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 Foundation

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.

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.

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Bhaskar Ghosh, Partner at 8VC, reflects on his journey from Calcutta to Silicon Valley, spanning influential roles at Oracle, Yahoo, LinkedIn, and NerdWallet before moving into venture capital. Now a leader at 8VC, BG introduces his “geometry framework” (persona, product, budget) for enterprise startups, shares insights on the opportunities in generative AI and data infrastructure, and talks about why managing uncertainty is the core skill in zero-to-one journeys. He also emphasizes intentional networking, the long-term nature of venture relationships, and his deep passion for music through his support for Ragas Live.

In this episode, you’ll learn:
[01:56] BG’s early journey from Calcutta to Silicon Valley and his career in academia, Yahoo, Oracle, LinkedIn, and NerdWallet
[06:10] Why he calls himself a “secondhand entrepreneur” and what excites him most about venture capital
[11:22] 8VC’s focus areas and why incubation is core to the firm’s strategy
[14:05] The “geometry framework” for evaluating enterprise startups: persona, product, budget
[19:30] Where BG sees opportunity in generative AI: orchestration, knowledge graphs, semantic layers, observability
[25:12] Why networking must be intentional and based on service, not transactions
[28:34] BG’s advice to founders on standing out and building authentic investor relationships

The non-profit Bhaskar is passionate about:  SACSA (Society for Arts and Culture of South Asia)

About Bhaskar Ghosh

Bhaskar Ghosh (BG) is a Partner at 8VC, where he leads investments in enterprise software, AI, data infrastructure, fintech, and healthcare, while incubating multiple startups. Previously, he held senior roles at Oracle and Yahoo, was the founding head of data infrastructure at LinkedIn, and served as CTO at NerdWallet, helping scale it to IPO. BG holds a PhD in Computer Science from Yale and is passionate about helping founders navigate zero-to-one journeys. Outside venture, he is deeply engaged in Indian classical music and supports community initiatives like Ragas Live.

About 8VC

8VC is a venture capital firm with approximately $7B in assets under management, investing in transformative technologies across enterprise software, AI, healthcare, logistics, fintech, and defense. With offices in Austin and San Francisco, 8VC partners with early-stage founders and also dedicates significant capital to incubation—building new companies alongside entrepreneurs. Its mission is to back ambitious founders solving global problems with scalable, science-driven solutions. 8VC’s portfolio includes category-defining startups that are shaping industries and tackling global challenges, including DataHub, Yugabyte, LightBeam, Tezi, OpenGov, Nile, AI21 Labs, AMP, Bedrock Robotics, 180° Insurance, Cambium, Candid Health among others.

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Zach Noorani, Partner at Foundation Capital, shares hard-earned insights from more than a decade in venture capital. He talks about why the most important question investors wrestle with is differentiation, why authentic conversations with founders matter more than polished pitches, and how the best founders demonstrate velocity of learning. Zach also reflects on the evolving nature of venture—how the industry has become more professionalized, what excites him about the new wave of innovation, and why empathy and due process matter in society as much as in business.

In this episode, you’ll learn:

[01:40] From Salem to Stanford to Silicon Valley: Zach’s journey into venture capital

[03:38] Why venture is a “blank canvas” and not a zero-sum game

[05:46] Foundation Capital’s early-stage focus and Zach’s typical check size

[06:58] “There’s no time too early”: When founders should reach out—and what Zach looks for

[09:43] What really happens in the first meeting (and why it’s about participation, not just Q&A)

[12:54] Should founders ditch the pitch deck? Zach’s advice might surprise you

[16:40] The Push Cash story: How one founder showed true differentiation from day one

[19:34] Why Zach says no—even after initial interest—and what makes a $10B story possible

[22:42] How venture has professionalized—and why AI brings back the excitement

About Zach Noorani

Zach Noorani is a Partner at Foundation Capital, where he invests in early-stage fintech and enterprise startups. With over 14 years of experience in venture capital, Zach has a background that spans corporate VC at Capital One and a passion for supporting founders who demonstrate velocity of learning and unique insight. Based in Los Angeles, Zach focuses on inception-to-Series A companies and has led investments in several innovative fintech ventures.

About Foundation Capital

Foundation Capital is a Silicon Valley-based venture capital firm with over 30 years of experience backing early-stage companies. The firm partners with founders from inception through Series A, providing hands-on support to help build transformative businesses. Foundation Capital’s portfolio includes category-defining companies across fintech, enterprise, and emerging technologies.

