Venture Unlocked: The playbook for venture capital managers

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

In this episode, I sat down with Logan Bartlett, Managing Director of Redpoint Ventures. We explore the evolving landscape of venture capital and startup investing and dive deep into the challenges facing unicorn companies post-2021, the transformative potential of AI, and the critical factors for successful startup investments. Logan shares insights on identifying promising founders, navigating market uncertainties, and the importance of adaptability in both founding teams and venture capital. Key takeaways include the need for founders with rapid learning capabilities, the potential disruption and opportunities in AI, the changing dynamics of startup valuations and exits in a challenging market environment, and so much more.

About Logan Bartlett

Logan Bartlett is a Managing Director at Redpoint Ventures, where he leads early-growth investments in enterprise software, with a focus on infrastructure, SaaS, and AI. Since joining Redpoint in 2020 after six years at Battery Ventures, Bartlett has backed high-growth companies such as Ramp, Cribl, Cyera, Monte Carlo, FloQast, Crossbeam, and Workato. His work has earned him recognition on both the Forbes 30 Under 30 and the Midas Brink lists.

Beyond investing, Bartlett hosts The Logan Bartlett Show, a podcast featuring in-depth conversations with top founders, operators, and investors. The show offers insights into startup growth, market cycles, and venture capital strategies, and has become a respected resource within the tech ecosystem.

Redpoint Ventures, founded in 1999, is a venture capital firm that partners with visionary founders to create and redefine markets. The firm invests in startups across various stages, from seed to growth, and has backed over 578 companies, including industry giants like Snowflake, Looker, Kustomer, Twilio, and Netflix. With 181 IPOs and M&A exits and managing $7.2 billion across multiple funds, Redpoint's expertise in guiding businesses toward success is well-established.

Timestamps:

In this episode, we discuss:

* Logan Bartlett’s Path into Venture Capital (1:46)

* The 2021 Unicorn Logjam and Future Outlook (4:38)

* AI’s Role in Reshaping Legacy Companies (8:32)

* Liquidity Challenges and Growth Stage Investing (11:16)

* Portfolio Construction and Risk Balance (17:16)

* Underwriting Series B Investments (22:41)

* Portfolio Composition and Risk Appetite (26:36)

* Evaluating AI Companies and Revenue Durability (30:01)

* Forecasting and Macro Underwriting (35:32)

* Key Investment Decision Criteria (40:11)

* Traits of Successful Venture Investors (45:28)

* Final Thoughts and Takeaways (49:58)

I’d love to know what you took away from this conversation with Logan. 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 to another episode of Venture Unlocked. In this episode, I had the pleasure of welcoming Villi Iltchev, founder and managing partner of Category Ventures. Villi has had a long history in tech, both in operating roles at companies like Box and Lifelock, as well as investing roles at August Capital and Two Sigma, where he departed in 2024 to launch Category Ventures.

We covered a lot of ground in our conversation, including his inspiration for starting a new firm and the experiences that informed his true north. We also spoke about the fragmentation of the market and what it means to win in early-stage investing in a heavily crowded market of dedicated seed funds & larger funds who are active in see and Series A. I really enjoyed the authenticity of the conversation and hope you do as well.

About Villi Iltchev

Villi Iltchev is the Founder and Managing Partner of Category Ventures, an early-stage venture firm focused on backing category-defining enterprise software companies. With over two decades of experience as both an operator and investor, Villi has held leadership roles at Box, LifeLock, and Salesforce, where he led investments and acquisitions in companies like HubSpot, MuleSoft, Gusto, and Zapier. As a General Partner at August Capital and later at Two Sigma Ventures, he backed standout startups like GitLab—turning a $20M investment into over $900M in returns. Originally from Bulgaria, Villi brings a global perspective and a founder-first mindset to every partnership.

Category Ventures is an early-stage venture firm founded in 2024 by veteran investor Villi Iltchev, focused on backing category-defining enterprise software startups. With a $160M debut fund, the firm invests in pre-seed and seed-stage companies across infrastructure, dev tools, AI, and applications. Drawing on Iltchev’s track record—including early investments in GitLab, Zapier, and Gusto—Category Ventures brings deep technical and go-to-market expertise to help founders build enduring businesses. Their approach centers on hands-on support and founder-first partnership to shape the future of enterprise software.

