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The Ultimate Gift Guide for Entrepreneurs: Perfect Picks for Every Small Business Owner

Writer's picture: Ashley ChivaletteAshley Chivalette

Updated: Dec 16, 2024

The holidays are upon us already - are you ready? Well, today, we're helping you out with the entrepreneurs in your life.


If you’re scratching your head wondering what to get that small business owner, business advisor, or budding entrepreneur in your life, you’ve come to the right place. This thoughtfully curated gift guide is filled with practical, fun, and inspiring ideas. We’ve got something for every kind of business mind: from the busy-on-the-go professional to the zen-seeking entrepreneur who craves a moment of calm, and even the caffeine-fueled business coach who’s always brewing up new plans.


girl in overalls handing a wrapped gift to the camera

So, pour yourself some cocoa, get cozy, and let’s find the perfect gift to support their journey!


 

For the Entrepreneur Who’s Always Bursting with Ideas


Moleskine Smart Writing Set

a smart notebook with glasses laying on them

This notebook allows you to digitize your notes! This Smart Writing Set combines a classic Moleskine notebook with their Ncoded paper, a redesigned Smart Pen, and the Moleskine Notes app to digitize handwritten notes instantly. Perfect for those juggling ideas and projects, this set turns every page into a shareable, editable digital file.


For small business owners, business coaches, or advisors managing multiple projects, this tool helps take handwritten ideas to the next level. Whether they’re mapping out their next venture or drafting the perfect email pitch, this set amplifies the power of pen and paper in a beautifully innovative way.


Aqua Notes

We absolutely LOVE this product. We are constantly recommending it to clients. It's super cheap too!


It's a waterproof notebook that allows you to capture all your great ideas even in the shower! We all know the shower is where some of the best brainstorming happens. Aqua Notes ensures that no great idea goes down the drain. It’s the gift that says, “I believe in your creativity—wherever it strikes.”

person holding up a iphone to take a picture of a lit christmas tree

For Entrepreneurs Who Are Always on the Move


Portable Phone Charger

This one's a given! Someone who is always on the go definitely needs a way to keep their batteries charged so they can stay connected. Small business owners live and breathe connectivity—client calls, social media updates, online invoices, and email marathons. A portable charger ensures their phone won’t tap out in the middle of a big deal, making this a simple but oh-so-practical gift.


smart activity watch laying on a laptop

GPS Watch or Activity Tracker

If your entrepreneur is also health conscious (or trying to get in the habit) a fitness or activity tracker is a great gift! I personally love Garmin watches, but an Apple or Android watch is also a fabulous choice! After all, a healthy entrepreneur tends to run a healthier business.


Stylish Laptop Bag

For stashing all their computer needs and keeping it safe. My personal faves are these from Kate Spade- so beautiful! A sleek, sturdy laptop bag is essential for hauling tech, documents, and that genius proposal they’ve been working on. Consider something chic and durable—Kate Spade.. wink wink—so they can show up to any meeting looking polished, professional, and ready to impress.


small business owner sitting reading a new book trying to relax during the holidays

For Entrepreneurs Craving a Little Chill & Relax Time


Headspace or Calm Subscription

Being a small business owner can be like riding a rollercoaster blindfolded. Give them a shot of serenity with a mindfulness app subscription. Guided meditations, soothing soundscapes, and sleep stories can help them recharge and hit “reset” whenever life gets hectic.


yoga instructor teaching a small business owner on the first time at yoga

Yoga Class Pass

This is my favorite gift idea (hint hint)! Especially if your business owner is into yoga, this is one gift that truly keeps on giving. Find out where their favorite studio is or invite them to yours! Balance—both on the yoga mat and in the boardroom—is vital for sustained success. A yoga pass encourages entrepreneurs to step away from their spreadsheets and into some deep stretches, helping them return to work feeling centered and refreshed.


Candles

Candles are awesome presents no matter who you're shopping for- look for unique candles this year, like these from this small business. Candles aren’t just about ambiance; they’re about creating a space that inspires calm and creativity. Seek out small businesses that craft artisanal scents.