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Jacques Benkoski, General Partner at US Venture Partners, shares lessons from decades of experience as an operator, CEO, and VC. He challenges common startup myths and offers a framework for market entry that emphasizes strategy over luck. Jacques explains why focus—not speed—is the key to building category leadership, and why the venture ecosystem has become noisier, faster, and harder to navigate. He also opens up about the psychological toll of startup leadership and why founders need thought partners, not just capital.

In this episode, you’ll learn:

[01:00] From Belgium to Israel to Silicon Valley: Jacques’ global path into tech and AI

[05:20] “This time it’s different” is rarely true—how founders should think about hype cycles

[11:00] Why more capital doesn’t mean an easier path for founders

[13:30] The venture industry is now a volume business—but founders need depth, not scale

[15:00] What founders get wrong about market entry—and why randomness is the enemy

[17:30] Focused beats first: how Medigate won in cybersecurity by narrowing in on medical devices

[30:00] The importance of reflection, walking without your phone, and finding a mentor

[37:00] Jacques' nonprofit passion: creating dialogue between communities in conflict

The nonprofit organization Jacques is passionate about: Technion

About Jacques Benkoski

Jacques Benkoski is a General Partner at US Venture Partners (USVP), where he invests in enterprise software, AI, and cybersecurity startups. He has over 20 years of experience as a VC, following a successful career as a startup CEO and tech executive. Jacques is also the author of Market Entry Strategy, a hands-on guide for founders navigating early customer acquisition. A passionate advocate for founder wellbeing and long-term thinking, Jacques mentors entrepreneurs around the world.

About U.S. Venture Partners

U.S. Venture Partners (USVP) is a leading Silicon Valley venture capital firm with a strong focus on early-stage companies in enterprise software, cybersecurity, and healthcare. With more than $4 billion raised since its founding in 1981, USVP has backed over 500 companies including Box, Guidewire, Trusteer, and Medigate. The firm brings decades of operational expertise and deep sector insight to help founders scale with clarity and discipline.

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Amit Garg, co-founder and managing partner at Tau Ventures, shares how he backs startups at the intersection of healthcare, enterprise, and automation.. Drawing from his experiences as an operator, VC, and nonprofit founder, Amit offers a pragmatic and deeply thoughtful perspective on what makes a venture-backable company, and why doing the right thing can (and should) drive valuation.

In this episode, you’ll learn:

[04:40] Why Amit believes _“VC is one of the most intellectually fulfilling jobs in the world”_—and how it blends empathy and long-term conviction

[11:40] Betting on uncomfortable timing: Tau backed Iterative Health before AI in gastrointestinal innovation was trendy

[17:40] "I value humility more than confidence." Amit’s surprising lens on what makes a founder trustworthy (and fundable)

[21:30] Understanding how to extend your runway to 24 months is the key to success in early-stage startups.

[25:20] What founders must understand about true VC alignment

[29:49] Value vs. valuation: The myth founders must unlearn to avoid being misled by hype-driven fundraising

The nonprofit organization Amit is passionate about: Hospital for Hope

About Amit Garg

Amit Garg is the Co-founder and Managing Partner at Tau Ventures, a Silicon Valley-based early-stage venture capital firm. With a background in engineering, product, and investing, Amit has built a career around intersecting deep tech with human impact. Prior to founding Tau Ventures, he worked at Google, Norwest Venture Partners, and Samsung NEXT. He’s also the co-founder of Hospital for Hope, a nonprofit hospital in rural India. Amit brings a global, grounded, and mission-driven lens to evaluating startups, with particular focus on AI, digital health, and enterprise infrastructure.

About Tau Ventures

Tau Ventures is a seed-focused venture capital firm investing in startups at the intersection of AI, healthcare, automation, and enterprise infrastructure. Founded by operators-turned-investors, the firm applies deep technical understanding and pragmatic business insight to back early-stage teams tackling real-world challenges. Tau operates with a lean fund model, high conviction, and a focus on value creation over hype. Its portfolio includes startups applying cutting-edge technology to improve healthcare diagnostics, workflow automation, and infrastructure scalability. Tau’s portfolio companies include 1Password, Absci, Alpaca Health, Autonomize AI, Iterative Health, Vecna Robotics among others.

