20VC with Harry Stebbings
Showing 526–540 of 691 transcripts.
- 1h 34m
Mike Salguero: How I Grew ButcherBox to $600M/year in Revenue; Tips for Influencer Marketing | E998
Mike Salguero, Harry Stebbings
ButcherBox CEO Mike Prieto is pivoting the bootstrapped $600 million revenue company from saturated influencer channels to media-stunt marketing and micro-influencer networks as traditional growth tactics fail. By abandoning asset-heavy infrastructure and VC-dependent growth models, the organization optimizes unit economics through a 5-month customer acquisition payback period to scale toward $1 billion while retaining full founder ownership. This strategy aims to establish a 100-year legacy institution that survives the current D2C correction by prioritizing operational efficiency over vanity metrics and rapid expansion.
- 1h 23m
Shopify CEO Tobi Lütke: Remote Work vs In-Person; The Benefit of Setting Constraints | E997
Tobi Lütke, Harley Finkelstein, Harry Stebbings
Tobias Lütke, founder of Shopify, presents a philosophy that prioritizes sustainable contentment over temporary happiness while advocating for decision-making based on 40% to 70% information and a commitment to truth over being right. He argues that maximum creativity and team effectiveness emerge from strict constraints and physical proximity for small groups, drawing parallels between jazz improvisation and modern remote work strategies that expand talent access despite minor productivity trade-offs. The presentation concludes that leadership success depends on maintaining an accurate model of the world to communicate effectively, rejecting traditional goal-setting in favor of craftsmanship and tangible output to navigate complex systems like AI and global markets.
- 8 min
Bill Ackman's Biggest Loss of All-Time
The speaker details the forced liquidation of Gotham Partners five years before the 2008 crisis following an MBIA white paper that triggered legal investigations and regulatory actions, alongside personal hardships during a 2015 to 2017 business downturn. Applying lessons from these structural failures regarding asset-liability mismatches, the founder established Pershing Square to invest exclusively in liquid large-cap companies while prioritizing rigorous internal reviews of both realized losses and missed opportunities like the Netflix position. Ultimately, the narrative emphasizes a resilience strategy combining physical health, supportive networks, and the discipline to reset after defeats, illustrated by a $2.8 billion interest rate hedge that remains regretted only for its insufficient capital allocation.
- 1h 19m
Jackie Reses: The Most Powerful Woman in Finance; Making $50BN for Yahoo on Alibaba | E996
Jackie Reses, former Square executive, founded The Bank We Wanted to See to build a scalable fintech infrastructure targeting high-growth tech and crypto sectors that existing providers fail to serve. Her leadership philosophy prioritizes innate grit and honest feedback over resume pedigree, fostering a high-performance culture while she negotiates deals by focusing on regulatory speed and long-term partner value rather than immediate economic leverage. Reses aims to establish Lead Bank as a global innovator by 2028, leveraging her expertise in compliance and finance to guide the next decade of fintech through an anticipated market rationalization and return to first principles.
- 1h 3m
Jag Duggal: How We Scaled Nubank to 80M Users; Google's Brutal Hiring Practices | E995
Jag Duggal, David Velez, Harry Stebbings, Kevin Systrom
Jack Borthwick, a former executive at Google and Facebook, relocated to Brazil to lead product strategy at NewBank, where he applies a hiring philosophy that prioritizes drive and clarity over traditional credentials to serve the bottom half of the global income pyramid. Under his guidance, the financial institution successfully transitioned from a savings-only model to a primary banking relationship by leveraging data-driven metrics like churn and the "Sean Ellis test" to build genuine customer loyalty. Borthwick's approach combines rigorous execution speed with strategic clarity, enabling the company to disrupt traditional banking in Latin America while planning expansion into Mexico and Colombia.
- 49 min
Dara Khosrowshahi: How I Became CEO of Uber; Uber Eats vs DoorDash; The Postmates Acquisition | E994
Dara Khosrowshahi, Harry Stebbings
Dara Khosrowshahi applies a philosophy of sustained excellence and calculated risk to guide Uber through its transformation from a crisis-ridden startup into a globally dominant logistics platform. By prioritizing marketplace technology over failed hardware ventures and correcting strategic missteps in delivery, he has successfully orchestrated complex supply-and-demand matching while shifting the board's focus from control to organizational success. His leadership approach emphasizes hiring for clarity of thought, maintaining a "plastic mind" to embrace mistakes, and allocating capital with a long-term perspective that balances Wall Street expectations with aggressive growth.
- 6 min
Bill Ackman wants to give $7000 to every baby
The speaker warns that rising post-crisis wealth inequality threatens societal stability by creating a divide where asset compounding vastly outpaces wage growth. To counteract this, the proposal combines a universal "Baby Bonds" program funding $6,500 accounts for every newborn with tax reforms targeting loopholes like like-kind exchanges and unrealized gains taxes. While rejecting a broad 25% tax on appreciation for risking a liquidity crisis in startups, the speaker argues that closing specific loopholes to fund these bonds is essential for providing every citizen a permanent economic stake without harming business formation.
