20VC with Harry Stebbings
Showing 406–420 of 691 transcripts.
- 52 min
Matt Rosenberg: Why You Should Not Hire Sales Leaders From Big Companies | E1068
Matt Rosenberg, Harry Stebbings
Former lawyer-turned-sales leader Matt outlines how accidental sales leaders from law and finance can build scalable enterprise motions by prioritizing discovery and "radical listening" over generic playbooks. He advises founders to hire senior operators capable of translating market needs into repeatable processes, quantify the economic cost of delay to drive urgency, and balance product-led growth with dedicated enterprise expansion strategies. Ultimately, the event emphasizes using data to diagnose rep performance, maintaining strict discount discipline, and diversifying leadership teams to include empathetic parents who excel at multitasking and time management.
- 1h 16m
Phin Barnes: The Services Model of Venture Capital is Broken, The Best Founders Do Need Help | E1067
Former First Round associates Finn Brosius and Dan Portillo launched The General Partnership to challenge the broken VC model by offering unbundled operational services like recruiting and go-to-market support in exchange for equity rather than management fees. The firm targets approximately 30 mature second-time founders through a concentrated, high-engagement approach that prioritizes operational execution and founder judgment over brand prestige or large check sizes. By structuring specific funds for sales and product verticals and utilizing formal Statements of Work, the partnership aims to align financial incentives directly with founder success while maintaining a scalable, high-context support system.
- 51 min
Kevin Niparko: Big Mistakes Founders Make When Hiring Product Teams | E1066
Kevin Niparko, Harry Stebbings
This session features insights from product leaders discussing a philosophy that prioritizes observing customer workflows over feature requests to drive major trends. The discussion outlines a framework for scaling product teams by balancing art and science, implementing weekly demos as a forcing function, and allocating resources across three innovation horizons. Additionally, the event provides strategic guidance on hiring generalist leaders, avoiding the build trap, and timing the introduction of secondary products to sustain core growth.
- 1h 16m
Christian Lanng: "How Being a Founder Almost Killed Me" | E1065
Christian Lanng, Harry Stebbings
Following a severe health crisis and realization of deep burnout after 14 years, TradeShift co-founder Christian resigned from his executive role to prioritize well-being and address a "valuation trap" caused by early high-finance decisions. Transitioning into a new venture called "Beyond Work," he now advocates for AI-first architectures that eliminate traditional software interfaces while arguing that proprietary data and trust are the primary competitive moats for future enterprise solutions. His revised investment philosophy favors second-time founders and a "Beyond Work" vision designed to automate corporate tasks by placing humans at the center of workflows rather than forcing them to adapt to rigid systems.
- 30 min
Marc Benioff: The Future of San Francisco and What He Would Do if in Charge | E1064
Salesforce CEO Mark Benioff outlined the company's strategic shift toward autonomous AI agents and the launch of the Einstein 1 platform while asserting its status as the leading enterprise AI provider. Benioff defended San Francisco's economic vitality through record office demand and proposed increased policing to address safety concerns, all while reinforcing the firm's hybrid work model and commitment to its philanthropic 1-1-1 legacy. Looking toward 2033, the organization aims to integrate generative AI and AGI capabilities across its CRM suite through collaborative futurist strategies and a core values framework centered on trust, innovation, and customer success.
- 47 min
Christian Kleinerman: Do OpenAI and Anthropic Have a Sustaining Moat? Who Wins the AI Wars? | E1063
Christian Kleinerman, Harry Stebbings
Christian, a veteran executive with deep experience at Microsoft, Google, and now Snowflake, outlines a strategic vision where generative AI serves as a fundamental disruption driven by proprietary data rather than model size. He warns that while creative industries are early adopters, widespread enterprise implementation is currently hindered by data maturity gaps and regulatory constraints, particularly in healthcare and the public sector. Looking forward, he predicts that incumbents with vast data reserves will capture the most value, as the industry shifts toward specialized, cost-effective models and integrated platforms that bring computation directly to existing data ecosystems.
- 1h 24m
Is the VC Model Broken? Jason Lemkin, Mike Maples, Eric Paley & Harry Stebbings Debate | E1062
Jason Lemkin, Mike Maples, Eric Paley, Harry Stebbings
The panelists analyze a market characterized by rationalizing seed valuations and a pervasive disconnect between fund valuations and actual returns, warning that the current AI boom and high valuation culture pose significant risks of a bubble. Speakers emphasize that over-capitalization at early stages often leads to premature scaling and poor founder decisions, advocating instead for non-consensus investing and long-term holding horizons to generate sustainable alpha. Looking toward the near future, the discussion predicts persistent gaps between total value invested and distributions through 2025, driven by compressing public multiples and a shift from momentum-driven speculation to fundamental business performance.
- 1h 44m
Miles Grimshaw: The 5 Pillars of Venture Capital & Why Co-Pilot is an Incumbent Strategy | E1061
Miles Grimshaw, Josh Kushner, Bill Gurley, Peter Fenton, Harry Stebbings
Matt Hargrave, a general partner at Benchmark Capital, articulates a philosophy of "impatient patience" and "founder respect" while critiquing early-stage market hesitations on companies like Figma and Plaid. He predicts a fundamental shift in computing architecture where AI moves from selling software to selling outcomes, positioning his firm's early backing of LangChain as a strategic play for the new ecosystem of millions of AI developers. Drawing parallels to his ultra-running endurance, Hargrave emphasizes that successful venture capital requires clinical curiosity and the ability to integrate holistic founder assessment over rigid metrics.
