Latest Interviews
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Clear all filters- All-In Podcast2h 17m
E109: 2022 Bestie Awards Live from Twitter HQ
Calacanis, Rudy Giuliani, Shellenberger, David Sacks, David Friedberg, Chamath Palihapitiya, Elon Musk
The All-In podcast team convened in Lake Tahoe in December 2022 to present their annual Bestie Awards, during which Jay Cal was unanimously voted the new Director of the All In Summit. The episode featured extensive analysis of 2022 political winners like Ron DeSantis and Xi Jinping, business shifts involving defense stocks and generative AI, and critical discussions with Elon Musk regarding his Twitter acquisition. Additional guests included Michael Schellenberger, who detailed FBI influence on content moderation, while the panel also recognized top investors, identified worst performers, and selected the year's most significant scientific breakthroughs.
Outbound Sales Tips from Maggie Hott, Director of Sales at Webflow
Founders are advised to initiate immediate outbound sales motions to build brand awareness and secure referenceable customers rather than targeting broad segments without sufficient infrastructure. Companies like Webflow implement a 10-80-10 outreach framework and rapid response protocols to scale personalized engagement while aligning sales and marketing under unified leadership. This strategy prioritizes securing high-value logos in specific verticals to validate the business model before expanding into complex enterprise markets.
FOUNDER ADVICE: How to Create a Category | a16z's Martin Casado
Martin Casado, Harry Stebbings
This discussion outlines the strategic complexities of creating new technology categories, emphasizing the necessity of "market annealing" and rigorous narrative development led by practitioners like Dave McJannet and Steve Mullaney. Participants analyze the critical impact of macroeconomic trends, noting that while sheer resilience can sustain a company through difficult market conditions, alignment with positive first derivatives significantly improves survival odds. Furthermore, the event establishes that capital efficiency must coexist with category creation, advising founders to prioritize operational replanning over immediate layoffs to maintain long-term strategic agility.
How to Hire Salespeople | Sales Tips from Maggie Hott
Webflow employs a cluster-based hiring strategy and a rigorous interview process designed to identify sales professionals who thrive in ambiguous, chaotic environments while minimizing the costly impact of mis-hires. Their multi-stage assessment replaces product demos with passion pitches and live coaching sessions to evaluate growth mindsets, accountability, and the ability to accept feedback without defensiveness. Specific behavioral inquiries focus on ownership of failures, self-reflective analysis of performance gaps, and proactive preparation, ensuring new hires align with the company's long-term culture and operational goals.
Barry McCarthy: From Netflix CFO to Peloton CEO; How Netflix Beat Blockbuster | 20VC #962
Barry McCarthy, Harry Stebbings
After joining Peloton as CEO to execute a strategic turnaround, Barry McCarthy leverages his extensive background at Netflix and Spotify to implement a high-performance culture that prioritizes talent density over loyalty. Drawing on a "professional sports team" philosophy and insights from his past direct listing experiences, McCarthy aims to restore profitability and regain operational control before eventually transitioning to a successor. His strategy centers on leveraging Peloton's brand equity and user base while avoiding the scaling pitfalls that previously challenged the company's growth trajectory.
Product-Led Growth Tips | Maggie Hott, Director of Sales at WebFlow
Industry analysis identifies that successfully scaling Product-Led Growth (PLG) into enterprise sales requires introducing a dedicated outbound motion only after achieving $1–2 million in ARR to prevent product cannibalization. Effective differentiation strategies must prioritize legal negotiability, dedicated support, and granular security features over basic SSO, which often proves insufficient for Fortune 500 contracts. Founders are advised to validate their ability to quantify ROI for external prospects and distinct market segments before attempting to layer traditional sales structures onto self-serve platforms.
How My Parents Shaped Me | Billionaire Founder of Mailchimp Ben Chestnut
Drawing from his mother's salon experience and his father's stoic military upbringing, the speaker shaped MailChimp's philosophy to empower entrepreneurs with big ambitions rather than labeling them as small businesses. This internal drive is fueled by a maternal legacy of unfulfilled scaling potential and a paternal lesson that resilience requires enduring hardship without complaint while masking internal stress with a calm exterior. The resulting leadership model combines the belief that business growth is a means to realize dreams with the discipline that true capability is forged through silent, relentless persistence.
Hadi Partovi: How I Became an Advisor to Mark Zuckerberg; Lessons from Steve Ballmer | 20VC #961
Hadi Partovi, Mark Zuckerberg, Steve Ballmer, Harry Stebbings
Venture capitalist and Code.org co-founder Randy Farmer leveraged his background at Microsoft and early investments in Facebook to pivot from wealth accumulation to a global mission for educational equity, aiming to integrate computer science into school curricula worldwide. Drawing on high-performance leadership frameworks developed during his time with Steve Ballmer and Bill Gates, Farmer prioritizes rapid decision-making and strategic hiring to drive the organization's goal of having twenty-five U.S. states mandate computer science graduation requirements within five years. His approach fundamentally reshapes education by advocating for a curriculum focused on AI-relevant skills and project-based learning rather than obsolete subjects like calculus, addressing the mismatch between traditional schooling and the future technology-driven economy.
