Khosla Venture's Samir Kaul on building an iconic, durable firm, and the role of non-consensus decision making

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape. Welcome back to another episode of Venture Unlocked, the podcast that takes you behind the scenes of the business of venture capital. In this episode, I have the pleasure of welcoming back Oren Zeev of Zeev Ventures to help unpack the current world of venture. As many know, Oren has remained a one-man firm since inception, and manages nearly $3B in assets. We dove into the growing disconnect between private and public valuations, how FOMO and massive fund sizes structurally push large platforms into chasing a handful of companies, and why Oren intentionally avoids playing that game in favor of high‑conviction, early‑stage investing with smaller, more focused funds. Oren shares his views on the first wave of AI (infrastructure, models, and chips) versus the underappreciated application layer, the real moats in “vertical AI” beyond thin wrappers, and how to separate healthy, durable growth from momentum and creative accounting. We also discuss his decision to lean in on companies like Navan through extreme uncertainty, how he thinks about getting to follow on conviction, when it’s not obvious. This was a fun one to record as Oren is uniquely transparent and honest in his views. Hope you enjoy it. Oren Zeev is the Founding Partner of Zeev Ventures, a highly successful early-stage investment firm focused on backing exceptional founders and category-defining technology companies. Over his career, Zeev has been an early investor in companies including Audible, Chegg, Houzz, Tipalti, and Navan, with several growing into major technology businesses. Before founding Zeev Ventures, he was a General Partner at Apax Partners, where he developed extensive experience investing in technology companies. Topics in this conversation include: * Market Bifurcation and Disconnect Between Public and Private Valuations (2:46) * FOMO, Large Funds, and the Cost of Omission for AI Deals (5:07) * Two Investor Camps: Playing With House Money vs. Chasing Missed Winners (8:00) * Parallels and Differences Between the Dot-com Bubble and Today’s AI Boom (17:39) * Moats in Vertical AI, Thin Wrappers, and the “SaaS Apocalypse” Narrative (25:59) * Capital Availability for Solid but Non-Hypergrowth Companies (33:40) * Biggest Investing Misses, Lessons From Proptech and Chips (41:27) Thanks for listening to another episode of Venture Unlocked. I hope you enjoyed this conversation with Oren. If you’d like to get Venture Unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or head over to Apple Podcasts or Spotify and subscribe.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape. Welcome back to another episode of Venture Unlocked, the podcast that takes you behind the scenes of the business of venture capital. In this episode, I sit down with Carter Reum, Co‑Founder of M13, to explore his journey from Goldman Sachs and a shelved Oaktree offer to founding and exiting a beverage company and building a multi‑billion‑dollar venture platform. We discuss how Carter reframes “risk” through probability‑adjusted outcomes and asymmetric upside, his “microscope and telescope” framework for balancing execution with long‑term vision, and the idea of “wins above replacement” as a way to assess founder‑ and investor‑fit. Our conversation dives into what it means to build a truly operator‑led VC firm, the wide gap between value‑add and “negative value” VCs, and how M13 uses discipline, retrospectives, and portfolio construction to separate process from outcomes in an AI‑driven, increasingly frothy market. Carter Reum is M13’s Co-Founder and Managing Partner. After building and selling VEEV Spirits, Carter and his brother Courtney co-founded M13 in 2016, designing it as the firm they wanted as founders. M13 has since backed 18 unicorns at seed or Series A and ranks #3 globally by HEC Paris–Dow Jones. Before M13, Carter was an investment banker at Goldman Sachs and co-authored the bestselling Shortcut Your Startup. He serves on the board of LACMA. Topics in this conversation include: * Rethinking Risk and Probability-Adjusted Outcomes (2:02) * Using a Microscope and Telescope to Build Enduring Companies (8:56) * How M13 Was Designed as a Different, Operator-Led VC Firm (12:58) * Operator to Investor and How VCs Should Work with Founders (17:08) * Early-Stage Investing, Imperfect Information, and Wins Above Replacement (20:06) * Travis Kalanick, Negative Value VCs, and Why Most Investors Miss (26:26) * Building an Institutionalized VC Platform, Culture, and Process (31:56) * Separating Decision Quality from Outcomes and Doing Retrospectives (34:52) * Fund Size, Portfolio Construction, and Competing with Multistage Giants (44:11) * Risk Spectrum, Asymmetry, and the Sammy Sosa vs. Mark McGwire Analogy (47:55) * Excitement and Anxiety in Today’s AI-Driven, Frothy Venture Market (50:16) * Fear vs. Greed, LP Behavior, and Closing Thoughts on Building a Decacorn (52:53) Thanks for listening to another episode of Venture Unlocked. I hope you enjoyed this conversation with Carter. If you’d like to get Venture Unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or head over to Apple Podcasts or Spotify and subscribe. Thanks again for listening.