Three years ago, 15 people met up to talk about the creator economy in the corner of a New York City bar.
Today, Brett Dashevsky's Creator Economy NYC is a six-figure business with 12k newsletter subscribers, over 8,000 lifetime event RSVPs, and presenting sponsors backing events at $20-30k a pop.
In this episode:
📰 How a bar meetup builds to a six-figure media and events business
🤝 How to design and grow a high-quality weekly newsletter
📧 Securing year-long brand deals and running five-figure events
— Natalia Pérez-González, Assistant Editor
00:00 Introducing Brett Dashevsky
01:16 Biggest challenges growing a newsletter from scratch
07:00 Scaling multiple newsletters to the masses
12:44 A community built out of passion
20:00 Why consistency always wins
26:21 Building something bigger than himself
29:33 The best advice for creators
33:56 Revenue breakdown
36:19 How hosting events makes money
42:41 Securing long-term deals with brands
48:33 Defining the digital economy
50:52 Event cost and attendance
56:36 Building tools for creators
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The connector’s playbook
“Everything I’m doing today came out of Creator Economy NYC.”
Is New York City the center of the creator economy? Brett Dashevsky would have you think so.
Creator Economy NYC is a six-figure business built around a newsletter and event series. For the first iteration, 40 people RSVP’d. In total, 15 people showed up to chat over drinks at bar on New York City’s Lower East Side.
Brett spent most of the night doing exactly what he does at a larger scale and in fancier surroundings now: weaving between conversations, making introductions, making sure the right people found each other — he’s a consummate host.
Then, he went home and manually BCC’d everyone a follow-up email from his laptop. A newsletter was born.
"Community-building is incredibly difficult. You have to want it. You need to build it knowing that this probably won't make money — and ask yourself, ‘would I still be doing it if it wasn't?’"
There was no grand business plan then, no sponsor or ticketing system — just a Twitter group called “Creator Economy Meetup NYC” and a goal of bringing together fellow builders in the creator economy.
Fast forward three years, and Creator Economy NYC events have garnered over 8,000 lifetime RSVPs. The accompanying newsletter has over 12,000 subscribers and a 56% open rate (at the time of our interview, they’d just hit 100 weekly sends).
From dive-bar happy hours to fully sponsored, open-bar events
By the time of the first Creator Economy NYC meetup, Brett had already been working in the creator economy for three years.
He is the second Dashevsky we’ve had in the Spotlight. In April 2024, we interviewed his brother Jared about Healthcare Huddle, a newsletter the two Dashevskys (alongside a friend) launched together in 2019. Jared, in medical school, supplied the expertise. Brett — still in college at the time — handled growth.
The early days of Healthcare Huddle were scrappy.
They used MailChimp as their email service provider, and whenever someone followed their Instagram account, Brett would manually DM them to request their email (this was before automation tools, such as ManyChat, were available). When Instagram restricted link-in-Stories to accounts with 10,000 followers, Brett improvised: he used the question sticker as a signup form, collected email addresses there, and then manually copied each one into the backend.
It wasn’t elegant or automated; it got the job done.
“There weren’t really platforms like beehiiv yet. You had to grow by being scrappy.”
That period of hand-built systems taught Brett how to directly build creator-led media, from the inside out. So when Healthcare Huddle was eventually acqui-hired by Workweek in November 2021, Brett found himself applying those same instincts at scale as a creator manager across the company’s creator roster, helping people like Trung Phan and Nick Sharma launch and grow their newsletters.
It was an education in working with talent — managing deadlines, navigating sponsor commitments, understanding how creators actually operate.
All this time, Brett craved to build something fully his own, so when Workweek laid him off at the end of 2023, he took it as a sign and launched the Creator Economy NYC newsletter on beehiiv within weeks — finally creating a central platform for the community he'd been building online and through his bar meet-ups.
How Creator Economy NYC makes money
Today, about 90% of Creator Economy NYC's revenue comes from events and brand partnerships. Presenting sponsors — like Teachable — pay as much as $20-30k per event, which covers the $15K+ production costs (venue, catering, videographers, merch) and leaves room for CENYC to profit. At this point, if there isn’t an event sponsor, there is no event; the dive-bar days are long in the rearview.
