Hi,

I have worked with, interviewed, and sold to extremely successful people following a few simple principles. It can be scary, but preparation will help you manage the fear.

Here are my thoughts:

First, consider why you want to work for him. How will you benefit from a job with him? Don't assume that it is a good fit for you just because he is a billionaire. Are you doing it just because you need income? Or do you want mentorship? Get really clear on why this would be good for you.

Once you are convinced that this is a good fit for you, think about why it would be valuable to him. Why would working for him be a mutually beneficial situation? Are there any gaps in his business that you would be able to fill? Do you see an area that would be improved if you were working on it for him?

Once you have determined that working together would be a good situation for both of you, then ask for a phone or video chat meeting. From here, you want to have some quality questions for him that both demonstrate your expertise and help you confirm it is a good fit.

One last piece of advice: The purpose of your meeting with him is not to convince him to hire you, it is to find out if it is a good fit for both of you. This mindset will help you make a decision together instead of you being at his mercy.

If you would like extra help with the specifics, I would be happy to have a call with you. I have done this many times, and I know that it can be intimidating. Let me know if I can help in any way.

What kind of job are you looking for? Show him you are a forward thinker and are capable, and surprise him by taking action. Maybe you see something that needs a fresh eye or input ie copywriting, design, or a system restructure. Impress him.

Just ask. I doubt he's never had a project go sour, so admitting an idea (or two) didn't work out doesn't hurt your credibility. Honestly, it might HELP your credibility.

One of my closest friends landed his first writing job at 19 by emailing the then-editor of his favorite magazine and asking, "How can I get your job?"

I thought he was nuts. No way he'd get a response. But he did. And then he got a job offer.

I also went to a friend of mine, the CEO of a large company — after turning down a job offer years ago — asked him if he'd still be interested in working with me. I had to swallow my pride to do it. But he was, and I got a long-term contract that's hugely improved my quality of life.

If you never ask, you may protect your pride, but you'll definitely never get the job. So you really have nothing to lose: if you ask, you might not get the job; if you don't ask, you'll definitely not get the job.

You're probably better off playing the odds, and I'd say your odds of getting a job are significantly higher if you take a chance, be honest about your situation, and ask. :)

Good luck!

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

Don't assume the billionaire is the best person in general for you to be talking to about your path or next step or he/she will have The Thing for you any more than someone you know very well or in your closer network.
That said if he/she has company(s) then find one you fit best in and perhaps a role that they are looking to fill that you fit well. Then apply for it or reach out to other people that are in that company.
Once you apply or connect THEN ping your billionaire with "hey just wanted to let you know, I've always be intrigued with your success/companies etc and I applied (or trying to connect with) to join...."

I think you have a powerful opportunity here. Yes, he is a billionaire, but that means he is also human. Communication is a powerful tool, so this will be a great learning experience regardless of the outcome.

I would just reach out to him and let him know all of the things that you learned on your projects, what you did to try to save them, what you are interested in now, and then tie that into what he is doing (do your homework). If you tell him how you can fix HIS problem then he will be open to your work.

Worst case scenario, you are in the same situation. This is just a good way of acting in a place of diplomacy. Boldness, yet humbleness.

Also, because you are feeling the way you are about this particular individual, I would challenge you to start having conversations with "power players" on a weekly basis. This will help you to get out there, get some bumps and bruises, and play in the arena.

I can help you come up with a full "grand strategy" if you are interested.

Everyone puts on their pants one leg at a time, so we're all roughly the same.

Just ask him if there's some task he just has a hard time getting done, that maybe you can help him accomplishing.

If not, ask him to just let you know if something comes up.

I've had many conversations like this over the years. Sometimes a conversation cooks/percolates for years, before the person converts to a client.

So...

Be relaxed. Just ask.

Oh... And ask a massive number of people.

Here's a trick...

Target looking for 100 no answers. (Geez, I think I heard this in Amway in another life.) Once you have 100 no answers, you have enough yes answers to have a very comfortable income.