learn the lessons and move on.
I would encourage you to hire a career coach who can help you craft a compelling story about your experiences. They will help you identify your core strengths and provide some coaching. Your challenges are not technical, but mental/psychological (and btw it’s normal for someone who has been through what you’ve).
I wish you the best in your next adventure.
Start your own start up. You will never look back by the sounds of it.
I’m 35, over the last decade I have failed and failed and failed at my previous businesses. I use those failures to show investors that I know what I’m doing in my latest venture.
Perseverance is the key. You fail until you don’t.
“With three short-term roles my resume is a wreck.” - I think this is the biggest concern that is holding you back. While this might be true in some circumstances, it only IS true IF you make it so. Don’t. Don’t let anybody tell you what to think, and write your own story.
It might be difficult to believe right now, but if you look at your last couple of years and try to revert every negative into a positive, you will come out with a unique resume. Nobody else will have a resume like yours!
Think about it. You went through all these turbulent times, delivered AND surpassed your goals, maintained your own sanity and your team moral, and have had experiences in not just one, but multiple industries. Who else, if not you, is better prepared to wade into the rough seas and succeed?
All the things that made you jump around were completely outside of your control, but everything in your control, you crushed it!
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Take a long break. Don’t work. That will set in a new perspective which will help with better decision making
Get out of doing other peoples startups and create your own
My feeling reading your post is that your experience at startups that have failed is such a great asset! Imagina how much time and money can be saved with having someone who has experienced failling so can know better.
The data I see from successful startups says that there is a bunch of trying and failing at the beginning, especially if the founders haven’t failed a bit yet.
I don’t have that much experience in the startup industry yet (I came from 10 years in the marketing industry), but still, I think that people in the startup world are familiar with this situation and would completely understand your CV.
With that much experience, maybe you would feel motivated to create your own?
Anyone that can score a 500k + equity offer is killing it, startup successful or not…I’m very envious and inspired
You’re gonna have to find work by leveraging relationships with past founders where you were successful. Three short unsuccessful stints is gonna be a huge red flag to recruiters, so they are unlikely to give you a chance since they don’t really understand how often startups fail. Even if you get to explain the situation to them, they’re gonna be skeptical as will founders who don’t want that stink on their baby. But one if your former founders vouching for you to another founder wipes that stink right off. But your options will be greatly limited and you’re probably looking at a huge oaycut unless you get super lucky. Just the reality.
This is the unpleasant truth that haunts me.