The Path profiles people working in what we think of as "dream jobs," living their best professional life, and looks at the people and practices that helped get them there. We talk to these amazing folks about how goal setting, great managers, tough conversations, and key moments of praise helped set them straight or lift them up at instrumental moments and take them where they are now running the show.
Name: Ian Kaplan
Job Title: Partner / Executive Producer
Company: The Custom Family
Today, it’s become less likely to stay at a job as long as previous generations. Though it was once common to join a company and stay put until retirement, modern work culture has normalized the act of jumping from job to job in search of different things—from bigger pay stubs to more impressive titles to a better culture fit. A recent Gallup poll called millennials the “job-hopping generation,” finding that a staggering 21% of them say they've changed jobs within the past year — more than three times the number of non-millennials reporting the same. And yet, even though millennials are the most likely generation to switch jobs, that doesn’t mean everyone’s doing it.
Case in point: Ian Kaplan. In 2011, Kaplan was a young college graduate with a dream of breaking into the photo industry. He found an internship at a production company called The Custom Family and decided to get his feet wet in the profession of his dreams. But the summer internship became more than Kaplan initially bargained for, and within nine years, he went from college intern to executive producer and is now a one-third owner and partner in the company. Within that time, Ian has accumulated an impressive stack of accomplishments, including spearheading a global Levi’s campaign and a campaign for the launch of Facebook’s ‘Live’ Feature.
In our interview with Kaplan, we wanted to learn about what it’s like to become a partner at a production company and, more generally, grow up within a company for the long-term. In a time where so many people hop between jobs, Kaplan sheds light on the benefits of putting down roots within an organization, why he thinks mental health is a priority (and strives to start each day with meditation), and why he believes that listening and empathy are keys to strong leadership.
What did you go to school for and what did you think you wanted to do at that time in your life?
I graduated from Florida State University with a major in Business Marketing and a minor in Communications. Photography had been my passion all through high school and into college, but in the end, I decided against the idea of a pricey out-of-state BFA program (a decision I have never regretted once to this day). At the time, I was confident that I’d figure out another angle of entry into the photo industry.
How did you end up getting hired for the position you’re currently in?
It was summer 2011, I was still in college, and I decided that I wanted to find a [air quotes] “photography internship” in New York City. At the time, I had no idea what a producer even did, or how the industry as a whole functioned. Nevertheless, I came to New York in search of my first stepping stone into the world of photography, and was serendipitously pointed in the direction of a production company called The Custom Family.
They were boutique in size but had their hand in some of the most impressive photography work in magazines and on billboards across the globe since the mid-90s. I was stoked. Over the next seven years, I worked my way up from intern to production assistant to coordinator to manager to unsure-of-job-title-but-did-a-little-bit-of-everything. Then, in 2018, I became a one-third owner/partner in the company. It’s been equal parts loyalty, working my ass off, and being fortunate enough to have been in the right place with the right people at the right time.
Tell me about someone who’s made a significant impact on your career trajectory.
With the rigor of this industry (as well as many others) and the amount of responsibility that was being put on my shoulders at a young age, I would have been paralyzed from the stress of it all and thrown in the towel a long time ago if it was not for the support and counsel I received from my parents and my closest friends. I am a big believer in externalizing when it comes to life’s biggest challenges.
What are some daily habits you absolutely make sure to schedule into your day?
While I am borderline OCD when it comes to the management and running of a production, I am pretty terrible when it comes to taking good care of myself and my mental health. This year, I am making a conscious effort to eat three square meals a day (I am the self-proclaimed king of the late breakfast, followed by 10-12 hours of feverish working at my computer, followed by dinner right before bed—yikes!) and to start every day with meditation — both of which I have found to be immensely beneficial.
What do you love most about your job?
I get the chance to work with incredibly driven and talented people on a daily basis (no one stays in this industry long if they don’t love it!). The work takes me to amazing places that I’d never have the ability to see otherwise. And, above all else, no two shoots are the same. Yes, many productions require many of the same things (everyone needs to be fed, everyone needs a method of transportation to and from set, etc).