In this episode, we discuss:

* Villi’s Background and Journey (1:50)

* Lessons from Venture Capital Firms (5:35)

* Market Fragmentation in Venture Capital (8:47)

* Flexible Investment Strategy (12:24)

* Challenges with Traditional VC Models (13:26)

* Product Market Fit and Founder Support (17:35)

* Counterpoints on Large VC Firms (21:40)

* Winning in Venture Capital (24:07)

* Kindness and Community (26:24)

* Components of Success (30:00)

* Decision-Making Process (33:21)

* Intellectual Honesty in Investments (36:16)

* The Role of Fresh Perspectives (40:08)

* Acting on Great Ideas and Final Thoughts (42:27)

I’d love to know what you took away from this conversation with Villi. 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.

Today, I sat down with Victor Lazarte, a Benchmark partner who transitioned from founding a billion-dollar mobile gaming company in Brazil to becoming a venture capitalist in Silicon Valley with Benchmark in 2023. Victor shared Benchmark's unique investment philosophy, which focuses on deep, meaningful partnerships with entrepreneurs, with each partner doing only 1-2 deals per year.

We also spoke about the equal partnership Benchmark has, and what that means in practice day to day from a decision making and culture standpoint. This was a fun one so hope you enjoy!

Throughout our conversation, Victor provided a nuanced perspective on company building, technological innovation, and the evolving role of venture capital in bringing transformative ideas to market.

About Victor Lazarte

Victor Lazarte is a General Partner at Benchmark, a renowned venture capital firm focused on early-stage technology investments. With a background in entrepreneurship and investing, Victor brings deep operational expertise and a founder-first mindset to supporting high-growth startups.

Before joining Benchmark, Victor co-founded Wildlife Studios, one of the world’s largest mobile gaming companies, where he helped scale the business to global success. His experience in building and leading companies gives him a unique perspective on product development, scaling operations, and long-term strategy.

Victor is passionate about partnering with visionary founders to build category-defining companies. He holds a degree in engineering and is committed to fostering innovation across industries.

Benchmark is a leading venture capital firm specializing in early-stage technology investments. Known for its hands-on, founder-first approach, Benchmark partners with entrepreneurs to build transformative companies across industries like software, marketplaces, and infrastructure. The firm operates with a unique equal partnership structure, ensuring deep collaboration and long-term commitment to its portfolio companies. With a track record of backing iconic startups such as Uber, Twitter, eBay, and Snap, Benchmark continues to be a trusted partner for ambitious founders looking to scale breakthrough ideas into world-class businesses.

Timestamps:

In this episode, we discuss:

* Victor's Background and Journey (1:29)

* Wildlife Studios and Its Growth (3:59)

* Bootstrapping Success (6:53)

* Understanding Venture Capital (9:48)

* Benchmark's Unique Model (12:17)

* Decision-Making in Venture Capital (17:05)

* Open-Minded Yet Disagreeable (20:29)

* Benchmark's Equal Partnership Model (22:20)

* Dynamic of Disagreement (25:24)

* Betting on the Jockey (30:38)

* Adapting to Changing Environments (34:59)

* Providing Value to Entrepreneurs (37:14)

* The Current AI Technology Shift (39:26)

* Identifying Fast-Improving AI Areas (42:04)

* Final Thoughts and Takeaways (44:33)

I’d love to know what you took away from this conversation with Victor. 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.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

Had a great conversation recently with Tomasz Tunguz Founder and General Partner at Theory Ventures. We dug into how AI is reshaping venture capital and everyday life, from the rapid advancements in the space to what it all means for startups and the broader market. We covered everything from the declining cost of training AI models to the open vs. closed-source debate and how enterprises are starting to adopt AI in real ways. A really insightful discussion—hope you enjoy it.

About Tomasz Tunguz

Tomasz Tunguz is the Founder of Theory Ventures, where he invests in early-stage technology companies with a focus on SaaS, data infrastructure, and machine learning. Renowned for his deep analytical insights and data-driven approach to venture capital, Tomasz helps founders navigate growth, product-market fit, and scaling challenges.

Prior to founding Theory Ventures, Tomasz was a Managing Director at Redpoint Ventures, where he led investments in several high-growth software companies. He is widely recognized for his blog on SaaS metrics, startups, and venture capital, which serves as a valuable resource for entrepreneurs and investors alike.

Tomasz holds a degree in Mechanical Engineering and Economics from Dartmouth College. His passion for technology, strategy, and helping companies succeed has made him a respected voice in the venture capital community.

