20VC with Harry Stebbings
Showing 676–690 of 691 transcripts.
- 1h 6m
Q-Commerce in Emerging Markets with the CEOs of Airlift, JOKR, & Zepto | 20VC #892
Usman Gul, Ralf Wenzel, Aadit Palicha
Executives from Airlift, Joker, and Zepto outlined how quick-commerce ventures in emerging markets leverage high population density and lower labor costs to achieve profitability faster than Western counterparts. These companies are pivoting from pure delivery models to vertically integrated operations that control supply chains, optimize unit economics through reduced wastage, and generate significant revenue via proprietary advertising platforms. By capitalizing on local ad-hoc purchasing habits and navigating unique infrastructure challenges, the sector is transitioning toward "e-commerce 3.0" with a focus on free cash flow generation rather than capital-intensive growth.
- 42 min
Keith Rabois: The End of Woke Capitalism; Time Allocation Tips; Silicon Valley vs Miami | 20VC #891
Keith Rabois, Mike Moritz, Vinod Khosla
Venture capital insights differentiate early-stage "art-like" investments from later-stage "greater fool" dynamics, emphasizing that multi-stage funds like Founders Fund can sustain contrarian strategies while single-tranche investors must rely on derivative consensus for future funding. The discussion highlights shifting market conditions where in-person collaboration is prioritized over remote work, and geographic capital is migrating away from Silicon Valley toward hubs like New York and Miami due to safety and network concerns. Key financial takeaways include the necessity of focusing time only on high-leverage winners, avoiding reliance on public market comparables for early ventures, and recognizing that valuation cycles are driven primarily by inflation and interest rate environments.
- 48 min
Aydin Senkut: How I Scaled from a $4M Angel Fund to $900M AUM | 20VC #890
Founded by former Google executive Aydin Ocalle after facing rejection from traditional firms, Felicis Ventures evolved from a $41 million seed fund into a $900 million global entity that prioritizes investing in high-quality companies over optimizing for initial valuation or ownership percentage. Operating under a "success with empathy" culture, the firm differentiates itself by accepting smaller initial checks to secure positions in top-tier ventures before doubling down, while deliberately mitigating market volatility through vintage and geographic diversification. Ocalle continues to shape the firm's strategy by focusing on critical sectors like climate technology and advocating for rigorous decision-making processes that navigate the tension between late-stage market inflation and the need for early-stage conviction.
- 54 min
Oliver Jay: How To Create and Execute a World-Class Sales Playbook | 20VC #889
Former Morgan Stanley and NEA executive OJ Herzberg outlines a strategic framework for scaling sales teams that emphasizes distinct go-to-market approaches for emerging versus established categories. His methodology prioritizes hiring individual representatives over sales leaders in new markets to define product-market fit before codifying a repeatable playbook, while advocating for hybrid models that integrate Product-Led Growth with traditional enterprise sales. Herzberg further details critical operational tactics, including specific onboarding sequences, equity compensation strategies to foster long-term retention, and the necessity of maintaining a continuous feedback loop between sales and product teams to ensure scalable growth.
- 1h 1m
Oren Zeev: How I Raised $1 BILLION in 12 Months | 20VC #888
Independent venture capitalist Oren Zeev distinguishes his 27-year career by rejecting traditional partnership structures to prioritize rapid capital deployment and concentrated portfolios of nine to ten companies. He argues that current market corrections reflect valuation adjustments rather than fundamental business failures, advocating for aggressive investment in high-growth opportunities while advising founders to avoid prolonging the inevitable decline of failing ventures. His strategy emphasizes securing top-tier founders over satisfying limited partner optics, a philosophy illustrated by his successful bet on Riverside despite early product flaws and his admission of past missed opportunities like Facebook.
- 1h 7m
Fabrice Grinda: The First Person to Predict the Collapse of Credit Suisse? | 20VC #886
FJ Labs founder Fabrice Grinda details the firm's evolution from a sole-operator angel fund to a structured organization managing 31 professionals, while outlining a revised due diligence process that screens approximately 200 weekly deals against core criteria of team quality and market economics. Grinda analyzes the current macroeconomic landscape as a 60% probability of "Great Stagnation" driven by high inflation and interest rates, yet maintains an optimistic view that technology will drive long-term productivity growth despite a heightened 20% risk of a catastrophic sovereign debt crisis. To navigate this environment, the firm has reduced its average check size to capture value in early-stage markets while advising founders to prioritize unit economics and cash efficiency over rapid expansion.
- 41 min
Sid Sijbrandij: How I Founded GitLab; Remote Work vs In-Person; CEO Coaches | 20VC
GitLab CEO Sid Sijbrandij outlines the evolution of his fully remote DevOps platform, detailing how a 2,000-page handbook and mandatory informal "coffee chats" enable asynchronous collaboration across 60 countries while mitigating the fragmentation risks inherent in hybrid work models. Beyond internal operations, Sijbrandij advocates for a unified DevOps market and shares governance strategies involving situational leadership and specialized board feedback to support the company's growth from 300 to over 1,500 employees. The discussion concludes with insights into OpenCore Ventures, a new initiative aiming to build open-source companies around core projects, as the organization navigates the scaling challenges of cross-functional initiatives.
