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I was 30, had never taken a business or marketing class, and I had never used PowerPoint. I bought a Mac to use Persuasion and tried to create a company presentation for venture capitalists. My first official day of work was my thirtieth birthday, February 17, and we got the company funded. We met every day, the three of us, in one founder’s townhouse in Fremont. There was nothing to do at first—just talking about what we did yesterday, what we had for dinner, or where to go for lunch. For several months, the big daily decision was whether to have Philly cheesesteaks or Chinese food, and eventually whether to put donuts in the fridge in the morning. That period lasted a few months. I read books about starting companies and tried to figure out how to raise money and what a venture capitalist is. I then met a lawyer at Cooley Godward who helped us incorporate. He asked how much money we had in our pockets; I said $200. He took $200 and got 20% of Nvidia for it. I went back to the house, and my two partners each gave me $200, each getting 20%. And that’s how it worked, liberally. I never finished my business plan. I know it. We never finished a business plan, to tell you the truth. If I had finished that thick Gordon Bell book, How to Start a High-tech Company, I would have been dead now; we would have run out of money and time. I read the first three or four chapters, then had to go to work. We incorporated, and they introduced us to two venture capitalists. I went to their office and explained what I wanted to do. The key to getting funded, I learned, is not a business plan; VCs don’t invest in business plans because business plans are easy to write. They invest in great people, and your reputation and history matter. Because I had done significant work with Andy Bechtolsheim, another Stanford graduate and founder of Sun, and because we had connections with the founders of Synopsys and LSI Logic, we were in a strong position due to our track record and relationships, even if my business plan writing skills were inadequate. Another crucial factor is the vision. They want to know there is a market large enough to justify the investment. The market size matters: if the market is $20 billion, an investment of $10 million may not be justifiable; but if the market is $200 billion, the dynamics are different. The size of the market is important, and having a clever idea that the market has never done before is compelling. Yet, the last point, perhaps the least important, is the market itself—because you may need to reinvent yourself over time. If you’re going to reinvent yourself, you need great people, which is why great people are so important.

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The speaker discusses notable figures and firms in Silicon Valley, focusing on Peter Thiel and the venture capital world. They begin by mentioning two cyber companies, Lookout and Palantir, and note that Palantir is Peter Thiel’s company. The conversation clarifies the spelling of Palantir and Thiel, though there is some back-and-forth about the correct letters. The speaker indicates that Thiel would put you on the board of Palantir, expressing that Peter Thiel is one of the best they’ve never met, and mentions that Thiel is expected to come here next week. The dialogue shifts to Andreessen Horowitz, the venture capital firm co-founded by Marc Andreessen and Ben Horowitz. The speaker explains that Andreessen Horowitz pays Larry a million dollars a year to advise them. The firm is identified as Andreessen Horowitz, with the correct spelling of the names confirmed. The conversation then asks what the firm is, and the answer given is that they are lobbyists. The speaker notes that Andreessen Horowitz are the biggest venture capital people in Silicon Valley, asserting they are bigger than Sequoia or Kleiner Perkins, describing them as the “new” power players in the industry. A broader characterization is provided: these two entities—Palantir (Peter Thiel’s company) and Andreessen Horowitz (the prominent venture capital firm)—are highlighted as pivotal players in the tech ecosystem. The speaker emphasizes the influence and reach of Andreessen Horowitz by describing them as the biggest venture capital people in Silicon Valley and comparing them favorably against other legendary firms. In closing, the speaker remarks that these two companies are key players to consider, suggesting that involvement with them would be significant within the next three weeks if there is a potential departure or change in status.

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In 2008, I faced a tough decision with around $30-40 million left. I had two options: invest it all in one company and let the other one fail, or split the money between both companies and risk losing both. It was like choosing which child to let starve. Unable to make that choice, I decided to divide the money between them. Luckily, both companies managed to succeed in the end.

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I purchased my music catalog from Scooter Braun's Ithaca Holdings. The deal was funded by the Soros family, 23 Capital, and the Carlyle Group.

