Bill Gates’ Private Party

Bill Gates and Jason Hewlett

Imagine having “Bill Gates’ Private Party” on your resume of events you’ve performed for!

Yes, it may sound glamorous, and heck, it was amazing to be there.

I mean, just picture in your mind’s eye seeing tennis legend Andre Agassi on the front row, laughing and high-fiving other billionaires, who also happens to be Bill’s tennis coach…

Wacky stuff!  Yes, this is a true story.

I’ll never forget the expectation I had upon receiving notice that I would be performing for this event –

“This will lead to so many events with Microsoft and his charitable organizations! I can’t wait for all the doors this will open!” 

I killed it at the event – remember, this was years ago when I was solely focused on doing entertainment, each event leading to another one – and Bill ran up to tell me all of his favorite things I did, asking also why I had excluded other impressions he hoped I might do, and then said let’s take a photo of you doing the Raptor.

Bizarre, right?


Bill Gates and Jason Hewlett Raptor


What an awesome night!

And then, as I waited by the phone, and even reached out to the event planners, guess what came of it?

Nothing from Microsoft.

Nothing from the Gates Foundation.

No, all that came from it was…more private parties for more billionaires!

Now, that might sound all high and mighty and really cool, but that wasn’t what I wanted.

Billionaires are billionaires for a reason.

They are sticklers on price, and even worked hard to get discounts out of me for their events.

It was very deflating, knowing they spent more on their pocket swatch than they’d give me for my time and expertise.

And I did some really cool parties, NDA stuff, where the FBI would fly through my ceiling and kill me if I told you about the wild and crazy gigs I’ve done through the years.

But that’s not the point of this post.

The point is this: I had a certain expectation as to the desired result of my discounted performance for a billionaire’s private party.

That never came to pass.

The attendees did not see me in the light of: Let’s have him come to our company to perform! 

The attendees saw me for what I did: Private Party Billionaire approved Entertainment!

That’s a very specialized niche.

And that’s what it led to: More billionaire parties!

Sometimes opportunities lead to others we aren’t expecting, and that’s a delight, but when we accept the opportunity and hope it leads to a different result, that can truly kill our spirit.

5 years later I was speaking for Microsoft.

It didn’t come from Bill Gates, or his team, or anyone at that party. Heck, I don’t even imagine Bill would remember me if he saw me ever again.

It was a referral from a friend in my acting class from 20 years ago who is an event planner there now.

A local friend.

For the local Microsoft.

She had seen me speak at another local event for another company, where I shared The Promise…so that’s what she determined I could do for her event.

Go figure.

The Promise is to deliver wherever we are hired, and offer discounts only with the expectation that is communicated as to the reason for it, or else we will be disappointed.

But a Promise we make, and the expectation for keeping it, must be in alignment.

In all fairness, the best thing I got out of the Bill Gates party was a great story and some funny photos that amazes people when they ask, “Who’s the most famous person that has seen you perform?” 

And then I show them the photo above and they are stunned.

Was it worth it?

It depends upon your Promise.


~ Jason Hewlett

Husband, Father, Writer, Mentor, Hiker

  • Speaker Hall of Fame * Award-Winning Entertainer * Coach & Mentor
  • World’s Only Keynote Speaker utilizing entertainment, musical impressions, and comedy to Create Legendary Leadership through the Power of Commitment
  • Author of “The Promise To The One”



Share this post

14 thoughts on “Bill Gates’ Private Party”

  1. Important for me to read this today. I recently spoke for an important company at a lovely venue, did a great job and now reflecting back, did have an expectation of future work from the same company ( which has not happened). I do hope I planted some seeds which can have value to them moving forward.
    Once again, I appreciate your authenticity and really appreciate your last line…”Was it worth it? It depends upon your Promise”.
    Sending many blessings,

    1. This means a lot my friend. You’re awesome to always find something within these articles. Thank you for lifting me up!

    1. Thank you Eric. Yes sir, many times, I write about it in my book The Promise To The One. It cuts both ways – there are expectations we hope for that don’t happen, and then those we expect and they do! Pretty great.

  2. That is why the rich get richer and the poorer get poorer
    because the rich penny pinch and pray on the Poor and the Poor are all so generous and give all they have to others and are very humble

    and you can have any thing you want it just depends on how bad you want it money is all just priorities

    I will stick with the poor and stay humble and keep my awesome fun and loving life with my family

    your cousin
    Jeaneen Moffat

  3. You may want to consider your discounts only on the back end, giving them a referral fee for booked events. It may be a meaningless offer to a billionaire. Nonetheless, you can’t find any better entertainment at any cost than what you offer. Never discount yourself. You’re awesome!

    1. Thank you Mike! That means a lot. This was of course many years ago, and they wouldn’t accept my full fee. It was one of those decisions that had to be made. I agree with you and appreciate your kind words.

Leave a Comment

Your email address will not be published. Required fields are marked *

Latest Tweet