Theory Ventures is an early-stage venture capital firm focused on investing in transformative technology companies across sectors like SaaS, data infrastructure, AI, and machine learning. Founded by Tomasz Tunguz, Theory Ventures combines deep analytical expertise with a founder-first approach, providing hands-on support to help startups achieve product-market fit, scale operations, and drive long-term growth. The firm is committed to backing visionary entrepreneurs who are building the next generation of technology solutions, offering both capital and strategic guidance to turn bold ideas into successful businesses.

Timestamps:

In this episode, we discuss:

* AI's Impact (1:18)

* Cost Reduction in AI Training (2:18)

* Impact of DeepSeek on Market Dynamics (5:01)

* Open Source vs. Closed Source AI (10:57)

* Enterprise Decision-Making in AI (13:19)

* Defensibility of AI Applications (17:27)

* Efficiency in Growing Companies (21:01)

* The Path to AGI (25:46)

* Impact of AI on Labor Market (28:58)

* Excitement and Concerns About AI (30:55)

* Non-Consensus Views on AI and Final Thoughts (33:29)

I’d love to know what you took away from this conversation with Tomasz Tunguz.

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.

We recently had the pleasure of hosting Zal Bilimoria, Co-Founder of Refactor Capital. Zal has had a fascinating career from building products at Microsoft, Google, Netflix, and LinkedIn to making the leap into being a VC. His story is one of relentless curiosity and a deep passion for technology, something that started early in his life while working in his family’s computer business.

In our discussion, Zal walked us through his transition from product management to venture, his time at Andreessen Horowitz, and what ultimately led him to launch Refactor Capital. As a solo GP, he’s taken a unique approach to investing, navigating the challenges of fundraising while staying laser-focused on backing founders tackling complex, high-impact problems. We covered everything from the evolution of his investing philosophy to the importance of founder relationships and how he thinks about the future of life sciences and technology.

About Zal Bilimoria

Zal Bilimoria is the Founding Partner of Refactor Capital, a venture firm investing at the intersection of life sciences, technology, and sustainability. With a background in both software and healthcare, Zal brings a unique domain expertise and lens to investing. Before launching Refactor, originally with his partner David Lee, he was a partner at Andreessen Horowitz, where he focused on emerging technologies.

This was a fun conversation—if you're interested in what it takes to build a venture firm from scratch, how product thinking translates into investing, or where the future of innovation is headed, this episode is a must-listen.

Timestamps:

Topics in this conversation include:

* Zal's Early Life and Background (2:00)

* Career in Product Management (3:06)

* Starting Refactor Capital (6:03)

* Challenges of Starting a New Firm (9:36)

* Portfolio Construction Strategies (13:12)

* Solo GP Model (18:06)

* Advice on Hiring Associates (20:12)

* Fund Size Philosophy (24:32)

* Investment Entry Points (28:34)

* Return Model Considerations (32:04)

* Understanding Ownership Thresholds (36:31)

* Market Influence on Investments (38:44)

* Navigating Investor Relationships (41:08)

* Quick Decision-Making with LPs (43:25)

* Parting Thoughts and Future Outlook (46:32)

I’d love to know what you took away from this conversation with Zal Bilimoria.

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.

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

Today I had the pleasure of speaking with Brian Ascher, a veteran venture capitalist at Venrock, a firm with a storied history dating back to 1969 as part of the Rockefeller family office. Brian, with nearly 30 years in the industry, shared his journey from product management at Intuit to becoming a key partner at Venrock. We dove into the firm's evolution, investment strategies, and decision-making processes, highlighting how Venrock maintains its edge as it evolves.

About Brian Ascher:

Brian Ascher is a Partner at Venrock where he focuses on early-stage investments in enterprise software, SaaS, and consumer internet companies. With a deep passion for partnering with visionary founders, Brian is known for helping businesses scale through strategic growth, operational insights, and innovation.

Since joining Venrock in 1998, Brian has played a pivotal role in numerous successful investments, including Vocera, 6sense, Personal Capital, and Inrix. His expertise spans go-to-market strategies, product positioning, and building high-performing teams.

Topics in this conversation include:

* Brian’s Career Journey (1:34)

* The Evolution of Venture Capital (6:25)

* Venrock’s Decision-Making Model (10:09)

* Balancing Investment Decisions and Team Dynamics (14:42)

* Empowered Accountability in Deal Decisions (20:44)

* Cultural Norms in Venture Capital (22:38)

* Investment Strategy and Risk Management (25:12)

* Portfolio Construction and Returns (30:22)

* Opportunity Funds vs. Core Funds (33:01)

* Adapting to AI's Impact on Investment (36:15)

* Advice for Aspiring VCs (41:28)

* Final Thoughts and Takeaways (43:48)

I’d love to know what you took away from this conversation with Brian Ascher.

