Venture Unlocked: The playbook for venture capital managers by Samir Kaji

September 9, 202655 min

Wins Above Replacement: The New Way to Judge Founders

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. This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

August 11, 202654 min

From the early days of Facebook and learning from Zuck to building a $2B+ VC franchise w/South Park Commons

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 . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

July 28, 202648 min

Has venture capital lost the plot?

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 operator s. 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 . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

June 4, 202653 min

Deep Tech Gold Rush: Smart Boom or Future Bust?

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 and A and IPO Outcomes Still Matter For Smaller Funds (26:53) * Fund Proliferation, New Managers, and What Will Prove Transient (28:49) * Access Capital, Hollywood-ization of Venture, and Coming Bust Risks (33:34) * Consensus Growth Obsession, 10x Expectations, and Metric Distortions (38:02) * How Seed Managers Adapt and Curate Downstream Capital for Portfolios (41:01) * Founder-led Investor Selection and Power Shifting To Specialist Seed GPs (44:53) * Myths About VC Impact, Trend Surfing, and Overstated GP Influence (48:18) * Final Thoughts and Takeaways (53:11) 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 . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

December 3, 202537 min

Betting on Founders Who Build the Real World

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 Lior Susan from Eclipse to explore his journey from building companies in the physical world to founding and scaling a unique venture firm. We discuss the importance of high-conviction investing, assembling elite teams from operator backgrounds, and staying adaptable in a rapidly shifting market shaped by technology and AI. Lior shares lessons on discipline, honesty, and the realities of venture investing, offering actionable insights for anyone interested in building resilient companies or understanding what it takes to succeed in today’s venture landscape. Thanks for listening to another episode of Venture Unlocked. We hope you enjoyed our conversation with Lior. If you’d like to get Venture Unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or go to Apple Podcasts or Spotify and subscribe. Thanks again for listening. About Lior Susan Lior Susan is the founder and managing partner of Eclipse, a venture capital firm focused on backing entrepreneurs who are building companies to transform physical industries. He began his career as a co-founder of Intucell, a software-defined networking startup that was acquired by Cisco in 2012. After that, he led the hardware investment platform Lab IX at Flextronics, deploying capital across energy storage, additive manufacturing, robotics, and wireless infrastructure. In 2015, Lior launched Eclipse to invest in startups transforming critical industries like manufacturing, logistics, supply chain, transportation, energy, and on. He draws on experience as an operator, investor, and former Israeli special forces serviceman to support founders tackling complex, real-world problems. Eclipse is a firm headquartered in Palo Alto (with a New York presence) that partners with entrepreneurs building category-defining companies in physical industries. The firm builds and invests in companies at all stages, combining hardware, software, and systems to modernize “bits and atoms.” Since its founding in 2015, Eclipse has built and backed over 100 companies and helped accelerate startups like Bedrock, VulcanForms, True Anomaly, and Cerebras — companies driving innovation in construction, digital manufacturing infrastructure, defense capabilities, and AI infrastructure. During the conversation, we discussed: * Lior’s Career Path and Founding Eclipse (3:38) * Reflecting on the Fund’s Origins and Initial Fundraising (6:46) * Adjusting Firm Size and Strategy as Opportunities Grow (9:49) * High-Conviction, High-Ownership Investment Approach (12:45) * Decision-Making Process and Team Dynamics (14:57) * Patterns Among Founders of Large Companies (17:27) * The Evolution of Eclipse’s Value Proposition (20:23) * Operator-to-Investor Transitions and Internal Training (24:49) * Market Shifts and Macro Changes in Venture Capital (27:07) * Exit Challenges, IPOs, and Long-Term Private Markets (30:27) * Alignment Between LPs and Managers Around Exits (33:44) * Lior’s Investment Lessons and Reflections on Power Law (35:17) * Thoughts on Deglobalization and Future Predictions (36:32) I’d love to know what you took away from this conversation with Lior. 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 . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

