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Are You Still Loving It? Self Reflecting as a Founder/CEO


Today, Volition Capital Venture Partner Jenny Fleiss answers a question submitted by a friend: When should a founder consider stepping aside as CEO? Do you have a question for Jenny? Shoot her an email at or submit your question in the form below.

ASK JENNY ANYTHING: How Can a founder grow as a company scales?

FULL Transcript

Hi, this is Jenny on Ask Jenny Anything. We’ve gotten some great questions. Thanks for emailing in. You can email if you have any questions about starting a business, investing in businesses, hiring for your business…really anything in the startup world. And, I’ll try to give you some quick tips.

This last week, Tom C. wrote in and asked, “how do you know when it’s time as a founder to call it quits being a CEO?” Well, first off, the skill of founding a business is often quite different than being a CEO, especially as a company scales. So, there is nothing wrong…and I’d even say it’s pretty typical…that at some point a founder may not be the best person to lead as a CEO.

The first piece to consider is if you as the CEO are still enjoying it. So, are you having fun and happy with scaling a company versus the founding, building, and creating the early stages. Because it’s a different sort of muscle. And, if you’re not enjoying it and you’re not passionate about what you’re doing, it’s less likely you’re going to put your all into it and be successful. So, I think the first is kind of introspective question.

The next becomes a question of hitting metrics and key KPIs for the business. Is it actually that we’re tracking towards revenue, bottom line growth team hiring, retention, all the key metrics that you lay out with your board? If at some point for an extended period of time you’re feeling that you can’t reliably hit goals and metrics that you’ve signed up for, I think that should be a moment where everyone calls to question is there something wrong with the whole mix? And maybe that’s the team supporting you. Maybe it is the CEO. But, I think starting to ask those questions and diagnose the pieces is in part the responsibility of the CEO themselves, but also the board to try to encourage and help the CEO to ask themselves the hard question about is it time to hire someone to either support them in scaling the business or potentially to have the founder take a different role as the company continues to scale?

At the end of the day, you want to optimize value for everyone, including yourself. So, everyone has the same goal here. If you’re the founder of the business, you should want it to be the biggest business possible and just be really humble, open minded and self-aware about the right leadership to get you there. This has been Jenny and ask Jenny anything. 

Hope this was helpful. And please send your questions to or fill out the form below.