Gary Land never disappoints. Jovial, imaginative, friendly, expert, talented, accomplished, humble, knowledgeable, and fun. In this episode of Creative How, we learn from a guy who is an elite photographer but also a DP (director of photography or cinematographer) on film and the head of a creative agency and production company.

The conversation ranges widely, and you’ll hear stories about early failures in Gary’s career, shooting famous athletes and entertainers like Allen Iverson and 50 Cent, creating a collaborative environment, mentoring teammates, the best steps to take to get into his industry, and also how awesome Sean and I are.

Gary said, and I quote, “Instagram is my favorite thing on the planet right now.” (Mine is pizza, but that’s beside the point.) For a photographer to say this is somewhat rare. Years ago, it was unheard of, but today it’s still a bit odd given it can arguably diminish the skills of a trained photographer. But that’s how Gary thinks. He learns from what he sees and he doesn’t limit sources of inspiration. 

Quick anecdote that doesn’t show up in the episode:

The day before a big shoot with Gary and his team, we finished the standard pre-pro meeting and the details were in place. At this point, the various people (photo team, client team, agency team, etc.) usually go their separate ways and get ready for the next day. This can mean sleeping, drinking, exercising, whatever. But on that day, Gary suggested we have a big Whiffle Ball game in the dilapidated tennis court of the hotel we were all staying in. And that’s what we did.

The sum of the comments above is that Gary Land is a different kind of creator. Open to ideas from everywhere and everyone, but also a fine craftsman with a sharp point of view. A renowned photographer, but also the head of both a production company and an ad agency. There are few like him. Here are Three Big How’s from a guy who shouldn’t be NEARLY as down-to-Earth as he is after accomplishing so much:



Obvious but poignant, and particularly relevant to aspiring young photographers. In Gary’s words, “Get off your couch, stop playing Fortnite, and shoot!” Photography and shooting video have never been more accessible, and testing out new ideas is there for the taking. Fact is, you need to go do it. What do I shoot?, you say. Shoot what you like! Gary says that’s what you’ll know best and that’s what you like most. For him, the beginning was shooting his friends skateboarding and snowboarding…and look how that turned out.


Gary said if he had it to do all over again, he would’ve started out as a PA (Production Assistant) on photo and video sets. PA’s do all kinds of things on a set…from getting coffee to moving props to basically anything anyone asks. Being on a set is being in a different world. Literally knowing where to walk and where not to walk is complicated, so you can imagine with the level of equipment and expertise on any given set there is A LOT to absorb and learn. As you begin to see the machinations of set and the various roles of the personnel, you could—like many of us—become enthralled by it. So look online for PA jobs somewhere near you, and get your name in there. 


No offense to other brands, but Gary’s a Canon guy. That’s the camera that works for him, but you should explore (once you have the financial resources, of course). One thing he strongly believes is that he needs to see a real representation of what he’s shooting, so he doesn’t like electronic viewfinders. As important as the camera—and possibly more important—are the lenses you use. Without getting too technical here, you’ll need to educate yourself on what lenses do and how they work…and then get the best you can afford. Finally, and shockingly, Gary said everyone already has a great camera…on their phones. Most photographers don’t say this, but that’s what makes Gary Gary. It’s not the photo editing you can do with your phone as much as it is the literal ability to go out and shoot ANYTHING and constantly try new things. Not something that was available to past generations.

While these show notes are actually a bit longer than usual, they don’t even scratch the surface. This episode is packed with details from someone who is a true giant in photography and beyond. The anecdotes from Gary’s career and the insights he shares about so many aspects of his business can help you think differently and probably better about your pursuits.

It’s always a pleasure to spend time with Gary, so don’t cheat yourself. Listen!

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