Sandy Cass brings an unusually fundraising-centric perspective to seed investing, having personally raised over $200M in equity and venture debt as an operator and explicitly positioning himself to coach founders through fundraises and round structuring rather than just writing checks. His deep operating background includes scaling Artsy from 0 to over $100M GMV as COO/CFO and helping grow Bonobos through its $330M exit to Walmart, giving him hands-on experience with marketplace dynamics and unit economics that he now applies as an investor at Red Swan Ventures.

• Preference for productivity software that breaks down data silos and allows for cross-platform context. He has expressed frustration with meeting apps that trap data in isolated environments, instead praising tools that allow him to query transcripts alongside his other files and emails to get a complete picture.
• Strong scrutiny of go-to-market strategies that rely too heavily on paid acquisition. He suggested that founders who immediately cite paid ads as their primary growth lever signal a major red flag, preferring instead to see businesses that grow by reinvesting profits and avoiding the customer acquisition tax imposed by major ad platforms.
• Personal passion for running and endurance sports which informs his view on company building. He connects the delayed gratification of long-distance running to brand building, referencing his appreciation for specialized running gear and wearable health monitors that can withstand heavy sweating during workouts.
• Focus on clean deal terms and sustainable financial planning. He has advised founders that taking a valuation cut is often better than a flat round with complicated terms like high liquidation preferences, and he actively looks for financial planning products that outperform the legacy tools he used during his time as a CFO.
• Interest in the intersection of technology, art, and culture. Drawing on his past professional experience, he frequently engages with art exhibitions and praises platforms that help creators, modernize the art buying process, or create liquidity for cultural assets.