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This transcript presents an exchange highlighting how Jeffrey Epstein allegedly acts as a “fixer” to help former government officials convert their public power into private wealth as they leave office. Context and people: - The discussion centers on a February 2013 meeting involving Jeffrey Epstein, Ehud Barak (then head of Israeli military intelligence, later prime minister and defense minister), and Larry Summers. The timing is notable as Barak was transitioning to the private sector and leaving government work in March 2013. - Tom Pritzker (chairman of the Pritzker Foundation and head of the Hyatt chain) is referenced; the conversation references Tom Pritzker asking someone named Douglas about mentoring and a list of IOUs. - The speakers describe Barak’s career trajectory and Epstein’s role as a facilitator in converting government influence into private sector opportunities. Key claims and dynamics: - Epstein’s role as “outside fixer” helping a previously high-ranking official navigate the private sector and monetize government power. - The explicit strategy discussed: compile a “people index”—a list of people who owe you favors, owe you their lives, or owe you jobs. This IOU list is presented as the crucial asset for post-government opportunities. - The stated consequence: after leaving government, the official can secure lucrative board seats, funding from foundations and philanthropies, startup capital, and high-level consulting or venture capital opportunities, all because people owe favors from their time in government. - Barak’s situation is framed as an example of converting cresting government power into personal business leverage, with Epstein mediating connections to private-sector roles. - The conversation suggests Epstein has facilitated similar arrangements in the United States with CIA director Bill Burns, in the United Kingdom, and possibly with Saudi actors, framing this as a general pattern. - Specific monetization ideas discussed for Barak include pursuing board roles; Lookout (a cybersecurity company) is mentioned as a potential board opportunity that could pay “a couple million dollars.” - There is a mention of Palantir (Peter Thiel’s firm) being discussed in the context of Barak’s potential involvement, though Barak had not heard of Palantir at the time, and Epstein notes the possibility of approaching Thiel or related circles. - The dialogue compares Epstein’s brokerage function to a talent agent in the music industry—handling the money side, negotiations, and access to platforms—so that the individual can focus on the expertise itself. - The two cyber companies mentioned include Lookout and Palantir, with a note that Thiel’s Palantir was not familiar to Barak or Epstein at that dinner in 2013, despite Palantir’s 2003 founding. Additional context: - The dialogue references an attempt to reach Peter Thiel and to surround him with “spooks,” suggesting ongoing efforts to connect Barak and Epstein with Thiel’s network. - The overall theme is a firsthand depiction of how high-level government experience can be leveraged into private-sector power through a carefully curated network of IOUs and official-to-private transitions.

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Raytheon's Chris explains that In-Q-Tel is the strategic investment arm of the CIA and the broader intelligence and national security community. It was established in 1999 as an investment vehicle to access certain companies. In-Q-Tel is celebrating its 20th anniversary and has experienced the various stages of a startup. They have made successful early investments in companies like Palantir.

20VC

Peter Lacaillade: Why Now is the Best Time to Invest in Emerging Managers | E1096

Guests: Peter Lacaillade

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You just have unfair advantages over the public market. When I joined SCS, we had $7 billion under management. I was investing maybe $100 million a year. Now it's like about a billion and a half. It's amazing to me that the wealth management industry continues to be so fragmented. The platform at SCS was built to scale private markets for multi-family offices and families, turning a fragmented advisory world into a private markets program with direct investments, co-investments, and a focus on venture alongside buyouts. 2011 was quite a fortunate time to be coming in. In 2011, people were still reeling from the global financial crisis, and there was a dearth of capital on the LP side, an environment that made it easier to scale a private program. I backed emerging funds like Thrive, Founders Fund, and Andreessen; we were among the early institutions in some of those vehicles. The emphasis was on high conviction and taking risk on next-generation managers, with support from leadership like Steve Sago and Pete Mattoon. On the fund side, I talk a lot about the LP view of risk and return. The barbell approach mixes big, established managers with many niche funds, while maintaining diversification across industries. We emphasize direct investments as a core part of the program—over 100 direct investments—with a fee structure that is favorable: 'the carries like 7 or 8%' and 'over 100 direct investments.' Our investment committee for co-investments operates on a 48-hour clock, enabling rapid decisioning and execution. Co-investments typically range from 10 to 25 million, with flexibility up to 50. Liquidity planning is crucial. The LP landscape includes endowments, multi-family offices, and fund-of-funds; the incentives sometimes diverge, affecting how capital is allocated and deployed. The secondary market is evolving, with new structures to provide liquidity, and the tide is going out on frothy vintages, while disciplined managers aim for durable, scalable returns. The conversation emphasized patience, disciplined selection, and long horizons, acknowledging that private markets penetration remains relatively small but expandable.

My First Million

The Crazy Story of Google’s 7 Angel investors

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In this episode, hosts Saam Paar and Shaan Puri explore the early investors in Google, highlighting the unique stories of seven individuals who made significant contributions to the company. They begin with the "karma building" at 165 University Avenue in Palo Alto, where Google was founded, alongside other notable companies like PayPal. The first investor discussed is Andy Bechtolsheim, co-founder of Sun Microsystems, who, after a brief meeting with Google founders Larry Page and Sergey Brin, wrote a $100,000 check to "Google Inc." without even a formal valuation, ultimately owning 2% of the company. Following him is David Cheriton, a Stanford professor who also invested $150,000, later becoming a billionaire through his shares. Ron Conway, another key figure, is introduced as a legendary angel investor known for his generous approach to helping founders. He invested in Google after being introduced to it by Cheriton at a holiday party. Conway's philosophy centers on supporting entrepreneurs, which has built his reputation and network in Silicon Valley. The discussion also touches on other notable investors, including Shaquille O'Neal, who accidentally invested in Google after a chance encounter, and Susan Wojcicki, who rented her garage to the Google founders and later became the CEO of YouTube. The hosts emphasize the importance of proximity in Silicon Valley, where casual interactions can lead to significant opportunities. They conclude with reflections on the nature of investing, the unpredictability of valuations, and the importance of recognizing potential in founders and ideas quickly. The episode encapsulates the serendipitous nature of early-stage investing and the transformative impact of these initial investments on the tech landscape.

