The playbook for a sustainable creator career

I sat down to write a piece summarizing Adam Krasner’s answers to my questions about fandom, ownership, and the future of creator businesses. But after writing 75% of the piece and rereading his responses, I realized that editing them down would be a mistake. Everyone who reads this newsletter will want the full detail of his brilliance and insight.

Adam is the founder of Two West, a management agency that represents some of today’s most impactful creators. My agency, Wonderly, has worked with several of Two West’s clients, and we consider Adam and his team to be an important partner in this work. We’re deeply aligned in our views on ownership, the necessity of building and protecting an email list, and the shifting role that social media and AI will play for creators in the years ahead.

Adam and I have had the chance to talk about these topics at length - including a long lunch in LA where we traded notes on what we’re seeing across the industry. What I admire most about Two West is how seriously they take the diversification of their clients’ businesses. Their model is innovative and, in my opinion, one of the most important approaches in the creator economy today.

Instead of me telling you about it, here is Adam in his own words.

Allie: Two West uses the term category leaders — how do you define that, and what makes someone a leader versus simply a popular creator?

Adam: A category leader isn't just someone with a big following; it’s someone who fundamentally shapes how their audience thinks. A few of Two West’s clients provide great examples. Caroline Chambers didn't just build a food newsletter; she redefined what weeknight cooking means for over half a million subscribers. Dan Pelosi transformed the idea of entertaining from something stressful into joyful celebration. The Brownstone Boys aren't just home renovation content creators - they're preserving architectural history while making home restoration accessible. Category leaders create movements, not just content. They have pricing power, brand loyalty that transcends platforms, and most importantly, they solve real problems in ways that become the standard everyone else follows.

Allie: What patterns do you notice across your roster in how they attract and maintain fandom? And how do you measure the “health” of a client’s fandom beyond follower counts?

Adam: Consistency paired with vulnerability. There is a direct correlation between our most successful clients and those that show up reliably for their audience. For example, Caroline shares at least two newsletters with her subscribers each week and they know exactly what they will receive and on what day: Wednesday is the So Into That edition with life updates and product recommendations, every Saturday a new recipe is shared. But she also lets people in on the messy, more personal parts of her life, revealing a more complete picture of her world. We measure fandom health through the depth of engagement, not just follower count or numbers without context. Are people pre-ordering books months in advance? Are they showing up to events? Converting to paid subscriptions? Healthy fandoms engage, purchase, and evangelize - they don't just watch.

Allie: When a creator begins to tip into “fandom territory,” what signals do you see first? What’s the most surprising thing you’ve seen fans do to support or amplify one of your clients?

Adam: The first signal is when the audience starts creating their own language and rituals around the creator's content. Dan's fans call themselves "Grossy Girls" and Caroline's readers grocery shop for their family around her recipes and monthly meal plans. The shift happens when people stop consuming content and start participating in a community. I'm not sure if anything truly surprises me anymore, but one moment comes to mind recently.

Our client Haley Hoffman Smith's Dreamway community vibe-coded a prototype custom mobile app to bring Haley's content experience off of its host platform (Kajabi). This is something we had discussed with Haley as a team, but receiving an unsolicited proof of concept from a community member validated our product roadmap and shifted our priorities. This is quintessential fandom - when your audience becomes your advance team.

Allie: Two West’s ethos is revenue diversification. What are some of the less obvious revenue streams that have proven most impactful for creators? And how does diversification protect a creator’s career long-term compared to the traditional reliance on brand partnerships or ads?

Adam: Licensing deals where creators get equity in a business or ongoing royalties - not just one-time fees. Caroline has developed limited-edition products with Skout Organic and GroundUp. The Brownstone Boys licensed a rug collection to NuStory and developed a lighting line with Blueprint. These aren't just one-time brand deals - they're ongoing revenue streams tied to actual product sales with physical and digital distribution that the talent is not responsible for maintaining.

What some creators miss is that top of funnel free newsletters are incredibly valuable not just for selling their own products but for leveraging affiliate platforms to share product recommendations. Platforms like ShopMy and LTK have gamified affiliate marketing and have become the sole business focus of many influencers, but the real power for creators is integrating it into a broader strategy. Every recipe, weekly dispatch, and gift guide can drive passive revenue.

