20VC with Harry Stebbings
Showing 361–375 of 691 transcripts.
- 7 min
Moving from Founders Fund to Khosla with @Khosla Managing Director Keith Rabois
After a five-year tenure at Founders Fund, the speaker rejoined Coastler Ventures, drawn by a persistent desire to return to the firm's rigorous collective debate model and deep technical education environment. Unlike the individual manager strategy previously employed, the new arrangement restores intensive weekly partner sessions where figures like David, Samir, and Vinod engage in structured arguments to sharpen analytical skills across financial, founder, and data science domains. This transition resolves a long-standing gap in professional development that the speaker had missed despite maintaining frequent co-investment activities with the original partners during their departure.
- 1h 16m
Keith Rabois on Rejoining Khosla Ventures | E1102
Keith Reboy is returning to Coastal Ventures after six years at Founders Fund to re-engage with the firm's rigorous partner-led investment model while defending its $4.1 billion fund structure. His strategy emphasizes early-stage conviction over price discipline, prioritizing seed and Series A deals where founder alignment allows for meaningful intervention before companies solidify. Reboy plans to leverage his extensive experience and network to navigate a volatile growth market without launching a new fund, aiming to maximize impact through high-conviction allocations rather than pre-allocated reserves.
- 1h 15m
Ed Sim & Jamin Ball: Did Figma Kill M&A Markets & 3 Requirements to IPO in 2024 | E1101
Ed Sim, Jamin Ball, Harry Stebbings
Venture capital market dynamics have shifted from the 2021 funding bubble to a restrictive 2024 environment where late-stage valuations have contracted by 90% and antitrust scrutiny limits large-scale M&A. Founders and investors like Ed Sim and Jarmin Ball now prioritize cash-flow breakeven and realistic growth metrics over inflated multiples, forcing a strategic pivot toward "acqui-hires" and private-to-private transactions. Looking ahead, the industry views 2024 as a critical vintage for deploying capital at adjusted prices in emerging sectors like AI security and data infrastructure, emphasizing manager selection over vintage timing to generate sustainable returns.
- 55 min
Crypto Roundtable with Nick Tomaino & Kyle Samani: US Elections, NFTs, and Trump | E1100
Nick Tomaino, Kyle Samani, Trump, Harry Stebbings
Multicoin Capital managing partner Kyle Samani and crypto purist Nick Tamaino debate the roles of speculation versus utility in the blockchain ecosystem, contrasting Samani's aggressive commercial approach to Solana's high-performance architecture with Tamaino's focus on long-term authenticity and social innovation. The participants analyze the collapse of major entities like FTX and Luna as warnings against greed-driven markets while discussing the divergent regulatory paths for Ethereum and Solana under potential changes to the SEC chairmanship. Looking toward the next five years, the speakers envision a future where financial infrastructure integrates directly into consumer devices and NFTs bridge mainstream culture with decentralized finance.
- 1h 33m
Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099
Jason Lemkin, Trump, Harry Stebbings
Jason Lemkin's 2023 Venture Capital Market Review analyzes a conservative funding environment characterized by high unicorn failure rates, aggressive efficiency drives by public SaaS firms, and a strategic pivot toward decacorns. He forecasts a delayed IPO wave extending into 2025 while warning that enterprise AI adoption will initially remain limited by functional budget constraints and geopolitical shifts. Simultaneously, Lemkin outlines Sastra's transformation into a $100 million IRL marketplace to replace traditional media models with direct transaction facilitation between software buyers and sellers.
- 1h 10m
Dave Powers: The Meteoric Rise of Hoka Running | E1098
Deckers Brands leveraged a disciplined strategy to transform Hoka from a niche running label into a $1.4 billion revenue driver while managing UGG's transition from over-distribution to a premium position. Executive Dave Powers drives this performance through a "kind but aggressive" culture that prioritizes profit margins over raw growth, actively divesting weaker assets like Sanuk to fund innovation against rising Asian competitors. The company navigates market volatility by maintaining a cautious direct-to-consumer approach and balancing resource allocation between its two primary growth engines to ensure long-term brand viability.
- 56 min
Roundtable #7: Spotify, Adobe and Linkedin on How AI Changes The Future of Product & Design | E1097
Gustav Söderström, Scott Belsky, Tomer Cohen, Harry Stebbings
Product leaders from Adobe, Spotify, and LinkedIn converge on an AI-first paradigm that prioritizes specialized long-tail models and proprietary data over general-purpose mega models to secure competitive moats. This strategic shift necessitates a redesign of user interfaces into probabilistic AI personas, transforming design roles to encompass model mechanics, prompt engineering, and cost-efficient infrastructure management. While traditional seat-based licensing remains prevalent, the industry anticipates a future where value-based pricing replaces headcount metrics, driven by the need to simplify complex workflows through intelligent model routing and verticalized hardware.