November 12, 202538 min

Unpacking "A Crisis Moment In Seed"

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. Today, I sat down with Rob Go , Co-Founder and Partner at NextView , to discuss the shift in seed-stage investing and what seed funds need to consider to remain viable. The conversation was sparked by a series of Posts Rob wrote, the first of which was called a Crisis Moment in Seed. We spent a lot of time talking about what inspired the post and how seed managers should adapt to the shifted market. For anyone investing at seed, this is a must listen as Rob shared so many insightful views. Thanks for listening to another episode of Venture Unlocked. We hope you enjoyed our conversation with Rob. If you’d like to get Venture Unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or go to Apple Podcasts or Spotify and subscribe. Thanks again for listening About Rob Go Rob Go is the co-founder and partner of NextView Ventures, a thematic seed-stage venture capital firm focused on investing in founders solving meaningful problems for everyday people. Before launching NextView, Rob was a venture capitalist at Spark Capital, where he focused on the intersection of media, technology, and entertainment. Earlier in his career, Rob led the “Finding” business unit at eBay, where he helped design and launch over 20 products that transformed the platform’s search and merchandising experience. He also worked in strategy consulting at The Parthenon Group, focusing on consumer and retail industries, and held product management roles at Fidelity Investments and BzzAgent. Rob holds a B.S. in Economics from Duke University and an MBA from Harvard Business School. Beyond venture, he’s a founding member of Highrock Church in Brookline, MA, and a dedicated husband and father who values family and faith as deeply as entrepreneurship. NextView Ventures is an early-stage venture capital firm founded in 2010, with offices in New York, Boston, and San Francisco. They focus on seed-stage investments, typically ranging from around $250K to $4M, in companies building consumer, fintech, digital health, and B2B SaaS solutions that reshape what they call the everyday economy The firm has backed a number of notable companies, including ThredUp, Grove Collaborative, WHOOP, and TripleLift, all of which have achieved significant exits or growth milestones. Their hands-on, founder-first approach and thematic focus have helped them build a strong track record in seed investing. During the conversation, we discussed: * The Venture Landscape’s Evolution Since 2011 (3:27) * The Entry of Accelerators Like YC and Mega Funds (6:21) * The Role of YC’s Offer Structure in the Seed Market (9:14) * Mega Funds and the Influence of the Power Law (12:21) * AI’s Market Impact and Opportunities for Seed Investors (15:18) * Defensibility and Differentiation in AI Applications (18:17) * The Importance of Distinct Strategies for Seed Funds (21:37) * Super Compounder Versus Classic Venture Approaches (24:26) * Adjusting Capital Allocation for Non-Consensus Companies (27:26) * The Role of Optionality in Navigating Downstream Capital (30:35) * NextView’s Tactical Shift Toward Data and AI Tools (33:27) * Lessons on Discipline, Dogmatism, and Missed Opportunities (36:22) I’d love to know what you took away from this conversation with Rob. 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 . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