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Dave McClure, founder of Practical Venture Capital and co-founder of 500 Startups, dives deep into the growing role of secondaries in venture capital. Dave explains how today’s longer startup cycles and liquidity droughts have created opportunities (and confusion) around secondary markets. He breaks down what secondaries actually are, how Practical VC operates, and key trends shaking up the system. With his trademark candor, Dave also shares hard truths for both founders and VCs navigating this next chapter of private markets.

In this episode, you’ll learn:

[03:55] Dave’s journey to becoming an investor
[06:30] The early evolution of accelerators and why “lots of little bets” took off
[09:50] How cloud, open source, and low CAC changed the startup funding game
[12:49] Why startup liquidity timelines have doubled—and what that means for founders and LPs
[14:56] What secondaries really are (hint: not just one thing)
[19:31] Does venture’s illiquidity attract the right kind of investors—or just the most patient?
[22:06] The discipline of public markets vs. the opacity of private ones
[26:37] What Practical VC looks for in a secondary opportunity (and the $50M–$100M revenue rule)
[29:14] How Dave screens funds and companies for possible exits
[33:37] What’s exciting (and worrying) about secondaries, stablecoins, and emerging markets

The nonprofit organization Dave is passionate about: New Story

About Dave McClure

Dave McClure is the founder of Practical Venture Capital, a firm focused on liquidity through venture secondaries. Previously, he co-founded 500 Startups, one of the world’s most active early-stage venture funds. A PayPal alumni and self-described nerd turned investor, Dave has worked across engineering, marketing, and venture roles, investing in hundreds of startups globally. He’s known for his honest insights and bold bets on opportunities before they’re ‘cool’.

About Practical Venture Capital

Practical Venture Capital is a Silicon Valley-based VC secondary firm providing liquidity to GPs, LPs, and founders through targeted secondary investments. Specializing in fund-level and company-level secondaries, Practical VC aims to shorten the venture capital time horizon by backing mature, revenue-generating companies with clear exit paths. The firm focuses on portfolios nearing liquidity and brings a flexible, creative approach to valuation, pricing, and structure.

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Brian Frank, the founder and general partner at FTW Ventures, shares why he left his founder career to invest in startups solving real-world problems starting with the global food system. He explores the climate risks, supply chain fragility, and health challenges driving the need for innovation in food and agriculture. From AI and biotech to automation, Brian highlights where the biggest opportunities lie. He also offers candid advice for founders navigating slow-moving, regulation-heavy industries and calls for a more collaborative, mission-aligned approach to venture capital.

In this episode, you’ll learn:

[03:35] How startup success as a student got Brian hooked on innovation early

[05:54] Why Brian left startup life after seven companies to support founders solving global problems

[09:18] The urgent reasons our food system needs reinvention—from climate to national security

[12:33] FTW Ventures investment philosophy and focus areas

[22:50] Hard truths for founders in food and agriculture

[31:13] The story of a founder who proved his market, didn’t wait for funding, and built trust

[37:05] What needs to change in VC: stop party rounds, leave space for small funds, invest with purpose

The nonprofit organization Brian is passionate about: World Central Kitchen

About Brian Frank

Brian Frank is the founder and general partner at FTW Ventures, a venture capital firm focused on technology solutions in food, agriculture, and health. A serial entrepreneur with a background in computer science and product development, Brian has launched and scaled seven startups. He brings that hands-on experience to founders tackling real-world challenges, backing science-backed and mission-driven companies that aim to improve life on the planet.

About FTW Ventures

FTW Ventures is a Silicon Valley-based venture capital firm investing in the future of food, agriculture, and human health. With a thesis grounded in problem-first investing, FTW backs early-stage startups applying biotechnology, artificial intelligence, automation, and sustainable systems to global challenges. Their portfolio includes companies advancing biomanufacturing, food-as-medicine, CRISPR-based crop innovation, and more—pursuing returns across people, planet, and profit. Companies in FTW’s portfolio include Boston Bioprocess, ALTR, Sylvan Health, FreshFry, Izote Biosciences, Arise, Quorum Bio, Earthodic, Heritable, Brilliant Harvest, VoltAir, Geltor, Spoiler Alert, Plantible Foods, Galley, Phytoform, Nfinite Nanotech, Yali Bio, and Debut Biotechnology.

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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 key focus areas for innovation. Geoff also shares advice for founders navigating this fast-evolving landscape and reflects on how thoughtful investment today can shape the future of humanity.