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.

In this episode, I have the pleasure of conversing with Gaurav Mathur, Partner at Pinegrove Capital Partners. Together, we dive into the evolving venture capital landscape, focusing on liquidity solutions and the rise of secondary markets. Gaurav shares insights from his extensive experience, discussing the growth in assets under management, the trend of companies staying private longer, and the changing dynamics for limited partners. We explore mechanisms for generating liquidity, such as continuation funds, strip sales, and secondary tenders, emphasizing the importance of alignment between general partners and limited partners.

About Gaurav Mathur and Pinegrove:

Gaurav Mathur is a Partner at Pinegrove Capital Partners. Gaurav Mathur is a seasoned finance professional with extensive experience in investment banking and venture capital. In 2023, he co-founded Pinegrove with Brian Laibow through the backing of a $500 million commitment from Sequoia Heritage and Brookfield.

THE ORG

Prior to founding Pinegrove, Gaurav spent 18 years at Goldman Sachs as a Managing Director in the Investment Banking Division, leading the US Equity Private Markets. He began his career at PwC in the Dispute Analysis & Investigations Group. Gaurav holds a Bachelor of Science degree in Business/Commerce from the University of Virginia.Pinegrove Capital Partners is a venture investment platform that offers tailored solutions for fund managers, founders, and limited partners within the venture capital ecosystem. Their expertise includes fund of funds, venture debt funds, venture secondaries, and co-investments.

With combined assets under management exceeding $10 billion, Pinegrove is supported by sponsors such as Sequoia Heritage and Brookfield Asset Management. In May 2024, an affiliate of Pinegrove, backed by these sponsors, entered into a definitive agreement to acquire SVB Capital, the investment platform business of SVB Financial Group. This transaction was completed in September 2024.

Topics in this conversation include:

* Growth of AUM in Venture Capital (3:53)

* Data-Driven Insights on Liquidity (6:11)

* Private Markets Growth Forecast (11:03)

* Mechanisms for Generating Liquidity (17:00)

* Alignment in Continuation Structures (21:28)

* Sizing Continuation Funds (29:44)

* Exploring Strip Sales (31:36)

* NAV Lending as a Liquidity Tool (34:00)

* Growth of Liquidity Solutions (37:35)

* Technology's Role in Liquidity (41:14)

* Final Thoughts and Takeaways (45:55)

I’d love to know what you took away from this conversation with Gaurav Mathur. 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.

Today I’m excited to speak with the founding team of Chemistry, a new venture firm led by Kristina Shen, Ethan Kurzweil, and Mark Goldberg, who recently spun-out of blue chip firms Andreessen Horowitz, Bessemer, and Index Ventures, respectively. The firm just announced a significantly oversubscribed $350MM debut fund. 

As a new entrant to the market (in the toughest time to start a new firm in over a decade), I wanted to ask them about their blueprint for building a firm, including how they chose to partner up and the work they did beforehand, LP strategies and selection, and what they felt was their unique reason to exist in a highly competitive market.

About Kristina Shen

Kristina Shen is Co-Founder and Managing Partner at Chemistry Ventures, overseeing a $350M fund focused on early-stage software investments.

Formerly a General Partner at Andreessen Horowitz (2019-2024), she led significant investments in Mux, Pave, Wrapbook, and Rutter. Kristina specialized in high-growth startups.

She began her venture career as a Partner at Bessemer Venture Partners (2013-2019), working with companies such as Gainsight, Instructure, and ServiceTitan. Previously, she worked in investment banking at Goldman Sachs and Credit Suisse, focusing on technology sectors.

About Mark Goldberg

Mark Goldberg is Co-Founder and Managing Partner at Chemistry Ventures since, investing in seed and Series A software startups. Previously, a Partner at Index Ventures (2015-2023), he worked with companies such as Plaid, Pilot, Intercom, and Motive, establishing a strong fintech and software portfolio.

Prior to Index, Mark worked at Dropbox in Business Strategy & Operations and Strategic Finance (2013-2015), where he contributed to growth strategies during Dropbox’s scaling phase.

He started his career as an Analyst at Morgan Stanley (2007-2010) before joining Hudson Clean Energy as a Senior Associate. Mark holds an AB in International Relations from Brown University.

About Ethan Kurzweil

Ethan Kurzweil is Co-Founder and Managing Partner at Chemistry Ventures, leading investments at the seed stage for tech-driven startups. He also serves as a board member for companies like Intercom and LaunchDarkly.