- 1h 22m
Peter Lacaillade: Why Now is the Best Time to Invest in Emerging Managers | E1096
Peter Lacaillade, Harry Stebbings
SCS, now managing $30 billion in assets, has scaled its private equity deployment to $1.5 billion annually by leveraging a post-GFC strategy that favors emerging managers over established funds. Led by Harry Peter Mattoon, the firm employs a barbell approach combining venture and buyout allocations while utilizing rigorous "off-list" diligence to identify "force of nature" entrepreneurs. This methodology supports a diverse portfolio of 10 to 15 niche funds and includes a co-investment program yielding significant cost advantages, all designed to navigate current industry challenges like compressed deployment timelines and market volatility.
- 1h 13m
Davis Smith: From Selling $6M of Pool Tables to Scaling Cotopaxi to $150M in Revenues | E1095
Davis Smith leveraged over a decade of entrepreneurial experience, including a failed $40 million Brazilian venture and Cotopaxi's successful growth, to challenge conventional fundraising strategies and the structural misalignment between mission-driven founders and traditional venture capital. He details Cotopaxi's evolution from a purpose-built movement to a profitable B-Corp that tripled revenue while prioritizing employee well-being through pay cuts instead of layoffs, despite his eventual transition to lead a church mission in Brazil. Smith advocates for a new paradigm in commerce where capital supports long-term social impact rather than short-term exits, ultimately urging leaders to align business growth with personal values and global poverty alleviation.
- 55 min
Steve Goldberg: Core Questions All CFOs Ask Today When Buying | E1094
Steve Goldberg, Harry Stebbings
A recent industry analysis highlights a decisive market shift toward performance-driven sales cycles where CFOs rigorously scrutinize renewals as new deals, necessitating a move from legacy relationship-building to data-backed strategies. To navigate this landscape, organizations are prioritizing Revenue Operations roles and implementing "hunter-hunter" models alongside intensive hiring processes that assess candidate grit through multi-hour case studies and third-party validation. Furthermore, the consensus advocates for replacing adoption metrics with outcome-based results and restructuring discounting negotiations to focus on long-term value, ensuring companies optimize operations for efficiency before pursuing further scaling.
- 7 min
How To Engage With An Investor with Level CEO Sam Corcos
The speaker details a strategy for maximizing value from a large angel network of approximately 100 investors by replacing vague networking requests with over 3,000 highly specific, actionable asks. This data-driven approach, which includes concrete metrics and social accountability mechanisms like shared Google Sheets, achieved a 50% conversion rate compared to the industry average of five annual requests. Furthermore, the presentation emphasizes the critical need for founders to explicitly document needs and define engagement expectations early to distinguish between strategic partners and those unable to provide tangible support.
- 1h 20m
Sam Corcos: Why Founders Should Take as Many VC Meetings as Possible | E1093
In a detailed discussion on operational strategy, the founder of Levels outlines a fundraising approach that prioritizes broad investor outreach and transparent performance metrics, aiming to secure partners who already understand the company's vision rather than converting skeptics. The company implements radical transparency internally, utilizing the Netflix "Keeper Test" to maintain a lean team of 50 high-performing employees and eliminating functional titles to foster a culture where contribution outweighs hierarchy. Looking toward 2028, the leadership team targets a 40% retention rate while advocating for intentional leadership practices that balance rigorous professional execution with a dedicated focus on family life and societal epistemic stability.
- 1h 7m
Sanjit Biswas: Samsara's $18BN Market Cap & $1BN in ARR in 8 Years | E1092
Sanjit Biswas, Harry Stebbings
Samsara employs a 70-20-10 capital allocation strategy and a "market-first" methodology to scale products by tenfold while rejecting technology-led pivots in favor of organic customer demand. The company expands through concentric product circles and hybrid workforce models, leveraging AI for tangible operational value rather than speculative growth. Serial founder leadership drives this compound growth by prioritizing problem-solving over raw IQ and reinvesting billions into long-term infrastructure to maintain scalability.
- 1h 0m
Geoff Charles: How To Hire Product Teams & Increase Product Velocity | E1091
Geoff Charles, Harry Stebbings
Ramp executives outline a rigorous early-stage framework emphasizing direct founder-led sales, scrappy hiring practices, and a two-speed development cadence to validate product-market fit before scaling. Their methodology prioritizes observing actual customer usage over verbal feedback, utilizing professional services tactics to drive customizations that foster deep loyalty among initial design partners. Furthermore, the leadership strategy advocates for a hypothesis-driven product culture where clear goals and leading metrics guide decisions, balancing the "art" of design with the "science" of rigorous execution.
- 6 min
How to Make Marriage Work as a CEO w. Procore Founder and CEO Tooey Courtemanche
Tooey Courtemanche, Brian, Will, Harry Stebbings
In a candid discussion about leadership and longevity, a Procore founder and his wife of 25 years advocate for a strict firewall between professional life and family, arguing that marital stability relies on persistence rather than the pursuit of happiness. The speaker challenges the myth that life should be safe and predictable, positing that resilience and voluntary exposure to adversity are the true drivers of success and that current global economic shifts may ultimately harden younger generations similar to the impact of World War II on the Greatest Generation. By rejecting the notion that challenges diminish over time, he asserts that both business and marriage are perpetual struggles requiring agility to navigate constant change.