If you’re like me, you think a fair amount on how to maximize your 20s and often find yourself questioning wether you’re doing the right things.
As conventional wisdom goes, spending time before family responsibilities kick in is best spent developing yourself. Our 20s are for maximizing how much we’re learning, experiencing, and trying things out. Then, the eventual goal is to consolidate all of it into one big swing, one focused journey that you can tie your life output and identity to.
So, if I’m preaching that you as a twenty something should be constantly learning and exploring, then I’m an advocate for the multidisciplinary young mind. I’ve spent the last few years obsessed with people across every sphere, and trying my best to sit at the intersection of each of them. I’m at a point now where I know a handful of people in every industry which makes me sort of relevant everywhere. But, I’m not the guy anywhere. Having one toe in means I get invited to a lot of birthday parties but I’m left out of industry news, late to trends, and not privy to insider insights as I’d like to be.
The beauty of being multidisciplinary is that it reduces the risk of picking wrong. Carl Jung (a renowned Swiss psychiatrist who wrote on human archetypes) talks about becoming who you actually are instead of who society programmed you to become. And to achieve that, you need to spend time exploring. Nietzsche’s famous quote “He who has a why to live can bear almost any how.” emphasizes the importance of choosing right. It also sets an exciting ceiling of fulfillment if you choose well
Not to simplify it with 18th century European wisdom, picking is hard. Søren Kierkegaard (godfather of existentialism) believed the source of all anxiety comes from infinite possibility. When applied to career and life direction, a young multi-disciplinarian suffers because they can imagine too many lives at once. Especially after taking taste bite sized tastes of many different outcomes.
There’s a beautiful world though where the swing is to combine everything into one. Steve Jobs was obsessed with intersection points. Apple succeeded because it existed at the intersection of technology and arts. As everyone knows, Jobs studied calligraphy, design, architecture, storytelling, Zen Buddhism, etc. He built Apple on the premise that creativity comes from synthesis rather than isolation. But even Jobs eventually concentrated all of his curiosity into one singular mission. At some point, you will too.
In choosing a swing, I’ve always defaulted to the simple Ikigai thought framework of finding the intersection of what you love, what you’re good at, what the world needs, and what sustains you. If you subscribe to the framework, Ikigai would say your 20s are for discovering where your curiosity, competence, and contribution overlap.
Exploring many paths and getting good at many things allows us to have an easier time picking our eventual end goal. David Brooks writes about “resume virtues” versus “eulogy virtues.” Resume virtues are what the market rewards: achievement, status, wealth, whereas Eulogy virtues are what people remember about you when you’re gone: character, generosity, depth, warmth, impact. Picking your path correctly ensures you’re moving towards each outcome simultaneously.
I think many ambitious people spend their 20s accidentally optimizing for resume virtues before realizing they’re emotionally craving a path that builds their eulogy virtues too.
Once you’re exposed to enough forms of success, you start realizing some of them feel spiritually unattractive to you, even if they’re objectively impressive.
For me, startups created that feeling.
I’ve spent years around founders and venture-backed companies. Smart people with high agency. The feeling that the future is being engineered in front of you. But startup success often gears toward one primary event: the exit. And then what? You sell the thing you spent a decade building. Maybe you stay on for a retention package. Maybe you don’t. Maybe you start over from scratch searching for another idea worthy of your life. The liquidation event doesn’t magically solve all your problems, regardless of how big the check is. The founder of Loom exited for $1 Billion+ and lost all his purpose. He said it was the worst thing to ever happen to him and now he’s an intern trying to find his footing again. (real story)
Just as startup success has its own unique trajectory, so does art, film, VC, media…If you look at music, management specifically, you don’t build toward one liquidity event. You build a roster and a world around it over time. You can have many hits (which isn’t unique to music of course) but you’re always hunting and always taking bets. Similar to VC, except you don’t have to talk to b2b saas founders all day!
But seriously, in music you can shape culture and touch hearts repeatedly. That feels infinitely more alive to me than spending fifteen years optimizing toward a singular acquisition and then asking what comes next.