And yet, nearly every shoot has something unique about it that needs to be figured out, and that unique element is oftentimes something you’ve never done or figured out before. Including, but certainly not limited to: figuring out how to capture a humpback whale breaching in the background of a photo at the very moment that talent is in the foreground mid-blink with 12 hours notice and 24 hours to get the shot; managing a production that’s capturing ten commercials and shooting in eight cities across two continents, simultaneously, with all content being captured by non-professional talent on cell phones and remotely beamed to an HQ space; exploring lowrider bicycle associations in Buffalo, New York; sourcing a sloth, a zebra, baby leopards, and many, many rabbits, and becoming deeply familiar with the exotic animal laws that govern upstate New York; building a forest set in the middle of Times Square; and not freaking out while working with Bill Murray.
Has there been a time when someone took a chance on you? What happened? Do you think it’s important to take chances on others?
Just as I would not have gotten this far without the support of my family and friends, I would not have even begun this journey if it was not for the leap of faith that my now-business partner took on me when I was a 19-year-old greenhorn intern. After he saw that I had the motivation to learn, and we built just a bit of foundational trust, he began to give me responsibilities that would’ve had major client-facing consequences if the tasks were botched. It was those first instances of having been thrown into the gauntlet — and learning how to thrive while surrounded by things unknown to you — that built the backbone of everything that has happened since.
How do you integrate critical feedback and praise into your work?
I try to never lose sight of how rewarding it once felt to receive praise on my performance from a superior. Also, I try to remember that I make mistakes as often (if not more often) than the person or people who I am giving constructive feedback to. The main thing I am looking for is that someone treats a mistake as an opportunity to learn and grow.
Mistakes are par for the course, and, of course, I identify them when I see them happen, but I try to do so in a constructive way and highlight successes just as often. It’s only when the same mistake is made over and over again that it becomes indicative that either something’s not the right fit or that the individual does not have the desire to improve.
What’s been the biggest learning lesson in your career so far?
Learning that balance is everything, prioritizing mental health, and learning that giving oneself the opportunity to step away regularly to recharge is crucial in becoming the best you can be at what you do. I’ve learned not to feel shy about broaching the topic of taking the time and space that you need when you need it. I was for many years, and it weighed on me as well as the relationships in my life.
I believe that this pressure people feel in the United States (especially in cities like New York) to provide unwavering and unlimited devotion to their occupation for fear of being perceived as weak or unmotivated (or being replaced by someone who’s that much more willing to work every waking hour of their lives) is incredibly toxic.
Tell us about your first experience as a manager. What have you learned since then?
As I mentioned, I got a very early start in this industry, and because of the circumstance and the trust that was built early on, I was given an unusual amount of responsibility for my age. This amounted to situations on productions where there were crew members that technically reported to me who were 10-20+ years my senior. At first, it was very difficult for both me and those crew members to get comfortable with this age gap. In time, though, I learned that, by being as much of a student as I was a ‘teacher’ and letting my authority speak for itself (versus trying to accentuate it), respect and comfort naturally followed suit.
What do you think makes a good leader?
Someone who listens as much as they speak. Someone who has walked in the shoes of the people that they lead. Someone whose passion for what they do motivates the people around them to find that same passion within themselves.
What does empathy mean to you vis-a-vis the workplace?
I have always been a deeply empathetic person, so to me, managing a team and a sense of empathy go hand-in-hand. I don’t think that I could ever be an effective leader without also being able to understand and share the feelings of the people that I work with.
How do you approach difficult conversations with your team and other colleagues?
There are many ‘right’ answers to this question, but in most situations, I prefer to first lay the foundation for difficult or complex topics in writing before discussing them, especially if it’s a message that the other person might not be expecting to receive. I feel that it benefits everyone involved to be able to review and mentally process words on a page (which are then memorialized and are less likely to be misinterpreted or misremembered), and then discuss.
How has goal-setting played into your career?
Goal-setting is an everyday aspect of my work, but in regards to the big picture, I have never really looked at it like ‘I want to be in X kind of job by Y date.’ I just made a commitment with myself to work hard, kept my eyes and ears open, identified doors that could be opened, and walked through when they presented themselves. I stayed loyal to those who gave me opportunities, and tried to remain humble every step of the way. The advancements I have made and promotions I have received along the way are a product of the consistent execution of all of the things above.
What’s been the value for you in growing in one company instead of moving around like so many others in your generation?
I owe most of the credit for my rise from intern to partner to loyalty. Growing in your skillset at one company allows for you to be able to build a deep trust with those around you and vice versa. I have nothing against moving from company to company; it’s just undeniable that doing so prevents one from being able to spread their roots as much.
What advice would you give to your younger self?
Take time off after you graduate college before going straight to work, dummy!