September 24, 202548 min

Platform Shifts, AI, and the Future of Consumer Investing

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 had the pleasure of speaking with Mercedes Bent about her fascinating journey from a tech-driven upbringing to becoming a leading venture capitalist. We discussed how her unique background informs her investment philosophy and the importance of originality and non-consensus thinking in today’s VC landscape. Our conversation also covered the challenges and opportunities in consumer technology, the transformative impact of AI, and strategies for portfolio construction. One of my key takeaways was the critical role of intuition in identifying exceptional founders, as well as the value of building compounding networks and staying ahead of platform shifts. It was an insightful discussion that offered practical lessons for anyone interested in the future of venture capital. We hope you enjoy the conversation. Thanks for listening to another episode of Venture Unlocked. We hope you enjoyed our conversation with Mercedes. If you’d like to get Venture Unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or go to Apple Podcasts or Spotify and subscribe. Thanks again for listening About Mercedes Bent Mercedes Bent is a Venture Partner at Lightspeed Venture Partners and Co-Founder of venture firm Premise. At Lightspeed, she focused on early-stage investments in consumer, fintech, multicultural markets, and Latin America. She began her career at the Federal Reserve and Goldman Sachs before moving into the education technology sector with General Assembly. At General Assembly, she helped expand one of the company’s key product lines from $2M to $100M in revenue over four years. She joined Lightspeed in 2019 after developing a strong investment perspective in areas such as edtech, VR, and multicultural consumer products. At Lightspeed, she has invested in and worked with companies including Stori, Honeylove, Forage, Magic Eden, Outschool, and Flink. She has also been recognized in industry publications for her contributions to venture capital and efforts to broaden access to entrepreneurship. Lightspeed Venture Partners , founded in 2000, is a global venture capital firm managing over $25 billion in assets with offices across the U.S., Europe, Israel, India, and Southeast Asia. The firm invests from seed to growth stage across enterprise, consumer, fintech, healthcare, and emerging tech. Over the years, Lightspeed has backed more than 500 companies, including Snap, MuleSoft, Affirm, Carta, and Anthropic, and has been part of notable exits like AppDynamics and Nest. With a strong record of helping founders scale and succeed, Lightspeed is recognized as a leading partner for building category-defining companies. During the conversation, we discussed: * Mercedes’s Background, Upbringing, and Early Career (1:45) * How Background Informed Firm Values/Culture (4:19) * The Gap in Consumer Technology Investing & Identifying Founders (8:40) * Non-Consensus Investing in Early Stage VC (10:01) * Startup Mentality and KPIs in Fund Management (15:06) * Sourcing vs. Winning Seed Deals – What Matters? (16:19) * Seed Manager vs. Large Fund Business Models (21:21) * Gifted TVPI vs. Earned TVPI, Portfolio Philosophy (26:22) * Consumer Sector’s VC Downturn & New Tech Cycles (32:21) * The AI Consumer Technology Wave & Opportunity (35:33) * Identifying Product-Market Pull and Early Leading Indicators (37:08) * Shifts in Distribution Channels in AI (40:09) * Future-casting, Platform Shifts, and AI Companions (43:50) * Lessons from Years in VC & Trusting Intuition (44:27) * Final Thoughts and Takeaways (47:46) I’d love to know what you took away from this conversation with Mercedes. Follow me @SamirKaji and give me your insights and questions with the hashtag #venture unlocked. 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 . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

August 20, 202547 min

The GP of 2030: AI, Automation, and the Future of Capital Formation

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 had the pleasure of speaking with Alex Robinson , CEO and Co-Founder of Juniper Square . We talked about the evolution of private markets and the transformative role of technology and AI in fund administration. We also discussed the inefficiencies that inspired Juniper Square’s founding, the challenges of scaling operations for both institutional and individual investors, and the ongoing push for greater transparency between GPs and LPs. Alex shared insights on how AI is set to revolutionize knowledge work in the industry, streamline workflows, and enhance the investor experience. Key takeaways include the critical importance of embracing technology to drive efficiency, the growing impact of AI on fund management, and the need for adaptability as the private markets continue to evolve. Thanks for listening to another episode of Venture Unlocked. We hope you enjoyed our conversation with Alex. If you’d like to get Venture Unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or go to Apple Podcasts or Spotify and subscribe. Thanks again for listening Bio of Guest: Alex Robinson is the CEO and Co-Founder of Juniper Square, a leading investment management software platform transforming private markets. With a background in engineering and business, Alex previously held product and leadership roles at top technology firms, including Microsoft and Boston Consulting Group. His own experience as a limited partner inspired the creation of Juniper Square in 2014, aiming to modernize and simplify the private investment process. Under his leadership, the company has grown to serve over 2,500 GPs and over 600,000 LPs, managing tens of thousands of investment funds. Alex is recognized as a driving force behind digitizing private markets and expanding investor access through innovation and transparency. Juniper Square is a leading investment management platform designed to streamline operations for private equity, real estate, and venture capital firms. The platform helps General Partners (GPs) manage fundraising, investor reporting, and fund administration through intuitive, data-rich software. Since its founding in 2014, Juniper Square has become a trusted partner to over 2,500 GPs and supports more than 600,000 Limited Partners (LPs) across more than 40,000 investment funds. By replacing outdated systems with modern, transparent tools, Juniper Square is transforming how private markets operate and expanding access for investors worldwide. Timestamps: In this episode, we discuss: * Founding Motivation for Juniper Square (2:00) * Early Focus on Real Estate and LP Trends (6:13) * Complexity and Lack of Standardization in Private Markets (11:40) * Impact of Technology on LP Experience (15:34) * Transparency Evolution in Private Markets (19:15) * Differences Across Asset Classes and Regulation (23:15) * Strategic Decisions and Market Surprises (26:09) * Bundling and the Future of Wealth Channel Access (30:43) * AI’s Impact on Private Markets and Fund Operations (33:44) * The GP of 2030: AI and Capital Formation (37:49) * AI and Labor Market Disintermediation (42:07) * Future Vision and Company Outlook (44:07) * Final Thoughts and Takeaways (47:07) I’d love to know what you took away from this conversation with Alex. Follow me @SamirKaji and give me your insights and questions with the hashtag #venture unlocked. 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 . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