In this episode, you’ll learn:

[02:05] Why Geoff believes AI is not ‘just’ a tool but a cognitive force reshaping humanity
[06:29] The subtle but profound difference between tools and intelligent agents
[13:56] Who wins and who loses in an AI-driven future, and what roles must investors play?
[20:36] Can we still design a utopian future with AI?
[24:06] The types of founders Geoff wants to back through SAIF
[26:30] Why mission-aligned safety startups still need product-market fit
[28:46] What happens when AI does everything—and what humans will still choose to do

The nonprofit organization Geoff is passionate about: AI Venture Lab

About Geoff Ralston

Geoff Ralston is the founder of SAIF (Safe Artificial Intelligence Fund) and former President of Y Combinator. A longtime startup investor, entrepreneur, and thought leader, Geoff previously founded Imagine K12, an edtech accelerator later merged with YC. With decades of experience launching and scaling category-defining startups, Geoff now focuses on funding companies that ensure AI becomes a force for good, addressing challenges around safety, security, and the future of human work.

About SAIF

SAIF (Safe Artificial Intelligence Fund) is a venture capital firm dedicated to building a safer future with AI. Founded by Geoff Ralston, SAIF invests in startups focused on AI safety, biosafety, interpretability, and information integrity. The firm supports mission-driven founders creating scalable solutions to counteract risks and ensure that AI technologies empower rather than endanger society.

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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 conviction and better partnerships. Nadav also shares his views on why venture capital needs to evolve and how a flexible, founder-first approach can reshape the industry.

In this episode, you’ll learn:

[01:49] From building treehouses to model airplanes: Nadav’s early love for tech and tinkering
[03:26] How informal advising turned into full-time investing
[04:57] The meaning behind the name at.inc and how it reflects the firm’s thesis
[10:01] “What kind of company will this be in 30 years?”—the power of visionary questions
[13:30] Building conviction: fast no’s, thoughtful yes’s
[15:51] How early-stage founders can build a relationship with Nadav
[20:14] Why Nadav says no: timing and fit

[24:07] How venture capital should evolve to serve today’s founders

The nonprofit organization Nadav is passionate about: Tel Aviv University

Nadav Eylath is the founder and managing partner of at.inc, a venture capital firm that invests at the very inception of startups. With a background in data science, marketing, and company-building, Nadav brings an operator’s empathy and a long-term investor’s lens to early-stage ventures. His career spans roles at startups acquired by companies like Intuit, as well as over a decade of deliberate, hands-on venture investing. Nadav’s approach is grounded in trust, curiosity, and a passion for helping founders bring technically ambitious and globally relevant ideas to life.

at.inc—short for “at incorporation or at inception”—is a Silicon Valley-based venture capital firm that backs startups from day zero. The firm invests in deeply technical companies with global potential, often writing the first check when founders are just forming their ideas. Generalist by design, at.inc partners with entrepreneurs across sectors, emphasizing long-term vision, high trust, and a hands-on approach. With a focused investment pace and founder-first philosophy, at.inc supports startups throughout their full journey, from inception to global scale.

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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 candid advice for founders on articulating impact, leaning into community support, and navigating a healthcare landscape that's increasingly collaborative.

[02:00] Why Silicon Valley’s "uncertainty and possibility" drew Tomoko from Japan

[04:06] Venture capital as a humble act of early belief—and why VCs are deeply interdependent

[06:46] Kicker Ventures' mission to create a happier and healthier world through science-backed innovation

[12:31] What founders must do in the first meeting to excite impact-driven investors

[19:19] Why founders should build strong communities early and ask for help

[26:00] Tomoko’s call to eliminate barriers to global innovation and unlock hidden talent worldwide

The non-profit organization Tomoko is passionate about: Kadampa Meditation Center SF

Tomoko Ishikura is the Managing Partner at Kicker Ventures, where she leads investments in science-backed innovations shaping the future of healthcare. Originally trained as a pharmacist and molecular biologist, Tomoko transitioned into business development, consulting, and now venture capital. Drawing from her global experience across Japan and Silicon Valley, Tomoko brings a distinctive focus on empathy, impact, and community-driven success to the startup ecosystem.

Kicker Ventures is a San Francisco-based venture capital firm investing in transformative solutions for the future of healthcare. Kicker backs science-backed innovations that foster happiness, empower individuals, amplify the work of health professionals and researchers, and create meaningful human connections. With a deep commitment to measurable impact, Kicker Ventures partners with visionary founders reimagining health and wellbeing for future generations.

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