Ben Skaar was a Massachusetts-raised photographer and digital artist attending NYU in Manhattan, known for his aerial cinematography and his work in the NFT and digital art space. Isaac and Ben had first connected through Clubhouse during the pandemic, and the episode covered Ben’s journey from building an Instagram photography portfolio to hosting Twitter Spaces about digital art after school, creating the Cinema in the Sky series on SuperRare, and a Samsung-sponsored trip to Iceland that became a short film about his father — and what it means to have people in your corner while chasing a creative life.
How Ben Skaar Found the NFT Space
From 2017 to 2021, Instagram was Ben’s primary platform — posting photography, treating it like a gallery, building connections. Then Clubhouse happened. He was in high school, classes had moved online, and between sessions he’d hop into rooms to talk about photography. One Friday night he stumbled into a room about NFTs and crypto.
“It felt like a really an opportunity for us to own the work that we were putting out — as social media creators a lot of the time when we posted one of our photos or videos we’re almost like giving up ownership of it to the platform.”
He started hosting his own rooms. Then, at 17, he got banned from Clubhouse — his age violated the platform’s policy. Twitter had just launched Twitter Spaces, a near-identical format.
“I was like all right I’m just gonna take what life has given me here, make lemonade, and just start hosting these.”
After school every day, he’d open a Space — type “let’s talk digital art NFTs” as the title and hit go. Sometimes he had an itinerary; mostly he let people filter in and talk for hours. He was the host but felt more like a participant — people who knew far more than him were joining, and he was absorbing it all. Photography names he’d followed for years on Instagram were suddenly in the same room. Digital barriers he’d felt on the feed were gone.
“Even as like a host of the room I was more just a participant — I was just learning from all these people and getting to meet all these cool artists — people that I had like followed for years on Instagram.”
The daily habit also sharpened his speaking. Hosting strangers, navigating rooms of adults as a teenager — he came out of it with confidence he hadn’t had going in. He carried it further, traveling to Miami twice for digital art gatherings and to Lisbon, Portugal to speak at a conference. Face-to-face was always the deepest tier, he said — and a major reason he later chose New York City.
Cinema in the Sky
Ben’s aerial photography and drone work had always been central to what he made. When he entered the digital art space in earnest, he built a series that brought those two things together: Cinema in the Sky, short aerial films shot at locations around the world — Hawaii, Italy, Massachusetts — each paired with original music composed specifically for the clip. The goal was immersion.
“Our number one goal with this series was immersion — I really enjoy the process of sharing that with people and being able to give them like a glimpse — the work that I create is very centered around the experience and feeling that I have at a location.”
He released the series on SuperRare, an invitation-only platform for digital art. Getting accepted there at 19 felt significant. What he was chasing in the work wasn’t realism — it was translation. The feeling of being somewhere, amplified and made transferable.
“I care about how a place makes me feel and I want to amplify that through my photos and videos.”
His first NFT sale from this body of work outpaced every client job he’d ever done.
“It was the largest amount of money that I had ever made from my work — it immediately outmatched every single client job that I had ever done, which felt crazy.”
He reinvested a large portion back into the ecosystem, buying work from other artists in the space.
The Samsung Iceland Film
Samsung found Ben through Cinema in the Sky. They were producing 8K content — their TVs could display it, but there wasn’t enough footage being made — and they’d seen what he’d done with aerial cinematography. They sent him to Iceland for eleven days with a Cinema drone, told him to bring someone, and trusted him to make something he wanted to make.
He brought his dad.
“They were like hey we have this overarching mission, we trust you to make something that you want to make — and that was like okay, you see my creative vision is of value to you.”
The short film he was cutting from the footage was called Full Circle. It was about their relationship — specifically the years when Ben was too young to drive, and his father would get up at sunrise to take him somewhere he wanted to shoot, sometimes biking thirty miles with him. The Iceland trip flipped that dynamic: Ben was now the one bringing his father somewhere.
“This trip was almost like a testament to the fact that they let me continue to chase my delusions of being an artist.”
He’d grown up with parents who never steered him toward a safer path. The film was partly a way of acknowledging that.
The Digital Art World as a Movement
Ben held a strong thesis on where digital art was headed — and held it with the kind of conviction that required tolerance for looking delusional.
“I kind of compare it almost to like graffiti and Hip Hop in New York in the 1980s and 90s — everybody frowns on it at the time — but it kind of looking back becomes like a small little cultural revolution that impacts future culture.”
The community he described wasn’t the profile-picture NFT market most people associated with the space. It was a smaller subsection — illustrators, 3D artists, photographers — trying to build something closer to a recognized art movement. The blockchain, in his framing, was a way of permanently placing digital work somewhere that couldn’t disappear the way a centralized platform could.
He spread his own work across platforms by medium: SuperRare for the aerial Cinema in the Sky videos, Foundation for his nature photography, OpenSea for urban work from Boston and New York, and Manifold for pieces that needed their own smart contract structure.
His advice to anyone looking to enter:
“I think your initial focus should be giving before you take — because it’s going to come back and people are going to remember how you started.”
The artists sustaining real income in the space weren’t extracting — they were on Twitter every day, contributing to conversations, supporting others’ work. Success tracked your presence and your impact on the people around you more than the quality of the work itself.
He also pushed back on utility as the primary value driver in digital art:
“There’s a phrase that I like where it’s like the artist is the utility — by buying a digital artwork it’s almost like you’re placing your trust in this artist that they are going to continue to create, they’re going to hone their skills, because they are an artist.”
Creative Control and the Long Game
The NFT income had given Ben something he hadn’t had before: the ability to say no. Before, a trip meant building client deliverables before he could focus on what he actually wanted to make. Now, revenue from his own projects funded the personal work, and he could turn down commissions that didn’t align creatively.
Samsung was the exception that proved the rule — he took that job because they handed him the wheel.
“I want somebody that picks me to create what I want to make because really the stuff that I’m super passionate about making is going to result the best for the brand.”
He was at NYU studying digital media and business, and found that the locked-in structure of school — class hours, academic deadlines — had made him more productive in the remaining time, not less.
“Because I’m aware of this limitation that I have I am more wise with how I spend the time that is allotted.”
He’d also built a two-week social media detox into the start of the year, driving around the Arctic Circle in Norway with his grandmother and getting his screen time down to thirty minutes a day. In seven years of posting, it was the longest break he’d ever taken.
The long-term goal was the same one that ran through everything else: freedom — to make what he wanted, go where the work took him, and sustain it.
“Photography started as like a form of documentation for me and now it’s almost like a soul storytelling medium — I’m always seeking for ways to better explain how I feel and the stories that I want to tell.”
Key Takeaways
- Give before you take in the NFT space. The people sustaining real income in digital art were contributing to the community — not just posting work and waiting to be discovered.
- The artist is the utility. In fine digital art, collectors aren’t buying a promise — they’re betting on the person. Your commitment to keep creating is what holds the value.
- Platform switches can open better doors. Getting banned from Clubhouse pushed Ben to Twitter Spaces, which turned out to be a better vehicle for what he was building anyway.
- Face-to-face deepens every digital relationship. Ben moved to New York City partly because the space he was building in happened there — in-person connection was always the highest tier.
- Creative freedom is a filter, not a luxury. The Samsung project worked because they gave full creative latitude. That’s the version of commercial work worth pursuing.
- Less available time can make you more productive. The structure of school forced Ben to be more intentional with the hours left over — a constraint that worked in his favor.
Visit Ben’s work at benskaarphoto.com. Connect with Isaac at isaacjarnagin.com.