Perhaps this is ultimately what your 20s are for: Not finding yourself or prematurely locking into a lane, but exposing yourself to enough worlds that you can eventually make an informed decision about which game deserves your life.
Eventually you will have to choose. No matter how good at being multidisciplinary you are. And when that moment comes, the goal is not simply to become successful. The goal is to know exactly why the thing you choose is worthy of your devotion in the first place.
Jobs I think are interesting
None of these jobs are publicly accessible. Each of them are shared exclusively from the founders direct to their networks. When you email, let them know where you found it.
Brand and content associate @ Apollo Bagels
Joey Scalabrino (Vol 18), is the chef and mastermind behind the brand identity of Apollo Bagels. He just returned from a successful popup in Japan. Now with 7 stores across Manhattan and Brooklyn (and 3 more soon to open), Apollo’s success has been entirely driven by word of mouth and quality of product. Joey needs help creating and producing content. You’ll get to work with him out of his office at WSA
Joey is one of the warmest, most thoughtful, generous people I’ve ever met. He’s uniquely approachable, and makes time to care for a long list of people in his life. If I was just graduating school and looking for someone to work and learn under, Joey would be at the top of my list.
Junior Creative Director @ Four Four Entertainment
Kian Mchugh (vol 24) has been building Four Four company for 2.5 years now. They’re a creative agency built on the idea you can create art with big tech companies, financial institutions, etc. A way to redirect big sums of capital to artists. You likely know him best from their work building the ultra-viral Poly Market grocery store. They’ve also worked with Complex Con, Netflix, Disney+, JP Morgan Chase, ESPN, Panera, Lacroix, and Coinbase. Their deck is great.
Kian is hiring junior creative directors to work on lifestyle and product based campaigns. They’ve scaled to a 20 person team. They’re also hiring an executive assistant to support the 3 partners.
Paid Intern for Digital and A&R @ &Friends
Danny Serebrennikov (vol 25) started the company 4 years ago as a music platform covering genre fluid left music. Think underground alternative including Lexa Gates, The Hellp, CC Natalie, Underscores, Sophia Stel, and Zulan. They grew to 180k followers on all platforms in year one. Danny wanted to get involved with artist development and expanded out of media alone and into a label model. His first two years were entirely self funded but in the last 6 months & friends is now with AWOL as their exclusive distributor and financier of the label.
I have some friends who’ve interned for Danny in the past who have set themselves up in very nice music industry roles. Great hands on NYC summer internship.
Paid Intern @ Anemoia Records
Ian Hunter (vol 23), formerly at WMG for 15 years (at Atlantic for a decade). Anamoia started as an imprint of Atlantic where they asked Ian to build out his own label. his first signing was the hellp, who he also managed. Last year, he got the rights from WMG to go on as a fully indie label. They just signed the quickly exploding The sound chalk makes.
Ian is looking for artists similar to TSCM and The hellp who fit into a genre but aren’t defined by it. He looks for people who did what 100 Gecs did in electronic, Skrillex in Dubstep, or Pop Smoke to rap. Stand alone acts. As an intern you’d directly assist to Ian and do A&R work under his wing. The goal is that he’d hire you full time.
Creative Director @ Triptych Management
Jon Schulder (vol 19) founded the company to build better entertainment infrastructure for artists and creators. They manage 5 artists across music and content. It’s a young team built from 6 Harvard and Yale grads, all pushing the needle in the business of media and entertainment. You may know Wacomo, Yami Club, or Jev. Who also each hold equity in Tryptich.
Jon is incredibly connected with legacy players and leaders at big companies. He’s 25 with one of the largest independent networks I’ve ever seen. If you want to be around smart people (who need a creative director) and are extremely profitable, email Jon.
People to watch
Katie Lever, 26, vol 18
Katie (Kitty) grew up as an army brat, moving through 15 towns as a kid. She relied on social media early as a way to keep in touch with all the relationships she would build and then move away from. When she was 12 she ran a Tumblr account with 50,000 followers. Curating a world always came natural to her. Today, she is the personification of whimsy and eccentric as they come. You probably know her from her “Can I have a piece” series and then followed along into the iconic world she’s built around herself.
