This was a treat and a true highlight of my Dialectic project so far. Jack is wise and totally infectious. Here’s to helping and witnessing creative people do their thing.
If you enjoy it, please share with a friend and rate / review wherever you listen.
Available on Dialectic.fm (transcript), Spotify, Apple, YouTube, Twitter/X, and LinkedIn.
Dialectic 52: Jack Conte - Draw the Next Page
22 of My Favorite Lessons from Jack
Stop polishing your B-minus. Early on, Jack chose a pure growth mindset, hammering at everything he was bad at, until he hit the ceiling: a year or two might drag a weakness from B-minus to B-plus. Now, he hands that work to someone excellent and pours more of himself into the few things he thinks he can uniquely crush—and more importantly, the things that give him energy.
Prolificacy needs an operating system. Jack made 100 music videos a year while running Patreon by turning one weekend a month into eight recorded songs, then letting production teams carry them across the finish line. Meanwhile, his Chief of Staff Nicole keeps everything in check across Patreon and life. What resembles impossible stamina online is often excellent operations backstage.
Get post-chaos. Many people read chaos as a sign of failure, something to fix. Jack accepts it as the baseline of life and company-building: disorganization, changing schedules, changing priorities, and the feeling that things are always a little stretched. He’s getting better at relaxing into that instead of waiting for a calm that isn’t coming.
Burnout can be five solvable problems in a trench coat. Jack’s worst lows usually turn out to be a few gnarly problems arriving together, impersonating the end of the road. His method is to separate facts from the stories in his head, write crisp problem statements, then take the first three plausible actions against each one until a path reappears. He’s learned not to trust the permanence of emotions: sometimes all is lost until he has a snack and realizes it was low blood sugar. “I don’t want to be Charlie Brown again.”
Your most joyful work may not be your most meaningful work. Making music gives Jack such immediate, bodily joy that he can disappear into Ableton for six hours and forget to eat or use the bathroom. Patreon’s daily work is nowhere near as pleasurable, but its creator-focused mission gives him immeasurable meaning and purpose.
Art carries a feeling. Content carries an objective. Most work lives in a wide spectrum, but at the ends, Jack thinks content is made to produce an intended result, while art begins with something the artist felt and wanted another person to feel. The same film can therefore be art to its director and a means to subscriber growth for Netflix’s infinite content machine.
Every artist has a different appetite for business. Jack and Patreon sort creators into three personas: the purist who just wants to play guitar, smoke weed, and be left alone; the operator who’ll handle the business work because it unlocks the life they want; and the builder whose eyes light up at the machinery itself—who says “I’m a media company” and studies exactly where the New York Times greys out its paywall.
Getting paid is the opposite of selling out. Many artists worry that making money off their work makes it dirty. Jack calls that backwards, because asking to be paid is knowing you made something of value and wanting to build a future where you can make more. He thinks selling out is doing something other than making art.
Don’t let the dashboard tell you what your work is worth. For twenty years, platforms have taught artists to read revenue per view as a verdict of value. Jack doesn’t buy it: when three million views pays eighteen dollars, the number is measuring the system’s extraction, not the art’s worth. He hates the term “influencer” because it names only the monetizable part of a person—their reach—and turns artists into commodity suppliers of eyeballs.
The history of art is direct support. For most of history, art did not run on ads, feeds, or subscriptions to infinite libraries. It ran on patronage: churches, governments, and rich people saying, “I like what you make; here’s a bag of coins, go make more.” Recording tech let art hitch a ride on scarce physical objects for a century, then the internet erased the scarcity, and that model collapsed. Jack sees Patreon as a return: direct support, now distributed across individuals instead of concentrated in institutions.
Free wins distribution. Artists pay the difference. Free experiences helped the internet reach billions of people, but a system solely optimized for the consumer keeps pushing art toward all-you-can-eat abundance at ten dollars a month. Patreon exists to muscle in the opposite direction, and its primary KPI is not attention, engagement, or subscriber growth. It’s dollars sent to creators.
Align incentives before asking for trust. Patreon’s take-rate model means the company succeeds when creators get paid. Values matter, but they are easier to uphold when the economics point in the same direction.
Buy the hot dog factory. When Costco could no longer source its famous hot dog cheaply enough to preserve the $1.50 price, it rebuilt the supply chain instead of breaking its promise. Jack sees trading short-term revenue for long-term trust the same way, because he wants Patreon fighting for artists a hundred years after he’s dead.
Some forms of capital don’t fit the spreadsheet. In tech, the product is the thing, and even Jack concedes that. But brand, narrative, creativity, and storytelling can matter even when they don’t show up cleanly in the P&L. Companies that only believe what they can cleanly attribute will struggle to earn what Jasmine Sun (Dialectic 49) calls other forms of capital: attentional, social, or cultural.
