Trust, Velocity, and Building the Answer Engine: Dmitry Shevelenko of Perplexity speaks to Farouk Hussein
In this fascinating conversation, Perplexity's Chief Business Officer Dmitry Shevelenko reveals how a company barely three years old is mounting the first credible challenge to Google's search dominance in two decades. Shevelenko shares the counterintuitive distribution strategy that led Perplexity to partner with mobile carriers and device manufacturers rather than chasing browser deals, explaining how creating mutual value with partners became their path to 22 million monthly active users.
The discussion centres on execution velocity as Perplexity's primary competitive advantage, with Shevelenko openly admitting that six months from now he'll have a top priority he can't even imagine today. From eliminating internal presentations entirely to making hiring decisions "physically hurt," he paints a vivid picture of how Perplexity maintains startup intensity while competing against trillion-dollar tech giants, offering invaluable lessons for anyone navigating the AI transformation.
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The long road to the last mile : Nic Humphries and Matthew Brockman reflect on 25 years of Hg
In this candid anniversary conversation, Hg's leadership team of Matthew Brockman and Nic Humphries reflects on 25 years of building one of Europe's most focused software investors. Humphries shares the challenge of convincing colleagues to abandon multiple sectors for pure software focus, while Brockman opens up about his leap of faith in 2010, leaving Apax Partners for an uncertain bet on Hg's vision and the turbulence of 2012 that eventually led to success.
The conversation hones in on AI as the next major platform shift and Brockman's concept of the "last mile"—the deep understanding of customer workflows required to transform AI capability into practical business solutions. Their discussion reveals a firm that has spent 25 years accumulating the pattern recognition, operational capabilities, and entrepreneurial culture perfectly suited for an era where success depends less on investment judgement and more on building products that solve real workflow problems—making this milestone feel less like a celebration of the past and more like preparation for the defining challenge ahead.
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AI, Control Points, and the Next Wave of Vertical SaaS with Tidemark Capital founder, Dave Yuan
In this compelling conversation, Tidemark Capital founder Dave Yuan shares his journey from Bain consultant to building one of the most thoughtful voices in vertical SaaS investing. Yuan reveals his "control point" philosophy—identifying the mission-critical systems that small businesses would turn off last before going bankrupt—and explains how this approach has guided Tidemark's investments in category leaders like ServiceTitan, