20VC with Harry Stebbings
Showing 646–660 of 691 transcripts.
- 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.
- 56 min
Tony Fadell: Why You Can't Be a Solo Founder; Mercenary vs. Missionary Operators | 20VC #910
Tony advocates for resilience and anti-helicopter parenting by leveraging his own history of frequent relocations to foster adaptability, a philosophy that extended into his career by compelling him to create unique roles at major tech firms like Apple and Phillips. His leadership framework distinguishes between "Coach," "Parent," and "CEO" modes, urging professionals to seek co-founders with complementary skills and to invest counter-intuitively in long-term sectors like green technology before market data validates them. Ultimately, Tony aims to serve as a scalable mentor through his book *Build*, guiding others to navigate cyclical economic downturns and establish mission-driven cultures without succumbing to the isolation of sole-founder status.
- 54 min
Kyle Samani: Why Bitcoin is Not a Hedge Against Inflation | 20VC #909
Founded by Kyle Noller in 2017, Multicoin Capital has evolved into a distinctive venture firm that prioritizes token-based thesis formation and aggressive information consumption over traditional portfolio diversification or founder pedigree. The firm's investment philosophy centers on analyzing network effect curves and capital formation mechanisms, utilizing a high-intensity culture of active disagreement among a lean core team of ten to stress-test hypotheses before deploying capital. While rejecting SaaS models and dual equity-token structures, Multicoin leverages the liquidity of crypto assets to achieve lower loss rates and rapidly exit positions, aiming to bootstrap decentralized infrastructure like Helium through carefully timed incentive mechanisms.
- 57 min
Sam Taylor: How I Became VP of Sales at Loom; Lessons from Dropbox | 20VC #908
Sam O'Sullivan, currently leading sales at Loom, outlines a strategic evolution from rigid sales scripts to adaptive frameworks that prioritize understanding customer workflows and cross-functional collaboration. He argues that early-stage sales leaders should focus on gathering market insights rather than immediate quotas, using high base salaries and take-home video assessments to identify curious talent capable of bridging product development with go-to-market strategy. This approach enables companies to successfully transition from product-led growth to enterprise sales by addressing complex organizational hurdles, such as category creation in large enterprises, through deep relationship building and iterative deal reviews.
- 1h 13m
Des Traynor: How I Founded Intercom; Product Marketing Tips; Feature Creep | 20VC #907
This discussion features Intercom co-founder Brian Intercom exploring product strategy, venture capital investment philosophies, and operational leadership through specific case studies like Miro and Figma. The conversation details critical frameworks for building defensible moats via execution rather than first-mover advantage, distinguishing between features and standalone products, and adapting go-to-market approaches for B2B enterprise clients. It concludes with insights on navigating founder-investor dynamics, avoiding hiring biases like "logo bias," and the author's personal roadmap to transition out of operational roles by 2027.
- 52 min
Peter Singlehurst: The Most Powerful Investor You've Never Heard of | 20VC #907
Bailey Gifford leverages its unique partnership structure and the evergreen Scottish Mortgage Fund to execute a growth investment strategy that blends public and private market analysis across a concentrated portfolio of mid-to-late-stage companies. By prioritizing cognitive diversity over traditional financial backgrounds and rejecting the standard venture capital label, the firm deploys capital to founders who focus on long-term value creation rather than immediate liquidity events. This approach has yielded substantial returns from over a dozen decades of investing while maintaining strict alignment with the philosophical conviction that share prices are merely uncontrollable outputs of fundamental business progress.