July 30, 202545 min

Jack Altman on the transition going from building a Unicorn with Lattice to starting a venture firm

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 Jack Altman, Managing Partner at Alt Capital. We unpack Jack’s journey from Lattice CEO to venture capitalist . We dive deep into the nuances of venture investing, exploring how operators transition into investors, the importance of founder relationships, and the critical elements of successful early-stage investing. Jack shares candid insights about evaluating talent, providing tough feedback, and navigating the current AI technology landscape. His most compelling advice centers on the importance of backing founders you truly believe in, regardless of market fluctuations. As we discuss everything from fund strategies to valuation challenges, the conversation reveals the complex art of venture capital – a world where relationships, intuition, and long-term vision matter more than short-term metrics. Thanks for listening to another episode of Venture Unlocked. We hope you enjoyed our conversation with Jack. If you’d like to get Venture Unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or go to Apple Podcasts or Spotify and subscribe. Thanks again for listening About Jack: Jack Altman is the founder and Managing Partner of Alt Capital, a $150 million early-stage venture fund he launched in February 2024 that has invested in Antares, David AI, Legora, and Owner, among others. Jack is also an investor in companies like Figma, Rippling, Writer, and Vanta. Prior to his career in investing, Jack co‑founded and led Lattice, an HR and people-performance platform that grew to serve thousands of global companies and reached a $3 billion valuation before he transitioned into his role as Executive Chairman. With a background that includes roles in corporate finance and business development, Jack honed his startup expertise at Teespring and Hydrazine Capital before building Lattice from the ground up. Now at Alt Capital, Jack combines his founder-to-investor experience to back innovators in B2B software and hard tech. He's launched initiatives like the Generate accelerator, offering expert mentorship and resources to AI-driven startups—underscoring his commitment to pragmatic, conviction-led investing. Alt Capital is an early-stage venture firm focused on backing exceptional founders across industries, predominantly B2B software and hard tech. With a $150 million debut fund launched in 2024, Alt Capital takes a founder-first, conviction-driven approach to investing—leveraging Founder Jack Altman’s experience scaling Lattice into a $3B company to support startups through their earliest and most pivotal stages. Alt Capital prioritizes long-term partnership, practical guidance, and high-conviction bets over volume-based investing. In a short time, Alt Capital has already positioned itself as a go-to firm for ambitious founders building the next wave of category-defining companies. In this episode, we discuss: * Jack’s Transition: Operator to Investor (1:47) * Early Surprises in Running a Venture Firm (4:05) * Types of Venture Capitalists and Motivations (6:37) * Brutal Honesty vs. Founder Friendliness (9:51) * Earning the Right to Give Advice (13:19) * What Makes a Good Venture Capitalist (18:22) * Evaluating Founders: Motivations and Outlier Traits (21:20) * Measuring Success in Venture: Feedback Loops and KPIs (26:53) * Big vs. Small Venture Firms: Different Models (29:47) * Venture as Different Financial Products (32:35) * AI, Market Size, and Valuation Inflation (34:13) * Underwriting and Fund Size Strategy (37:45) * Biggest Lesson Learned in Venture (43:19) * Final Thoughts and Takeaways (44:55) I’d love to know what you took away from this conversation with Jack. 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 . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

