The Sure Shot Entrepreneur

Geoff Ralston, founder of SAIF (Safe Artificial Intelligence Fund), and former President of Y Combinator, shares his vision for building a safer AI future. Geoff discusses the risks and promise of AI as a force beyond traditional tools, posing AI as a set of entities that will reshape the way we work, live, and relate to each other. He talks about biosafety, interpretability, and misinformation as...

Nadav Eylath, founder and managing partner of at.inc, shares his philosophy of early-stage investing rooted in trust, long-term thinking, and technical rigor. Nadav talks about backing founders at the very inception of their startup journey—sometimes even before they’ve left their jobs. He explains how asking questions like “What kind of company will this be in 30 years?” leads to deeper convictio...

Tomoko Ishikura, Managing Partner at Kicker Ventures, shares her unique perspective on investing in the future of healthcare. She talks about building a venture firm rooted in empathy, humility, and measurable impact. Tomoko explains how Kicker Ventures seeks science-backed innovations that move the heart, not just the market, and why strong communities are vital for startup success. She offers ca...

Mahesh Ram, serial entrepreneur and former Head of AI at Zoom, shares his journey from building pioneering companies in education and AI to helping launch FUNDA, a vibrant founder-to-founder community. He discusses the evolution of AI-first startups, lessons from working closely with Zoom founder Eric Yuan, and what it takes to build enduring tech companies today. Mahesh offers real-world advice o...

Andrew Cleland, Chief Investment Officer at Techstars, shares how the world’s leading accelerator invests in early-stage startups. He breaks down what makes a great founder, how Techstars selects startups from tens of thousands of applicants, and why a strong technical differentiator is crucial. Andrew reveals the most common reasons startups get rejected and how Techstars mentors founders to avoi...

Stephen Crook, Executive Director at Achieve Kids, explains how the organization supports students with special needs through individualized education, behavioral support, and vocational training. For over 60 years, Achieve Kids has provided a structured and supportive environment where students can develop independence. By working closely with school districts, educators, and families, the organi...

Allen Taylor, Managing Partner at Endeavor Catalyst, shares how Endeavor is fueling the rise of world-class startups in emerging markets—places often overlooked by traditional venture capital. Allen reveals how Endeavor identifies and supports high-potential founders before investing, why scaling talent is just as critical as scaling products, and how global ecosystems are evolving to produce unic...

Connor Ryan, Partner at Bridge Venture Fund, shares his insights on investing in overlooked markets and the importance of sustainable unit economics. He explains why he prioritizes revenue quality over aggressive growth, the difference between projected and demonstrated product-market fit, and how Bridge Venture Fund supports startups tackling inefficiencies in industries like legal tech and sport...

David Hornik, founding partner at Lobby Capital, shares insights from his 25-year journey in the industry. David discusses the evolution of venture capital, the growing importance of relationships over transactions, and his structured yet practical approach to investing. He highlights how liquidity challenges impact founders and early investors. David also shares his take on what makes a startup t...

Pablo Srugo, partner at Mistral Venture Partners and host of The Product Market Fit Show, shares his journey from co-founding startups like Gymtrack to becoming a venture capitalist focused on seed-stage investments. He reflects on the lessons learned through his and other founders' entrepreneurial highs and lows, including raising $6 million for a wearable tech company and navigating the challeng...

Felipe Camposano, Managing Partner at Taram Capital, shares his journey as a pioneer in Chile's venture capital ecosystem and his efforts to support startups across Latin America. He discusses his transition from entrepreneur to investor, emphasizing his focus on mission-driven founders and leveraging networks for deal sourcing and evaluation. Felipe highlights Taram Capital’s unique approach to s...

Neil Devani, founder of Necessary Ventures, shares his journey from healthcare and healthcare policy to venture capital, focusing on mission-driven startups tackling societal challenges. He discusses his investment strategy, offering insights into evaluating startups for transformative potential, talent retention, capital efficiency, and impactful storytelling. Neil highlights the importance of cu...

Dave Anderson, founding general partner at Beat Ventures, discusses his approach to investing in tech startups targeting overlooked legacy industries. He highlights the role of AI in revolutionizing these industries, giving examples of predictive AI application in meat processing and generative AI in finance. Dave stresses the importance of building Silicon Valley networks for funding and hiring w...

