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Actionable
Takeaways

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.

Conversation
Highlights

 

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

 

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