Caswell created a powerful exercise where she strips names from 12 top-tier VC websites and challenges people to identify firms by their messaging alone. Almost no one can. This "madlibs" approach to positioning reveals that when everyone uses the same formula ("we back [adjective] founders to build [adjective] companies"), differentiation comes from the "how," not the "what" or "who."

Rather than claiming to "add value to portfolio companies," Operator Collective tracks every introduction, connection, and piece of support they provide. They literally "show up with receipts" at year-end, creating tangible proof points that differentiate them from competitors making identical claims. This accountability-based approach builds trust and provides concrete content for marketing efforts.

Caswell uses Operator Collective's "collective venture model" as a decision-making framework for all marketing activities. Every event, piece of content, or initiative must showcase how operators, portfolio companies, and institutional investors benefit from aligned incentives. This creates consistency across touchpoints while ensuring marketing activities reinforce core value propositions.

In venture marketing, the VC shouldn't be the protagonist telling the future story—portfolio founders should be. Caswell's role involves shepherding founder narratives while ensuring they connect to the firm's broader thesis. This requires understanding how individual company stories create through-lines that reinforce the venture firm's investment philosophy and market positioning.

Coming from Pramana Collective, Caswell applies strategic communications frameworks that look at messaging "from all different angles." This holistic approach prevents tunnel vision and allows her to context-switch between crisis communications for portfolio companies, fundraising materials, thought leadership content, and event marketing while maintaining narrative consistency.

As a team of one managing content, social, PR, events, newsletters, and portfolio support, Caswell has developed systems for rapid context switching and strategic prioritization. Her approach of being involved "soup to nuts"—from setting event strategy to placing name tags—provides deep operational knowledge that informs strategic decisions and ensures nothing falls through the cracks.