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?