I have had plenty of opportunities to convert "failures" into opportunities to
learn and grow - which they are, one way or another.

Remember neither failure nor success is ever final...

Here are two things to consider:

Q1: What did you learn from those failures? No one will dish for you failures, but most will respect you for having
transparency and clarity about what you learned and how you will apply this learning to your future goals.

Instead of asking for a job - ask yourself:

Q2: "How can I add value to him / his company/companies? (You'll want to do research around this)

When you are able to answer that cogently - and how what value you can offer is in alignment with your future goals and trajectory, then I would consider yourself ready to craft a communication to him to reach out with a clear offer and request.

I hope this helps, and would be happy to talk more if you feel inspired.

Best,
Mathias