Remember which audience matters. Patreon is Jack’s first real job, and he entered technology from music and YouTube rather than through the Valley’s usual doors. He thinks Patreon is partly dismissed in tech because it has spent thirteen years building trust with creators instead of focusing on the insider tech audience and the engineers it might impress.
Say the thing you’re ashamed of. The best advice Jack has for making real fans comes from screenwriter Charlie Kaufman, who said to say who you truly are, out loud, especially the thing you are ashamed to admit. He points to Prince: Don’t like it, go away. The honesty that repels the wrong people is often what lets the right people recognize themselves.
Aim ambition outside yourself. Jack likes intensely ambitious leaders, but first asks where that force is pointed: toward individual advancement or the company’s mission. The related trait is what he calls the “passion muscle,” the capacity to fall in love with a customer, problem, or cause beyond yourself.
Fascination outlasts talent. For all his output, Jack doesn’t feel naturally talented. The first time he recorded his guitar, he assumed the equipment was broken; after reviewing the recording, he discovered the malfunction was him. What kept him going was not conviction that he was gifted, but an obsessive desire to understand how the music was made.
You better be proud of what you upload. The internet has enough stuff. Jack once found publishing itself exciting, but the web has been saturated. He’s no longer interested in adding to it unless he feels deeply proud of the work and thinks it is unbelievably great.
Leave room for the thing you can’t explain. Jack is skeptical of extraordinary claims, yet music feels closer to the supernatural than anything else he has known. Like consciousness, it seems to occupy some aphysical, uncharted space: impossible to fully explain and impossible to stop exploring. For all his business-building, Jack’s deepest loyalty is still to that mystery.
Anxiety is a risk key. Lucid dreamers use reality checks to notice that they’re sleeping. Jack knows he tends to catastrophize, so he uses anxiety the same way: a cue that his risk meter may be miscalibrated, not proof that disaster is coming.
Draw the next page anyway. Thirteen years ago, as a full-time YouTuber and musician who’d never had a real job, Jack sketched plans for Patreon across fourteen sheets of printer paper. Despite feeling like a fool, he repeated aloud, “This isn’t going to work. That’s okay. Draw the next page.” The company began when he gave himself permission to feel stupid without putting down the pencil.
Description
Jack Conte (Patreon, YouTube, YouTube Pt2, X, LinkedIn) is the co-founder and CEO of Patreon. He is also a lifelong artist and musician, and releases nearly 100 music videos per year between his bands Pomplamoose (a duo with wife Nataly Dawn) and Scary Pockets (a funk collective), and was a longtime YouTuber.
Jack is not a tech CEO who happens to like music. He is an obsessive, prolific artist whose first conventional job is running Patreon. This has shaped him as a founder and executive, and his mission at Patreon is to build an enduring and truly creator-first company that empowers creators to earn a living from their work.
We began with how he manages to do it all, where his energy comes from, and what it’s like to be “post-chaos.” Then, we talked about art, content, and commerce, Patreon’s model (that isn’t actually pure patronage), and why Silicon Valley undervalues art, brand, and narrative — and Patreon. Jack shared the benefits of a business model that is fully aligned with creators, why he hates the word influencer, and why he’s still the right man for the job after 13 years of leading Patreon. We also covered what great leadership looks like, building fans and community, filmmaking, authenticity (from Charlie Kaufman to Prince), and remembering to take risks until the very end.
I hope you’re inspired to make things you are proud of and to draw the next page even when you have no business doing so.
While I have you: I’d strongly recommend Jack’s recent SXSW talk on AI, creativity, and change.
Full transcript and all links: dialectic.fm/jack-conte
Dialectic is presented by Notion. Notion is an AI-powered connected workspace where teams think together and create their best work. Learn more about Notion’s new developer platform and workers here. You can learn more at notion.com/dialectic.
Timestamps
(0:00) Opening Highlights
(1:38) Intro to Jack & Thanks to Notion
(3:44) Start: Prolific Output, Energy, Juggling, Endurance, and Becoming Post-Chaos
(22:04) Combining Creativity and Business and Art vs. Content
(33:21) Advertising vs. Membership & Patronage vs. Patreon
(44:06) Jack’s First and Only Job, and Silicon Valley’s Undervaluing of Creativity, Brand, and Storytelling (and Patreon)
(55:17) Building for Creators First, Incentive Alignment, Trust, 100 Years of Patreon, and Why Jack is the Right CEO for Now
(1:04:49) Leadership: Types of Ambition, Obsession, Self Reflection, Bias to Action, Learning from Others
(1:12:59) Talent vs. Enthusiasm, Being Proud of What You Make, Making Fans and Being True, Managing Parasociality, and Community
(1:28:30) Filmmaking, Labels and Collectives vs Individuals, Breaking Patterns, Creative Intimacy, Music, Patreon’s Origin, Persistence, Lucid Dreaming, and Taking Risks
(1:49:26) Thanks Again to Notion
Links
All links & transcript: https://dialectic.fm/jack-conte