Aromatherapy Diffuser

This one is a great idea for the more holistic minded business owner. An essential oil diffuser transforms a home office into a personal oasis. Energizing peppermint for pre-pitch pep talks, relaxing chamomile after marathon meetings—this is aromatherapy tailored to an entrepreneur’s work-life flow.


santa holding a letter from a child who is standing in front of him.

For Entrepreneurs Who Need More Time in Their Day


Clothing Subscription Box

Dressing the part is important, but so is not wasting time rummaging through closets. A service like Stitch Fix or Trunk Club curates outfits, shipping them directly to your business owner’s doorstep. Less time browsing racks = more time landing clients.


mom helping a child prepare a pie while family cooks together
The mess might take some time though...

Food Subscription Box

Food subscription boxes are a great way to bring peace and fun back to dinner time. These boxes send all the ingredients you need to create a delicious and easy meals throughout the week. Meal kits like HelloFresh, Blue Apron, or Sun Basket deliver fresh ingredients and easy recipes so entrepreneurs can enjoy a nutritious, home-cooked dinner without the hassle of meal planning.


Virtual Assistant Services

Time is money, and a virtual assistant can free up hours for strategic thinking rather than administrative tasks. Gifting a VA trial subscription is like handing them a personal productivity boost—perfect for entrepreneurs who need more hours in the day.


top down view of a red tinted latte surrounded by winter decorative items

For Coffee or Tea Lovers


Tea of the Month - Tea Subscription Box

We, at Out of the Box Advisors, LOVE our Tea subscription boxes! It allows us to try all kinds of tea that we might not have otherwise had. Atlas Coffee Club curates a variety of teas based on personal taste profiles, introducing your entrepreneur to new blends they never knew they needed. It’s a cozy adventure in every box.


Coffee Gadgets

Coffee gear for coffee lovers is always a great idea. For the coffee-obsessed business owner, consider a French press, pour-over set, or even a fancy espresso machine. Pair it with locally roasted beans to support another small business and make their mornings smoother (and tastier). These coffee mugs are super cool, plus you're supporting a small business. Also, check out this awesome coffee company.


small family putting together a chistmas tree under a stairwell in their home

For the Tech-Savvy Entrepreneur


Smart Speaker (Amazon Echo or Google Home)

"Hey Alexa, what’s the best gift for a tech-loving small business owner?" Answer: a smart speaker! These clever gadgets do it all—play productivity playlists, set reminders, answer random business questions, and even tell jokes. It’s like giving them their very own assistant who never calls in sick.


External Hard Drive or Cloud Storage Subscription

Because no entrepreneur should have to play “Where’s that file?” This gift is like a safety net for their precious spreadsheets, client presentations, and top-secret business plans. Bonus points for saving them from the “I forgot to back it up” panic.


Ring Light or Video Kit

If your entrepreneur is the next YouTube sensation, a webinar wizard, or just wants to look fabulous on Zoom, a ring light is the MVP of their video game. It says, “I see your brilliance, and I’ll make sure everyone else does, too."


small business owner sitting in a window sill reading a book in a cozy blanket with snow outside

Bonus Ideas: For the Bookish Business Owner


Inspiring Business Books

From classics like “Think and Grow Rich” to contemporary gems like “Atomic Habits,” books offer insights, inspiration, and a wealth of knowledge. A well-chosen business book can spark fresh perspectives and new strategies.


Online Course or Membership

Consider gifting them a subscription to a business coaching community or a specialized online course. Learning from seasoned entrepreneurs, business advisors, or industry experts can arm them with the skills to take their small business to new heights.


woman in overalls unwrapping a gift

And Now for the Ultimate Gift…

Drumroll, please! The ultimate gift for any small business owner (or aspiring entrepreneur) is… us! That’s right—what’s better than unwrapping a game-changing business coach and advisor?


out of the box advisor's logo

At Out of the Box Advisors, we’re here to help business owners untangle those messy spreadsheets, conquer that looming to-do list, and turn brilliant ideas into real results. Think of us as the gift that keeps on giving—support, strategy, and solutions wrapped up in one neat little package (and no awkward holiday bows required).


Give them the gift of success this holiday season by scheduling a free consultation (see below to book it for them!) with us. Whether they're ready to grow, streamline, or just need someone to help figure out the next move, we've got their back.


Because let’s face it—every small business deserves the VIP treatment.


Merry Christmas and Happy New Year, friends!



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