For #1, it wasn’t hard at all. Here’s why:
At some point, and this happened around maybe 50 employees for me at my first company, you have to accept the fact that your company is no longer just “yours” – it belongs to your team, your customers, your community, your investors, etc. If you fail to do this, you will struggle to scale. Moreover, if you build a successful company and sell it, you will be intimately involved in the “what happens next” discussion, including who runs it at the acquirer (likely you for a while), how your team is structured, where the product vision is going, etc. It’s just another phase in the life of your company.
My first company RJMetrics was acquired by Magento, which itself was then acquired by Adobe. Our software, and much of our team, is now part of the Adobe Digital Experience Cloud. I’m so proud of that, even though I haven’t been involved there for years. That’s the mentality that makes it easy.
For #2, I think it took me a long time to develop a true sense of intellectual honesty and to be risk-seeking rather than risk-averse while operating an early-stage company. Both are core requirements in a startup entrepreneur, as you have to chase down the high-risk, high-upside chess moves and then be honest with yourself quickly when you screw them up and need to pivot. This was a mental journey more than anything. I’ll talk more about other frameworks in another question.