These diversified revenue streams also create stability. When [insert social media platform here] makes yet another change to its algorithm or a brand cuts budgets, creators with multiple revenue sources can better weather those storms and disruptions. The most successful creators aren't choosing between advertising, subscriptions, licensing, or affiliates - they're building businesses that include all of them.

Allie: Can you share an example where a nontraditional revenue path (book tour, licensing deal, community building) fundamentally shifted a client’s trajectory?

Adam: Dan Pelosi's GrossyWorld membership is the perfect example. We launched it by tying it to his Let's Party cookbook pre-order campaign this summer: buy the $35 book, get a free 3 month membership. This accomplished two key goals: drove book pre-orders and seeded a paid community with recurring revenue. Within weeks, he had over one thousand paying members. But more importantly, it changed how he thought about the idea of building an owned community. And, as an indicator of the campaign's success: Dan's book made the New York Times bestseller list, debuting at #8 this week!

Allie: What role do physical experiences (events, tours, pop-ups) play compared to digital products in today’s fandom economy?

Adam: Physical experiences validate the digital work of creators and provide a meaningful point of connection for the most engaged members of a community. Whether it is 500 people showing up to a client's book signing or 30 people attending a 3-day in-person retreat with their favorite creator, it's data brands can't ignore. Digital products can scale infinitely, but physical experiences create the moments that turn customers into superfans. The smartest play is using physical experiences as tentpole moments that drive digital product sales for months afterward. Every tour stop becomes content that further drives sales and contributes to a "fear of missing out" on the next event. Bonus points for offering exclusive products and merchandise that are only available to event attendees.

Allie: Coming from a legal background, what do you think creators overlook most when it comes to protecting their IP? Are there outdated industry norms (contracts, licensing, ownership structures) that just don’t work for creators with strong fandoms today?

Adam: What I value most about my law education is how it reframed how I problem-solve and approach business decisions - always thinking through best case and worst case scenarios to find the comfortable middle ground. That framework is essential in creator representation. The biggest mistake creators make is granting usage rights in perpetuity and allowing brands to put paid media behind your content without additional compensation. Creators need to understand exactly what they're permitting others to do with their name, image, and likeness. Once those rights are granted, they're nearly impossible to claw back. Every contract decision has opportunity cost - what impact will today's agreement have on potential business opportunities down the line? We can't predict the future, but we can make informed decisions. Knowing the value of your work is more than half the battle. Too many creators undervalue themselves because they don't understand their worth in the market.

The most crucial realization a creator needs to have is: you don't own your relationship with your audience on any social media platform. The algorithm decides who sees your content, when, and how often. This is why email is so critical - no one's inbox is algorithmically organized. You have direct access to your audience without interference.

Allie: How do you prepare clients for the inevitable ebbs and flows of attention in the fandom cycle?

Adam: This goes right back to our discussion about revenue diversification since the direct revenue from fandom (paid memberships, merchandise sales, etc.) should never be the only revenue stream. Beyond that, we normalize the peaks and valleys of the cycle - even Taylor Swift won't tour for years at a time or engage directly with her fans. One result of this intentional pulling back is it puts the creator in the control of the relationship with its audience while creating scarcity, which ultimately drives future demand. The key is using quiet periods for strategic planning, product development, and deepening the community relationship. A 20% drop in views doesn't matter if your core community is more engaged than ever.

Allie: Looking ahead, what do you think fandom-driven businesses will look like in the next 5–10 years?

Adam: The future is direct ownership of your relationship with your audience. Platforms will become discovery engines, but the real business will happen in spaces creators control - their own apps, membership sites, and newsletters. We'll see more creators becoming media companies, partnering with and acquiring other creators, and building portfolios of stand-alone brand businesses. The parasocial relationship will evolve further toward genuine community participation. Think less "follow me" and more "join us." AI will likely handle more of the content distribution and optimization, freeing creators to focus on what only they can do - create original perspectives and foster human connection. The winners will be those who build infrastructure now for the ownership economy that's coming - and, for the strategic creators of today, already here.

You can view the Two West deck and client roster here.