Doak Sergent
Career Endurance

VP, Strategy, 23 Stories
Instagram: @DOAKER
BEST Treat: Best Breakfast Burrito


Doak taught me the articulate way to use the term “pedestrian,” which I now throw around in design critiques weekly. This month’s Friend of BEST is anything but. Mia and I were lucky enough to work under him at DETAILS where we observed this New York cultural and career icon in his natural habitat — Condé Nast.

Doak is the boss everyone wants to be, and has likely been your boss at some point. He’s sharp. He’s confident. He’s intelligent. He’s the manager with the open door; ready to listen to your wild creative idea, brainstorm a “360” rollout on “multiple platforms” and then find the budget to pay for it ;) Hailing from the South, he’s seen the City's industry evolve, and has managed to weather the storm signet ring fully tact. Here we talk to him about staying power — what it takes, what it’s worth, what’s the back up plan. In a fashion world of peanuts, he’s our cocoa dusted almond. 

First thing’s first, you’re originally from Texas. How long have you been living / working in New York City, and what brought you here?

I’ve been living/working in the city for nineteen years.  When I met my better half we were both working for a bank in a conservative southern town and when we got serious it became clear that we seriously had to get out of there.  He wanted to stay in finance and I wanted anything but... so New York seemed like the obvious choice. Plus, it’s New York!


What makes “real Mexican food” real?

How about intent?  Growing up on the border I always thought that our version of Mexican food was the real deal, not Santa Fe style or SoCal style Mexican. But then as I traveled around Mexico I learned more about the many amazing regional cuisines, which if you want to be extra inclusive could maybe even include those from Santa Fe or SoCal or Texas since all were part of Mexico at one time...


What went into deciding to have a family knowing that you still wanted to work full-time?*

In a word: ignorance.  I’m the first person in my family to work for a large corporation, in a big city, with conventions like a standard work week. Needless to say, my availability is far different than what my parents had.  And yet, I don’t think my kids are any worse for it. I’m usually first-in, first-out and bolt home to fix and eat dinner with them more often than not and then plug back in after they go to bed if needed.  I firmly believe that a happy parent is a better parent and I find my job to be very stimulating – the work itself and especially the people.



What is the 23 Stories elevator pitch? What titles did you work at before that?

Good marketers make good advertising, great marketers make culture.  Born from Condé Nast, making culture is what we do best.

As for my previous stints, the way this business is I feel I should list the brands by those that are and those that aren’t.  I’ve worked at Vogue, W, Harper’s Bazaar, Rolling Stone, Details, Cookie, Lucky and House & Garden.


What has changed at Condé Nast (and at “jobs” in general) since you started in the “workforce?”

When I first worked in media, in New York, there were still vestiges of long-established homophobia. I had one boss who wasn’t out at work and the gay employees at another company where I worked had a semi-secret club/support group. We still have a long way to go for sure, for everyone who is underrepresented, but there has been progress.


It seems like Condé Nast attracts a lot of hard-working, talented, funny people. Why do you think that is? (is it the Condé Café?)

As a person whose admiration for creativity far outpaces my own creative abilities I consider myself so lucky to work with some of the most creative people in the world.  Saying that Condé Nast makes culture is not just a quippy line. It makes me think of the amazing blue sweater monologue that Meryl Streep’s character(!) gives in The Devil Wears Prada. We have brands that are 125 years old and still killing it in a world that is overrun with content choices but we also have amazing, unexpected new brands like Them that are giving a voice and recognition to a previously little served audience.


In your seniority, you have managed a lot of said hard-working, talented, funny people. What are the challenges in that, and how have you found is the best to handle them?

Everything I need to know about managing people I learned by raising toddlers. I don’t mean that my staff is prone to tantrums, but everyone wants to be heard, acknowledged and have their unique contributions recognized. Of course, some of the most creative, funny, energizing people can be the hardest to wrangle. A little dissonance can be good for a creative organization so sometimes you have to accommodate those personalities, if it benefits the work, but it’s a fine line and I’ve learned the hard way that one bad apple does spoil the bunch.


Besides the people, what are some other reasons you have stayed working for the same company?

The media business is changing at such a rapid pace that even within stints at one title or another my job description often changes multiple times in a year.  That certainly keeps it interesting. I’m also a textbook introvert-extrovert so I definitely operate better in a situation where I know the people, the processes and how to get things done.  Plus, having that kind of institutional knowledge has served me well both in getting things done but also in building a track record and fostering relationships with mentors who believe in and promote you.




What are the benefits for the youth these days to stay put in one job?

As long as you are getting the stimulus, learning, and growth that you desire there is something to be said for building a reputation internally, as long as you keep an eye to making sure that it will translate externally as well.


When you feel stagnant, where do you find the motivation to keep it up?

Your job is what you make of it. If you’re bored, look around you, there’s always something that can be done bigger or better.  If that doesn’t do it, move on or get a hobby.


Have any tips on bringing a fresh eye to doing relatively the same thing every day?

I’m not a natural seller, but I get passionate about great ideas so I tap into that and for me it becomes about telling those stories. Good storytelling requires knowing your audience, so if you’re doing your job right, even if the material is the same, the delivery changes.


Let’s talk lunch. What are you eating these days?

Flatbread with a little hummus topped with shredded carrots and radishes, something green and leafy, red pepper flakes, lemon and olive oil.


Let’s talk coffee break. What gives you the afternoon boost these days?

Oat “milk” latte and a couple of cocoa dusted almonds


Let’s talk happy hour. Where are you hanging out these days?

Went to Due West on W. 10th just last night: chic banquettes, good bites and big windows that open up to the street on a nice spring evening.  Near work, it’s Weather Up and at home we’ve got a hoppin’ new spot, The Cassidy.


At the end of the day, none of us have “job security” even at a conglomerate like Condé Nast. What’s your backup plan? Is it the same as your Retirement Plan?

No one has job security, especially at a big conglomerate. I probably don’t put enough thought into my backup plan but I like the idea of combining two of my favorite things: entertaining and interior design with a coffee/wine bar in which everything, including the furnishings, is for sale.


Briefly describe who you are and what you do and why you like BEST:

I am a ninth generation Texan who has learned to love living in New Jersey. Also known as Daddy to Loulou and Ollie (as opposed to “Dad” which is what they call my better half). I am head chef of the household and at work I help run Strategy and Accounts for 23 Stories, a creative and experiential agency owned by Condé Nast -- which in simplest terms means I’m the conduit between commerce (sales/clients) and creative with insights and positioning sprinkled on top. I like BEST because these amazing women are blazing their own trail, going wherever the creative winds take them. Because in a world of “not my job” the limits of their creative thinking knows no bounds and thanks to that they’ve saved the day for me more than once.



You made it! Here’s a treat from Doak—
the Best Breakfast Burrito (a future highlight at the coffee/wine bar).


Every month BEST interviews a cool person they know doing a good job at Life.
Learn something you didn’t know about someone you might have heard of. Plus treat.