Uncapped

The Next Generation of Software | Mamoon Hamid, Partner at Kleiner Perkins

Guests: Mamoon Hamid

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Gold rush energy filled Silicon Valley in the late 1990s, and Mamoon Hamid describes arriving there in 1997 as a first‑time engineer taking his first job at XYlinks. He watched the rise and fall of the internet from the cubicle, surfing Netscape, reading books on Amazon, and witnessing the emergence of Google. He notes that XYlinks, Netscape, Sun, Google, and Amazon were all backed by Kleiner Perkins at the Series A, which sparked his curiosity about venture capital as a vocation. Those boom years felt exuberant, with parties, momentum, and a palpable sense of progress. Hamid reflects on the bubble era’s exaggerations and the shift toward building versus monetizing, then recounts his move from engineering to business school and back. He left the Valley to study at Harvard (2003) and returned in 2005, after Google and Facebook were already changing the landscape. Back then cloud and web 2.0 consumer apps were emerging; he joined venture capital focused on semiconductors but pivoted to software and productivity apps. The horizon expanded with Box, Slack, Figma, and the broader move to browser-based productivity, even as consensus around cloud and AI was still forming. We move to Mamoon’s framing of AI as a 'super cycle,' two and a half years in, since the ChatGPT moment in 2022. He outlines a pyramid of jobs, prioritizing highly paid, highly skilled roles like doctors, lawyers, and engineers, and explains investments in co-pilots for these roles—Ambience for clinicians, Harvey for lawyers, Windsur for engineers. He discusses automation that can handle repetitive tasks, but acknowledges slower progress on low-skill physical work and robotics. He mentions Dexterity and the limits of today’s capability, while imagining a future where prompting could spawn new businesses and even robotic labor at scale. On Kleiner Perkins itself, Hamid describes joining in 2017 to revive a storied firm through a lean, early-stage approach, returning to the unit-level craft of venture capital. He highlights John Doerr’s relentless founder focus and the firm’s mission to be the first call for founders who want to make history. The strategy centers on 35 companies per fund, with a select fund doubling down on top performers and a growth path for missed opportunities. He frames leadership as servant leadership, emphasizes team culture, and balances work with family and faith, including a Mecca pilgrimage that anchors his ethics and humility in every meeting.

Sourcery

How Marc Andreessen, Ben Horowitz, & David Ulevitch Started a16z’s American Dynamism Fund

Guests: David Ulevitch

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The episode traces the origins of the American Dynamism Fund at Andreessen Horowitz, describing how Mark Andreessen and Ben Horowitz fostered a culture that would allow a specific team to pursue defense and national-interest opportunities. The guests recount the consolidation of a defense-focused investment approach after early ventures into companies like Anduril, and how strategic partnerships—including collaboration with Katherine Boyle and cross-firm dynamics—helped shape the fund’s direction. They explain that the initiative began as a movement within the firm before crystallizing into a formal fund, highlighting the role of private capital in accelerating defense and technology programs while reducing the overhead and delays associated with government procurement. The discussion covers the supply and demand shifts that make this moment favorable: advances in AI-enabled software, autonomy, and affordable hardware, plus a wave of talent leaving established tech companies to start new ventures. The guests emphasize the importance of Washington engagement, policy support, and a dedicated policy team to align startup funding with national interests, arguing that bake-offs, flexibility in solving problems, and outcome-based procurement can improve efficiency and innovation in defense, space, public safety, and energy resilience. They also reflect on the scale of private commitments, including a purported $1.5 trillion from JP Morgan, and how such capital signals broader recognition of the need to invest in strategic capabilities, while acknowledging ongoing complexities around regulation, liquidity, and exits for this evolving category.

20VC

Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft

Guests: Larry Aschebrook

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Larry Aschebrook describes an unconventional path into venture capital. He moved from academic fundraising to buying private shares in private tech, starting with Twitter, Uber, Spotify, and Alibaba. He created a one-page form to request stock from private holders and learned liquidity constraints of private markets the hard way. He launched his first fund around 2010-2013, deploying about $35 million over three years, funded by his own capital and classmates, driven by a belief that fewer institutions could help companies go public after the financial crisis. Momentum came with Alibaba in 2014 and Spotify, which became central to his strategy. He and Spencer Mloud traveled to Stockholm to pitch Spotify, after meeting a lawyer who finally arranged a meeting; they bought stock through Jack Ma's family office and later built a large position, even posting buy-signs in their break room. The third fund, about $380 million, included 40% in Spotify, delivering a billion-dollar-plus outcome for LPs and cementing Spotify as a cornerstone of his approach. By 2021 the model changed. They raised a massive $1.4 billion in a few months while working from home, and later faced a flood of capital—turning down $700 million. The period exposed the fragility of overpaying in private rounds, and they adopted guardrails to curb overreach. They describe the pivot to structured equity deals with IRR hurdles and concentrated bets, aiming to preserve liquidity velocity and protect LPs when markets turned. The value of the discount returning to favor was a key realization. They recount major wins and losses across a dozen companies. They profited on Lyft while Uber underperformed, and exited many positions before IPOs. They scored big with Spotify, Alibaba, Coursera, Airbnb, SpaceX, Impossible Foods, Postmates, Instacart, and Palantir; they endured losses from Theranos and 23andMe. They describe the co-investment frenzy of 2020 and 2021, the importance of primary versus secondary deals, and the need to keep the backbone of the business tight to avoid overextension. Looking forward, the focus shifts to AI and other mega-trends. They emphasize concentrated bets on foundation models like OpenAI and Anthropic, while maintaining exposure across SaaS, fintech, and consumer sectors. They discuss LP communications, the value of the logo, and the desire to preserve the firm's longevity. Money, while meaningful, is framed as a tool to fund the chase for the next win rather than a destination. He emphasizes discipline, LP trust, and avoiding herd mentality.

