My favorite thing about writing this newsletter is that I get to write about whatever I want. I don’t have a boss, editor, or anyone else telling me what topics to pick. Instead, this newsletter has become a creative outlet to explore what I find most interesting.

In some way, you guys are my boss. Subscribers are essential, and the business has to be a business. I want to create insightful content that is worth your time. But when I find something interesting, it typically leads to better writing. That writing then aligns our interests, allowing you to see what I was so enamored with in the first place.

This is precisely what happened with the photo above. We’ve all seen it by now — an aerial shot of a B-2 Spirit Stealth Bomber during the flyover at this year’s Rose Bowl.

This photo has gone insanely viral over the last few days, with hundreds of millions of views on social media and broadcasters talking about it on TV. There is no great way to accurately track these metrics, but I bet nearly half a billion people have seen it.

Much of that discussion has revolved around a few things. Some people just love the photo, of course. Others say that military flyovers at sporting events are a waste of taxpayer money, and then you have aviation enthusiasts, me included, who tend to lose their minds whenever they see a $2 billion B-2 Stealth Bomber in action.

The taxpayer stuff is interesting, but we’ll get to that later. The more interesting part to me is the photo itself. Several people have asked me what type of drone could capture such a clear image or how the photographer received clearance to fly his drone above a military aircraft and 100,000 fans at the Rose Bowl in Pasadena.

But the photographer didn’t use a drone. He has been taking this same photo every year since 2009. It involves several weeks of planning, a private plane, discrete radio frequencies, some acrobatic moves in the air, and absolutely zero margin for error.

This is Mark Holtzman. Mark has always loved two things: photography and aviation. As a kid growing up in California, Mark and his dad spent thousands of hours taking and developing photos in their makeshift darkroom. Mark then went on to get his private pilot license through the Boy Scout Explorers program when he was just 17.

Mark and his brother bought a small prop plane in their 20s. They traveled all over the West Coast, taking photos of whatever they thought was interesting. This small plane then became a slightly larger plane, a Cessna 206, which Mark still owns today.

Mark needed a larger plane for his growing family, including his wife and two kids. What Mark didn’t realize, though, was that this larger plane would change his life.

“My wife informed me one night at dinner that the airplane costs a lot of money to maintain, and I needed to either have it earn its keep or needed to sell it,” Mark told me. “So, one night, after a glass or two of wine, I decided to be an aerial photographer. Not much thought or research went into this, but I figured, what the heck.”

At first, this was a part-time gig. Mark used his sales background to land jobs through cold calling. A real estate company would hire him to take aerial photographs of a house, or a construction company would pay him for aerial updates on a project.

Back in 2000, this was super challenging. Mark would load up his Cessna 206 and fly to the location. He was using film cameras at the time, so he carried multiple rolls of film with him while flying, and it would take a day before he knew how the pictures turned out. That’s if Mark could even find the location, as this was before GPS and required him to use Thomas Guides — a series of spiral-bound, paperback maps.

This part-time job eventually became a full-time job. Mark brought on his son, Stephen, to help. They named the company West Coast Aerial Photography and started offering various services, including everything from aerial shots of a local university to 3D digital elevation models required during an aerial mapping project.

But while Mark’s company primarily focuses on commercial projects today, the California native has also become the go-to guy for aerial shots at the Rose Bowl.

This started in 2009. Mark plays the trumpet and was interested in seeing how the band formations looked at the Rose Bowl on gameday. So, Mark got flight clearance to take his Cessna 206 a few thousand feet above the Rose Bowl for pictures. He heard the Air Force was sending a B-2 Spirit Stealth Bomber for the flyover, so he stuck around for a few more minutes and captured the perfect shot as fireworks went off.

After landing, Mark and his son emailed the photo to an editor at Sports Illustrated, saying, “We think our photo would look great on the cover!” Sports Illustrated didn’t end up putting Mark’s photo on the cover, but they did the next best thing: They published it as a two-page spread in the following week’s print magazine edition.

Mark and his son Stephen have returned to the Rose Bowl nearly every year since. The game was canceled during the pandemic, and bad weather occasionally messes up his plans, but Mark still returns every year to photograph the flyover on New Year’s Day.

The process is simple yet complex. A few weeks before the event, Mark requests approval from various agencies, including Air Traffic Control and Pasadena Air Operations. Those agencies set a pre-approved altitude limit, like 4,500 feet this year, which left about 2,500 feet of vertical separation between Mark and the B-2 Spirit.

Mark flies his Cessna 206 from Van Nuys Airport to the Rose Bowl, then has a copilot take over while he takes the photographs.

It’s not as easy as point-and-shoot, though. Mark does left orbits around the stadium, attempting to time his shot perfectly with the flyover. He has to rotate the plane so the camera looks down on the field. He keeps the lens inside the window so the wind doesn’t impact the shot. And even if he times everything up perfectly, Mark has less than two seconds to get the photo, as the B-2 is flying at 250 knots (287 mph) in the opposite direction of Mark’s plane, which is doing 100 knots (115 mph) the other way.

Mark previously took the photos using a DSLR camera but hasn’t looked back since switching to a Sony mirrorless camera and Sony G Master lens five years ago. He also used to communicate only with Air Traffic Control during the flight, but after a few of his photos went viral over the years, the B-2 pilots reached out to him over email.

Mark now starts talking to the flyover pilots about a week before the game. He is still in constant communication with Air Traffic Control from the second he leaves the hangar until he returns, but Mark has since added a separate discrete radio frequency, allowing him to speak with the B-2 pilots and police on the ground during the flight.

The entire process takes about an hour. That includes take-off, landing, and more than 100 photos in between, including everything from the crowds cheering and the mountain backdrop to the marching bands lining up in formation and the B-2 flyover.

Mark follows essentially the same process for the Rose Bowl Parade earlier in the morning. However, he told me the parade can sometimes be more challenging, as the B-2 is designed to hide behind buildings and blend in with highways and city streets.

As for potential problems or issues, Mark’s been fortunate. The worst he’s had to deal with was when the wind closed his window shut one year just moments before the B-2 crossed into the stadium. Mark instinctively pushed the window open with one hand, holding the camera in his other hand, and managed to take a single shot of the B-2.

“When I talked to the pilot of the B-2 afterward, he mentioned that it was some of the worst turbulence he had experienced while flying in the B-2,” Mark told me over email.

Despite this being a fun behind-the-scenes story you won’t read anywhere else, someone will inevitably email me saying flyovers are a waste of taxpayer money.

That’s technically true. The Rose Bowl and its competing teams don’t pay a dime for these flyovers, with the operational costs being funded exclusively by the government.

However, these flights are often scheduled more than a year in advance. The military uses them as a recruitment tool. The aircraft requires a certain number of flight hours each year. The pilots use them as Time on Target (TOT) training, and if these flights weren’t happening above the Rose Bowl, they would be happening somewhere else.

For example, the B-2 Spirit Stealth Bomber used at this year’s Rose Bowl came from Whiteman Air Force Base in Missouri. If you look at the flight map that day, the pilots logged training hours between the parade in the morning and the game in the afternoon. And given that the planes are just 75 miles outside Kansas City, the Chiefs typically treat their fans with several B-2 Stealth Bomber flyovers each NFL season.

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