The Thrive Questionnaire with Zach Iscol

This CEO and former Marine Officer discusses the importance of structure and support from his family.

When you have the opportunity to ask some of the most interesting people in the world about their lives, sometimes the most fascinating answers come from the simplest questions. The Thrive Questionnaire is an ongoing series that gives an intimate look inside the lives of some of the world’s most successful people.

Thrive Global: What’s the first thing you do when you get out of bed?
Zach Iscol: I’m a big morning person. Like really, really early morning person. Depending on the day, I either get up and help get my kids ready, or head to the gym. My wife and I tag team and alternate so one of us can get in a morning workout while the other is on kid duty, making their breakfast and getting them dressed for the day. Structure is big for me. I really need it to function and it is a huge part of my day, even for breakfast. I typically eat 3 eggs, a piece of Ezekiel bread toast and drink cold brew coffee from La Colombe with heavy cream.

TG: What gives you energy?
ZI: My family. I love spending time with my wife and kids and do so whenever I can. On the weekends, I try my best to completely sign off from work so my family gets my full, undivided attention. Our kids are at a really fun age and I get serious FOMO when I travel or if I don’t get to spend a lot of time with them for a few days.

TG: What’s your secret life hack?
ZI: I need structure in order to survive. Without it, I’m like a jellyfish out of water – I totally disintegrate! So, I take steps to self-impose structure. I put everything on my calendar. I try to schedule all my meetings on Tuesdays – every other week I either have a team meeting with a specific division in my company (sales, marketing, client success, partnerships, etc.), or a one-on-one meeting. I also set a separate day aside to focus on management and how each member of the team is growing. I find that compartmentalizing like this helps me stay organized and work more efficiently.

TG: What’s a book that changed your life and why?
ZI: James Joyce’s A Portrait of the Artist as a Young Man. I read it for the first time in college and there is a point in Stephen’s story (the main character) that shifts from third to first person. He’s struggling to figure out his loyalties, whether to his family, his religion, or becoming an artist, and that shift in narration really resonated and stuck with me over the years. At the end of the day, you have to be true to yourself. There’s a similar shift in William Finnegan’s autobiographical Barbarian Days. He’s a surf bum and lands in South Africa and becomes a school teacher in an apartheid shanty town. Suddenly Finnegan transitions from a “barbarian” with no responsibilities, traveling the world and surfing, to a citizen, someone who wants to make positive change in the world.

TG: You unexpectedly find 15 minutes in your day, what do you do with it?
ZI: It depends on the time of day, but I would likely take a walk and call my wife. I love bugging her during the day. Our offices used to be across the street from each other and I’d be able to pop over.

TG: When was the last time you felt you failed and how did you overcome it?
ZI: At the end of 2017, I realized I was spread too thin and felt like I couldn’t devote the necessary time or energy to everything on my plate. At the time, I was basically the CEO of four companies – in addition to running Headstrong Project, a non-profit that provides high quality, free mental healthcare to Iraq and Afghanistan veterans, we had just added a third company to Grid North’s portfolio of brands owned and operated by veterans. I was focused on building up Grid North as the umbrella company, but was also working to grow the three brands underneath it – our career site Hirepurpose, our news platform Task & Purpose, and MilSpouseFest, the events series we acquired last year. It’s fun and exciting to be involved in so many projects you’re passionate about, but sometimes having a hand in everything can slow the team down. That’s a good time to delegate and bring in some more help. Ultimately we hired an Executive Director to come in and run the day-to-day operations of Headstrong, so I could fully focus on growing Grid North and its properties. Though it was difficult to take that step back and trust someone else run to the organization, I am so glad I did. It gave me the time back to dedicate to these growing brands and, honestly, our new Executive Director is simply remarkable.

TG: Share a quote that you love and that gives you strength or peace.
ZI: I’ve always liked these two quotes:

“The fox knows many things but the hedgehog knows one thing.” –Isaiah Berlin

“The test of a first-rate intelligence is the ability to hold two opposed ideas in mind at the same time and still retain the ability to function.” –F. Scott Fitzgerald

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