July 16, 202552 min

How to win in seed stage investing today

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 today’s episode, we are joined by Nakul Mandan , who is the founding partner of seed-stage firm Audacious Ventures. Having known Nakul since the early days of his journey in starting the firm in 2020, I was excited to dive deep into his unique path, from his roots in India to venture capital, working at firms such as Battery and Lightspeed before starting his own firm. As venture capital has evolved and grown, the stakes of being a successful early-stage manager have increased dramatically. In our chat, we discussed how managers should think about navigating competitive markets and how a proper system around sourcing, picking, winning, and building a brand through delivering for founders requires a machine-like approach. Audacious has created its own system, which is unlike most firms, providing a nice juxtaposition of more traditional models. This was a fun and candid deep dive into seed stage investing, and we hope you enjoy my conversation with Nakul Thanks for listening to another episode of Venture Unlocked. We hope you enjoyed our conversation with Nakul. If you’d like to get venture unlocked content straight to your inbox, go to ventureunlocked.substack.com and sign up, or go to Apple Podcasts or Spotify and subscribe. Thanks again for listening About Nakul Mandan Nakul Mandan is the founder and managing partner of Audacious Ventures, a pre-seed and seed-stage venture firm he launched in April 2020—right when the world was locking down. A student of greatness, Nakul is inspired by extraordinary journeys, whether in business or beyond. Previously a Partner at Lightspeed and Battery Ventures, he led early investments in category-leading software companies like Gainsight, People.ai, Multiverse, WorkOS, 6Sense, and Marketo. A graduate of IIT Kanpur, Nakul combines deep technical insight with a founder-first mindset—and a passion for helping entrepreneurial "force-of-nature" founders assemble A+ teams. Audacious Ventures is a next-generation seed-stage investment firm that reimagines venture capital as a systematic, founder-focused platform. Founded in 2020 with a $90 million fund, the firm distinguishes itself through a unique four-pillar approach: strategic sourcing, precise deal picking, competitive deal winning, and comprehensive founder support. Unlike traditional venture models, Audacious prioritizes talent recruitment and team building, with half the team dedicated to helping founders construct exceptional organizations. The firm's data-driven yet intensely human approach has quickly positioned it as an emerging leader in the seed investment ecosystem, attracting founders seeking more than just capital, but a true strategic partner in their entrepreneurial journey. In this episode, we discuss: * Nakul’s Early Life and Ambition (2:16) * Entry into Indian Venture Capital (4:00) * Transition to US-Focused VC and Lightspeed (6:41) * Becoming a GP and Founding Audacious Ventures (7:35) * Identifying Gaps in the Seed VC Market (10:34) * Audacious Ventures’ Differentiated Model (12:34) * Functional Organizational Design (16:12) * Traditional vs. Platform Seed Fund Models (19:24) * Ensuring Consistency in the Platform Model (24:41) * Hiring for Intensity and Culture (29:55) * Measuring Success and Feedback Loops (35:33) * False Positives and Markups in VC (41:30) * Ranking the Four Pillars: Sourcing, Picking, Winning, Helping (45:13) * Advice to 2006 Self: Focus on Asymmetric Upside (49:54) * Final Thoughts and Takeaways (51:44) I’d love to know what you took away from this conversation with Nakul. 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 . This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit ventureunlocked.substack.com

Venture Unlocked: The playbook for venture capital managers

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