- 56 min
Mike Maples: Lessons from SVB; Crisis Management Tips; USD's Status as the Reserve Currency | E993
Venture capitalist Mike Moritz warns that excessive currency printing and Federal Reserve errors have destabilized the global banking system, predicting a shift toward capital centralization in the "Big Four" banks by late 2023. He advises founders to mitigate these risks through rigorous scenario planning, maintaining liquidity across at least three non-correlated financial institutions, and adopting a crisis communication framework rooted in radical transparency. Furthermore, Moritz outlines shifting venture capital trends, noting that the capital-intensive nature of AI requires longer fund deployment timelines and a strategic focus on product-market fit over traditional board governance.
- 1h 2m
Frank Fillmann: How I Boosted Revenue by $500M at Salesforce; Tips for Hiring Salespeople | E992
Frank Fillmann, Zhenya Loginov, Harry Stebbings
Sales leader Frank synthesizes decades of experience, from door-to-door knife sales to managing teams of 75, into a methodology prioritizing potential over experience and the creation of latent demand. He advocates for "servant-leader" managers who build repeatable playbooks starting with financial metrics to cut ramp times to weeks while aligning sales with customer success through early integration. This approach emphasizes hybrid forecasting, deep discovery, and selfless leadership to navigate economic uncertainty and secure high-value enterprise deals in a transparent, remote-first market.
- 1h 7m
Bill Ackman: SVB Collapse, Biden vs Trump, How I Lost $400M on Netflix, Bill's 10-Year Long
Bill Ackman, Biden, Trump, Harry Stebbings
Bill Ackman and David Berkowitz launched their partnership with a $3.1 million fund by leveraging a shared track record of high achievement and living together to minimize initial costs. Following significant setbacks during the 2008 financial crisis, Ackman restructured Pershing Square to invest exclusively in liquid large-cap public companies while maintaining a disciplined approach to position sizing based on the risk of permanent capital impairment. In current markets, Ackman advocates for immediate federal guarantees on all bank deposits to prevent runs, argues that persistent inflation requires the Federal Reserve to pause rate hikes, and proposes policy reforms such as universal baby bonds to address wealth inequality.
- 9 min
How the FDIC Saves Failed Banks
Jackie Reses, Kris Dickson, Harry Stebbings
Following a weekend takeover by the FDIC, bank staff will analyze Silicon Valley Bank's balance sheet to prioritize repayment to the Federal Home Loan Bank, administrative expenses, and insured deposits up to $250,000. With 98% of depositors holding uninsured funds, the agency aims to stabilize the institution by selling super-liquid assets for immediate dividends or attracting a buyer like Morgan Stanley to assume liabilities, thereby preventing a protracted liquidation similar to Lehman Brothers. The final recovery amount for uninsured claimants will be determined on Monday based on asset sales, with speculation suggesting a potential 50% payout if no buyer emerges immediately.
- 7 min
Will there be more bank runs?
Jackie Reses, Kris Dickson, Harry Stebbings
Financial experts warn that secondary bank runs are highly probable and driven by panic psychology rather than fundamental weaknesses, with specific risks concentrated in institutions lacking diversification. To mitigate this, the FDIC plans to announce a buyer by Monday morning offering full deposit guarantees and immediate liquidity to stabilize markets before the U.S. trading day begins. While small businesses face the most severe threat of operational failure due to an inability to meet payroll, aggressive intervention is expected to prevent a worst-case scenario of widespread corporate insolvency.
- 1h 2m
Ophelia Brown: How We Raised $432M in a Pandemic; What's New in European Venture Capital | E990
Ophelia Brown, Harry Stebbings
Blossom, a $475 million Series A venture fund co-founded by Ophelia, Imran, and Alex, concentrates its European portfolio on 15 to 20 companies to provide high-touch operational support without relying on traditional investment committees or board seats. Diverging from industry norms, the firm rejects scout models and lead-investor syndication to maximize founder ownership while securing capital through a disciplined strategy that prioritizes speed and growth potential over investor brand prestige. Having overcome initial skepticism as a solo female general partner, Ophelia has established the firm with an explicit goal to become the top-performing venture fund in Europe or globally by 2028 through its concentrated, founder-centric approach.
- 7 min
COMMON MISTAKE: Confusing Metrics and Goals
This discussion examines the evolution of measurement standards from early-stage "registered users" to modern "monthly active users" while warning against the pitfalls of Goodhart's Law where metrics become targets. Founders are advised to adopt proven frameworks from industry leaders like Meta and eBay rather than reinventing strategies, ensuring their goals align with economic viability rather than mere forecasts. The session further highlights the necessity of human judgment in auditing these systems to prevent gaming, ultimately arguing that disruptive success often stems from singular visions rather than consensus decision-making.
- 8 min
Why did SVB collapse?
Jackie Reses, Kris Dickson, Harry Stebbings
The collapse of Silicon Valley Bank resulted from a critical maturity mismatch between its long-dated mortgage portfolio and a concentrated base of tech startup depositors, exacerbated by aggressive Federal Reserve interest rate hikes in 2022. A failed $1.5 billion capital raise announcement triggered a self-fulfilling liquidity crisis where depositors withdrew over $40 billion in hours, forcing the FDIC to seize the institution. This failure highlighted systemic vulnerabilities in the banking sector, where unrealized losses across the insured system reached a record $620 billion in the fourth quarter of 2022.