Harry Stebbings
Showing 556–570 of 632 transcripts.
How to Structure Sales Comp
The session outlines critical strategies for structuring early-stage sales compensation by prioritizing risk-tolerant hires and aligning incentives through collaborative, iterative plan development. It further details methods for maintaining team morale during market downturns via strategic transparency and the tactical use of gamified "small wins" to sustain momentum. Finally, the discussion defines effective Sales Performance Incentive Funds, illustrating their application through activity-based goals and monetary multipliers like Twilio's "Pipe Pipe Week" to drive non-routine business objectives.
Orlando Bravo: Raising Kids as a Billionaire; VC vs PE; Is Warren Buffet Wrong? | 20VC #974
Orlando Bravo, Warren Buffet, Harry Stebbings
Toma Bravo, a software-focused private equity firm founded in 2008, generates alpha by acquiring profitable B2B market leaders and systematically improving cash flow margins through rigorous operational discipline and consensus-driven decision-making. Under the leadership of founder Orlando Bravo, the firm rejects speculative venture valuations in favor of a "value plus growth" model that prioritizes future yield, recently navigating a challenging interest rate environment by targeting high-quality assets trading at reasonable multiples. Looking ahead, the firm plans to scale its mission impact by 2028 while expanding its foundation's support for emerging entrepreneurs, maintaining a focused portfolio strategy that avoids the operational pitfalls of excessive diversification.
Income Inequality & The Knowledge Revolution
Albert Wenger, Harry Stebbings
The event examines the transition from an industrial to a knowledge economy, arguing that attention has become the primary constraint necessitating a shift toward Universal Basic Income to stabilize inequality and provide a societal floor. It advocates for leveraging AI and automation to shrink the market-driven economic sphere, thereby expanding a non-economic domain focused on childcare, arts, and social connection. Furthermore, the presentation critiques the industrial-era education system while proposing new frameworks to secure informational and psychological freedom against modern digital distractions.
Alex Bouaziz: How We Became a $12B HR Company with 2,000 Remote Employees | 20VC #973
Founded in 2019 by Alex Bouaziz and Shuo Yang, Deel has scaled to 2,000 employees across 100 countries by pivoting from freelancer trust tools to a comprehensive global compliance and payroll platform. The organization leverages a fully distributed model and aggressive acquisitions to deliver rapid "Deel Speed" in execution while maintaining deep infrastructure for legal and payroll services. With a vision to help hundreds of millions of people work globally, the company combines its cross-cultural founding team with the operational discipline of its CFO to navigate complex international labor markets.
Ultimate Guide to Interviewing a Growth Candidate
Founders are guided to define specific growth models and North Star metrics before drafting job descriptions to attract expertise in either channel amplification or full-funnel optimization. Candidates undergo a rigorous evaluation process involving take-home assignments that assess their ability to audit user journeys, propose experiments, and analyze real data, while interviewers specifically screen for ego and reliance on outdated playbooks. The final hiring decision is made by a cross-functional panel comprising leadership, technical teams, and functional partners to ensure strategic alignment before extending an offer.
Homebrew’s Hunter Walk & Satya Patel: Why $100M is Not Enough to Execute a Seed Strategy | 20VC #972
Hunter Walk, Satya Patel, Harry Stebbings, Robbie, Sacha, Kieran, Eric, Jason Lampkin, Larry
Founded in 2012, Homebrew operates as a two-partner investment firm that transitioned to a self-capitalized model in late 2022 to maintain total decision-making autonomy and strict consensus governance. By funding their own operations through recycled carry rather than external limited partners, co-founders Satya Nadella and Hunter walked away from fixed fund sizes to pursue price-agnostic, long-term portfolio building focused on founder alignment over rapid exits. This strategy allows the partners to prioritize deep operational support and early secondary liquidity for founders while navigating a market correction that favors companies with genuine product-market fit over those reliant on inflated valuations.
Canva's Cliff Obrecht: How We Turned Our Yearbook Company to $40B Business | 20VC #971
Cliff Obrecht, Mel, Keith, Harry Stebbings
Canva co-founders Melanie Perkins and Cliff Obrien describe their journey from rejecting over 100 venture capital offers to building a global design platform by prioritizing user delight, rigorous technical restructuring, and a unique hiring philosophy that values "distance traveled" over pedigree. The leadership team outlines their strategic shift toward AI-driven co-pilots, their commitment to bundling interoperable creative tools, and their decision to donate 99% of their equity to the Canva Foundation to address global poverty. Looking ahead to 2027, the founders aim to unify fragmented visual workflows while actively challenging the startup ecosystem's geographic biases and promoting sustainable, transparent leadership practices.
