This is the third post in our 5-part series, Undivided December: A Holiday Survival Guide for Founders & Operators. Each week from now until Christmas, the Plumb team will explore how startup founders and operators can use AI and automation to get more done and be more present this holiday season. So grab a cozy sweater, a cup of hot tea or cocoa, and settle in around our figurative fireplace — it’s time for festivities! ☃️
Chief Cheer Officer, Reporting for Duty 🫡
There’s no better feeling than giving someone the perfect gift. But, as a startup operator with limited time to shop (and an admittedly Type A approach to just about everything, including the holidays) I’ve spent many Decembers agonizing over the details. Occasionally I’ll get lucky and stumble across a gift guide that nails it. But more often than not, I find myself procrastinating until the very last minute, then running around like a delirious over-caffeinated elf, trying to find excellent gifts for everyone.
It’s a lesson I’ve learned too many times. So naturally, I had to find a solution. This year I decided to try something totally different: I decided to pthat I would employ AI as my team of delirious elves. Here are a few ways I’m skipping the chaos this holiday season, so I can funnel my energy into the moments that matter most.
Read on to steal my strategy (Grinch style!) so you, too, can achieve CCO (Chief Cheer Officer) transcendence.
Done (and Delivered) Is Better Than Perfect 📬
Before we dive into my methods to stop the madness, let’s align on a very simple truth: A good gift delivered is better than a perfect gift contemplated.
Fellow founders and operators, I know how badly you want to approach gift-giving with an eye toward optimization. I do too! And maybe one day we’ll have an AI for that. But I've learned the hard way that the perfect gift isn't the one that scores highest on your carefully weighted criteria. It's the one that arrives in time, brings joy, and doesn't cause you to lose sleep over whether the hand-crafted artisanal whatever-it-is is actually marginally better than the other hand-crafted artisanal whatever-it-is you also considered.
Don't get me wrong — I still love a good system. But these days, my goal is to be thoughtfully efficient rather than exhaustively just-right. And guess what? The results have been better, the process has been smoother, and I haven't stayed up until 3 AM comparing Danish modern candlesticks.
Let AI Do the Heavy Gifting 🎀
First, let’s tackle two of the most challenging of all archetypes to shop for:
The Person Who Has Everything ™️
Someone you don’t know much about
Whether it’s a coworker, a client, an in-law, or another member from your book club who you hardly know — we’ve all been stumped by a Secret Santa recipient who seems impossible to shop for. You know the feeling: staring at your screen at midnight, 17 browser tabs open, wondering what kind of scented candle they might be into. My advice? Skip the gift they’ll give away, and before you start panic-buying generic gift cards faster than reindeer on Red Bull, let's explore how AI can help you sleigh your gift-giving game.
The “Interest Expansion” Technique 🌌
This one’s very effective for finding gifts for folks you know decently well. Instead of asking AI for gift suggestions directly, start with what you know about the person and prompt AI to expand those interests into adjacent areas. For example, "they really love artisanal coffee" becomes:
Region-specific coffee bean tasting flights
Hand-forged coffee accessories (mugs, coffee scoops) from makers on Etsy
Coffee-infused chocolate bars from small-batch artisans
Vintage coffee artwork from specific decades they love
This is even more fun when you highlight multiple seemingly unrelated interests and let AI make unexpected connections. My personal favorite product for this kind of AI-augmented searching is Perplexity. It’s like a better way to scour and sort through the whole internet.
The "Lifestyle Pattern" Method 🧘
Feed AI multiple data points about someone’s daily life or habits — or just one, if that’s all you know — and nudge it to uncover gift opportunities. Try something like “they work remotely and do yoga” and see what AI conjures up. Better yet: ask AI to ask you some clarifying questions. Treat LLMs like Claude and ChatGPT like collaborators, and brainstorm together. Just by flipping the dynamic on its head and being asked (instead of asking), you may discover that you know more about the gift recipient than you think!
The "Passion Project" Deep Dive 🎨
I love this method for finding excellent hobby-related gifts. When someone is deeply into a specific hobby, use AI to:
Map out all the sub-components of their interest (super helpful when their hobby is something you don’t know much about yourself!)
Identify the pain points or gaps in their current setup
Find specialized tools or limited-edition collectibles they might not know exist
For instance, "amateur astronomy enthusiast" could reveal:
Specialized star chart journals from independent publishers
Vintage celestial maps from their birth year
Making Your List (and Checking It Twice) 🎅
A few pro tips for the holliest and jolliest results:
Always include price range in your prompts
Specify "no Amazon listings" to surface more unique items
Ask for items from independent makers and small businesses
Request background context on why each suggestion might resonate (this is great for finding the right words for your holiday cards)
Use AI to generate specific search terms for platforms like Etsy
The Extra Mile: Personalization ✨
Once AI has helped you generate ideas, take it a step further to make sure your gift really hits home:
Ask AI to research the story behind the item or maker
Generate unique presentation ideas or gift pairings
Find ways to connect the gift to future plans or shared experiences
That’s A Wrap 🎁
Remember: while AI can help you wrap your head around gift ideas (pun absolutely intended), the most meaningful presents come from combining its suggestions with your own personal touch. And, if all else fails: gift receipts! 🧾
From all of us at Plumb, happy holidays!
The Magic of Plumb
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