Yiğit Ihlamur, co-founder and general partner at Vela Partners, shares his unique venture capital approach, which combines data analysis with personal connections to identify exceptional founders. At Vela Partners, an algorithmic scan of companies helps narrow down investment choices, but final decisions hinge on assessing founder resilience and motivation during meetings. Yiğit explains that, typ...

Jessie Guo, an investment partner at Next Legacy Partners, shares her journey from early life in the northern China town of Dingxiang to a chance meeting with co-founder Russ Hall and joining the team at Next Legacy Partners. The firm supports mission-driven, early-stage tech startups and funds. Jessie discusses their approach to backing both emerging and established managers, highlighting the imp...

Lochan Alagh, co-founder of VC Nest, shares her journey from India to Silicon Valley, her work with nonprofits, and her transition into entrepreneurship and venture capital. She explains how VC Nest is addressing gaps in the VC ecosystem by supporting emerging fund managers through collaboration, networking, education, and thought leadership. Lochan emphasizes the need to prioritize founder suppor...

Shreesha Ramdas, a successful serial entrepreneur and angel investor, shares his investment approach, which focuses on the individual stories of entrepreneurs rather than just their business ideas. He discusses the changing face of entrepreneurship in India and highlights the significance of community for founders through the story of how Funda, a thriving community of founders, investors, and ope...

Rajan Maruthavanan, Cofounder and Managing Partner at Upekkha, shares deep insights into the dynamics of building B2B startups from India for global markets, particularly in the US. He discusses the strengths and challenges of Indian founders, such as thriving in vertical, niche markets versus struggling with infrastructure and dev tools for global adoption. Rajan emphasizes the importance of foun...

Raed Masri and Rama Chakaki, general partners at Transform VC, discuss their unique approach to venture capital, focusing on impact-driven investments and supporting diverse, underrepresented founders. Drawing from their diverse backgrounds as entrepreneurs and investors, they discuss how they evaluate startups, form investment convictions, and challenge traditional industry norms. Raed and Rama a...

Aaron Webster, Managing Director at Cameron Ventures, shares his experience in the dynamic world of venture capital, with a focus on InsurTech, FinTech and Enterprise Technology investments at seed and Series A. He explains the evolving trends within these sectors and emphasizes the critical role of data infrastructure in driving innovation. Aaron shares insights into what he looks for in potentia...

Ben Black, co-founder and managing director of Akkadian Ventures, shares insights into the venture capital secondary market. He highlights the distinct approach Akkadian Ventures takes, focusing on businesses with proven customer economics and strong technology moats. Ben elaborates on their strategy of gradually increasing positions and leveraging discounts from secondary investments. He also dis...

Venktesh Shukla, Founder and General Partner at Monta Vista Capital, shares his journey from a reluctant immigrant to a successful entrepreneur and venture capitalist. He outlines his investment strategy at Monta Vista Capital, emphasizing deep due diligence, expert validation, adaptability, continuous learning, and leveraging networks. Additionally, he highlights the significant role of TiE (The...

Gayathri Radhakrishnan, partner at Hitachi Ventures, shares profound insights from her journey and perspectives on venture capital and technology. Gayathri reflects on her early life in India and how her competitive spirit and supportive family shaped her path to challenging norms in male-dominated fields. She delves into her focus on impactful investments in AI, utilizing Hitachi Ventures' corpor...

Dan Kimerling, founder and managing partner at Deciens, talks about key principles that shape his current approaches to startup investments. He explains Deciens' strategy of leading financing deals with a concentrated portfolio, allowing for deep partnerships with entrepreneurs. Dan critiques the average venture capital returns and promotes a bold, non-orthodox strategy to achieve exceptional outc...

Vishal Tripathi, investor at Next Legacy Partners, delves into venture capital dynamics, spotlighting Next Legacy Partners' unique blend of philanthropy and athlete-focused strategies. Vishal shares his journey into venture capital, underscoring the industry’s allure for innovation and human connection. He also discusses key insights including the importance for emerging managers to define their u...