2021 Holiday Gift Guide

Janine Sickmeyer
7 min readNov 26, 2021


Put together by Janine Sickmeyer of Overlooked Ventures.

Dropping just in time for Black Friday.

Another year, another startup gift guide. I’m excited to share my 2021 gift guide, created with startup people, investors, founders, and friends in mind. Finding the perfect gift for your tech-forward friends can be tricky. I curated this list to ease your holiday shopping stress and to offer thoughtful gift ideas for the ones who matter most.

The Overlooked Ventures gift guide is a great resource for sustainable, mindful, and helpful gifts for the founders, VCs, and others in your life. Plus, you might even find a gift for yourself.

A note: Before you continue, the Overlooked Ventures team and I want to recognize the challenges and stressors that arise during the holiday season. No one should have to feel guilty for not being able to give gifts. We also want to recognize those who have lost a family member or friend and might be struggling during this time.

Lastly, but certainly, not least importantly, we encourage you to pay special attention to yourself and your well-being around the holidays as it can be a stressful time. If you need someone to speak to this holiday season, please reach out to the National Suicide Prevention Hotline 24/7: 1–800–273-TALK (8255) or text HOME to 741741 and someone will always respond. Sometimes the gift we need is a reminder that we’re not alone and we can reach out for help.

Before we get into the holiday gift guide, here are some words from the Overlooked Team:

“You matter. You’re important” — Janine

“The world is better because you are here” — Brandon

“If you’re feeling alone, burned out, or like a burden, just know that we are here to listen.” — the OV team

Encourage Mindfulness and Self-Care

  • Tisbet: Give the gift of charity with an e-gift card that your friend can redeem at the charity of their choice. This is the perfect gift because your friend can donate to a cause they’re passionate about.
  • AeroGarden: This indoor garden is perfect for your friends in the city or gardening novices. The Harvest Slim makes growing vegetables, herbs, or even flowers easy with an LED light and indicators for when to water and add plant food.
  • Be Sustainable: It’s no surprise that there’s an increase in waste during the holiday season. Consider cutting down on waste this year by gifting an experience or service like a spa day, tickets to a play, cooking, or art class.
  • Matchaful: Matchaful takes premium matcha and botanical nutrition to make products that improve your well-being. Shop their accessories to powder and snacks.
  • Online Therapy Session: There are a number of online therapy providers that make mental health care more accessible than ever. TalkSpace, just one of many online therapy platforms, has two gift options — a virtual session and unlimited chat therapy.
  • House of Wise CBD Gummies: CBD offers tons of health benefits, without the side effects. House of Wise makes three lines of CBD products, Sex, Sleep, and Stress to help your friends and loved ones master self-care and wellness.
  • Keychron Keyboard: Grab a keyboard that works perfectly for your gift recipient. The Keychron Custom Mechanical Keyboard allows for complete customization again and again.

For Your Team

  • Couplet Coffee: Give your team the gift of energy this holiday season. Couplet Coffee makes specialty coffee both fun and accessible. Shop their light/medium roast beans as well as limited-edition coffee accessories and apparel. (disclaimer: angel investment portco)
  • Seshie: Provide your team with modern learning and development. Seshie has interactive and live workshops led by industry experts. These sessions are based on what your team wants to learn so that they are meaningful and useful.
  • Professional Development Course: Invest in your people this year with a professional development course. LinkedIn Learning, MasterClass, Udacity, and many other platforms offer specialized courses for any employee.
  • Ember Mug: It’s easy to forget about your warm cup of coffee. Ember keeps coffee warm so your team can enjoy it without trips to the microwave.
  • Brydge Vertical Docking Station: Reduce desk clutter with this vertical docking station. This docking station passes the connection to the MacBook from two USB-C ports and helps to give your employees a clean working space.

For Startup People (Founders, VCs)

  • Bluelight Glasses: Let’s face it, your startup friends are spending a lot of time staring at a screen. Bluelight glasses from Ocushield ease eye strain and improve sleep.
  • Daylight Lamp: During the darker winter days, it might be hard to get outside while the sun is shining. A daylight lamp provides similar benefits to the sun by improving mood, boosting energy, and regulating sleep with exposure to LUX.
  • Airtag: Your founder friend has a lot to keep track of, they shouldn’t have to spend their time finding their keys or personal items. The Apple Airtag makes it easy to locate items on Find My, right from your iPhone.
  • Away Backpack: As we start to attend more in-person events and take vacations, a good backpack is a necessity. The Away Front Pocket Backpack gives you peace of mind while traveling knowing that your belongings are secure and in place.
  • Cobble: Have a friend that’s always chatting about starting their next venture? Cobble’s all-in-one app for entrepreneurs helps founders of ANY stage build their businesses with business planning, pitch deck creation, financial models, and more. (disclaimer: built by me)
  • Apple Cleaning Cloth: There’s nothing better than a clean display. The Apple Cleaning Cloth is the perfect gift for your friends who are always on their devices.
  • NFT Digital Canvas: What’s a better gift for your tech-forward friend than a non-fungible token? Grab them a unique, digital canvas from Blackdove that they can hang in their home.
  • Growthmentor: Give your founder friend the gift of mentorship. Growthmentor is a platform for entrepreneurs and leaders to find startup and growth marketing experts.

For anyone. Love, a founder

  • Healthy Roots Dolls: Zoe is the first healthy roots doll that encourages young girls to celebrate their curls, beauty and tech self-love. She also helps new friends learn how to wash and style their hair.
  • Ugg Tasman Slippers: Perfect for your loved ones who want to stay cozy, this Ugg Slipper Boot serves multiple functions. With the durable outsole, these shoes can be worn on a quick trip to a store or to get the mail.
  • Know Headphones: When it comes to noise-canceling headphones, it’s hard to find ones that are comfortable for long periods of time. The Know Calm headphones make listening more enjoyable.
  • Bespoke Gift Box / Fab Fit Fun Box: You can’t go wrong with a subscription box. Both of these boxes are a great and easy way to gift a variety of items to your friends and family.
  • The Adventure Challenge: Go on an adventure with your friend, family significant other, or even yourself with guides from the adventure challenge. You won’t know what activity you’re doing until you scratch it off!
  • Purple Cushion: Give the gift of comfort this year with cushions from Purple. We spend a lot of time sitting at a desk, why not be comfortable and supported?
  • Books: Dive into some reads that help you and your peers learn about the Black experience in the workplace and history. A few books I suggest adding to your startup bookshelf include The Sum of Us, Right Within, Four Hundred Souls, So You Wanna Talk About Race, Hood Feminism, and The Memo.
  • London Jumpsuit: Sold by Taylor Jay, the London Jumpsuit is one of the most versatile pieces of clothing that you’ll ever own. In a wrap style, the jumpsuit is flattering and perfect for any occasion.
  • Support Women-Owned Businesses: West Tenth is an app that helps you find women-owned, home-based businesses in your neighborhood. You can find just about anything on this platform perfect for gifting!
  • A Book from A Kids Company About: It’s never too early to start having conversations with children about topics such as diversity, anxiety, emotions, privilege, death, and more.
  • Nude Barre: Nude Barre makes underwear and hosiery for all skin tones. They offer 12 shades of nude so that everyone can find garments that work for them.

Happy holidays,

Janine + Overlooked Ventures team



Janine Sickmeyer

Founding Partner at Overlooked Ventures