Sourcery

$635M Exit → $600M Fund: David Ulevitch on Building a16z’s Hottest New Fund

Guests: David Ulevitch

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The episode centers on David Ulevitch’s perspective on American Dynamism and how a16z is building a portfolio around mission-driven, capital- and talent-attracting founders. Ulevitch emphasizes that the core of successful ventures is the ability of the leadership to magnetically attract both capital and great people, and he recalls his own path from OpenDNS to a venture-capital approach that prioritizes team quality and execution speed. He notes that while product ideas matter, the people behind them—founders and executives who can recruit top talent—drive the trajectory of these companies and determine whether they can scale, particularly in capital-intensive, hardware-oriented sectors like defense, energy, and manufacturing. He also highlights the importance of strategic, long-term partnerships with government customers, learned from his Cisco experience, where wins depend on ongoing relationships rather than transactional deals. The chat delves into Ulevitch’s view of national competitiveness, arguing for a shift toward domestic manufacturing, mining, and energy diversification to reduce reliance on foreign supply chains. He cites specific portfolio bets in nuclear energy, grid resiliency, and unmanned defense technologies as examples of how software-minded founders can transform legacy industries. Throughout, there is a clear focus on authenticity in marketing as a tool to attract talent and policymakers alike, with Anduril’s approach illustrating how a defense company can maintain transparency while building public goodwill and influencing policy. Looking ahead, the conversation touches on Kōshī’s prediction markets and the upcoming American Dynamism Summit, underscoring an optimistic view of continued growth in talent, capital, and innovation. Ulevitch emphasizes ongoing momentum in the portfolio and anticipates concrete inflection points as products move toward customers, alongside a broader expectation of a robotics wave and potential breakthroughs in nuclear energy.

Uncapped

Inside the Mind of the Investor Who Backed Josh Kushner, Peter Thiel, and Marc Andreessen | Ep. 34

Guests: Josh Kushner, Peter Thiel, Marc Andreessen

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This conversation with Mel Williams, co founder of True Bridge, centers on how exceptional investors pick not just the companies they back but the investors who back them. Williams and host Jack Altman discuss two core traits they’ve observed in top venture minds: a contrarian, first principles approach to the market and rock‑solid conviction to double down when a winner emerges. Williams explains that True Bridge’s strategy blends exposure to large branded platforms with a disciplined, concentrated seed and early‑stage approach, arguing that fund size matters less than how it amplifies the firm’s capabilities, access, and conviction. The dialogue unpacks how concentrated portfolios, often 11 to 13 core managers, can generate outsized returns as winners dominate NAV over time, while still preserving room to back distinctive first‑munder managers who bring proprietary deal flow and unique angles to the market. A central theme is the power‑law nature of venture: the magnitude of wins can dwarf the rest, driven by decreasing marginal costs of software, widespread AI adoption, and signal creation by premier firms like Sequoia, Founders Fund, and Andreessen Horowitz. Williams notes that outside AI, valuations look more reasonable, yet AI remains the dominant force shaping capital deployment, talent acquisition, and market signaling. The discussion also tackles the durability of venture brands, the difficulty for LPs to distinguish luck from skill, and the long lead times required to evaluate fund performance, all while emphasizing the importance of network building and choosing managers with the rightConviction, track record, and an ability to build brands that attract founders and capital. The episode ultimately frames investing as a blend of selecting the right people, the right opportunities, and the right structural scale to participate in an era where technology, capital, and talent are co‑evolving in unprecedented ways across AI and beyond.

Uncapped

The Benchmark Partnership: Peter Fenton, Eric Vishria, Chetan Puttagunta, Ev Randle | Ep. 41

Guests: Peter Fenton, Eric Vishria, Chetan Puttagunta, Ev Randle

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The episode centers on Benchmark’s distinctive approach to venture investing, emphasizing deep founder proximity, long-term relationships, and a model that prizes happiness and meaning over sheer capital deployment. The guests discuss why Benchmark has remained small and founder-focused while others scaled, arguing that true alignment with entrepreneurs comes from entering companies at or before launch and maintaining a hands-on, equal-partnership ethos. They describe how this proximity translates into trust, authentic communication, and a shared sense of purpose that endures across cycles. The panelists reflect on the costs of scaling, noting that increased capital and more formal structures can erode the very joy and differentiated experience they seek to deliver to founders. They also stress that being the first, most trusted partner and maintaining an environment where bad news is faced openly are core to helping founders flourish rather than merely survive. A recurring theme is how Benchmark’s culture and governance—built around equal partnership, unconditional regard, and a stance of “first call, most impactful partner”—shapes every investment. The speakers contrast this with other firms’ approaches, particularly the hands-off “do no harm” ethos, arguing that founders benefit most when investors act as sparring partners who ask tough questions, push for clarity, and stay relentlessly focused on the entrepreneur’s growth and well-being. They emphasize that great investors are not just dealmakers but co-founders in spirit, whose commitment lasts across multiple years and leadership transitions. The conversation also dives into how AI’s rapid evolution has intensified the importance of founder-centric investing, with Benchmark chasing teams that can adapt to shifting substrates and who bring unique insight to bear on fast-moving markets. Throughout, the panelists highlight how culture, trust, and authentic partnership drive durable outcomes for both founders and investors, shaping the steady, long-horizon strategy that Benchmark aims to uphold.

