🔴 A Webby executive's take on building a creator career

Happy Tuesday, all 🎧. Our guest this week is Jesse Feister, the recently appointed Executive Director of Webby Media Group, the organization behind the prestigious Webby Awards. Before joining the Webbys, Jesse spent four years at Twitch, most recently as the Global Head of Creator Marketing.

Our launching this interview today is intentional — the winners of the 29th annual Webby Awards are being announced today, marking the first year that creators have their own dedicated category.

In this episode:

• 🎸 How Jesse's decade as a musician gave him a business education

• 🏆 Why the Webbys created a dedicated category for creators this year

• 💼 Three skills that help creators transition to business careers

— Natalia Pérez-González, Assistant Editor

P.S. We always welcome your feedback on these stories. There’s a poll at the bottom of the letter if you want to share your thoughts!

• 00:00 Introducing Jesse and the Webby Awards

• 00:47 Jesse's mandate as Executive Director

• 03:37 How the Webbys define “creator”

• 11:35 Understanding the grind of the entrepreneurial creator

• 16:00 Being a musician in the MySpace era

• 21:19 The 3 most valuable skills as a creator entrepreneur

• 30:20 Sustainable business models for small creators

• 34:04 The evolution of brand building online

• 38:46 AI and creativity: Creativity always wins

• 42:08 The biggest opportunities in the creator economy

• 44:56 The instant feedback loop — use it wisely

• 48:15 Plans for the Webby Awards’ 30th year

🎧 If you prefer a podcast platform other than YouTube, we’re on Apple Podcasts, Spotify, or wherever you tune in to your podcasts.

From DIY musician to Webby executive

Growing up in Cincinnati, Ohio, Jesse Feister was encouraged to “get a real job" rather than pursue his creative ambitions. However, the outlaw spirit of the early aughts internet opened up an entirely new path for him.

At 16, he downloaded Napster and used platforms like MySpace to connect directly with fans. MySpace was at its peak at the time — they even had their own record label, MySpace Records, which Jesse describes as "one of the early creator programs." To him, building a DIY fanbase from the ground up was an invigorating part of the experience.

He spent nearly a decade as a full-time musician after college, working odd jobs to make ends meet while playing as a drummer in rockabilly, pop punk, and radio pop bands. Eventually, his band landed a deal with Island Records, validating his music career to family members who didn't understand his choices. This marked the beginning of the end; his band was shelved within a year.

This experience, however, taught Jesse valuable lessons about the power of direct audience relationships versus traditional gatekeepers — lessons he'd later apply to his role at Twitch and now the Webby Awards.

Jesse joined Webby Media Group as Executive Director earlier this year, shortly after applications closed for the Webby Awards’ 29th annual edition — the first to include a dedicated set of awards for creators. To no surprise, the creator categories saw a record turnout for People’s Voice voting. There’s The Webby Award, selected by a formal judging body, and The Webby People’s Voice Award, selected by the internet — winners of both were announced today.

As I listened to this conversation, I found it worthy of noting some of Jesse’s thoughts around the evolution of the creator economy as it pertains to the Webbys:

• While the Webbys have recognized creators within other categories for years, Jesse notes that today’s creator content has evolved beyond regular social media posts. The creator's unique self-expression and entrepreneurial approach aren't just additions to the content — they're fundamental to what audiences are actually consuming and connecting with.

• The Webby Awards, like many other prestigious platforms, including the Grammys and Emmys, have a submission fee of around $500. A dedicated creator category acknowledges that creators are mature businesses that can justify such fees — an evolution from 10 years ago when an Instagram influencer might not have considered this worthwhile.

Connect with Jesse on LinkedIn.
Learn more about this year’s Webby Award nominees.

The artist-to-business pipeline

Last year, Jesse co-authored an article for the Harvard Business Review, examining how artist skills translate to business success. They sourced 150 individuals with similar backgrounds who began their working lives as creatives before entering the traditional business market. Through this research, Jesse and his co-authors identified three key transferable skills:

A bias for innovative action

Artists develop what Jesse calls "a pursuit of personal vision" — the ability to identify what you want to create and take entrepreneurial steps to make it happen. This drive to bring creative work to market independently is directly transferable to business innovation.

• Example: Alex Burkhart leveraged his decade as a touring drummer and successful recording artist to become both a startup founder and Fortune 100 product leader. The self-driven initiative he developed as a musician translated directly into his business career, enabling him to innovate, challenge conventional thinking, and identify opportunities for system improvement.

Growth mindset through practice

Creators must constantly learn new skills to survive. A musician might need to learn video editing to promote their work, or a visual artist might need to understand marketing to reach new audiences.

This practical approach to skill acquisition embodies what corporate environments call a "growth mindset." Artists don't just learn in theory — they learn by necessity and through direct application.

• Example: Jessica Nguyen translated her disciplined ballet background into a successful business career, rising from administrator to senior operations executive at a medical investment firm. Though initially feeling behind when entering business, her perfectionist mindset and openness to refinement helped her learn faster than peers. This pattern was common among creative professionals, whose practice-oriented approach to skill development accelerated their advancement into leadership roles.

Intrinsic motivation

Perhaps most importantly, artists develop deep intrinsic motivation by connecting their identity to their work. They create because they feel compelled to, not just for external rewards.

"As a creator, you really identify with what you're doing in a way that's like you're intrinsically motivated," Jesse observes. In business settings, this translates to employees who bring passion and a sense of purpose to their work.

If you're an artist, creative, or creator considering a transition to a more traditional business role, Jesse recommends focusing on these transferable skills in your interviews and applications. The challenge isn't that creators lack business skills — it's that they often lack the language to explain these skills in terms businesses understand.

• Creator language: "I built an audience from scratch by creating consistent content."

• Business translation: "I identified market opportunities and executed strategic plans to build engagement."

With more people gaining experience in the creator economy, these insights about transferable skills become increasingly valuable. As Jesse explains, "The creator economy is new, but the creative sort of experience is not. But now you're going to have 10, a hundred times more people who had this experience that we had.”

• American soccer marketing should steal a page or three from this creator collective (Creator Spotlight)

• How a Discord community became a $1M business (Creator Spotlight)

• A fictional groupchat TikTok series has had the internet in a chokehold (TODAY)

• YouTube’s superstar creators are literally taking over mainstream television (The Guardian)