20VC with Harry Stebbings
Showing 661–675 of 711 transcripts.
- 45 min
dLocal CEO Sebastian Kanovich: The $8BN Company You Might Not Know | 20VC #926
Sebastian Kanovich, Seba Kanovich
Seba Sacerdotte guides D-Local, a Latin American payment processor with a lean workforce of 650 across 35 countries, toward a long-term transformation into a comprehensive financial services provider for emerging markets. Having navigated a transition from a bootstrapped entity to a publicly traded company with General Atlantic's backing, the firm prioritizes rapid execution and customer-led product development while avoiding reliance on established corporate affiliations. Sacerdotte's leadership philosophy centers on aggressive market entry in high-friction regions and a culture of extreme frugality that evolved into a 100-year strategic mindset following the company's 2021 IPO.
- 49 min
Eleanor Dorfman: How We Scaled Retool to $50M ARR; Red Flags for Sales Hires | 20VC #925
Eleanor, a seasoned leader who rose from an unpaid intern at Clever to Head of Customer Success at Retool, advocates for prioritizing character and curiosity over pedigree when hiring early-stage sales talent. She advises founders to defer building sales playbooks until product-market fit is achieved and to compensate teams using bell-curve logic that ensures at least 80% of representatives can meet their targets. Emphasizing the shift from transactional selling to behavior change, she urges organizations to invest in sales infrastructure and diverse leadership before scaling, while rejecting discount-heavy strategies in favor of validating customer ROI.
- 1h 9m
Will Quist: Why 95% of Venture Capital is Not Really “Venture Capital” | 20VC #924
Will Quist, Harry Stebbings, Don Valentine
Will, a sixth-generation Bay Area native, launched SLO after a decade at Industry Ventures to challenge an industry he argues has abandoned true venture for consensus-driven growth capital. Operating with a "Special Forces" approach for early bets, the firm applies Charlie Munger's five enterprise value levers to identify founders and markets capable of converting hypotheses into first-party data. SLO remains a focused classic venture firm committed to avoiding multi-stage dilution while educating the market on which business models genuinely require venture funding.
- 1h 5m
Michael Mignano: How I Founded Anchor; Why TikTok could be a $2 TRILLION Company | 20VC #923
Venture partner Mike Volpi joins Lightspeed Venture Partners in New York to lead its new consumer team, leveraging his extensive experience to advocate for greater industry candor and transparency in founder-investor relationships. Drawing on his background with Anchor and past angel investments, he plans to execute early-stage capital deployments within 60 days while focusing on defensible social media innovations and direct creator monetization tools. His strategy emphasizes moving beyond traditional social graphs toward recommendation engines, aiming to help startups navigate the shift from viral hype to sustainable, algorithm-driven growth.
- 50 min
Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921
Former Expert Financial product lead and Calendly executive Annie shares critical insights on navigating product strategy from initial market fit to enterprise-scale growth. She outlines a framework for identifying the optimal timing to hire a CPO based on organizational maturity while warning against premature diversification or reacting impulsively to competitor moves. Her analysis further details a three-phase hiring process for product leaders and emphasizes the necessity of aligning go-to-market incentives with new product launches to avoid revenue shortfalls.
- 1h 0m
Logan Bartlett: WTF is Happening at Growth Stage Investing? | 20VC #920
Logan Bartlett, Harry Stebbings
Redpoint Ventures partner Logan Williams discusses his career trajectory from Battery Ventures to Redpoint and outlines the firm's distinct strategy of balancing individual partner brands with deep domain expertise. Williams analyzes the current venture landscape, noting a capital shift from late-stage Series B and C rounds to earlier seed and pre-seed stages that has driven valuation inflation while creating a dearth of mid-market deal flow. He further details Redpoint's investment discipline, emphasizing a focus on ownership in high-conviction winners over "spray and pray" tactics, advocating for transparent portfolio mark-downs, and stressing the critical role of board governance in guiding founders through market corrections.
- 54 min
Wesley Chan: How I Created Google Analytics; The Founding Story of Gmail & Canva | 20VC #919
Wesley Chan, Wes Chan, Larry, Sergey, Aydin Senkut
Former Google executive Wesley Chan leverages his decade of product experience to lead FPV Ventures, a $450 million fund managed by a small team that prioritizes "market creation" and 100-year founder visions over traditional metrics. The firm targets 20 core investments with checks between $10 million and $20 million, explicitly excluding crypto while focusing on revenue-generating businesses like Canva and Plaid to provide a safe harbor for charity-focused limited partners. By rejecting dogmatic ownership requirements and intervening only when requested, Chan's strategy aims to identify outlier companies capable of adapting the world for a century.
- 1h 4m
Jordan Van Horn: 3 Reasons Salespeople Fail; How to Make a Sales Playbook | 20VC #918
Jordan Van Horn, Head of Revenue at the billion-dollar data observability firm Monte Carlo, leverages his diverse background from Gala Winery, Dropbox, and Segment to refine go-to-market strategies for high-growth startups. He advocates for founders to own a disciplined sales playbook that clearly defines the problem, target audience, and urgency while ensuring multi-threaded relationships to mitigate churn risks during scaling. Van Horn further emphasizes building culture through transparent hiring practices, rigorous behavioral interviews, and a "User Guide" approach to align team expectations and foster rapid onboarding efficiency.
