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I’m the lead (acting CEO, technical, largest shareholder) of 3 co-founders. I’ve brought my startup through multiple rounds of funding and 30x increase in valuation in 3.5 years. But I feel that I don't have a comparative advantage being the CEO to lead us to the next phase - I'm too unstructured and don't have any job experience to feel confident managing a bigger team. Besides, I'm starting to feel physically worn out with an 80-110 hour work week and my creativity is increasingly stifled by managerial duties and email inflation.

However, I feel that my co-founders are even poorer managers, lack enough domain knowledge to chart a vision, and will need more experienced 'adult supervision'. So my plan is to install a new CEO from outside the company. This led to me thinking that there's reasons I should take a cleaner break: (1) A four-way management will come to more deadlocks in decision-making. (2) The incoming CEO won't have a strong mandate to boss my co-founders and revamp the company if I'm still around.

Hence, I'm planning to transition to a 1-day-per-week role at my firm, and to leave the day-to-day management work to the new CEO. During my free time, I want to keep my mind occupied with another startup idea. If fate has it, I might return to a full-time role in 2-4 years' time.

I have a few fears about my plan: There's very few success stories of people dabbling in 2 startups. Elon Musk, Jack Dorsey and Steve Jobs are often cited, but I feel that they had larger, more stable companies before they made 2-way commitments. Moreover, I don't feel that 4~ years is enough input from the original lead founder to keep the company's core culture and vision alive. And I'd rather suffer through the success of 1 company than enjoy through the failure of 2 companies.

Is this a good idea? What are some solutions or shortcomings that I haven't thought of?

closed as off-topic by paparazzo, Masked Man, Rory Alsop, Vietnhi Phuvan, The Wandering Dev Manager Dec 26 '16 at 14:09

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    @Paparazzi I'm sorry that you feel that way about my question. I've floated the idea around a few of my closer employees and mentors but I think it's a pretty big decision to alarm everyone for now. I got some useful advice from this SE before (this is a throwaway account) so I was curious to see other perspectives. – eudaimonia Dec 26 '16 at 13:19
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    As for future funding, our operating agreement just requires a certain portion of votes and board members to agree to further dilution. I'm technically not needed, though it's entirely possible for me to participate in the decision from a board chairman role without needing to be in the trenches and pitching or meeting investors. Lastly, we're at the cash flow breakeven point so it's not necessary for us to go through another round. I hope this helps make sense of the question. – eudaimonia Dec 26 '16 at 13:35
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    @MichaelKaras Certainly, however that can happen whether under my watch or under another's watch. – eudaimonia Dec 26 '16 at 14:01
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    @MichaelKaras Would've upvoted your point if you had made it an answer. You're probably right. It seems that my plan is highly improbable without a replacement who is highly in sync with me on the vision, and yet a good successor CEO is usually one who has a lot of autonomy. I'll mull over the paradox for a bit, but thank you for articulating this point. – eudaimonia Dec 26 '16 at 14:20
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    You sound like you're burned. Sell your share to your partners and move on cleanly or stay put, learn-by-doing, and soldier on. Best of luck. – Bob Jarvis Apr 9 '17 at 1:41
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It's good that you recognize your weakness in execution and for that reason alone you should hire an executive whose strengths include seeing initiatives all they way through to completion and an ability to focus on the day to day operations to bring your vision to fruition. If one of the three founders is not that ideal person, then you owe it to your company to find someone who is.

It's entirely up to you what you do with your free time. If you do hire an executive to provide the day to day leadership, you and your co-founders need to get out of the day to day management of the company and focus more on vision, culture, industry relationships and funding (if needed).

If you can start a new company in your free time, more power to you. This will depend on the people you have leading the day to day activities at both companies.

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