Read Time = 5 Good Minutes

It’s been a unique year. AI hype threatened to replace us all, LinkedIn selfies took over timelines and promises of growth were somehow just as elusive as your Q4 forecast. Despite the chaos, the holidays are here — and we shouldn’t let budget cuts or burnout dictate how we celebrate, how we spend and how we give.

This year’s list (the 1st edition) is packed with all the things your favorite tech sales rep wants but feels guilty buying for themself or didn’t know they need. Regardless of how deep your pockets are, this is the only holiday gift guide you’ll need — from the practical to the fantastical.

Inspired by the 2020 Goldman Sachs Guide — here’s your 2024 Tech Sales Guy Holiday Gift List

For The Office (WFH):

If you work in tech and aren’t WFH or hybrid, you are doing it wrong. For the office, start with some pictures or memorabilia from your favorite city, team, athlete or artist ($150). Throw it in the background to engage conversations and small talk during video calls. Sitting is the new smoking so get a standing desk ($275). When you’re seated, get a chair that’s comfy and sturdy ($300) and stay hydrated on back-back call days with this jumbo Yeti tumblr ($35). I take most calls with no headphones, however, I’ve considered these Apple headphones ($450) for focus time and flights. If you work late nights, get some red light glasses ($100) - easy on the eyes.

For The House:

There’s something nostalgic about listening to a full album start to finish. I got this record player ($200) last year and have enjoyed collecting classics - Queen, The 1975, Traffic, Outkast, Fleetwood Mac, Dead & Co ($25-$50)… to newer ones like Tyler the Creator, Dominik Fike, Khruganbin and Zach Bryan. For commuting from your bed to the home office, throw on a paid of these UGG slippers ($115). And since everyone else has one, you might as well get a cast iron skillet ($165). Finally, takeout food is overrated. Turn your back yard into a pizzeria with this Ooni pizza oven ($599).

For The Subscription Aficionado:

The ability to watch live TV on the go is revolutionary. YouTube TV ($700) is worth every penny. Throw in NFL Redzone ($100) for when the kids soccer tournament falls on an NFL Sunday. Whether you are trying to negotiate your new salary or perfect your Christmas cookie recipe, Masterclass ($20 / month) has a course for you. Lastly, Rent the Runway ($90 / month) is great for the fashionista in your life or the guy that doesn’t know how to shop for his significant other.

For Life Outside Work:

Business travel is back, which means so is business golf. If you are new to the game and looking to buy clubs, look for a good used set ($500) or you can try these trendy Takomo irons that are affordably priced ($750). If you are a golf nerd, check out The Golfers Journal ($150). For traveling, TSA precheck ($85) is a no brainer - it has saved me 10s of hours each year. Lastly, treat yourself and your significant other to some live music. Find an artist you like in a city near you and plan a future date night ($500). For an epic experience, check out Dead and Co at the Sphere.

For The Library:

Candidly, I’m not a huge reader. Typically, I’ll start the year with a good self-help book like Atomic Habits ($20), 5AM Club ($20), or The Gap and The Gain ($20). For the spring/summer beach trip, I like to read classic books ($20) and biographies ($20). Some people read fiction before bed - I prefer something psychological or philosophical like The Creative Act ($20). The book I refer to most for selling is Never Split the Difference ($20). If we’re being honest, most sales books stink.

For The Creator:

Shortly after spinning up a side hustle I bought a Macbook Air ($1350) to separate my W2 work from my solo venture. I’d recommend you do the same. For building a brand, I turned to social media. After grinding through daily posts on Twitter and 2-3 times a week on LinkedIn, I decided to invest in tools and tech for scale. Like most people, I started with Justin Welsh Operating system ($150) to understand basic frameworks around creating and distributing content. For scheduling posts I use Hypefury ($200). The “power ups” like the auto retweet and newsletter plugs keep things running when I’m away. For journaling, you can’t go wrong with these Pilot pens ($15) and a Moleskin notebook ($30).

For The Midlife Crisis:

Although I’d like to think I’m ~15 years away from getting here, I’ve come to the realization that we’re not getting any younger. I’d settle for sitting behind the wheel of a Porsche Panamera ($125k) or this Ferrari Testarossa ($200k).

For The Kids to Inherit:

Other than a a wedding ring, a watch is the only other acceptable form of jewelry for men. For the nice guy with money to spend, consider this Rolex watch ($13,500). Now, I’m not going to sit here and pretend to know women’s jewelry but I do love this Cartier watch ($11,900). Finally, if you’re not into material things and have an appetite for risk — invest in Bitcoin and hold it to pay for your kids college or leave them with a nice nest egg for when they enter the real world.

Honorable mentions

Lastly, if you need a few more things to help you get through time with the in-laws, I’d recommend TRX bands ($150) for on the go workouts, a bottle of Blantons ($145), HBO Max to rip through Season 1 of The Penguin ($10 / month) this alarm clock ($130) to stop sleeping with your phone next to you and Kiva sleep gummies ($40) if you’re really struggling to sleep. Also, for your friends or family with dogs, this harness ($90) is great for training and walks.

That’s it! Over 50 items so you’re guaranteed to find something for everyone.

While it’s important to enjoy the fruits of all our success this year.

There’s nothing better some time off work with people you love.

Happy Holidays!

Until next Thursday,

TSG

P.S. I reply to all emails.