Guest: Priya Saiprasad — Co-Founder & General Partner, Touring Capital Host: Peeyush Upadhyay — Managing Partner, Pekamiar In this episode of The Scale Up Flight, Peeyush Upadhyay sits down with Priya Saiprasad, Co-Founder and General Partner at Touring Capital, a $330M early-growth fund backing SaaS and AI companies. Priya shares how her global upbringing—having lived in 12 countries by age 12—shaped her resilience, adaptability, and founder-first investing philosophy. Drawing from her experience at Square, Microsoft M12, Mayfield, and SoftBank Vision Fund, she unpacks what truly drives scale in today’s AI-powered economy. The conversation goes deep into what venture investors underestimate, why technology moats are eroding, and how capital efficiency, talent, and go-to-market defensibility are becoming the real differentiators. Priya also offers candid advice for founders on choosing the right investors, navigating board dynamics, making tough people decisions, and building companies that compound over time—not just ride hype cycles. This episode is a must-listen for SaaS and AI founders, operators, and investors navigating the Series B/C transition in an increasingly volatile market. Chapters with TimeStamps 00:00 – 02:15 Introduction: Highlights & Welcoming Priya Saiprasad 02:16 – 06:10 Why diversity in VC is essential to finding true alpha 06:11 – 09:55 The M12 female founders initiative & uncovering overlooked founder talent 09:56 – 13:55 How a global childhood shaped resilience, adaptability, and founder empathy 13:56 – 18:30 Why the founder journey is inherently nonlinear—and deeply lonely 18:31 – 22:40 Square, Jack Dorsey, and the power of true meritocracy 22:41 – 26:40 A painful early investing lesson: product strength vs. “why now” markets 26:41 – 31:40 Contrarian investing, herd mentality, and resisting FOMO in hot markets 31:41 – 35:20 Why “tech as a moat” is eroding in the AI era 35:21 – 39:50 Capital efficiency vs. growth at all costs (and the Zoom example) 39:51 – 43:30 Where AI investing is overcrowded—and where real opportunity lies 43:31 – 47:10 What Priya looks for in a 30-minute founder pitch 47:11 – 49:55 How founders should diligence investors (beyond the size of the check) 49:56 – 52:40 Why most scale-up failures ultimately come down to talent decisions 52:41 – 55:50 The VC as confidant: trust, vulnerability, and founder peer networks 55:51 – 59:30 How Priya competes, takes risks, and shows conviction 59:31 – 01:02:00 Advice for leaders in the AI era: GTM, pricing, and staying relevant Key Takeaways Alpha isn’t obvious upfront — finding it requires looking beyond familiar networks and consensus thinking. Diversity in decision-makers leads to better outcomes for both venture portfolios and founders. The founder journey is a zigzag, requiring resilience, adaptability, and constant reinvention. Technology as a moat is diminishing in the AI era; defensibility now comes from GTM, data, distribution, and product virality. Capital efficiency matters more than headline valuation — valuation isn’t money in pocket until exit. Restraint is harder than deploying capital, especially in hot markets driven by FOMO. Great founders are intellectually curious, humble, and maniacally focused, not know-it-alls. Founders must diligence VCs on how they behave during downturns—not just when things go well. Everything ultimately boils down to talent — hiring, upgrading, and making tough people decisions at the right time. In AI, speed and relevance matter — pricing, packaging, and continuous innovation are critical to long-term retention. Hosted on Acast. See acast.com/privacy for more information.
