Don’t Overstretch; Raise The Right Amount of Funding

Tim Guleri, Managing Partner at Sierra Ventures, reflects on 25 years in venture capital and his journey from Chandigarh to Silicon Valley. He shares how hands-on experience as a founder shapes his investing philosophy, why early-stage VCs must guide founders toward long-term fundamentals, and why raising too much capital too soon can hurt a company. Tim explains Sierra’s disciplined approach to partnering with entrepreneurs, the power of unique customer insight, and his hope that America preserves its structural advantage in entrepreneurship. In this episode, you’ll learn: [02:10] From Chandigarh to Silicon Valley: Tim’s path to venture and entrepreneurship [04:09] Lessons from Scopus and Octane: Why lived experience matters more than spreadsheets [06:07] How venture “reinvents itself” and demands a learning mindset [11:43] Sierra Ventures’ early-stage focus and flexible check sizes [14:33] Why raising the maximum check can backfire [16:44] The Eudia story: Hundreds of customer interviews and unique insights win conviction [23:07] How Sierra selects only ~2 deals per partner each year [27:26] Tim’s message to Washington: Don’t overregulate America’s greatest gift—entrepreneurship The nonprofit organization Tim is passionate about: American India FoundationAbout Tim Guleri Tim Guleri is a Managing Partner at Sierra Ventures, where he focuses on AI, enterprise software, and emerging technologies. A successful founder turned investor, Tim led Scopus Technology to an IPO and later founded Octane Software, which was acquired for $3B. Since 2001, he has been a hands-on venture capitalist, backing transformative companies and guiding founders with lessons from both entrepreneurial wins and mistakes.About Sierra Ventures Sierra Ventures is a Silicon Valley-based early-stage venture capital firm with over $2B in assets under management and more than four decades of experience. Specializing in enterprise infrastructure and emerging technologies, Sierra partners with founders at seed and Series A stages, providing flexible capital, operational expertise, and trusted connections to help startups scale into market leaders. Portfolio companies include Eudia, Yalo, Spectro Cloud, Endor Labs, Phenom People, Planera, Quintessent, Cimulate, among others. Subscribe to our podcast and stay tuned for our next episode.