How I Saved $20K and Reignited My Passion For Photography

If you didn’t read the above photo’s caption, do so now — I’m still astonished by it.

I’ve been in love with photography half of my life — nearly 20 years. There was a burst of energy around it in my early twenties when I first discovered my eye for it. I purchased a 1980-ish manual Minolta SLR from a pawn shop for $100 to start a photography class and again in my late twenties, when some places were still developing and printing film. I fell back into the groove once more, again using an inexpensive manual SLR. Here are some examples, unretouched:

For the past nearly 10 years, though, I have been mostly bereft of the ability to practice the one true artistic talent I think I have, and a true passion of mine. This has mainly been due to life getting in the way, not having the time or bandwidth, and that digital photography — at least the kind I could afford — was just not doing it for me. To me, film feels like how records sound. Plus, I love the idea of having a finite number of shots to take to capture "the one."

Over the past year or so as my financial means changed, I made a decision to return to the hobby that sings to my soul and invest a significant amount of resources into getting the shots I see in my head on the daily. As I said in a recent podcast episode, I see the world in photographs. And I wanted to express myself in this way, creating art in the same way that I have started to collect it.

I had already spent around $3,000 on a great Fufjifilm camera and lens that is remarkably similar to the over $12,000 Leica cameras I’ve coveted for years. So I’ve been treating myself to lots of street photography and bringing it along on my many speaking trips for fun. I was never able to capture the feel I was going for though. The closest was when I rented a Leica for two days in 2017 and got some cool shots.

The next step was going to be to purchase an additional camera body, more (expensive) lenses and an iMac to teach myself how to edit. I was going to set aside a part of my new home office for complex lighting and background rigs, and was going to become your average Annie Leibovitz.

In total, this was going to cost me around $20,000 over a 24-month period and was going to come directly out of my book deal proceeds and speaking fees. I don’t own a car, so this was going to be THAT. And it would be worth it to me because of the pure joy photography gives me — I would be able to work with my hands, hone my craft and never ever get bored. Photography is also recession-proof. People find new ways to capture themselves, but the desire never goes away. So if I ever found myself needing to make ends meet, I figured photography could one day — years away — be something that helps.

A few weeks ago, I dropped my iPhone 6 on concrete and busted the screen. I tweeted about it. After a failed attempt to fix the screen, I decided to purchase a brand new iPhone instead. I had the old phone for at least two years, I think.

I noticed the iPhone X (Max) had great speakers (contrary to what I’d read online) and I loved the photos I’d taken at concerts. Overall, I was impressed with my new purchase and felt super fancy owning the phone. But I had no idea what was in store!

A few days ago, while sitting on the couch with my WIFE (we just got married so it’s fun to say that) Anna, I saw the sunlight strike her in a way that I wanted to capture while we spoke casually. She had just gotten a new hair cut and I thought it was super cute, so I wanted to capture it on the first day.

I decided to click over to the “Portrait” function of the iPhone since I had never used it, and play around a bit with the buttons and settings. I took several photos and loved what I was seeing. I took around 30 photographs and then we reviewed them. Keep in mind: she never stood up and we never stopped talking during this. Although 25 or so of them were what you’d consider your run of the mill photographs of the person you love, four of them stood out to us immediately. The ones that I had taken the most time on, and pretended I was using an SLR to capture:

I decided to do a little experiment. I used the iPhone’s browser to pull up Fedex.com and uploaded the unedited, unretouched, smartphone photo and ordered an overnight print of the first pic above as a whopping 24 x 36 in. poster. I thought I would receive a furled up poster of a low resolution version of the pic that — if I was lucky — would look cool enough to hang up somewhere around the house.

Anna agreed to run the errand and pick up the print for me about half a mile from our home. When she got back, I was sitting on the couch facing away from her. "Well that wasn’t your average trip through Hollywood,” she said. I turned my head and noticed she was out of breath because she had just hauled a giant, gorgeous, boarded photograph of herself down the streets of Hollywood. The combination of the iPhone X and Fedex printing services had shown up and showed out.

The same day, my mother Mrs. Sims, my brother Rook and my brother's fiancée Angel were visiting Los Angeles from Dallas. While we all chatted in our living room, I took a few snaps. Once again, several of the photographs look like the type you’d take on a phone, even in portrait mode. But I caught lightning in a bottle with one of them. Rook edited the tiniest blemish above his lip by my request, and then we had this printed as well.

The following day, this was the situation in my newly painted home office:

I also took a snapshot of my brother and his fiancee at sunset that turned out great. It’s particularly great because my brother has beautiful dark skin, and his fiancee has beautiful albino skin and wears electric colors, so you can see this side of things when printed. Again I did no editing, and I’m pretty sure the only editing Fedex Printing has done with these prints is make them cropped slightly to fit:

The next part of my fast-paced photography journey happened after I was asked to moderate a town hall-style event where Democratic presidential candidate Pete Buttigieg spoke in Oakland. I grabbed eight minutes with him afterwards to record my podcast, and we locked in for this shot that is turning heads. Literally had thirty seconds to shoot it. Can you see why I’m in love with this iPhoneX Portrait situation?

Most recently, I took several shots to capture a self-portrait. I just sat in a room alone and positioned the phone in different ways using my hand. No tripod. There are dozens of shots that are not good. There are many that are okay, but aren’t exceptional. And then there are some that I love:

The bottom line here is that I’m not buying any more camera equipment or the iMac for a while because these photographs are capturing people the way I wanted the other equipment to. It’s obviously muuuuch easier to carry my iPhone around and travel with it (I traveled 300 days in 2018) than with gear. The new camera backpack I bought will have to chill for a while. The biggest issue I’ll have is keeping the iPhone charged. But other than that, let’s go. I don’t know if I’ll use iPhones for the rest of my life, or if I’ll spend a few months on this particular phase, but I am stoked.

I will be creating a portrait for each of my podcast guests when possible to accompany their episodes, so keep an eye out for that. And I can’t wait to capture more of you.

Please send me samples and show me what you’re capturing. Let’s have some fun!

To learn more about Arlan, visit her venture fund website, podcast, Twitter and Instagram.