Holiday Gift Giving For Your M/Billionaire Boss

Holiday Gift Giving For Your M/Billionaire Boss

Giving someone a gift can already a brain-wracking process but what on earth do you give a millionairebillionaire who is your boss and can buy him or herself anything they want?

Don’t think Big. Think thoughtful.

Remember you know your boss’s likes and dislikes better than most. Grab a pen and paper. Start writing down the foundation of his or her interests.

Do they read? What’s the medium of entertainment? How do they dress? Are they involved in any charities or causes? Where do they own homes? Do they drink tea or coffee? Alcohol? Do they entertain? When have you seen them happiest inflight? What’s their luggage scheme? Do they enjoy sweets? What vacations did they go on this year? Pets?

Write all of this down. It will be your roadmap to a thoughtful and unique gift.

I recently watched the Netflix 3-part special “Decoding Bill Gates Brain”, in most scenes Bill is seen drinking diet coke. He is rarely seen NOT drinking diet coke.

I thought to myself, not only would I make sure a chilled can of diet coke was by his seat for every flight before he boarded but, I would take that and harness a silly, cheeky Christmas Present with it.

Here are some of my top picks for appropriate presents to gift your bosses that don’t break the bank but show genuine intention and thoughtfulness.

Private Jet Pool Floatie

Does your boss snowbird in South Florida? Or anywhere warm? How cute and cheeky is this Private Jet Pool Floatie? $94 at Amazon

Personalized Lip Balm


Best-seller / Personalized lip balm, made exclusively with natural ingredients that moisturize, repair and protect the lips and enhance their natural colour.

Monogrammed Small Leather Goods

Trust me, any avid traveler knows the value in a good toiletry case and pouch. I personally tend to go thru about 1 or 2 a year. This pouch comes in so many fun colors. I love this idea because it’s encompassed in the idea of traveling and they will use it every time you fly them somewhere. I also love a good monogram, its classic and timeless.

Travel Case Pouch

Out of all the wealthy folks I’ve flown, I have to admit its rare when you see them have a passport cover. I personally love my passport cover because it keeps my passport looking really nice and I have a safe place to put the important documents that some countries administer upon entry. A classic leather monogrammed passport case is chic and universal.

Passport Case

What do your bosses normally carry their laptop in when they travel? This clever accessory has a 13″ laptop sleeve, a pocket for all your tech accessories (chargers, chords) and snaps that hold everything securely in place. A padded interior keeps a trusted laptop in safe hands.

Tech Carry-All

For the bosses wife and or the Boss Lady herself, a lovely small jewelry traveling case + monogramed is classic and chic. It’s a small thoughtful gift that is luxurious.

Small Jewelry Case

Embroidered Cocktail Napkins

Does Mrs./Miss love a good martini? Is she absolutely fabulous? Here’s a cute gift idea:

Cheers Cocktail Napkins

Gemstone Cocktail Picks (For Her)

For the international jet setter who loves a good cocktail- these are my go-to gift throughout the year. It’s cheeky, luxe, without being too much.

Joanna Buchanan Bright Gem Cocktail Picks – Set of 6

Personalized Stationary

Take this idea and run with it, you could theme it “His & Hers” styled gifts. I love the website Papier as their quality is very high end with thickness of paper and posh styles. I’ve linked a few of my favorite sets below!

Painted Ornament

I love this idea because it is one thing that a person of high net worth wouldn’t necessarily buy for themselves and you can take in so many thoughtful directions.

  • Did your boss buy a new vacation home or house in another city? Have you seen it?
  • Does your boss have any beloved pets?
  • Is there a special place your boss likes to travel to that has a lot of sentimental value?
  • Did your plane go anywhere really cool or special this year and you took a nice photo of it there on the tarmac?
  • Maybe if your client doesn’t own the plane but charters a ton with you, you can still get a nice photo of the jet painted on an ornament.

All of the above ideas can be harnessed into a special ornament made for your boss!

Don’t be afraid to reach out to the assistant with any needed information or help to procure a thoughtful gift!

Here are some artists you can reach out to:


My first Christmas with my boyfriend, I gifted his parents with a custom painted ornament of their home as it was for sale that year and I thought it would be special reminder for the sons to always have their house they spent two decades in on their family Christmas Trees.

Custom Framed Photo

This is one of my favorite presents to give because in an age where we keep all of our photos on our phones and our galleries for them are social media, how refreshing is it to actually receive a beloved photo in a tangible way?

Keep it modern and classic and use your imagination when gifting it. Did your bosses daughter get married this year? Was he celebrated in any fashion at any charitable causes or galas? Did he and his family vacation anywhere special?

Use the same type of thinking of the ornament from above!

What was remarkable for your boss this year that you can help immortalize in a special photo?

My favorite companies to use for custom framing are Frame Bridge and Artifact Uprising because they allow you to send them a digital file to then create into a custom framed photo or choose a gorgeous picture frame like this one and frame a photo yourself quickly!

Charity Donation or Cause

Is your boss heavily invested in any charities or passionate about any causes? Think how you too can join efforts to help or make a donation in their honor.

Bake a Pie + Beautiful Cake Cutter

As you start to know where your boss and his family may be vacationing for their holidays, maybe you could source a beautiful pie and gift it with a pie cutter. If your boss likes rustic, homemade things, you yourself could bake a pie and send it off with him and his family to enjoy for the holiday.

I did this once for a family and it really meant a lot to them. Again, you know your passengers better than anyone, so be sure to think about if this is something they would enjoy or maybe it’s not so much their style. This a very American style present as well.

Engraved Jo Malone

This gift idea is a little safe and more universal in the sense that Jo Malone is a beautiful luxurious brand and if you know the scents are guests like based off their lavatory selections of soap and lotion you can not only get them a beautiful Jo Malone product, but also have it engraved.

Shop the Jo Malone Engraving Selection Here!

Portable Facial Humidifier

For the Mrs. or the Boss Lady, have her skin looking super fresh and moisturized for every landing by gifting this USB Portable Humidifier.

Hey Dewy Humidifier

Wine or Liquor

Need I say more? This is always a safe bet and makes a great gift.

Luxury Websites To Check Out for Inspiration:
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