Venture Unlocked: The playbook for venture capital managers

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.Welcome to another episode of Venture Unlocked. In this episode, I had the pleasure of welcoming Villi Iltchev, founder and managing partner of Category Ventures. Villi has had a long history in tech, both in operating roles at companies like Box and Lifelock, as well as investing roles at August Capital and Two Sigma, where he departed in 2024 to launch Category Ventures.We covered a lot of ground in our conversation, including his inspiration for starting a new firm and the experiences that informed his true north. We also spoke about the fragmentation of the market and what it means to win in early-stage investing in a heavily crowded market of dedicated seed funds & larger funds who are active in see and Series A. I really enjoyed the authenticity of the conversation and hope you do as well.About Villi IltchevVilli Iltchev is the Founder and Managing Partner of Category Ventures, an early-stage venture firm focused on backing category-defining enterprise software companies. With over two decades of experience as both an operator and investor, Villi has held leadership roles at Box, LifeLock, and Salesforce, where he led investments and acquisitions in companies like HubSpot, MuleSoft, Gusto, and Zapier. As a General Partner at August Capital and later at Two Sigma Ventures, he backed standout startups like GitLab—turning a $20M investment into over $900M in returns. Originally from Bulgaria, Villi brings a global perspective and a founder-first mindset to every partnership.Category Ventures is an early-stage venture firm founded in 2024 by veteran investor Villi Iltchev, focused on backing category-defining enterprise software startups. With a $160M debut fund, the firm invests in pre-seed and seed-stage companies across infrastructure, dev tools, AI, and applications. Drawing on Iltchev’s track record—including early investments in GitLab, Zapier, and Gusto—Category Ventures brings deep technical and go-to-market expertise to help founders build enduring businesses. Their approach centers on hands-on support and founder-first partnership to shape the future of enterprise software.In this episode, we discuss:* Villi’s Background and Journey (1:50)* Lessons from Venture Capital Firms (5:35)* Market Fragmentation in Venture Capital (8:47)* Flexible Investment Strategy (12:24)* Challenges with Traditional VC Models (13:26)* Product Market Fit and Founder Support (17:35)* Counterpoints on Large VC Firms (21:40)* Winning in Venture Capital (24:07)* Kindness and Community (26:24)* Components of Success (30:00)* Decision-Making Process (33:21)* Intellectual Honesty in Investments (36:16)* The Role of Fresh Perspectives (40:08)* Acting on Great Ideas and Final Thoughts (42:27)I’d love to know what you took away from this conversation with Villi. Follow me @SamirKaji and give me your insights and questions with the hashtag #ventureunlocked. If you’d like to be considered as a guest or have someone you’d like to hear from (GP or LP), drop me a direct message on X. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

Victor Lazarte, a General Partner at Benchmark and co-founder of the billion-dollar Wildlife Studios, shares insights from his leap from gaming to venture capital. He discusses Benchmark’s unique philosophy of fostering deep partnerships and making fewer, high-impact investments. Victor reflects on his entrepreneurial journey, the evolution of mobile gaming, and the critical role of VC in tech innovation. He also explores the rapid evolution of AI, emphasizing the need for sustainable growth amidst new technologies.

Tomasz Tunguz, Founder and General Partner of Theory Ventures, dives into the transformative power of AI and its implications for both venture capital and everyday life. He highlights the significant cost reductions in AI training, debates the benefits of open versus closed-source models, and discusses the rise of AI applications. Tomasz also shares insights on navigating investment challenges in this rapidly evolving landscape and addresses AI's potential to reshape employment while balancing the need for sensible regulation.

Zal Bilimoria, Founding Partner of Refactor Capital, shares his journey from tech titan to venture capitalist. He discusses the unique challenges of being a solo GP and emphasizes the importance of strong founder relationships. Zal explains his philosophy behind maintaining a $50 million fund, aligning strategy with investment integrity. He delves into the nuances of managing investments amid evolving market dynamics, such as the impact of AI on decision-making. His passion for technology and sustainability shines as he navigates the future of venture investing.

Brian Ascher, a Partner at Venrock with nearly 30 years in venture capital, shares insights from his impressive journey. He discusses how Venrock has adapted since its inception in 1969, focusing on modern challenges and strategies in tech and healthcare investing. Brian explains the significance of team collaboration in decision-making and the challenges of higher fund sizes. He also delves into navigating inflated valuations and the transformative potential of AI, making this conversation both timely and inspiring for aspiring investors.

Gaurav Mathur, Partner at Pinegrove Capital Partners and former Goldman Sachs veteran, discusses the evolving landscape of venture capital. He addresses the increasing importance of liquidity solutions as companies remain private longer. Gaurav shares insights on continuation funds, strip sales, and the role of technology in enhancing transaction transparency. He highlights how these innovations align the interests of general and limited partners while adapting to the shifting dynamics of the venture market.

In this engaging discussion, Kristina Shen, Ethan Kurzweil, and Mark Goldberg, co-founders of Chemistry Ventures, share insights on launching a new venture firm with a focus on strong team dynamics. They emphasize the importance of building meaningful relationships with founders and navigating the complexities of venture capital. The trio dives into their rigorous co-founder dating process, ensuring cultural alignment, and addressing uncomfortable truths early on. They also discuss the unique advantages of new ventures in supporting early-stage startups and fostering collaborative partnerships.

Sam Heshmati and Vincent Timoney from Citizens Private Bank dive into the shifting landscape of venture banking post-2023 crisis. They share insights on how rising interest rates and increased competition are reshaping strategies for startups and venture funds. The duo highlights the importance of building relationships for emerging managers seeking financial support and discusses the need for banks to offer value-added services. Their expertise sheds light on the evolving requirements of the venture ecosystem as it navigates new financial norms.

Join co-founders Ben Braverman, Thomson Nguyen, and Max Altman of Saga Ventures, a new seed-stage investment firm, as they share insights from their recent fund launch. They discuss key strategies for fundraising and the importance of building strong partnerships in venture capital. The trio highlights the necessity of resilience in the face of competition, effective communication with investors, and the significance of complementary skills within their team. Additionally, they elaborate on how to cultivate successful relationships with founders and navigate a dynamic market.

Glenn Solomon, managing partner at Notable Capital, shares nearly three decades of venture experience, discussing his journey from tennis at Stanford to tech investing. He emphasizes the need for venture firms to adapt to a global landscape and rebrand for founder success. Glenn highlights innovative hiring practices, focusing on character over past performance, and the power of nurturing relationships in building a thriving venture ecosystem. His insights shed light on creating lasting firms by fostering agility and strong partnerships.