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?
You sounds like you could add a lot of value to start-ups in a non-exec role. Sitting on a board and offering guidance.
There’s roles like ‘entrepreneur in residence’ and mentors in accelerators you might enjoy and could be done around other commitments.
It sounds like you are very good at your job, but situationally things have not been ideal
I can relate to OP, and am very curious about the roles you’ve mentioned. Can you talk more about what they actually entail, and how you go about getting them? Thanks!
I’ll do my best
Non-exec director is basically someone who doesn’t do the work (non-execution) but has a legal responsibility for oversight of the business.
A non-exec will usually sit on a monthly board meeting, listen, give advice, make introductions, and help ‘direct’ the business.
These can be paid positions or done as a vesting equity stake (1-3% ish?) or a mixture of both.
These either come through relationships with VCs and investors who trust you and know you are looking so will aim to put you in position to help with businesses they are investing in, or through being a known part of the eco-system through involvement in mentoring, advising, being employed, exiting, or investing for example.
These roles are also often advertised you can find them on linkedin.
EIR- Entrepreneur in Residence is generally someone experienced in startups who is attached to an accellerator/venture studio/incubator. They tend to have weekly short meetings with each team to track progress and give advice or act as a sounding board and are part of the long term relationship with a company during a programme to help those that run it, as opposed to mentors who tend to be one off meetings to give advice on specific topics at specific times.
You get these usually by being a mentor on a programme, or having been through a programme and becoming part of the system. These can sometimes lead to non-exec roles in companies that you add benefit to, or investment opportunities as you get early access to teams and know their trajectory. This is usually a paid position for the length of a cohort or project
Mentoring is like the above but less involved, this if not always a paid position as it is drop in mentoring and scheduling occasional calls and meetings with teams on programmes. This can often lead to running specific workshops (paid) and better relationships with organisers if you are seen to add value, which then can lead to EIR roles.
All of the above can generally be done part time around other work, it keeps you in contact with the eco system and allows you to spot opportunities in companies you would like to either join as an employee, co founder or investor.
It generally starts with identifying the local ecosystem organisers, getting to know them and letting them know you are looking for opportunities.
I have had all of the above roles after having co-founded multiple businesses to varying degrees of success and am now Programme Manager on an accelerator that I took my 2nd business on 10 years ago.
Happy to answer further questions
Thanks for sharing this
Ideally need some successful exits to get these roles. Not always but definitely helps, especially for plum roles on boards and VC firms.