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Matthias Schilling

Matthias Schilling is a venture capital investor with deep expertise in identifying and supporting visionary founders and unconventional investment strategies. Through multiple podcast appearances, he has shared nuanced insights on venture investing, emphasizing the importance of personal capital discipline, comprehensive deal experience, and challenging traditional VC orthodoxies. Schilling's investment perspective is shaped by hands-on experience navigating market cycles and a keen interest in founders who build exceptional companies outside of traditional tech ecosystems. He frequently discusses the critical factors for startup success, including founder DNA, risk management, and the value of obsessive curiosity in identifying breakthrough entrepreneurial talent.

3episodes
1podcast

Featured On 1 Podcast

The Full Ratchet

The Full Ratchet

3 episodes

All Appearances

3 episodes
The Full Ratchet

Investor Stories 413: Visionary Founders (Schilling, Abel, Patel)

The Full Ratchet
6 minInvestor from Headline

AI Summary

→ WHAT IT COVERS Three venture capitalists share stories of visionary founders who defied conventional wisdom, from building global companies in unexpected locations to demonstrating extraordinary product obsession and perseverance. → KEY INSIGHTS - **Geographic contrarian thinking:** Ngo founder rejected Silicon Valley pressure, built world-class engineering team in Midwest proving talent exists outside traditional tech hubs, challenging VC orthodoxy about location requirements. - **Product vision patience:** Sonos founder maintained extreme product obsession through extended market development cycle, demonstrating that conviction and patience can overcome slow initial adoption in creating new categories. - **Founder mode longevity:** Marc Benioff exemplifies sustained founder engagement after twenty-five years, actively driving AI transformation at Salesforce while maintaining cultural values through Ohana philosophy and one percent giving model. → NOTABLE MOMENT A founder who grew up in a Brazilian favela built Pismo into global banking infrastructure, selling to Visa for one billion dollars cash after seven years of development. 💼 SPONSORS [{"name": "Ramp", "url": "https://ramp.com/partner/tfr"}, {"name": "American Arbitration Association", "url": "https://adr.org/tfr"}] 🏷️ Founder Vision, Geographic Diversity, Product Obsession

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The Full Ratchet

Investor Stories 411: Lessons Learned (Patil, Schilling, Abel)

The Full Ratchet
7 minInvestor at Headline

AI Summary

→ WHAT IT COVERS Three venture investors share career-defining lessons: investing personal capital first, managing asymmetric risk through market cycles, and maintaining financial prudence after near-bankruptcy experiences. → KEY INSIGHTS - **Personal Capital Discipline:** Swell VC founders invested their own limited money in 2008-2010 before raising LP funds, forcing extreme discipline to focus on founder DNA over hype cycles and market trends. - **Asymmetric Risk Management:** Headline's Matthias Schilling emphasizes staying consistent through market cycles—biggest mistakes come from not investing in high-risk opportunities and tightening up when markets collapse instead of accelerating. - **Financial Prudence Post-Crisis:** G2's Godard Abel credits near-bankruptcy experience for making him more careful about over-investing, maintaining closer focus on achieving profitability and positive free cash flow before expanding aggressively. → NOTABLE MOMENT Schilling observes half his VC peers stopped investing for six months after Silicon Valley Bank crisis, while he viewed the empty market as optimal timing for contrarian deployment. 💼 SPONSORS [{"name": "Ramp", "url": "ramp.com/partner/tfr"}, {"name": "American Arbitration Association", "url": "adr.org/tfr"}] 🏷️ Venture Capital Lessons, Risk Management, Founder Selection

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The Full Ratchet

Investor Stories 409: Key Advice (Terbell and Clark, Schilling, Abel)

The Full Ratchet
4 minHeadline

AI Summary

→ WHAT IT COVERS Three veteran investors share essential career advice for aspiring venture capitalists, emphasizing hands-on experience, in-person relationships, obsessive curiosity, and long-term commitment to the industry. → KEY INSIGHTS - **Deal repetitions:** New investors must prioritize completing full deal cycles from start to finish rather than fragmented research tasks, finding mentors or teams that provide opportunities for comprehensive transaction experience. - **In-person engagement:** Face-to-face interactions with partners, entrepreneurs, and colleagues prove more valuable than remote work for developing venture capital skills, despite current trends favoring distributed work arrangements. - **Obsessive curiosity:** Successful venture investors demonstrate animal-like intensity, driven by natural curiosity to meet every founder and hear every idea, treating venture capital as a lifestyle rather than quick financial opportunity. → NOTABLE MOMENT Matthias Schilling reveals his strongest professional relationships emerged from both spectacular successes and complete failures, highlighting how venture capital rewards long-term relationship building through business cycles. 💼 SPONSORS [{"name": "Ramp", "url": "https://ramp.com/partner/tfr"}, {"name": "American Arbitration Association", "url": "https://adr.org/tfr"}] 🏷️ Venture Capital Careers, Investor Development, Startup Relationships

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