In school, katie was a D1 soccer player and spent all her free time thrifting clothes, reworking them and then selling them to girls on campus and have her friends model. Her athletic program awarded her most likely to make it in hollywood.
A true story of grit, after graduating, she was living in puerto rico modeling and moved to LA to get signed. After struggling to find her footing, she moved home to Tennessee where she was Door Dashing and working as a barista. She saved up enough money to move to New York where she lived in a small studio and literally shared a bed with another girl (not even romantically). Before her 2024 breakout year, she was a door girl, an assistant, worked in nightlfe; Kitty did whatever she could do to stay afloat.
Her philosophy in building the Kitty character is “if that unusual thing is true, then what else is true.” If this girl has all these things are in her purse, maybe she has a pet Golum too (she does). Kitty has now done runway shows, modeled for MAC Cosmetics, Cosmopolitlian, and most recently starred on the cover of lady gun.
It’s an active goal of Katie’s to be a part of a shift in consciousness. More prople to be inspired to feel whimsey, optimism, and belief in the world. Kitty is also a poet and soon to release a big project.
Jack Westerkamp, 27, vol 27
Jack is New Media’s leader in advertising and marketing news. Think Sports Center for the ad industry. He built Breaking and Entering as a social first engine to give people digestible and entertaining content within the ad world. They recently got covered in the wall street journal “the ad world is obsessed with these 27 year old guys”. They’re now running 9 million monthly views across 40k ig followers.
I asked about his thoughts on new media and what will stand the test of time. Jack says he owns the niche well, and believes there will a behavioral shift from tv to Youtube. Playing the same game as Julian Shapiro Barnum and Kareem Rahma, they’re part of a new class taking big bets on Youtube to circumnavigate big institutions and long production timelines.
I also asked what their X factor is to scaling into a spot where ad agencies have THEM on tv as opposed to CNBC. Jack says its all about delivering great content. To do so, they’ve built the show around people who don’t take themselves too seriously, guests and hires alike. So much so, that when they hire, “not taking yourself too seriously” is the only thing listed under responsibilities.
Julia Fernandez, 24, vol 27
Julia’s an experimental animator who works across many mediums. She likes to make things move that “shouldnt”, like ceramics. She likes working with tiles and still vessels. She’s worked in collab with West Elm, Emma Chamberlain, F.fern. And now she’s doing a project for a major luxury fashion brand
She believes that people are less compelled by computer generated things, they’re stopped by unique handmade objects. She thinks long term tying the art to the artist will be the artists power in the world of AI and new art. It proves work is real and human and worthy of building emotion around.
Julia’s multidisciplinary in that her ceramics work is almost always accompanied by video and animation. I asked who inspires her and who she spends time around. She shares space with 3 other ceramic artists, limsclay, gubean, and jhuangstudio. She bounces everything she does off of them. She also made sure to note that everything she knows and has accomplished is credit to the generosity of the New York community she’s found in art. Her aesthetic is inspired by experiential animation heros, John and Faith Hubly who left Walt Disney to pioneer their own career.
Her work is incredibly unique. This post is worth looking at to get a sense of how she intersects pottery and animation
Ziad Ahmed, 27, vol 26
In 8th grade, Ziad started a non profit to have discussions about the impacts of stereotypes. He built chapters around the world that landed him in the White House, in rooms with CEOs, and in conversation with global decision makers, all as a high schooler. He made it his mission to advocate on behalf of diverse young people. Though, despite his non profit success, he credits everything in who he is to being a model UN kid.
If you’ve seen, heard, or met Ziad, it’s because he’s now UTAs youngest honcho. He started JUV consulting as a junior in high school before continuing at Yale. It was a Gen-Z marketing agency with the goal of understanding the demographic as a cohort. He worked with 30 fortune 500 brands including Coach, Eos, Spotify, Lionsgate, and Fujifilm. With the network he built, he then founded Zcon, the first major conference of only Gen-Z speakers filled with CEOs and CMOs in the audience. They’ve hosted the flagship conference 3 times now, with thousands of attendees, 100 plus speakers and dozens of major sponsors. Being so deeply engrained with the next gen landed him a partnership with Cosmopolitian mag for their gen zers of the year section.