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape. Welcome back to another episode of Venture Unlocked, the podcast that takes you behind the scenes of the business of venture capital. In this episode, I sit down with Aditya Agarwal of South Park Commons (SPC) to trace his journey from being one of the earliest employees at Facebook, becoming CTO at Dropbox, and then the inspiration of creating South Park Commons from his living room. The firm just announced a $575MM IV, it’s largest fund to date. We discuss his decision-making at key career forks including his learnings working with Mark Zuckerberg, the power of surrounding yourself with exceptional people, and the five founder traits SPC relentlessly optimizes for. We also covered what it means to invest at the -1 to zero stage, and his view on the current state of venture capital. Thanks for listening to another episode of Venture Unlocked. I hope you enjoyed this conversation with Aditya. If you’d like to get Venture Unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or head over to Apple Podcasts or Spotify and subscribe. Thanks again for listening. Aditya Agarwal is a General Partner at South Park Commons and a longtime technology leader and entrepreneur. He previously served as CTO and VP of Engineering at Dropbox, where he scaled the engineering organization from 25 to more than 1,000 people. Before Dropbox, Aditya was one of Facebook’s earliest engineers, helping build foundational products including News Feed, Search, and Messenger before becoming the company’s first Director of Product Engineering. Today, he invests in and advises early-stage startups, drawing on decades of experience building some of Silicon Valley’s most influential technology companies. Topics in this conversation include: * Choosing Oracle Over Bridgewater (2:31) * First Impressions of Mark Zuckerberg and Early Facebook (6:02) * Lessons From Oracle on Talent Density and Bureaucracy (9:38) * Five Founder Traits SPC Looks For (13:14) * Growing the SPC Community and Early Angel Checks (22:33) * AI, ChatGPT, and Rethinking Fund Size (35:15) * Investing Ahead of the Curve in AI and Robotics (39:11) * Aiming for 5x Net Per Fund (41:04) * AI Compared to Railroads and Heavy Capex (46:07) * AI’s High Usefulness Floor and Mass Adoption (49:10) * Concerns Around Hyperscaler Capex and Hiccups (52:01) * Closing Reflections and Takeaways (54:38) 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.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape. Welcome back to Venture Unlocked, the podcast that takes you inside the business of venture capital. I’m your host, Samir Kaji. My guest today is Micah Rosenbloom, Managing Partner at Founder Collective, one of the longest standing and respected seed firms in the industry, with early investments in companies like Uber, The Trade Desk, and Coupang. What makes Founder Collective atypical to most successful firms is their decision to keep fund sizes small. In fact, despite their success, they’ve never raised a fund over 100 million dollars, in a market where nearly every one of their peers has scaled up. In this conversation, Micah and I dig into why they’ve stayed small, and the data behind it, including a study his team ran on 25 years of venture exits that found the median outcome of the top 500 exits is about 2.7 billion dollars. We also spent time on his post that described why the industry may have lost the plot by obsessing over fund and firm strategy instead of simply focusing on the core of finding unique opportunities that early, priced appropriately, and led by great operators. Micah is a two time founder himself, a clear thinker, and someone who’s willing to say what a lot of investors only think. I think you’ll get a lot out of this one. Thanks for listening to another episode of Venture Unlocked. I hope you enjoyed this conversation with Micah. If you’d like to get Venture Unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or head over to Apple Podcasts or Spotify and subscribe. Thanks again for listening. Micah Rosenbloom is a General Partner at Founder Collective, a seed-stage venture capital firm built by founders for founders. Before becoming an investor, Micah co-founded multiple technology companies, including Brontes Technologies, which was acquired by 3M, giving him firsthand experience building and scaling startups. Today, he invests in early-stage companies across enterprise software, healthcare, and