Management · Recruiting

Can startup founders ever be happy as just employees?

Jessica Alter Entrepreneur & Advisor

May 20th, 2015

We're thinking of hiring someone that's run their own startup several times. They are awesome culturally and can definitely handle the job. One of the only concerns is whether or not a startup founder is OK with being a team member and not CEO/Cofounder. Even at a small startup it is a shift. If you've been in this position or hired someone similar would love your thoughts.

Sylvain Carle Partner @RealVentures. General Manager @FounderFuel.

May 20th, 2015

I have been in both positions (hired a co-founder as an employee and was hired myself too, in a later stage company) and I think that the most critical success factor is the awareness that this role will be only "for a while", it will be a transition to doing another startup "in time". Typically, this probably means 2-3 years.

Entrepreneurs are the best employees if you challenge them, make them part of your core team, offer stock option plans, and respect the natural cycle of ebb and flow, they come and go... Frame of mind/reference being "The Alliance" from Reid Hoffman.

Brian Costello Strategy, Product Development, Digital & Investment Professional

May 20th, 2015

There are times when even the most ardent entrepreneurs seek something other than being the CEO. I have found that moving back and forth has created in me an ability to be a better manager and a better listener. Certainly a bit better at seeing the many sides to issues. As a start-up founder (especially multiple start-ups) you've seen a lot of what makes company succeed and fail, and those learnings can certainly bring you to the next start-up. But I've always found that what the experience has given me is the ability to see opportunities and give advice to other entrepreneurs and business people. This means not always being the #1, but rather, putting yourself in roles that best suit the growth of a company that you have an interest or passion for that you didn't start. I've had the great joy of being on companies that I have not started but, once there, helped grow and succeed. My experience starting my own companies has given me - if anything - more humility and more understanding of how to work with all kinds of people, situations and anything else that has come across the table. Being there as an employee is not a negative - it can be great fun and a great opportunity. The key is just to align expectations - a lot of start-up Founders need the break and the consistently of NOT being the CEO for a change - find the ones that have this desire to personally and professionally grow without risk of their wanting to take your job (some of us sigh a breath of relief). One caution - we can't get it out of our blood - you may not keep our interest long if we start to see mistakes and advice not heeded. Plus we are always, ultimately, entrepreneurs, so give us the opportunity to help you grow and good things happen.

Joe Greenstein Entrepreneur Mostly

May 20th, 2015

I have a pretty strong founder mindset... But I loved my role at Edusoft bc I quickly felt a ton of ownership. I think key questions are whether they come in w attitude to have a founder mindset toward the thing they are doing and whether they are given enough autonomy to realize that. If so, great things. If not, bad fit.

Marc Rowen

May 20th, 2015

Have they previously been a regular employee? If so, they know a bit more what they're getting themselves into, and if they're a great fit, I would hire them without hesitation. 

 I've worked with a number of folks who previously founded their own companies. Other than those who joined via acquisition, they were all great. The founders whose companies got acquired were different, but I think that's to be expected.  

Justin Sherratt

May 20th, 2015

I have been in both positions and also have worked as a recruiter with this situation.

Having very clear expectations of the duration of the role and also the command structure is crucial to the success of the new teammate. 

Here are some questions to ask: 
Is the former entrepreneur looking to mentor and just be involved? 
Why would they come work for you if they are so successful on their own? A home? A change? A challenge? Less of a challenge? Stability? A launchpad? A personal/career inflection point?
How does their partner (if one exists) feel about it? 
Are they in a "resting period" while they work on their next idea or just taking a breather for the sake of it? Are they going to be treated as duke/duchess of their own castle within your kingdom, or are they going to be part of your royal guard. 
Beyond the role and work, are there any strategic reasons behind the hire? Are you relying on their connections? Does it affect funding and press? 
How have they "played well with others" in other orgs as a teammember who is not lead?

These need to be ironed out, understood and verified. Very clearly and early on. 

Mary Camacho Product & Develoment Management | UI/UX

May 20th, 2015

I think knowing your expectations for the person or job is critical.  Most people move on to other positions whether they are often founders or not. As others have mentioned, even the most serial entrepreneurs sometimes need a reset period and their skills and capacities can contribute hugely to an organization that knows how to best 'use them'.  

While we may all be different, I've yet to meet a serial entrepreneur who can stand being bored.

Sumit Gupta Co-founder of Rightster, Seasoned CTO

May 21st, 2015


Some excellent points have been made in this thread, specially that co-founders can end up being employees in their own businesses, as well as it being desirable for entrepreneurs to sometimes wear an employees shoes to get the full picture (and just do a reset). 

My own view is that what excites an entrepreneur is not just taking his/her own idea to fruition, but to generally accept the challenge of taking *an* idea to fruition. As a founder, it's their idea, but it could be just about anyone else's. Sense of ownership is the key, however, and it doesn't necessarily come from ownership - that's something your company will need to cultivate, and I think as long as any employee has that feeling of ownership, they will behave like a co-founder. This kind of puts your question on it's head: you would *want* him to work like a founder - in your company - and not really like an employee who watches the clock.

All the best!

Michael Barnathan

May 22nd, 2015

I'll chime in and say that sometimes you can find a company which aligns with your values, and may be satisfied playing a non-founding role in order to be a part of it. That may provide fulfillment up until the inevitable "the people running this outfit are making a lot of mistakes I wouldn't..." moment. But that depends on your reasons for going into entrepreneurship too. I get excited about building something that moves the world closer to my ideals. For some people it's the process of founding rather than the result which is exciting, or they may simply desire a different lifestyle than you can find anywhere in employment. There are lots of answers, and it's not a question with a universal answer.

Larry Shiller

May 20th, 2015

Everyone is different. Have you been transparent with him or her with your concerns and if so what was the response and did it ring true? And if not, have you reflected on why not?

Lane Campbell Lifelong Entrepreneur

May 20th, 2015

Some people want a return to "normal hours" after the startup grind.  As long as they are moving into an employee position it should be good.  I think you will get so much more skill out of a former startup person than a traditionally educated person that it's worth the risk.