Juv was acquired by UTA, where Ziad is now building UTA Next Gen and leads a team of 20 people. Ziad is a people person with an excellent understanding of delivering insights to brands but also creating company structure and leadership that scales. Anyone who works at UTA next gen talks about Ziad any chance they get. He’s slated to be a power voice in business, political advocacy, and leadership for a long long time.
Brandon Fogarty, 25, vol 24
Brandon started a class of his own in high school. He picked a teacher to run the class and he used it as a ploy to start a his first fashion business. It was a pass fail class where he carved time to teach himself to build a biz, cut and sew, design clothes, and create a space to tell the story of the brand.
Now the founder of LES’s Komune Space, Brandon wanted to make a communal space to represent a curation of designers that were East Asia and Euro based but couldn’t break into the US because they lacked physical retail space. He goes after narrative driven brands that he can tell a story around.
Before knowing Brandon, my first impression of the store when I went in a year ago was finding a cigarette roller from Korea that dispensed one cleanly rolled smoke with the press of a well designed lever. It was from Nice Workshop, a home goods brand Brandon found out of Seoul. I remember also finding jewelry with bugs in it that I wouldn’t typically be a fan of, but I was. Brandon only has so many bug jewelry brands, so he knew what I was talking about - Chitiner. He also has a curation of fragrances from Vietnam that I encourage anyone who stops by to do a sniff test on.
His vision is to expand their physical offering on Orchard street. They just opened their inaugural art gallery next door for NYC design week and launched with a Lebanese designer (who also designed their fitting room). Whenever storefronts open up on the orchard street block, they plan to buy it and turn it into a product beyond clothing.
He sees the purpose of Komune to set up financial opportunity for people. They’re now building a tailor shop to offer free tailoring and hemming on any purchase. Their store associate ran it for a year on the side but now he’s hiring her full time as she’s gotten good enough to build a book of business for herself but didn’t have the resources to start it as a company of her own. So, the tailor shop will be their next Komune project.
3rd Space Update
There’s a past 3rd Space music highlight that I’m incredibly bullish on. At a casual poker game a month ago, we chatted about their management and I told him I’d intro him to some replacement options that could give him the care and thought he deserved. Making a list felt like telling your crush who they should go on a date with. Instead, I sent a text in the am proposing myself as a manager. He sent me a screenshot back that their ban gc had talked about it literally that night. We’re now in a 60 day trial period with them in partnership with Jon Schulder (the one from the jobs section). If all goes well, I’ll continue building my roster alongside Jon and Triptych.
Lowlights
burnt out this month, happens to me twice a year. Sucks.
I charge tickets because it’s important that our ecosystem has skin in the game, as we get access to more impressive people, willingness to pay goes down. A Substack writer I really look up to recently got very upset at me when I sent him a $130 ticket.
Learning all about management from square 1 is exciting but I’m at the low point of the Dunning Kruger curve. (meaning, I’m conscious of how much I have to learn)
6/6 Event with McIntosh
My favorite person, Tina Tarighian, made an interactive puzzle for our invitation. See it here.
We’re taking over all 6 floors and I’m putting on what I believe to be a very well done experience.
We partnered with Bedroom 6, my single favorite experience in New York
Robbie Bent from Othership is sending us his favorite breath work facilitator
Our New Substack Section
The writing will intersect historical context and insight into a current industry, contextualized by the author themself
We have 5 more in the chamber and planning to post on a biweekly cadence
We released our first post of Social Studies with Noah Berghammer
Cannes Lions
Thanks to Collins and Eron Lutterman, I’m curating 3 dinners at Collins House in Cannes alongside a cast of incredible brand leaders. (my enthusiasm levels are where you’d imagine). Please do text or email me if you’ll be there.
Writing is therapeutic for me, so I leaned into writing more than usual. If you’re all the way down here, it means a lot to me. Cheers
Jake
oh this was so wonderfully insightful!!! well done jake!!! this is awesome!!! and thank you ❤️