20VC with Harry Stebbings
Showing 391–405 of 691 transcripts.
- 57 min
Roundtable #5 with Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings | E1077
Jack Altman, Auren Hoffman, Jason Lemkin, Harry Stebbings
This discussion analyzes the operational, strategic, and institutional evolution of founder-led investment funds, highlighting how operators leverage recent industry experience to provide superior "tough love" support and signaling value compared to traditional venture capital. The dialogue contrasts solo GP models with scaling team structures, addresses LP alignment on dual-hat roles, and examines capital migration trends alongside critical retention data showing 88% of SaaS IPOs remain founder-led. Participants also debate investment heuristics based on past performance and wager on the future trading performance of major public companies like Arm and Klaviyo to illustrate market sentiment.
- 7 min
Coinbase fired him. Now he runs a VC firm with over $1 billion AUM.
After being pushed out of Coinbase due to corporate friction, a former employee leveraged deep sector knowledge to transition into venture capital and launch the $26 million "Confirmation" fund. This capital formation relied on prior experience at Runa Capital, the reputation built through the high-demand "Token Summit" and *The Control* newsletter, and a conviction in crypto as a transformative social technology. The speaker utilized these established industry pillars to successfully raise significant investment despite lacking connections to traditional wealthy investors.
- 1h 16m
David Meyer: Why You Should Hire People Who Aren’t In Product Already | E1076
A seasoned industry expert critiques the dilution of product management quality, reframing the role as a discipline of negotiating impossible compromises between conflicting engineering and sales stakeholders rather than acting as a product CEO. The discussion details rigorous methodologies for truth-seeking customer research and organizational scaling, emphasizing that effective leaders prioritize learning velocity over shipping speed while navigating the tension between data metrics and human insight. Finally, the speaker outlines a philosophy where leadership success relies on tailored feedback, adversarial hiring panels, and maintaining deep customer intimacy to prevent burnout and preserve innovation as companies grow.
- 1h 17m
Nick Tomaino: The Future of NFTs, What Will Happen with FTX & Who Should be Held to Account | E1076
Nick, co-founder of One Confirmation and former Coinbase employee, outlines his strategy for a venture firm that has achieved a 5.13x return while maintaining a strict discipline against total losses. He attributes his success to grit and mimetic desire theories, using these frameworks to drive early investments in OpenSea and critique the current state of crypto fundraising. Ultimately, Nick forecasts a coming contraction in the sector where only funds with unique insights will survive, while advocating for greater transparency in venture performance reporting.
- 51 min
Ed Sim: Why Seed Has Never Been More Competitive & Why Pricing Has Never Been Higher | E1076
Venture capitalist Ed advocates for a shift from traditional pre-seed labeling to "Inception Investing," promoting lean capital structures of $2M to $5M to force operational efficiency and avoid the "death spiral" of hyper-growth without product-market fit. He outlines Bold Start's strategy of maintaining concentrated ownership through an "Opportunity Fund" that avoids leading A-rounds, ensuring follow-on participation while founders navigate a market where exit multiples are compressing to 10x–14x forward revenue. This approach prioritizes fair valuations and data-driven de-risking over preemptive funding, positioning the firm to capture value in specialized AI security and enterprise solutions rather than generic startup wrappers.
- 9 min
#1 Mistake To Avoid When Picking Your Co-Founder -- Cloudflare CEO Matthew Prince
Matthew Prince, Harry Stebbings
The speaker contrasts a failed early venture formed by three socially compatible but functionally redundant friends with the enduring success of Cloudflare, where co-founders Lee and Michelle were selected specifically for their opposing skill sets in execution and operations. By establishing a clear framework where final decision-making authority is delegated to the domain expert, the team minimizes internal conflict and ensures that critical roles in product, sales, and finance remain distinct. This strategy of prioritizing complementary professional strengths over initial social closeness allows the company to operate with a singular vision while resolving the power struggles that previously fractured the founder's earlier partnership.
- 1h 1m
Ely Lerner: Should Startups Hire Advisors & How much should they be paid? | E1075
The event outlines a strategic framework for high-growth companies, emphasizing that success relies on limiting top-level objectives to one or two core bets while separating autonomous product units from legacy infrastructure to ensure P&L alignment. It details a shift from abstract advisory to hands-on engagement where founders retain ownership of offensive growth strategies while utilizing data-driven resource allocation to prioritize compounding initiatives over defensive maintenance. Furthermore, the discussion highlights critical operational levers such as defining structural Ideal Customer Profiles, rejecting outdated growth hacks in favor of specific leverage points, and restructuring organizations to isolate core experiences from primary growth loops.
- 27 min
Harry debates Cloudflare CEO Matthew Prince: "Should startups target niche markets?"
Matthew Prince, Harry Stebbings
Cloudflare CEO Harry Stephenson challenges the prevailing startup dogma of starting with narrow niches by arguing that ambitious, broad visions are essential for attracting top talent and unlocking wild success outcomes. Drawing on Cloudflare's trajectory, he demonstrates how targeting a massive initial market rather than a pre-determined segment allowed the company to discover high-value users in civil society while avoiding the stagnant "slog" of incremental growth. Stephenson concludes that venture-backed founders must prioritize recruiting incredible people and setting non-trivial targets over optimizing for immediate efficiency, as only a expansive scope can justify the risk required for exponential scaling.
