How doable is this? Be BRUTAL. Be HONEST.

So a little about me to help set the stage. I am in my mid 30s and would consider myself a "younger executive" as in I am not at the senior level, but find myself in their company very often. If I stay in my present career track, it is not impossible to see a world where I am a SVP or in senior leadership by mid 40s-50s. A lot of senior management and executives have access to private planes or regularly travel business class. Here is where the business idea comes in.

While senior management would not want to fly in a smaller plane, I see an opening to recruit middle VPs (folks earning in the 200ish range) and have them cost-share charter flights to select destinations. Without getting into too much detail about my line of work, I think I could do this by networking and marketing the business to folks I meet on a regular basis. 

I enjoy my work, but when I view my career over the next three decades I am not sure if I want to stay in the corporate world. Entrepreneurship has always been an interest of mine, but hard to do in my line of work.

Here is where aviation comes into play. It's been an interest of mine for a number of years, and recently I have gone on a discovery flight and am considering a PPL with the intent of becoming a paid pilot and switching careers.

How possible would it be to: 

1. train for a PPL part-time with the goal of getting a license by the end of 2027

2. build hours either by joining a flight club or renting and flying as much as I can when time and funds allow it

3. build certification to qualify to fly passengers and more importantly bigger planes such as a King Air 

4. purchase a twin engine plan capable of transporting anywhere from 5-8 people 

5. launch a niche charter service 

Does anyone know of a pilot that has gone this route?