Between meetups, the newsletter keeps the community engaged, and gives Brett ad inventory he plans to monetize more independently in 2026. Each part of his business serves the next party:
Events feed subscribers into the newsletter.
The newsletter builds leverage for sponsorships.
Sponsorships fund better events.
Co-founding Siftsy, a social listening app
Brett doesn’t really identify as a creator — at least not first and foremost. “When I wake up in the morning, I consider myself a founder,” he told us. The newsletter, the events, the content: they all work to stay close to the problems creators and brands actually face, so he can serve both groups to the best of his ability.
At a 2023 Creator Economy NYC fireside chat, Brett interviewed creator Timm Chiusano, who’d been gaining traction. He asked Tim how he handled the negativity that inevitably floods the comments when a creator grows. Tim shrugged: he didn’t read them. His wife did, sharing useful notes and protecting him from any negativity.
An operator with a tech and analytics background sat in the audience, someone whom Brett had met months earlier at his second-ever meetup. After the event, he pulled Brett aside with a pitch: What if we automated what Tim’s wife handles for him?
He’d already mocked up a prototype.
Brett loved the insight, not the branding. He went home and stayed up sketching a new version in Figma with a cleaner design, stronger architecture, and a new name — Siftsy (think sift-C, since it literally sifts through comments).
After settling on the branding and direction, they started building together. Today, the tool analyzes comment sections for clients like Lyft, Taco Bell, and Hilton.
"I'm boots on the ground with creators and marketers, getting this genuine experience of being a connector and hearing true boots-on-the-ground stories. That makes me more than just a SaaS founder. It makes me more than just a tech vendor in the space."
Connect with Brett on LinkedIn.
Learn more about Creator Economy NYC and Siftsy.
Brett’s playbook for building a sustainable creator media business
Six years into building in the creator economy, across multiple newsletter products, Brett's approach still comes down to the same principles: show up consistently, deliver value before asking for anything, and let the relationships compound.
Here's the most actionable advice from our conversation, organized by category.
On newsletters
Don't overthink design before you understand your editorial voice. Brett's newsletter has evolved significantly over 100 issues. If he'd locked in an elaborate design early, it would have constrained what he could write about. Get the reps in first. Iterate on aesthetics later.
Write for yourself first. Brett doesn't obsess over open rates. He claims he’s never clicked through to analyze precisely who opened what. The newsletter is a creative outlet that also serves his business. If you're only writing to grow, you'll burn out before the growth compounds.
Aligned referral partners matter more than number of partners. Brett's biggest growth drivers are through beehiiv’s referral network with partners including Jack Appleby's Future Social and Brandon Smithwrick's Content to Commas — newsletters with genuine audience overlap.
Public accountability works. When Brett launched his newsletter in December 2023, he set a goal to publish one edition each week in 2024. He created a chart with 52 empty orange circles and posted it as a Twitter thread, updating it publicly each time he hit send. The thread became a running log of his consistency — and a source of pressure not to break the streak. Other creators started following along and adopting the same approach.
"I haven't done anything as consistent as my newsletter in my life."
On brand deals
Start small and deliver. Brett's year-long Teachable partnership started with a single $2,000 event sponsorship. He made nothing personally — it all went to production. But it proved he could execute, which opened the door to the next conversation and larger deals.
Show up where your sponsors are. Between sponsored events, Brett made sure to get some face time at South by Southwest, VidCon, and Vid Summit to build relationships with his partners. These relational investments paid off during annual deal discussions.
Bundle to increase value. A newsletter ad alone might not justify a $25K price tag. But event hosting, panel curation, newsletter placement, LinkedIn posts, plus lead access? That package sells.
On events
Pick a cadence you can actually maintain. Brett chose monthly because it was ambitious but sustainable. Weekly would have burned him out. Quarterly wouldn't have built momentum.
Start at zero cost. Brett's first events were bar meetups where he just picked a time and place. No venue fees. No catering. He asked in every follow-up email if anyone could host or contribute. People volunteered offices and small sponsorship checks.
Curate attendees. Creator Economy NYC events require applications, enabling more intentional, strategic event curation and a better experience for attendees, while generating more valuable leads for sponsors.
Your event list is your newsletter list. Every RSVP feeds into the newsletter. The events build the audience; the newsletter maintains the relationship between events. Both streams feed into each other and don’t exist as separate products.