- 54 min
Matthieu Rouif: The Story of PhotoRoom, Is This YC’s Most Capital Efficient Company? | E1074
Matthieu Rouif, Harry Stebbings, Francesc Campoy, Mark Mandelmann
Founded by Matt Campo, PhotoRoom leverages proprietary AI to deliver mobile-first, studio-quality image editing for small business owners, achieving $20 million in annual recurring revenue through extreme capital efficiency. The company differentiates itself by replacing complex desktop tools with intuitive workflows that enable non-experts to generate professional visuals, utilizing a viral watermark strategy and a focus on weekly active exports to drive growth. Positioned to challenge incumbents by moving beyond "co-pilots" to autonomous "autopilots," PhotoRoom is scaling toward a billion-dollar valuation while expanding its enterprise API and building a global, remote-first organization.
- 1h 1m
Beezer Clarkson: Are LPs Open for Business & Why Do LP Incentive Mechanisms Need to Change? | E1073
Beezer Clarkson, Harry Stebbings
Sapphire Partners general partner Pesar outlines a venture capital market shift toward $300–$700 million funds and a tightening of LP capital deployment amidst stalled IPO windows expected to remain closed until late 2025. The discussion highlights how power law-driven returns and misaligned fee structures are forcing institutional investors to rebalance portfolios, exemplified by Sapphire's new early-stage specialist mandate for CalSTRS. Industry data suggests a prolonged period of valuation discounts and liquidity constraints before the sector recovers to traditional growth models.
- 1h 7m
Matthew Prince: The Two Biggest Mistakes Every Founder Makes | E1072
Matthew Prince, Harry Stebbings
Cloudflare co-founder Matthew Prince details the company's strategic evolution from a spam-fighting project to a $19.6 billion enterprise driven by an ambitious vision to "run the internet." Under his leadership alongside co-founders Michelle Zatlin and Lee Holloway, the firm adopted a venture-backed model that bypassed narrow targeting to attract top talent and launched a free tier that inadvertently served high-risk civil society clients. This approach enabled Cloudflare to defend Ukrainian infrastructure against cyber probing in 2022, resulting in sanctions from the Russian government against Prince, Zuckerberg, and Benioff, while cementing the company's focus on massive societal impact and global infrastructure protection.
- 46 min
Michael Eisenberg and Adi Levanon: Israeli Resilience in Crisis | E1072
Michael Eisenberg, Adi Levanon, Harry Stebbings
Following an attack causing over 1,400 Israeli casualties and the abduction of more than 100 hostages, the nation mobilized reserve forces and civilians while the tech sector established command centers to coordinate rescue and maintain business continuity. Global venture capital firms and political leaders have rallied to affirm support against Hamas and Iranian threats, despite rising anti-Semitic incidents and perceived equivocation from certain academic institutions. Investors predict that Israel's demonstrated resilience will attract significant capital inflows in the post-conflict era, even as speakers warn that the situation may deteriorate further before eventual improvement.
- 55 min
Roundtable #4 with Jason Lemkin, Woody Marshall, Deven Parekh, Harry Stebbings | E1071
Jason Lemkin, Woody Marshall, Deven Parekh, Harry Stebbings
The current enterprise software market reflects a structural shift toward profitability and efficiency, characterized by a deal drought driven by valuation gaps and a slowdown in late-stage private funding. While recent activity includes the Cisco-Splunk acquisition and several scaled public offerings, the sector anticipates an IPO window reopening in late 2024 as investors prioritize free cash flow and normalized multiples over hyper-growth. Amidst cautious optimism regarding artificial intelligence adoption, firms like Insight and TCV are navigating capital needs with a focus on profitable growth assets and secondary liquidity rather than speculative valuations.
- 52 min
Scott Farquhar: Founding Atlassian; How We Scaled to a $50B Valuation; The 4 Jobs of a CEO | E1070
Scott Farquhar, Harry Stebbings
Atlassian co-founders Scott Dunn and Mike Cannon-Brookes built the company from 2001 to 2011 by bootstrapping through the dot-com crash and post-9/11 era, eventually securing a $60 million funding round at a $405 million valuation by utilizing a closed-envelope bidding strategy. Following a decade of independent growth that reached 11,000 employees and 250,000 customers, Dunn identifies past mistakes of omission regarding Bitbucket and Stride as catalysts for launching the new "Point A" incubation program to aggressively invest in emerging categories like AI and developer tools. The organization now operates as a fully remote-first entity leveraging historical data for strategic AI integration, with a vision to eliminate busy work and redefine team collaboration by 2033.
- 1h 14m
Guillermo Rauch: Why Great Companies are Defined by How Many Things They Say No To | E1069
Guillermo Rauch, Harry Stebbings
Vercel founder Guillermo Rauch leverages a background in open-source programming and early financial self-sufficiency to drive a hiring philosophy that prioritizes tangible code output and serial founder experience over traditional credentials. He outlines a strategic evolution from software 1.0 to AI-driven "software 2.0," arguing that the future of technology requires adaptive interfaces that manage probabilistic outcomes while maintaining a rigorous culture of rejecting feature creep. Ultimately, Rauch envisions Vercel transforming the software landscape over the next decade by elevating the baseline for developer productivity, positioning AI not as a replacement for human creativity but as a core component of a new operating system for product creation.