I did 5 years as CEO after 7 as CTO. CEO was managing sales, marketing and operations. It was fun while I was learning things, but ended up realizing that I was not happier than before: 1. I was/am just an average manager compared to an awesome CTO. I felt limited by mind own engineer training. Plently of people are/were better than me in managing other people/taking care of operations. 2. I didn't really enjoy it as much as I enjoy building products and tech stacks. After the learning rush goes, sadness prevails. So, if you are going to go in that journey, just remember that your career must become that something. You are now a business person and not a technical person anymore. Your career is then to build as many profitable companies as you can, regardless of how cool the technical products are. Your source of professional happiness must be to build amazing companies, not just products anymore.