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Can startup founders ever be happy as just employees?

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.

38 Replies

Larry Shiller
1
0
Larry Shiller Entrepreneur • Advisor
Grit: The new dimension in college admissions
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?
Sylvain Carle
16
0
Sylvain Carle Advisor
Partner @RealVentures. General Manager @FounderFuel.
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.
Lane Campbell
1
0
Lane Campbell Advisor
Lifelong Entrepreneur
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.
Justin Sherratt
2
0
Justin Sherratt Advisor
Founder of @SortBox
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.
Richard Ramirez
1
0
Richard Ramirez Entrepreneur
Director at Zumbox
Some Founders are made, some are born. Personality is a deep seeded thing ... And different from manners and courtesy. In my experience, including my own turn as both the CEO with a former founder/CEO as a team member and as a a team member to another CEO ..I have found this to be very difficult, unless there is great maturity and real respect. What are the circumstances that have brought this former CEO to this position? What was the history of managing down the line of command when they were CEO? If they did not respect the chain of command and operational responsibilities of the team as a CEO ... Evidence they will forget now. You hire senior people in early stage to drive specify outcomes over modest time horizons ... 12-18 months. Don't hire the executive to drive scale when it is POC or reference accounts that are needed. R Sent from my iPad
Sameer Babbar
0
0
Sameer Babbar Entrepreneur
Founder SVB Group; Board Member VEA; Founder @Bujbu, @Zapiator, @ Celevitation
Sounds like a Jena great value add to the team however plz make sure you engage the services - with focus on the outcomes and not hours - you offer them flexibility of time and location as long they can deliver - they are a good social fit to the company culture you are trying to create or envisaging - their compensation structure is geared towards long term value I am sure you have heard of the saying - the devil you know versus devil you don't . It will be much easier to deal with and manage someone you know really beell if you are transparent enough before engaging them Good luck Cheers Sameer
Mary Camacho
2
0
Mary Camacho Entrepreneur
Product & Develoment Management | UI/UX
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.
Marc Rowen
3
0
Marc Rowen Advisor
Founder & CEO at SquadFusion
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.
Brian Costello
4
0
Brian Costello Advisor
Strategy, Product Development, Digital & Investment Professional
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.
Steve Grigory
1
0
Steve Grigory Advisor
Self-starter specializing in new and disrupted markets
Why not?

Be open about and ask this person about it. There are so many factors at play and none of them will rule this person out or rule this person in.

Be open as you can and if the other person reciprocates, take the risk (just as you would be taking a risk with anyone else). If they don't. If they aren't open - then keep looking.

Keep it simple...
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