- 1h 0m
Suchit Dash: Scaling Dubsmash to 43M Users, Battling TikTok & Joining Reddit | E1060
Sujit, who transitioned from PayPal to founding Dubsmash, led a pivotal strategic shift that transformed the lip-sync app into a dance-challenge platform, ultimately driving retention from 5% to 30% before securing a 2020 acquisition by Reddit. Drawing on lessons from Dubsmash's organic growth and eventual sale against TikTok, he now applies his product philosophy at Reddit to prioritize interest-based community engagement over traditional social graphs. His career trajectory highlights the critical importance of rapid iteration and the courage to make unilateral pivots, such as shutting down established markets to capture a specific user niche.
- 1h 9m
David Velez: How AI Changes The Future of Finance | E1059
David Velez, Harry Stebbings, Doug Leone
David Vélez transformed Sequoia Capital's character-centric interview methodology into the founding philosophy for Nubank, a Brazilian digital bank that now serves nearly half the country's adult population by prioritizing deep market penetration over rapid geographic expansion. Facing an exit from Sequoia's Latin American division due to a lack of local investment opportunities, Vélez leveraged that direct feedback to build a "beginner's mind" culture focused on solving financial exclusion rather than mimicking Silicon Valley models. The company is currently capitalizing on AI as a second platform shift to democratize high-net-worth banking and evolve into a broader consumer marketplace, all while vigilantly avoiding internal complacency in a region where traditional financial incumbents remain vulnerable to disruption.
- 1h 2m
Doug Adamic: Why Discounting is BS; How to Reduce Sales Cycles and Create Urgency | E1058
Former Concur and Brex executive Doug outlines a sales methodology that prioritizes high-quality pipeline generation and disciplined listening over volume, asserting that demand creation is a shared responsibility across all departments. He advocates for precise stakeholder management, value-driven urgency, and AI-enhanced efficiency to transform sales teams into consultative partners who challenge the status quo rather than relying on transactional tactics. By shifting focus to profitable conversion rates and seamless executive handoffs, organizations can achieve greater predictability and sustainable growth even in challenging market conditions.
- 1h 8m
Nikhil Basu Trivedi: Why 99% of AI Investments Will Go Bust | E1057
Nikhil Basu Trivedi, Harry Stebbings
A venture firm led by a partner team advocates for a disciplined investment philosophy that prioritizes traction and founder resilience over market size projections or rigid thesis constraints. By operating with a $175M fund size, the firm targets outlier companies like Canva while avoiding large early-stage rounds that encourage stagnation, enforcing a strict voting protocol where deals require unanimous strong support. Their strategy focuses on capital efficiency, diverse LP relationships, and a hands-on operational model where both partners attend every board meeting to ensure true partnership and avoid diluting conviction in follow-on investments.
- 54 min
Mudassir Sheikha: The Meeting that Led to $3.1BN Buyout: The Battle Between Uber and Careem | E1056
Mudassir Sheikha, Harry Stebbings
Co-founded in 2011 by Muntaz Adib and Magnus Olsson to address regional infrastructure friction, Kareem evolved from an SMS-based ride-hailing service into a 2019 Uber acquisition that valued the platform at a deal allowing for significant employee wealth creation. The company differentiated itself through capital-efficient operations and hyper-local adaptations like cash payments, eventually pivoting to a diversified super-app model during the pandemic despite a contentious exit process. Looking toward 2033, the organization now prioritizes sustainable retention and high-margin growth over aggressive expansion to become a daily utility across the Middle East and North Africa.
- 37 min
Noam Shazeer: How We Spent $2M to Train a Single AI Model and Grew Character.ai to 20M Users | E1055
Noam Shazeer, CEO of the full-stack AI platform Character.ai, leads a direct-to-consumer initiative processing 450 million daily messages by leveraging neural language modeling to deliver flexible superintelligence to 20 million users. The company distinguishes itself through a B2C strategy that encourages user-driven innovation, successfully adapting to unexpected adoption trends where users employ AI characters for emotional support and companionship rather than pre-defined enterprise tasks. While prioritizing data privacy and treating hallucinations as creative features for engagement, Shazeer positions the platform at the forefront of an emerging technological wave comparable to the invention of electricity, where massive computational scale drives human-level conversation.
- 53 min
Cris Valenzuela: AI Creators vs Hollywood Writers; How We Grew Runway into a $1.5B Company | E1054
Cris Valenzuela, Harry Stebbings
Founded in 2016 by CEO Cristian and NYU ITP alumni, Runway has grown into a lean 55-person team dedicated to bridging the gap between generative AI research and creative workflows. The company aggressively iterates on video generation tools like Gen 2 while rejecting industry dogma in favor of a pragmatic, free experimentation model that treats creative "hallucinations" as features. By prioritizing compute infrastructure over perfect model architecture, Runway aims to establish itself as the foundational camera of the new medium within the next decade.