Stevie Case: World's First Female Pro Gamer; Hiring Tips for Sales; PLG vs Enterprise | 20VC #970
Former gamer turned CEO Ciara Vanta leverages her unique background in game design and federal litigation to advocate for a sales model grounded in vulnerability, mathematical rigor, and human connection rather than traditional aggression. She advises enterprise leaders to avoid simultaneous PLG and enterprise motions, recommending instead a staggered expansion strategy that incorporates early multi-threading with finance and security stakeholders to navigate capital constraints. Vanta further emphasizes hiring for grit and curiosity while restructuring compensation to gamify pipeline activities, ultimately urging the industry to pivot toward higher empathy and authentic engagement.
Liquid Death'a Origin Story | Co-Founder & CEO Mike Cessario
Mike Cessario, Harry Stebbings
Founder Mike Dryer launched Liquid Death after observing that health-conscious subcultures were underserved by brands lacking the irreverent marketing of junk food giants, a concept initially rejected by traditional venture capitalists. The company validated its viability before launch by securing more social media followers than Aquafina in four months, a metric that attracted tech and science-focused investors who understood digital traction despite skepticism from conventional CPG backers. Dryer now advocates for founders to rely on empirical data rather than the "nobody gets it" narrative, noting that most startup ideas fail regardless of their strategic intent.
The Ultimate Guide for Building a Two-Sided Marketplace | a16z's Jeff Jordan
This event analyzes the critical mechanics of successful marketplaces, emphasizing how aggregating fragmented supply creates defensible moats while avoiding the channel conflicts inherent in owning inventory. Participants examine unit economics and capital efficiency, contrasting sustainable models with long payment-to-execution cycles against capital-inefficient strategies that fuel destructive price wars. The discussion further details how specific cohort retention metrics and strategic timing can determine whether a platform overcomes the cold start problem or succumbs to negative network effects.
Albert Wenger: Elon & Twitter; Impact of SBF; Income Inequality; Will they ban TikTok? | 20VC #969
Albert Wenger, Elon, SBF, Harry Stebbings
Venture capitalist Albert Wenger critiques the failure of Industrial Age models to address the Knowledge Age's challenges, advocating for Universal Basic Income and decentralized education to mitigate inequality and mental health crises. He details his strategy for a dedicated climate fund and digital currency reforms while predicting a necessary 50% GDP reallocation to tackle thermal realities and enabling leapfrogging in developing nations. Wenger concludes that optimism remains viable as the private sector and new financial systems pivot toward programmable platforms and resource redistribution.
The Ultimate Guide to Brand Marketing | Liquid Death CEO Mike Cessario
Mike Cessario, Harry Stebbings
The discussion explores how powerful brands like Liquid Death transcend functional utility to forge deep emotional connections with diverse demographics through dark aesthetics and rebellion narratives. By strategically embracing polarization rather than seeking universal appeal, these companies cultivate a devoted following by validating specific cultural identities while allowing broader audiences to safely engage with a rebellious image. The analysis ultimately warns marketers against fixating on visible archetypes, urging them instead to recognize that true consumer bases often reside in unexpected groups driven by entertainment interests rather than the product's literal utility.
The Current State of Venture Capital | Jason Lemkin w/ Harry Stebbings
A prominent venture capital investor reports a strategic halt in new deployments for the past year while significantly raising investment standards to address a post-bubble market characterized by reduced capital availability and stricter efficiency requirements. Targets for SaaS IPOs have shifted toward $200 million in revenue, necessitating a "trifecta" of top-tier growth, capital efficiency, and profitability that is increasingly rare even at early revenue stages. Consequently, founders are now required to demonstrate precise competitive differentiation and segment dominance rather than relying on broad category growth or the inflated valuations of the previous boom.
Liquid Death CEO Mike Cessario: How I Turned Canned Water to a $700M Company | E968
Mike Cessario, Harry Stebbings
Mike Cessario founded Liquid Death by transforming canned water into a disruptive entertainment brand that leverages irreverent humor and high-impact marketing to challenge traditional beverage giants. Despite early investor skepticism and costly retail distribution mistakes, the company secured success by prioritizing a unique voice over product formulation, effectively building a loyal community while maintaining budget efficiency through creative partnerships rather than traditional celebrity endorsements. The organization now operates as a hybrid entertainment and beverage entity aiming to reach a multi-billion dollar valuation by 2028, fundamentally reshaping how healthy products compete for consumer attention in a saturated market.
How Recessions Affect SaaS Sales
Public software companies are navigating elongated sales cycles and heightened executive scrutiny driven by the withdrawal of pandemic stimulus, which is compressing revenue windows and threatening high net retention rates. In response, organizations are restructure their internal operations by dismantling dedicated overlay teams and converting SDR functions into renewal units to upskill general account managers and optimize quota density. Despite these headwinds and ongoing sales layoffs, the market remains tight for talent, with leadership projecting a return to normalized conditions and reduced volatility by the second half of 2023.