A Founder’s and CEO’s Guide to the 2022 Holidays

Heads-up: This Post is firmly Tongue in Cheek

The holiday season and year-end are challenging. There are lots of fun parties to attend, and dozens of people to give gifts to and toast with adult beverages. But hanging over all that cheer and merriment is next year’s Ops Plan – which is due soon (fuzzy, post-party head notwithstanding).  

Everyone knows that startup founders and CEOs need whole cadres of people around them in order to succeed in both good times and bad. And its key for leaders to provide their people with timely recognition and rewards.

Yet it can be very difficult to send the ‘just right’ message at this time of year.

Sometimes the gift is not enough. You must do and say something.

It’s difficult to figure out what to give them. (One might ask oneself: “Is the seven-foot black swan in obsidian too much? Not enough? Off the mark?”). So, what do you say to them and do with them at this time of year that’s not too big, corny, overly sentimental, patronizing, or off-putting in a million other ways? It’s tricky business indeed.

In some cases, your people are classmates or friends. You’ve met their partners or spouses, and pets. You have met in person with or seen their children, grandchildren, mothers, fathers and cousins via social media. In some cases, you have seen them in bathing suits, naked in the locker room at the gym (or elsewhere!), or in otherwise compromised positions. You have driven in their cars, or flown in their planes. You have read their career achievements and self-aggrandizing proclamations over LinkedIn. You’ve been present during their triumphs and loses. You know that their parent has passed, or a dear friend is sick, or their beloved dog has died. You have shared in some ways their glories and pain.

Now it’s time to mark that relationship, that familiarity, and encapsulate it all perfectly in a representative act. You need to do something, preferably a spot-on thing, that’ll ring true with the nature of your relationship. Tricky business, indeed!

But, as always, we’re here to help. To that end, the following is a short list (in order of importance) of things to do for all the positive people in your startup life.

1. For your life partner (husband, wife, boyfriend, girlfriend, lover, etc.) – bring them to dinner at a really nice restaurant, and give them a carefully chosen gift. Later, during pillow talk, do a thorough review your 2023 operating plan with them and make sure they agree with your T&E budget line items. Remember to say: “I couldn’t have done it without you.” Also, in the sincerest voice you can muster, say: “You complete me.”

2. For your Amazon driver and USPS mailperson, pharmacist or the dude or dudette at your pot dispensary, give them cash or a nice gift. They help you get through startup life in special ways. 

3. For a co-founder who has helped you and supported you, give them a hug for more than a minute, breathe-in and -out several times, but don’t tell them why. Bat your eyes a couple of times. Silent affection is beautiful thing.

4. Meet up with your favorite, most intelligent, most insightful, most wonderful advisor, investor or board member. Give her or him a memorable gift, such as a beautiful bottle of red wine from Bordeaux. (Don’t skimp. I know my wines. Consider: Domain Leroy Musigny Grand Cru, 2012.)

5. Go out for drinks with your favorite VC. Tell her how valuable she has been this year. This most sound sincere. She may not have a job next year.

6. Pay your lawyer’s bill.

7. Meetup with your best friend in the startup world. Give that person (me!) an exotic and expensive bottle of bourbon. Make it really, really special. (Don't skimp. I know my bourbons. Consider: Blanton’s Black Edition. I’m running low.)

8. Meetup with your best friend from outside the startup world. Go out for drinks and thank them for their friendship, love and support. If you don’t have a friend, see #5 above and say to yourself a dozen times: “I’m not a loser”.

9. For family members who have been short-changed because of your life style. Arrange for a lunch or dinner at a nice place. Chug three strong drinks rapidly, then say in the nicest possible way the following: “I’m a mutant. I don’t know who the f#ck you people are.” Then standup and leave the restaurant. Do not pay the bill.

10. For your colleague at work who has been granted more stock options that you: Send them an inscrutable video from Giphy via Slack with Santa Claus humping a reindeer. That’s all they deserve.

11. For your colleague at work who has been granted fewer stock options that you, fuggedabout it and dem if they can’t take a joke.

12. For your product manager, director of operations, community manager, controller and others who do really hard jobs and make them look easy, a Porsche Cayman Vs 911 makes a lot of sense. But it’ll be tough to find a stocking that it’ll fit in.

Next, identify all the negative, self-involved, egotistical, careless, rude, and unsupportive people in your startup life. (It’s worth adding pudden-heads.) For example:

• Your partner or spouse,

• Close family members,

• The startup CEO who spent all her funds that you helped to raise on swag, self-promotion and stupid GTM,

• Avid Facebook users,

• Unproductive VCs, board members, lawyers, advisors, investors and other leaches,

• Members of the media,

• Politicians from both parties, and…

• Elon Musk

Take a deep breath. Close your eyes for a moment. Count to 16. Turn off the stream of invective, vulgarities and negative thoughts floating through your mind. Say to yourself the following:

• I’m a positive person and not going to give these people a present, and

• I can get through my startup life without their help

You will feel better after this exercise. Repeat monthly – even after the holidays.

No matter what you decide to do during the holidays, gentle readers...seriously, enjoy your loved ones and whatever time off you can get. Next year is going to a hard one.