Ep 4: Marketing Ventures w/ Kera DeMars, Head of Marketing at Hustle Fund

The Front Lines

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Kera DeMars.

Head of Marketing · Hustle Fund

Kera DeMars is the Head of Marketing at Hustle Fund and a true master of messaging. Whether it’s marketing an event, developing partnerships, producing newsletters, or managing internal employee programs, she thrives at crafting the right message to make things resonate. With extensive experience across content creation, event production, employee communications, business strategy, and the art of juggling countless priorities at once, Kera brings both creativity and executional excellence to every initiative she leads.

Guest

Kera DeMars

Head of Marketing

Company:

Hustle Fund

Location:

United States

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In this episode of Marketing Ventures, we speak with Kera DeMars, Head of Marketing at Hustle Fund. Hustle Fund is a pre-seed and seed stage venture capital firm that has invested in over 600 portfolio companies globally, including notable companies like Gamma and Rupa Health. Kera brings a unique perspective to venture marketing, having transitioned from The Hustle where she managed dozens of high-stakes events annually to becoming one of the few marketing leaders in the venture capital space. Through tactical newsletters, strategic events, and community-building initiatives, she's developed a playbook for reaching both founders and investors in an increasingly competitive market.

Topics Discussed:

Transitioning from media/events to venture capital marketing
Building and scaling newsletter content at 40,000+ subscribers with 50-80% open rates
Managing dual customer bases (founders and investors) as a competitive advantage
Creating tactical, depth-focused content that cuts through venture capital jargon
Leveraging AI tools for content creation and scaling editorial workflows
Running 40+ annual events across virtual and in-person formats
Testing and sunsetting initiatives: lessons from failed podcast and education programs

Seven takeaways from this conversation.

Actionable for Marketing Venture (Coming Soon) marketers

Depth Over Breadth in Content Strategy
The Founder Playbook newsletter achieves exceptional 50-80% open rates by focusing intensively on single topics rather than covering multiple subjects superficially. Each weekly issue tackles one actionable strategy in depth - from cold email templates to pitch deck breakdowns - providing implementable value rather than surface-level insights.
Turn Internal Expertise Into Scalable Content
DeMars created a systematic content creation process where investors record 5-minute voice notes on topics from their daily conversations with founders. She then transforms these insights into newsletter content, leveraging the team's frontline knowledge while maintaining editorial control and consistency.
Use AI as an Editorial Amplifier, Not Replacement
After extensive testing, DeMars found success with Toolflow AI by having the founder create a custom GPT trained on her four years of writing samples. This approach produces 80%+ usable first drafts because the AI understands her voice and style, rather than generic content that requires complete rewrites.
Treat Dual Audiences as Leverage, Not Complexity
Rather than viewing founders and investors as competing priorities, DeMars leverages the fact that both groups want access to each other. This creates natural partnership opportunities, cross-promotional potential, and event programming that serves both constituencies simultaneously.
Make Complex Industries Accessible Without Dumbing Down
DeMars identified that most venture capital content reads like "Wall Street Journal" pieces when the audience needs something between that and "BuzzFeed." By simplifying language and structure while maintaining tactical depth, she makes sophisticated concepts accessible to busy operators.
Build Community Through Tactical Value, Not Networking
Hustle Fund's virtual events focus on showing actual workflows, templates, and tactical implementations from subject matter experts rather than high-level discussions. This approach drives both attendance (40-50% show rates for free events) and brand affinity by providing immediate implementable value.
Test Aggressively and Sunset Quickly
DeMars has killed multiple initiatives including podcasts, crypto education programs, and founder bootcamps when they didn't meet ROI thresholds or resource constraints. This disciplined approach to experimentation allows for rapid testing without organizational drag from underperforming programs.

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