- 54 min
Sheel Mohnot: Lessons from Investing in Flexport and Missing on Robinhood | 20VC #917
Sheel Mohnot, Jake, Justin Bieber, Harry Stebbings
Better Tomorrow Ventures, co-founded by Sheil and NerdWallet's Jake Gibson, operates as a concentrated FinTech-focused fund targeting 10 to 15% ownership stakes in approximately 30 portfolio companies while prioritizing capital efficiency. The firm leverages Sheil's founder exits and microfinance background to execute a disciplined strategy that increased follow-on allocations in Fund 2, despite acknowledging past regrets over missed exits in companies like Robinhood and Chime. Looking ahead to 2027, the partnership aims to solidify its position as a global partner for fintech founders, maintaining a concentrated portfolio approach even as macroeconomic headwinds reshape emerging market opportunities.
- 1h 2m
Kieran Flanagan: Hiring Tips for Growth; North Star Metrics; Hubspot's Mistake | 20VC #916
Industry experts outline a framework for scaling companies through three maturity stages, advising founders to prioritize retention over acquisition revenue until product-market fit is established. They contrast product-led and sales-led organizational structures while emphasizing rigorous hiring practices that favor execution skills over brand prestige and the necessity of cross-functional alignment to navigate internal friction. The discussion concludes by evaluating shifting marketing tactics, noting the decline of paid advertising effectiveness and the rising strategic value of building deep communities supported by durable channels like email automation.
- 1h 1m
Mo Koyfman: The Secret to Winning in Venture; Why Small Funds Outperform Large Funds | 20VC #915
Mo Koyfman, Fred Wilson, Philip Roth
Mo, a veteran investor who previously led M&A at IAC and joined Spark Capital before founding Shine, operates a $325 million venture firm structured around a hierarchical leadership model rather than traditional partnerships. His strategy prioritizes high-conviction "stock picking" in Seed and Series A rounds with limited portfolio sizes, enforcing disciplined capital allocation and rejecting deals that feature founder greed or exclusionary terms. By targeting 10–12% ownership stakes and avoiding blanket pro rata commitments, Shine aims to achieve top-10 early-stage status by 2027 through a rigorous focus on chemistry and rational market constraints.
- 56 min
Cambly CEO Sameer Shariff: Why I Raised $60M and Didn't Touch a Dollar | 20VC #914
Founded by Samir Arora and Kevin, Cambly operates as a data-driven global marketplace connecting 1.5 billion non-native English learners with native tutors to leverage the efficacy of one-on-one instruction. The company transitioned from intuitive growth to capital efficiency, securing cash flow positivity by 2017 through a "paid usage" model and strategic hiring that prioritized management aptitude over individual contributor skills. With a long-term mission to serve the fraction of the global population currently unserved, Cambly now focuses on scaling via improved matching algorithms and expanded affordability while navigating the complexities of maintaining speed as it grows from a lean startup to a structured organization.
- 1h 1m
Shreyas Doshi: The 6 Product Metrics You Need To Know; The 3 Types of Product Leader | E913
Shreyas Kasiviswanathan defines product management through a six-category metric framework and identifies three distinct leader personas—operators, craftspersons, and visionaries—to guide hiring decisions from the pre-product-market fit stage through scaling. He advises founders to prioritize strategic frameworks like the "Below, Table Stakes, Differentiation" model to avoid commodity traps while emphasizing that early-stage success relies more on qualitative feedback than quantitative perfection. Ultimately, the presentation underscores that founder responsibility for product strategy remains absolute and that successful investing hinges on identifying leaders with deep domain instincts rather than prestigious resumes.
- 49 min
Kirsten Green: The Biggest Challenges Scaling Both Teams and AUM | 20VC #912
Kirsten Green, Harry Stubbings
Kirsten, a former employee investor who launched Forerunner Ventures at age 40, leverages a unique non-linear background to drive a "Consumer North Star" investment thesis that increasingly targets B2B sectors serving shifting consumer behaviors. Operating a small, tightly-knit team with a leadership style defined by empowerment and rigorous quality standards, she navigates complex market dynamics by emphasizing strategic optimization and authentic decision-making over traditional credentials. Despite economic headwinds, her firm remains focused on building resilient companies through strict fundamentals, aiming to deliver top-quintile returns while fostering a culture where individuality and collective goals coexist.
- 58 min
Yahoo CEO Jim Lanzone: The Yahoo Turnaround Plan | 20VC #911
Jim Bankofman, a seasoned executive known for turning around Ask Jeeves and leading Tinder and CBS Interactive, assumed the CEO role at Yahoo in September following its Apollo Global Management buyout. He is executing a federal restructuring model that empowers vertical-specific General Managers while leveraging the company's 900 million monthly users and strong brand equity to drive long-term growth. Bankofman aims to position Yahoo for a public company return within five years by balancing immediate user experience fixes with strategic investments and avoiding the pitfalls of over-monetization.