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?
A) I think you are successful. B) For the next opportunity, pretend like you are an investor. You are investing your time. I heard one “I thought it would succeed”, I didn’t hear that for all the companies you worked with. I heard what you got out of some of the others. If I were you, my next opportunity would be self-led. Go to events in an industry you are keen on. Scope out the smartest person in the room and tell them why you can help them succeed, independent of whether or not they are hiring. Disclaimer: Easy for me to say what I would do, with no skin in the game.
I was reading and thought „man If I could afford it Id hire this guy“ and then you said your resume is „a wreck“? You’re doing good man. Keep going.
Can I even find a job? -> Yes, you can! You have to.
Is it time for me to get out of start-ups? -> Could be but it’s not necessary.
return to my old job as a mobile developer.
I’ve been in startups consistently for almost 30 years now. Sounds like a typical success path except one thing - attitude is everything. Reality is what you make it, enthusiasm goes a long way… find the success in all of these failures and turn it into the most positive experience. Focus on that and you’re going to be fine.
You’ll have to trust me when I say I have a lot worse ‘damage’ I’ve dealt with and have always been able to turn things into a positive.
| Can I even find a job with three short three short term roles on my resume over the past 2 years?
You clearly have tons of experience and would be a huge asset to many startups. Yes, you’ll be able to find a good job.
There are good founders but the hard part is finding them and filtering them. When you interview with a startup founder, you should be asking more questions than they ask. Interview them at least as much as they interview you. That might cause a few bad founders to not want to hire you (which is a great thing! saves you from joining a bad startup) and the really good founders will think more highly of you for being selective.
It’s totally appropriate to ask founders about questions about their business model, current / future investors, runway / cash flow, how they thinking about corporate culture, any key hires they are thinking about, examples of how often and specifics on when they changed strategy or pivoted etc.
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?”
Sounds like an Amway presentation.
You want to change your life? Spend an hour a day reading financial news and do good investments.
I’m contributing nothing to this answer. I’m only responding because the summary of your extensive (and impressive) resume fascinates me. In contrast to you, I’ve been in essentially the same kind of job at the same company for almost 42 years. The startup ecosystem is amazing and clearly it takes a certain magical kind of person. And I guess that is you not me.
I have no doubt you’ll be successful wherever you end up.
You are successful OP and you will Land a great job at a startup of your choice in no time. I would hire you
Fucking 2023 man. I’m in a similar situation with 2023 being failure across the board. It’s just the economy at the moment killing all the startups. Don’t take it to heart.
The big problem is you don’t have any peers with which to socialize. You’re alone and feeling schlubby.
> Can I even find a job with three short three short term roles on my resume over the past 2 years?
I don’t see why not. You seem to be able to line up new positions quite easily. One thing that you might not be doing right is demanding more information about the company and its funding status before signing on. At your level you need to start insisting on getting enough solid (documented) information to do your due diligence. Good luck!
I would say focus on more mature startups. I quickly found that a minimum series D+, 600+ employees, and a very healthy cash flow is the only way I’ll jump ship. It means there’s clear product market fit, hopefully clear path to liquidity, and while yes you’ll get a lot less equity, if it’s on clear learn to 10B, then a few basis points is still a retirement.
You’ve had more success and opportunities than most people. What you really should be doing is helping others and mentoring at this point. And for startups you should be consulting based on your ability to generate results quickly.
Also if you have some time I would love to have a chat, I myself am trying to transition out of freelance marketing into a in house role at a startup and I would love to have a chance to speak with someone who’s been a CMO.
Sounds like you have the battle scars to start your own consulting firm. You could probably make ridiculous money at a fraction of the stress.
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