Lenny’s holiday gift guide

50+ gift ideas for your friends, family, and coworkers

👋 Hey, Lenny here! Welcome to a ✨ special edition ✨ of my weekly newsletter. Normally I tackle reader questions about product, growth, working with humans, and anything else that’s stressing you out at the office. But this issue is a little different…

Happy holidays, everyone! For something a little different, I thought it would be fun to put together a gift guide to help you win the holiday season. Below I’ve curated 50+ products that I absolutely love, which would also make great gifts. Enjoy!

Focus and productivity

1. Centered: My main to-do app, and probably my most-used app period. It combines a simple task list with flow-inducing music, distraction reminders, and a community of fellow-concentrators. Use code FLOWWITHLENNY to get 50% off your first year.*

2. Taika Matcha Latte: My go-to drink when I want to focus. Delicious, effective, and goes great with Centered. It’s made from organic ceremonial-grade matcha, a blend of adaptogens and functional mushrooms, and is designed to keep you feeling awake, aware, and inspired. Use code LENNY to get 20% off (or use this link).

3. Magic Mind: My other favorite focus-inducing drink, made by my buddy James Beshara. Pairs well with green tea. Use code LENNY23 for 23% off.

4. Jabra Elite 85h Wireless Noise-Canceling Headphones: I’ve been using these headphones for years and can’t recommend them enough. No matter what’s going on around me, they help me focus and stay in the zone. Originally a gift from my mother-in-law.

5. Mailman: A Gmail plugin that batches your incoming email and keeps your lizard brain from getting distracted by the endless trickle of new email. It’s a game-changer. Use code LENNY for 50% off an annual plan.


1. Topo Designs Global Briefcase: My favorite travel bag. Fits 3-4 days of clothes, has plenty of room for electronics, and includes a special slot for a laptop. It also looks great, and you can wear it as a backpack.

2. Alaska Bear Pro Contoured Sleep Mask: For anyone who has trouble falling (or staying) asleep when there’s light outside. I’ve tried a lot of sleep masks, and this is my favorite because it leaves lots of room around the eyes.

3. Combo Lightning and Micro USB charging cable: Never make the mistake of bringing the wrong charging cables again.

4. Vacu Vin Wine Saver Pump: Removes air from your wine bottle to keep wine tasting new for a few extra days.

5. Atlys: Get a visa for 195+ countries in minutes (not days).*

6. K9 dog backpack: For any dog owner in your life. Here’s our little guy in action:


1. Am I Overthinking This? and Maybe This Will Help by Michelle Rial: An unofficial box set—my wife’s bestselling first book, Am I Overthinking This?, and the prequel, Maybe This Will Help, which just came out this week. They’re great gifts for the chart-lover in your life, and you can get both for under $30.

2. The Cold Start Problem: How to Start and Scale Network Effects by Andrew Chen: After three years of work, Andrew’s book is coming out in two weeks. It’ll be an instant classic, and a great gift for founders and growth teams.

3. A Short History of Nearly Everything by Bill Bryson: My current obsession. I’ve learned more about the world per-page than from any other book. A great fit for anyone who’s curious.

3. The War of Art by Steven Pressfield: For anyone in your life doing creative work.

4. Tiny Beautiful Things: Advice on Love and Life from Dear Sugar by Cheryl Strayed: For anyone in your life going through real-life sh*t.

5. Ready Player One by Ernest Cline: For anyone in your life trying to understand how the coming metaverse may look.

6. Finite and Infinite Games by James Carse: A mind-bending (and short) book that changed the way I looked at life.

7. Sum: Forty Tales from the Afterlives by David Eagleman: Short, hilarious, and infinitely creative.

Newsletters (that aren’t already free)

1. Drawing Links by Edith Zimmerman: A comics newsletter with short illustrated stories about her life.

2. Letters from an American by Heather Cox Richardson: A newsletter about the history behind today’s politics.

3. 2pm by Web Smith: Analyzing the intersection of media and commerce and how those principles are applied elsewhere.


1. iOttie wireless fast-charging stand for iPhone: Best device I’ve found to charge my phone at night.

2. COCOFLOSS Coconut-Oil Infused Woven Dental Floss: Seriously, try this floss.

3. Magnetic Measuring Spoons: Love these friggin’ spoons. Easy to keep together, easy to use, easy to wash.

4. U-Taste cooking tongs: Useful for mixing, grabbing, dropping, turning—basically, everything.

5. Italic: High-quality products from the same manufacturers as top brands, but without the brand name and for 50%-80% less. Great for sheets, towels, sunglasses, jackets, shoes, and so much more. Almost too good to be true.


1. Writer.com: A browser extension that helps you write better. Has completely replaced Grammarly for me.*

2. On Writing Well: The Classic Guide to Writing Nonfiction by William Zinsser: The book that taught me the most about writing well.

3. MUJI gel ink ballpoint pens: Hard to beat these pens for quality, reliability, and affordability.

Other great apps

1. Hand Mirror: See what you look like on camera before you start your Zoom.

2. PictureThis: Magically identify plants just by taking a picture of them.

3. Mem: My go-to note-taking app—and so much more. “As simple as Apple Notes. As powerful as Google Search for your mind.”*

4. Rocket: Easiest way to use emojis on a Mac.

5. AllTrails: An unbeatable gift for your outdoorsy friends.


1. Katie Gong

2. Meghan Shimek

3. Tricia Choi

4. Molly Kars

5. Nicole Lavelle

6. Donate on someone’s behalf to DrawTogether: Art kits to boost kids’ creativity.

Donate to a nonprofit

Each month I’ve been donating a portion of my job board’s revenue to a nonprofit that helps underrepresented groups learn tech skills (to eventually fill these open roles). Here are my five favorite charities:

1. BlackGirlsCode: Building pathways for young women of color to embrace the current tech marketplace as builders and creators by introducing them to skills in computer programming and technology.

2. Hidden Genius Project: Training and mentoring Black male youth in tech, entrepreneurship, and leadership skills.

3. /dev/color: A global career accelerator for Black software engineers, technologists, and executives.

4. Techtonica: Partnering with tech companies to provide free tech training, laptops, living stipends, and job placement to women and nonbinary adults in need in the Bay Area.

5. Code2040: Increasing the participation and leadership of Black and Latinx people in the innovation economy.

*If you see an asterisk, I’m an investor or advisor to the company. Mostly because I find a way to invest in the products I love most.

Got anything else to recommend? Leave a comment!

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✨ Happy holidays to you and yours ✨

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Lenny 👋