20VC

Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions"

Guests: Jake Saper

reSee.it Podcast Summary

In capital, we've returned a little over $8 billion in cash. We analyzed how our deals fared on graduation metrics relative to the market: nine out of ten of our deals have gone on to raise successful following rounds; one in five have raised rounds north of a billion dollars; and one in ten of our early-stage investments have gone public. The frame guides our approach to backing ambitious founders at meaningful scale, emphasizing strong product signals, repeatable unit economics, and durable growth trajectories. Zoom was Emergence's first major deal. The firm developed a thesis around replacing WebEx, and the Zoom opportunity arose with about 2–3 million in revenue in 2014, showing early product-led growth. The proposed check was $20 million from a $250 million fund at roughly a $200 million post-money. We uncovered churn data miscalculations—Eric counted upgrades and pauses as churn—and collaborated with a math-focused teammate to fix the model. We committed to helping build an enterprise sales motion on top of PLG, and we became the first institutional investor, which helped set the company on a fast growth path. Because our approach blends domain insight with fresh perspective, we’ve backed both experienced founders and naive, ambitious builders. Prepared minds can accelerate diligence, but real-world execution matters most. Chorus informed a broader thesis on voice AI, and Doximity illustrated a winner-take-all network in a professional vertical. We see substantial market pull in Bolt and Together, and believe open-source LLMs will be a dominant market factor; Together aims to offer open models for enterprise confidence, while others pursue specialized wedges that can become durable defensible products. Pricing and defensibility hinge on carving a wedge with a credible path to scale. Viva evolved into a board-level vendor; the notion of coaching networks suggests how a narrow, focused product can scale through deep customer value. Incumbents like Salesforce remain powerful but are not invincible; startups that solve a specific problem exceptionally well can outpace them and then broaden. Our diligence process—seven partners, a clear what-you-have-to-believe framework, comprehensive reference checks, and on-site visits—strives to reduce risk and improve odds of identifying outsized returns. On structure and risk, Emergence emphasizes governance and retention. They fund with a disciplined, high-touch approach, owning meaningful stakes and using reserve investments carefully. They acknowledge a VC ecosystem prone to a “merry-go-round” of partners, which can leave founders with orphan deals, yet highlight a track record of roughly $8 billion returned on about $2 billion deployed. IPO timing remains uncertain, with a view that deals resume next year, while the broader message remains: focused, evidence-based investing can bend odds and uncover generational winners.

The Ben & Marc Show

How Andreessen Horowitz Disrupted VC & What’s Coming Next

reSee.it Podcast Summary

Marc Andreessen and Ben Horowitz discuss the origins and evolution of their venture capital firm, Andreessen Horowitz, highlighting their unique approach to the industry. They began their journey after selling Opsware to HP and realizing that traditional venture capital was underwhelming for entrepreneurs. They aimed to create a firm that offered more than just capital, focusing on providing substantial support to founders. The conversation reflects on the history of venture capital, noting its roots in the 1960s and the legendary figures who shaped it. They emphasize the importance of having operators in venture capital, contrasting their experiences with those of traditional VCs who lacked operational backgrounds. The dot-com crash in 2000 led to a significant decline in angel investing and venture capital, but by 2004, Andreessen and Horowitz began ramping up their angel investments, helping founders navigate the challenging landscape. They describe their strategy for launching Andreessen Horowitz in 2009 with a $300 million fund, aiming to differentiate themselves through a platform approach that provided entrepreneurs with resources akin to those of large corporations. They faced skepticism from established VCs but believed in their vision of creating a supportive ecosystem for startups. The firm quickly gained traction, with successful investments in companies like Skype and Instagram, and they recognized early on that they could compete with top-tier VCs. They attribute their success to a deep understanding of the industry and the ability to adapt to changing market dynamics, including the rise of software as a critical component in various sectors. Andreessen and Horowitz discuss the evolving landscape of venture capital, noting that the asset class has become increasingly overfunded, leading to more competition among VCs. They argue that this influx of capital benefits entrepreneurs by providing them with more opportunities to secure funding. They also highlight the importance of personal relationships in venture capital, asserting that while AI may enhance certain aspects of investing, the human element remains crucial. The conversation concludes with reflections on the future of venture capital, acknowledging the potential for disruption but emphasizing the enduring value of relationships and operational expertise in the industry.