- 59 min
Shopify President, Harley Finkelstein on What is Being a Good Husband | Full Interview
Shopify President Harley Finkelstein draws on a history of early financial hardship and family resilience to shape a leadership philosophy that prioritizes radical transparency, empathetic communication, and the distinction between paralyzing anxiety and productive eustress. By maintaining a high-trust partnership with co-founder Toby Lütke while enforcing strict boundaries between work and family, Finkelstein has helped scale the platform to facilitate approximately 10% of all U.S. e-commerce while serving over two million entrepreneurs. Looking ahead, he aims to democratize entrepreneurship by encouraging individuals to commercialize their passions and normalize the path to self-actualization through business.
- 46 min
How I Built a Twitter Audience of 500K+ in 18 Months | Sahil Bloom Full Interview
Sahil Reddy Bloom transitioned from high-intensity private equity to content creation, leveraging his media platform to launch SRB Ventures, a $10 million fund that targets pre-seed and seed companies with a $50,000 to $250,000 check size. By rejecting the traditional model where capital is the primary differentiator, Bloom positions his fund to offer operational leverage and distribution support to founders, aiming to disrupt the "middle" of the venture capital landscape where mid-tier firms struggle to compete. His approach combines early-stage investing with a rigorous personal philosophy of "engineered serendipity" and disciplined consistency to maximize value for both investors and the companies they back.
- 31 min
How I Bought 12% of Google for $12M; How VC is Fixing Climate Change | John Doerr Full Interview
John Doerr, Tom Perkins, Larry, Serge
Kleiner Perkins validated its strategic bet on climate technology by investing over $1 billion across 70 companies, a portfolio now valued at $3 billion despite initial market volatility. The discussion highlights how specific successes like Enphase offset losses in broader solar ventures while reinforcing an investment philosophy that favors being early on transformative ideas like Google. Concurrently, the analysis calls for urgent global decarbonization through measurable objectives and private sector leadership to address the escalating climate crisis.
- 6 min
Mac the VC Answers a Quick Fire Round of Questions with host Harry Stebbings | 20VC
Mac the VC, Harry Stebbings, McKeever "Mac the VC" Conwell II
Rare Breed venture capitalist discussed the personal and professional challenges of balancing family life with the long-term demands of multi-fund operations during an appearance at the Harvard Club. The speaker advocated for increased diversity in venture capital and urged greater flexibility toward founders requesting non-disclosure agreements, while highlighting Unspun as a recent investment that leverages 3D printing to create zero-waste jeans. The conversation also emphasized the importance of founder conviction in deal-making and concluded with a call to return to pre-pandemic social norms through a public health message.
- 31 min
Cost Plus Drugs: EXPLAINED | Mark Cuban Full Interview
Mark Cuban's self-funded venture, Cost Plus Drugs, bypasses traditional Pharmacy Benefit Managers to sell generic medications at a transparent wholesale cost plus a fixed markup, leveraging a direct-to-consumer model with over 50,000 users and daily growth exceeding 10,000 accounts. By utilizing TruePill for fulfillment and prioritizing operational efficiency over profit maximization, the platform aims to force pharmaceutical manufacturers to lower prices once a critical mass of ten million customers is reached. Cuban supports this disruption with a "hiring slow" internal philosophy and a vision for future blockchain-based claims processing, all while facing regulatory hurdles and supply chain scaling challenges inherent to the complex healthcare market.
- 43 min
Mac the VC on the Journey from Homeless To Becoming A VC | Full Interview with Harry Stebbings
Mac the VC, Harry Stebbings, McKeever "Mac the VC" Conwell II
Mac, a former software engineer and two-time founder, launched Rare Breed in 2020 after raising $10 million through a public solicitation model that bypasses traditional general partner commitments and leverages rolling closes. The Baltimore-based firm targets pre-seed companies outside major tech hubs, prioritizing returns among underrepresented founders in the Americas and the UK rather than adhering to industry gatekeeping norms. By utilizing a flexible capital call structure and public marketing under Regulation 506(c), Rare Breed has established a non-traditional investment vehicle designed to democratize access for emerging managers and overlooked talent.
- 45 min
Snowflake CEO Frank Slootman on How To Narrow The Focus and Increase The Quality | Full Interview
Frank Slootman, Harry Stebbings
CEO Frank Slootman advances a career strategy prioritizing company trajectory over individual merit, a philosophy that guided his impulsive 2019 transition to lead Snowflake during a period of organizational revitalization. His execution framework mandates extreme focus, rapid decision-making, and a rejection of traditional performance reviews in favor of high-conviction resource allocation and aggressive compensation calibration. Furthermore, Slootman advocates for hiring maladjusted yet empathetic talent while fostering a culture of rapid failure correction where leaders maintain high anxiety to ensure competitive vigilance and strategic autonomy.
- 6 min
Chris Sacca Talks About His Fears For Kids Today & What Kind of Job Everyone Should Work | 20VC
Chris Sacca, Harry Stebbings, Crystal, Bill Gurley
The speaker critiques the hyper-anxious pursuit of elite education and early specialization in youth as drivers of a generational decline in empathy and basic social etiquette. To counteract the monoculture within the technology sector, their organization exclusively hires candidates with backgrounds in service industry or manual labor to foster real-world perspective and humility. Ultimately, the presentation argues that systemic pressures are producing entitled individuals disconnected from the human condition, necessitating cultural shifts in both family prioritization and corporate hiring practices.