Maggie Hott: 3 Questions You Must Ask When Interviewing Sales Reps | 20VC #960
Maggie Brown, who scaled Slack from $12 million to over $1 billion ARR as its first sales rep, now leads Webflow's sales organization from the ground up. She emphasizes that successful hyper-growth requires early investment in enterprise-grade tools, immediate outbound strategies, and cross-functional partnership to differentiate self-serve products for the enterprise market. Brown further advises founders to hire seasoned account executives, cluster hiring for efficiency, and utilize coaching-intensive interview processes to build high-performing sales teams capable of navigating complex negotiation landscapes.
- Goldman Sachs21 min
Carolyn Childers and Lindsay Kaplan, Co-founders of Chief
Carolyn Childers, Lindsay Kaplan, Asahi Pompei
Co-founded by Carolyn Childers and Lindsay Kaplan, Chief is a unicorn-level professional network that connects female executives through hyper-curated peer groups to combat the projected 200-year timeline to gender parity in senior leadership. Operating on a B2B model where most members are employer-sponsored, the platform bypasses traditional networking by facilitating deep cross-industry connections that address the unique isolation and compounded pressures faced by women at the apex of their careers. With membership spanning 80% of Fortune 100 companies and a 60,000-person waitlist, the organization is rapidly expanding its international presence while driving strategic shifts in workplace culture through its distinctive, non-gendered branding.
- The Diary Of A CEO1h 16m
Richard Branson: How A Dyslexic Drop-out Build A Billion Dollar Empire!
Richard Branson, Sir Richard Branson
Richard Branson outlines his entrepreneurial philosophy of diversification and delegation, crediting these strategies alongside his dyslexia for sustaining the Virgin Group through crises like the COVID-19 pandemic. He details the history of Virgin Atlantic's resilience against British Airways' legal and competitive challenges while describing the high-stakes risks and ultimate success of his personal spaceflight missions. Branson concludes by attributing his leadership style to early family influences and the strategic power of personal branding, which allowed him to transform individual ventures into a global empire defined by innovation and customer service.
- Goldman Sachs15 min
Maverick Carter CEO/Co-founder, SpringHill Company
Co-founded by LeBron James and Maverick Carter, the Springfield Company operates as a content and commerce entity designed to build enterprise value through owned intellectual property rather than traditional management fees. Following a strategic capital raise, the 50-50 male-female firm is evolving its flagship platform "The Shop" into a global franchise with international reach on YouTube, featuring high-profile guests and brick-and-mortar expansions. Guided by a poker-inspired risk philosophy and a "More Than" ethos, the organization structures partnerships as co-productions to empower individuals while securing long-term brand relevance in the media landscape.
- The Diary Of A CEO1h 47m
Billy McFarland: The Man Behind The Infamous Fyre Festival Disaster | E202
Billy McFarland, Andy king, Ja rule
Billy McFarland, the architect of the fraudulent Fyre Festival who defrauded investors of over $26 million with fake accommodations and false projections, was sentenced to six years in prison and now faces lifetime restitution and an SEC ban on public company leadership. Following his release, McFarland is navigating strict probation while managing severe psychological trauma from ten months of solitary confinement and attempting to rebuild his reputation through a new, small-scale experiential venture called Pirate. His ongoing efforts focus on repaying defrauded investors and avoiding the impulsive behaviors that previously led to the festival's catastrophic collapse, even as he remains banned from returning to the Bahamas where the original event took place.
Marty Cagan: Product Lessons from Steve Jobs and Elon Musk; Why do we idolize engineers? | 20VC #957
Marty Cagan, Steve Jobs, Elon Musk, Harry Stebbings
Marty Cagan, a former executive at HP, Netscape, and eBay, defines product management as a team-facilitation role focused on solving the primary risk of product-market fit rather than secondary business mechanics. He outlines a discovery framework built on four pillars—value, usability, feasibility, and viability—that requires 50 to 100 rapid iterations to validate whether a solution significantly outperforms alternatives. Cagan advises that organizations should hire dedicated product leaders when engineering teams reach 25 to 30 members, emphasizing that success depends on outcome-driven autonomy and deep customer immersion over process-heavy management.
Only 15% of Founders Listen to their VCs | Jason Lemkin
Jason and Harry argue that venture capitalists must shift from sugarcoating feedback to delivering direct, "ass-kicking" advice every two years to ensure founder accountability and prevent corporate failure. While Jason's blunt warnings about unsustainable burn rates often alienate 60% of elite founders and damage relationships, he contends that this harsh honesty is essential for identifying resilience and saving portfolio companies from inevitable collapse. This debate highlights a structural inefficiency in current VC models, where infrequent board meetings prevent the real-time course corrections necessary to address market realities before it is too late.