Sourcery

Carta CEO Henry Ward on Raising $1B, Path to ~$500M ARR, & the Move into PE

Guests: Henry Ward

reSee.it Podcast Summary

Henry Ward describes Carta’s core strengths as transforming service industries dominated by spreadsheets into software platforms, and focusing on moving problems that people currently handle in spreadsheets into the cloud. He outlines a decade-long journey to approaching half a billion in ARR and discusses a growth path toward a billion and beyond by expanding into private equity and private credit, with a belief that venture is part of a broader ecosystem rather than the sole focus. Ward emphasizes a flywheel-driven approach: measuring inputs like securities accepted, cap tables shared, and capital movements, rather than traditional outputs, arguing that disciplined attention to inputs sustains long-term growth and helps prevent performance slowdowns when markets shift. He explains Carta’s evolution from cap tables to fund accounting and private equity, outlining how the company creates value by building networks that link investors, startups, and funds, and how the go-to-market motion changes with each new asset class while the product remains a software-enabled version of spreadsheet-based workflows. Ward stresses the importance of a 10x product mindset rather than incremental improvements, noting that successful offerings sell themselves once they truly outperform incumbents and customer needs. The conversation also delves into AI as a strategic priority, with Ward describing dual tracks: using AI to enhance customer experiences and to improve internal operations. He shares concrete examples of AI-driven context-aware interfaces, error detection, and automation that reduce manual work and enable faster, more reliable processes. Ward also discusses leadership lessons, the value of a strong board (including Marc Andreessen and Joe from Silver Lake), and the ongoing challenge of balancing product exploration with a focus on building an institution capable of scaling. The episode closes with reflections on the love of building, the balance between product and company-building, and期待 transformative AI-driven product advances in the coming year.

Sourcery

Windsurf: The Making of a Billion-Dollar AI Company | Leigh Marie Braswell, Kleiner Perkins

Guests: Leigh Marie Braswell

reSee.it Podcast Summary

The episode presents Leigh Marie Braswell’s perspective on Kleiner Perkins’ evolution and the Windsurf investment, highlighting the firm’s focus on scaling through selective, founder-friendly partnerships. Braswell describes KP’s current structure, including the KP21 venture fund at $800 million and a growth fund called Select with about $1.2 billion, emphasizing that fund size alone doesn’t determine success; relationship-building and hands-on support remain central as KP seeks to partner with exceptional founders at various stages. She outlines the close-knit team—nine investment professionals who operate across early and growth stages, each with majors and minors in specific domains such as AI—allowing the group to share expertise and work collaboratively with portfolio companies. The conversation underscores KP’s long-term orientation, with a view toward the exit environment that leans toward durable, product-led growth rather than rapid, short-term returns. Braswell discusses Windsurf, KP’s portfolio company, detailing how the founders Varun and Douglas pivoted from Codium to Windsurf by owning the IDE and focusing on enterprise-grade, developer-focused AI tooling, a move she says has translated into rapid adoption and a growing user base. She explains Windsurf’s dual strategy of enterprise readiness alongside a strong product-led growth model, which helps capture both enterprise customers and individual users. The interview also touches on the importance of real-world usage data, speed-to-market as a competitive moat in AI infrastructure, and the need for pragmatic diligence. Braswell shares her approach to evaluating investments—watching for truthfulness, consistency in execution, and a founder’s ability to answer tough questions—plus the value of a robust CIO network to validate product-market fit. The discussion closes with reflections on talent acquisition as a differentiator in venture, her Scale AI experience shaping her eyes for “talent vortexes,” and the broader opportunity AI presents across industries, including finance, healthcare, and legal workflows. The episode ends on a forward-looking note about continuing to meet ambitious founders and help them build sizable, enduring companies in the AI era.

20VC

Peter Wagner: 27 Years of Investing Lessons of Picking Founders, Price Discipline & Reserve | E1123

Guests: Peter Wagner

reSee.it Podcast Summary

Peter Wagner describes the very best founders as those with high bandwidth engagement and glaring deficiencies in current approaches; he prefers founders who are 'pissed off' at how things are done. He joined Excel in July 1996 after a stint as a product manager at Silicon Graphics and says the late-’90s internet boom created fertile ground for early wins. He recalls joining as an accident that turned into a vocation, and he emphasizes the value of credibility gained from early hits. He explains two fundamental paths in venture: asset under management versus maximizing returns, and he favors being a lead, early investor who can shape a company rather than chasing volume. He stresses the 'sleepless night factor'—the intense personal accountability that sharpens judgment—and notes talent development at Excel was accomplished by a flat, non-hierarchical structure where even juniors had a voice. He warns against over-expansion into multi-geography growth funds, arguing focus preserves discipline and increases the odds of backing enduring builders. He reflects on lessons from Excel and Wing, including the primacy of pattern recognition tempered by the danger of overfitting, and the idea of a 'prepared mind'—being the world's leading authority in a focused area. He recounts a Snowflake seed investment and a missed Series B led by others as a costly growth miscalculation, illustrating how capital scale can outpace disciplined venture judgment. He remains optimistic about tech’s role but warns against capital-intensive bets that strain early-stage capital.

