Not dead against it though not my first choice. But how would one who has been technical with no people management skill make that change?

I think you can do it. Your age and maturity helps a lot and especially if you are very sound at technical it helps in many ways: 1) juniors respect technical managaers more that non technical ones 2) you can estimate better you can dig things yourself from a high level 3) CTOs, VP tech etc are techical people isn't it? It's just the extra polish

Thanks!. Like what you are doing with https://codeflow.co/ . Good luck with the venture. Always have a special respect for Entrepreneurs.