Previously, Ethan was a Partner at Bessemer Venture Partners (2008-2024), where he worked with companies such as HashiCorp, Twilio, and Twitch. His focus on software and digital platforms spanned roles as board member and investor, contributing to significant IPOs and acquisitions.

Early in his career, Ethan worked in business development at Linden Lab (creators of Second Life) and served as a Senior Manager in the CEO’s Office at Dow Jones. He holds an MBA from Harvard Business School and an AB in Economics from Stanford University.

In this episode, we discuss:

* (01:43): Importance of Team Chemistry and Partnership Formation

* (03:27): Challenges of Building a Firm in the Current Environment

* (08:00): Unique Value Proposition for Early-Stage Founders

* (10:18): Early-Stage Focus and Differentiation from Large VC Firms

* (16:12): Fundraising Insights and LP Relationship Building

* (19:00): Choosing Aligned LPs and Targeting Long-Term Partnerships

* (27:23): Single-Trigger Investment Decision-Making Model

* (30:12): Balancing Conviction with Collaborative Feedback

* (35:23): Independent Decision-Making for Follow-On Investments

* (39:19): Personal Contrarian Beliefs about the Venture Industry

* (42:18): Closing Remarks on Building a New Venture Franchise

I’d love to know what you took away from this conversation with Kristina, Mark, and Ethan. 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 Twitter.

Podcast Production support provided by Agent Bee

Follow me @samirkaji for my thoughts on the venture market, with a focus on the continued evolution of the VC landscape.

In this episode, Sam Heshmati and Vince Timoney from Citizens Private Bank stop by to talk about all things venture banking and how the industry is recovering from the 2023 regional banking crisis.

Sam and Vince, both of whom have extensive experience in the banking sector, share their insights on the challenges faced during this period, including the impact on startups and venture funds. They also discuss the significant changes in the banking industry since the crisis, such as the increased cost of capital, the fragmentation of fund banking services, and the shift in how banks serve emerging managers and venture capital firms.

The conversation provides a detailed look at the current landscape of banking for the venture ecosystem and how Citizens Private Bank is positioning itself to help clients navigate these challenges.

About Sam Heshmati:Sam Heshmati is an Executive Managing Director at Citizens Private Bank, heading the emerging VC and innovation practice. Previously, he co-founded and led programs serving the VC and tech community, cultivating and managing relationships with some of the nation’s top emerging managers, accelerators and entrepreneurs at the former First Republic Bank. He has over 21 years of experience in the technology ecosystem, serving clients not only as a banker, but as trusted partner with the expertise needed to help navigate important decisions within this space. Over his career, he has worked with more than 1000 early-stage VC firms and several thousand venture-backed startups. Prior to joining First Republic Bank in 2012, he spent 10 years as a tech banker at Silicon Valley Bank and Square 1 Bank. He earned a bachelor’s degree from San Jose State University.

About Vincent Timoney:Vincent Timoney is a Senior Managing Director at Citizens Private Bank, serving the fund finance and innovation economy nationwide. He has more than 12 years of experience working with VCs in business development, sales, lending and relationship management roles within the venture capital and technology ecosystem.

In this episode, we discuss:

(01:34) The evolving importance of banking, especially after the events of 2023.

(02:16) Banking Crisis of 2023 triggered by the collapse of Silicon Valley Bank and First Republic Bank.

(04:00) The impact of Silicon Valley Bank on the venture ecosystem and the rapid sequence of events leading to its downfall.

(07:00) How the banking industry has changed post-crisis, focusing on client expectations and digital banking.

(08:30) The increase in players in fund banking and the rise in cost of capital.

(12:00) Sam and Vince explain their journey of joining Citizens Private Bank, focusing on safety, stability, and continuing their work in the sector.

(18:00) Challenges faced by emerging managers, including capital call lines and banking needs.

(22:12) The importance of a seamless digital experience.

(28:16) Explanation of management company lines and their use by emerging managers.

(31:00) Advice for emerging managers on managing financial challenges and understanding the economics of running a fund.

(34:00) How technology and APIs are used to enhance banking services and integrate with third-party providers.

(38:00) Importance of offering personalized banking experiences tailored to individual client needs.

(40:00) Value-added services and why banks offer advisory support and strategic guidance.

(45:10) The long-term commitment required to build a successful banking franchise in the venture ecosystem.

I’d love to know what you took away from this conversation with Sam and Vince. 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 Twitter.

Podcast Production support provided by Agent Bee