20VC

Peter Singlehurst: Lessons from Turning Down Stripe, Coinbase and Losing Money on Northvalt

Guests: Peter Singlehurst

reSee.it Podcast Summary

Peter argues that 'you can build a better business by staying private for longer,' noting the rise of large company-facilitated secondary rounds. Bailey Gifford has not yet invested in any of the big AI LLM companies because they are still defining what 'competitive advantage' will look like at the large language model level. The firm remains focused on true growth-stage opportunities and a global reach, even after acknowledging painful investments that weren’t outright mistakes. Peter describes their investment framework: a '10 questions framework' that looks at growth potential over 5 and 10 years, enduring determinates of success, and organizational culture, plus financial analysis. Derisking on product and seeking high return on equity are central. The median portfolio company is around $200 million in revenue, growing about 70% year over year and only modestly unprofitable. They model upside to a five-times outcome and assess probability to determine whether a given bet makes sense. Peter says they invest in AI-relevant areas like infrastructure (Data bricks) and chip-related ventures, but 'we haven't taken the plunge into any of the big AI llm companies' because they are still defining 'competitive advantage' at the large language model level. He suggests that enduring competitive advantage often lies beyond a single product and cites Bendings Spoons as an example—a 'playbook for M&A' embedded in culture and founder leadership—rather than a lone widget. They discuss how capital cycles have shifted toward longer private ownership, with 'large company facilitated secondary rounds' becoming a feature and capital recycling through private rounds. They recount nearly missing Stripe: 'we first invested in Stripe at about a $30 billion valuation, but we didn't take part in the down round that they did whenever that was, 2022' and say they should have. They note ongoing debates about IPO timing as private markets evolve, and point to Wise as an example facing London Stock Exchange headwinds, while envisioning liquidity via private secondary rounds and potential dividends for mature private firms.

20VC

Pat Grady: Sequoia Partner on Investing Lessons from Doug Leone, Roelof Botha and Alfred Lin | E1174

Guests: Doug Leone, Roelof Botha, Alfred Lin

reSee.it Podcast Summary

Sequoia’s core framework rests on founder-market fit and the vector describing the founder. The market defines a company’s ceiling; the founder determines how high it can rise. On sourcing we’re eight or nine out of ten, on picking about six. If a wildly successful company excludes Sequoia from its cap table, that signals a miss in the process. Two signals drive founder selection: founder-market fit and the vector. Founder-market fit blends understanding of the problem with the ability to build a solution; the vector captures direction and magnitude—motivation and momentum. They cite Harvey in AI for Legal Services as an example, where one founder knows the problem and another builds the solution. Crystallize a thesis before diligence and stress-test it. HubSpot’s story shows one strong founder and market can overcome a mediocre product; a series of strategic moves matter. The market ceiling exists, but the right founder can extend it. In growth investing, the gap between a $1 billion company and a $10 billion one is often the result of an exceptional founder. VC operations unfold across sourcing, picking, winning, building, and harvesting. Arc, Sequoia’s accelerator, is described as a wild success: founders love it, LPs benefit, and the program’s NPS is effectively 100. The platform and data signals support meetings without replacing judgment. Hiring is rigorous—top-of-funnel outreach once drew about 9,000 applicants; decisions balance DNA versus experience hires, with apprenticeship as the method. Doug Leone is the ‘tip of the spear’ in early meetings; postmortems emphasize hunger and humility to prevent arrogance. A ServiceNow example shows Sequoia’s hands-on problem solving, including a 52 million investment for 20 percent. Sequoia’s premium branding creates signaling advantages in future rounds. The conversation closes on keeping many superstars aligned, choosing fewer, better bets, and staying day-one hungry.

20VC

Sonali De Rycker | How I Became a Partner at Accel; Type 1 vs. Type 2 Mistakes | 20VC #902

Guests: Sonali De Rycker

reSee.it Podcast Summary

Sonali De Rycker traces her path from socialist India in the 70s and 80s to a full scholarship in the United States. She describes fleeing limited choices—doctor or chartered accountant—and using the USIS library to pursue an abroad liberal arts education. She arrives debt laden but undeterred, landing at Goldman Sachs in 1995 and moving into a group that works with tech startups and IPOs, including Spyglass, the first internet software IPO. That encounter ignites a lifelong focus on entrepreneurship and technology. After business school she shifts to Europe, joining Atlas Venture, and in 2008 moves to Excel, where she has built her career. She recounts two defining downturns that shaped her approach. In 2000 she joined a tranche of e-commerce founders at the market’s low, where a phone call from David Bonderman on a satellite line recalled the value of detail and diligence, proving that even small stakes matter. In 2008 Lehman’s collapse forced fundraising with LPs arriving at the Four Seasons basement, testing the fiduciary duty to founders, LPs, and the fund. The lessons: never stop investing, and partner deeply with entrepreneurs through highs and lows, now especially with a watchful eye on profitability. She describes Excel London as the glue of the firm, hyper competitive on the outside and ultra collaborative on the inside. Real time feedback, a dedicated talent function, and a culture of openness anchor its global reach from London to Helsinki. The conversation moves to resilience, early stage focus, and the belief that great founders and outsized returns endure through downturns, with BeReal cited as a current example driving optimism.