frontier technologies, and has backed successful startups including Verkada, Lovevery, Talos, Plated, and Trusted. Known for his founder-first philosophy, Micah is a respected voice on capital efficiency, venture strategy, and building enduring companies. Timestamps: Topics in this conversation include: * Seed Capital Scarcity in Boston and Birth of Founder Collective (5:18) * Why Small Funds Create Optionality and Better Multiples (9:02) * Capital Efficiency vs Growth Treadmill and Founder Psychology (13:08) * Data on Billion Dollar Exits and 2.7B Median Outcome (18:20) * Can AI Change the Exit Math or Just Inflate Valuations? (23:59) * Profitability, Durable Growth, and Non AI Winners (30:28) * What Founder Collective Refuses to Chase in This Market (34:47) * Saying No to Great Founders at Misaligned Terms (38:10) * Has Venture Lost the Plot? Multiple VC Business Models (41:45) * Biggest Lesson Learned: Betting on Who, Not Just What (46:24) 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.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape. Welcome back to another episode of Venture Unlocked, the podcast that takes you behind the scenes of the business of venture capital. In this episode, I’m joined by three deep tech investors and friends of the show, Nate Williams, Sunil Nagaraj, and Guy Perelmuter, for a roundtable on the state of deep tech and the changing venture landscape. We dig into what deep tech really means today, why it’s suddenly attracting so much capital, and how economics, government tailwinds, and AI as a “killer app” have pulled these once niche technologies into the mainstream. We also explore the growing concentration of capital in a handful of hyperscale winners, the tension between consensus vs. non-consensus investing, and what all of this means for emerging managers, LPs, and founders operating at the zero-to-one stage. Thanks for listening to another episode of Venture Unlocked. I hope you enjoyed this conversation with Nate, Sunil, and Guy. If you’d like to get Venture Unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or head over to Apple Podcasts or Spotify and subscribe. Thanks again for listening. Nate Williams is the Founder and Managing Partner of DeepTech seed firm UNION (Union Labs, Union Peak VC funds) and formerly served as an Entrepreneur-in-Residence (EIR) at Kleiner Perkins focusing on vertical “Physical AI” opportunities across Climate/Resilience, PropTech, and Mobility. Nate has made over 40 early-stage investments, including Urban Sky, Butlr, Antimatter (acquired by Databricks), Proxy (acquired by Oura), Ruby Robotics (acquired by Intuitive Surgical) and Klue (acquired by Medtronic). Before transitioning to full-time VC, Nate built a track record as a hands-on operator with senior leadership roles across startup, growth, and turnaround stages, culminating in successful exits for 4Home (to Motorola, 2010), Motorola Mobility (to Google, 2012), Motorola Home (to ARRIS, 2013), and August Home (to Assa Abloy, 2017). Earlier in his career, Nate was an Analyst in the Digital Home Group at Intel Corp. Nate holds an MBA from UCLA Anderson School of Management and a Bachelor’s degree in Comms from the University of Connecticut. Sunil Nagaraj is the Founder and Managing Partner of Ubiquity Ventures, a seed-stage venture firm investing in “software beyond the screen,” including robotics, AI, industrial automation, and frontier technologies. Prior to founding Ubiquity, Sunil spent over a decade at Bessemer Venture Partners, where he invested in companies across cloud computing, developer tools, and emerging technologies. He is widely recognized for his early conviction in deep tech and infrastructure-driven innovation before it became mainstream in venture capital. Guy Perelmuter is the Founder and Managing Partner of GRIDS Capital, a venture firm focused on deep tech, AI, and advanced industrial technologies. With a background spanning engineering, technology, and investing, Guy has built his career around backing highly technical founders tackling complex global problems. He is known for his insights into the convergence of AI, infrastructure, and industrial transformation, as well as his emphasis on technical depth and long-term value creation in venture investing. Timestamps: Topics in this conversation include: * Definition of Deep Tech by Technical Prowess and Advanced Engineering (2:51) * Hardcore Technology, Difficulty to Build, and Hardware Misconceptions (3:51) * Drivers Of Deep Tech Tailwinds: Maturing Technologies and Government Push (6:12) * Excess Investor Interest After SpaceX and Other Breakout Successes (9:18) * Historical Analogy to Electrification and AI as New Infrastructure Layer (14:43) * Need For Specialized Deep Tech Expertise and New VC Org Structures (19:36) * Schizophrenic Risk-on Behavior and King-making of Consensus Winners (22:08) * Why Normal M an