One of the most knowledgeable angel investors out there, Jeff Stewart, told me that the definition of success as an entrepreneur was when you walk into work, and there's nothing for you to do. At that point, you've hired someone better than you at all of the tasks you did previously as a founder. You've built a well oiled machine and it works without kicking, prodding, or you being a key cog. I've always liked that idea, but wonder whether or not founders have put real plans in place for that to happen.
The other side of having a plan where you eventually become obsolete as a founder is having a plan for each key team member to grow in responsibility. Few startups I've seen do that. If you hired your first Director of Marketing, do you have a plan for that person to be CMO in 2-3 years. What skills do they need to develop to get there? What do they have to show you in order to gain more responsibility and trust? Where is there room for expansion in what they do that takes things off your plate in time?
Without plans, this is never going to happen, and your plate as a founder is never going to get smaller. Your team should help you scale by growing in responsibility and increasing their skillset. Without a plan for this to happen, it's unlikely for that to happen on its own. If you're an entrepreneur, I'd start writing up the playbook now about your succession plan and how you can get your team to replace you two years out. You may decide to stick around, but at least you'll know that your company is in good hands should you get hit by a VC on a bike.
You know, it's funny... I'm a terrible speller, mostly because of spell check, and I had to Google "succession" to make sure I was using the right word. It's interesting to me that the word "success" is in "succession". Just goes to show you that true success is when you built something lasting that enables people to grow and springboard to bigger and better things inside and outside of the company.