20VC

a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game

reSee.it Podcast Summary

The Thrive strategy was brilliant: buy the best property on every block. It plays like Monopoly. A fintech block here, an OpenAI block there, an infrastructure block and a database, tick. Then you go home and wait for the checks to roll in. It sounds ingenious: why chase 8x over 20 years in a seed fund when you can write one big check into a winner and realize liquidity in a quarter? The absolute return may be larger even if the multiple is lower. It’s tempting to call it a strategy for suits and doubters, but it’s compelling in practice. The SAS investing frame before is fading. The spreadsheet approach—look at net revenue, growth rates, predict quality—feels outdated. Nabil at Spark echoed this. Are our rubrics obsolete, and do we need to rethink them from the ground up? Rory, who first opened my eyes to this, described a rough ladder: “1 to 10 in five quarters or less” as S tier, with the Mendoza line looming behind. Late 2020 term sheets pushed valuations into the high nine figures without founder contact, pushing investors to question what “good” really means. The conversation tracks how the old playbook plateaued and how AI upends expectations, making scalable, defensible advantages riskier and more dynamic than in the past. PMF is transient and revenues are increasingly volatile. Gen AI enables rapid leaps to 20, 30, even 50 million, but often with sugar highs. Two things changed: model progress and the fact that we’re still figuring out what you can do. Absent progress, there’s drift and pivots. It used to take five years to find product-market fit; now a company can adjust in five weeks as AI capabilities expand, making PMF less stable and capital deployment more uncertain, especially when automation targets the head of the worker rather than just back-office processes. Private markets, exits, and governance: liquidity remains a friction. Founders, funds, and LPs wrestle with harvesting value when IPO windows are irregular and private valuations inflated. The conversation weighs liquidation preferences, side deals, and the risk that buyers sidestep VC terms. It argues for disciplined selection, longer horizons, and a mix of diversified yet concentrated bets on marquee assets. The broad view is that the venture ecosystem endures through selective winners, structural reforms, and continued appetite for top-tier, high-conviction bets, even as the terrain grows more volatile and scrutinized. OpenAI and foundation models: fundraising scales and the logic of backing teams with a hidden recipe for breakthroughs. OpenAI reportedly raised a 30 billion fund, and Anthropics’ multi-billion rounds illustrate capital chasing foundation models. The stance is pragmatic: fund people with the techniques that crack the code, because those deals can outsize traditional bets. Rippling’s fundraising at around 18 billion underscores the tension between aggressive deal-making and governance risks when high-stakes rounds collide with ethics.

20VC

Inside Accel's $4BN Growth Investing Machine | Miles Clements

Guests: Miles Clements

reSee.it Podcast Summary

In this episode, Miles Clements, who leads Accel’s growth investing practice, discusses how to assess value in an AI-driven world where technology feels transient and traditional revenue signals can be opaque. He outlines a framework built on time to value and durability of that value, explaining how different AI-enabled verticals can vary in deployment speed and long-term impact. For example, Basis, a legal and accounting AI, offers longer adoption cycles but transformational durability once integrated, whereas coding-focused tools like Cursor and Claude Code provide rapid value alongside growing durability as users deepen their reliance on the platform. The conversation delves into how multi-model, multi-tool strategies matter in development environments, with developers frequently switching models and adopting agent-based workflows, underscoring the importance of products that serve professionals with specialized coding needs. Clements addresses market sentiment and the debates around Cursor’s trajectory, noting that recent headlines about its decline overlook broader dynamics: market expansion, increased consumption, and the shift toward agents that enhance product usage. He emphasizes that Cursor’s multi-model approach and emphasis on engineering as a platform could yield lasting advantage, even as competitors emerge. The discussion moves to investment philosophy and the delicate balance between growth rates and the quality of founders, market, and ownership terms. The guests explore how Accel navigates valuation pressures, scarcity of mega-outcomes, and the reality that several private AI leaders may eventually become trillion-dollar platforms, while cautioning against overreliance on any single metric. The episode also covers practical aspects of running a multi-stage fund, such as diversification versus chasing momentum, the role of liquidity events, and when to seek exits or preserve capital for long-horizon bets. They compare private and public market dynamics, reflecting on the appeal and limitations of public stock markets for private-scale outcomes, and discuss the importance of founder alignment, board effectiveness, and the ongoing quest to identify the next breakout leaders. The conversation concludes with reflections on mentorship, culture, and how Accel aims to nurture young talent to sustain success across future AI waves and investments.

All In Podcast

E65: VC markup dynamics, Russia/US tensions over Ukraine, Altos Labs raises $3B, Stripe mafia & more

reSee.it Podcast Summary

The hosts discuss various topics, starting with Palmer Luckey and his potential syndicate launch. They reflect on their investment strategies during market downturns, emphasizing the importance of distinguishing between investments and trades. Chamath shares insights on emotional reactions to market fluctuations, while Sacks discusses the inverse relationship between entry and exit prices in venture capital, noting that current market corrections have led to more reasonable venture deal pricing. They analyze the implications of the Federal Reserve's upcoming rate hikes, suggesting that while the market may react negatively in the short term, historically, stocks tend to rally after rate hike cycles begin. The conversation shifts to geopolitical tensions, particularly the situation between the U.S. and Russia regarding Ukraine. The hosts argue that U.S. involvement in Ukraine is historically unprecedented and discuss the potential motivations behind Russia's actions, emphasizing the need for a nuanced understanding of the situation. They also touch on the complexities of NATO expansion and its impact on U.S.-Russia relations, suggesting that a more diplomatic approach could help de-escalate tensions. The hosts highlight the importance of economic factors in foreign policy decisions and the potential consequences of military conflict. Lastly, they discuss a significant investment in Altos Labs, a biotech company focused on cellular reprogramming for age reversal, and the challenges of large funding rounds in startups. The episode concludes with reflections on investment strategies and the lessons learned from missed opportunities in the venture capital space.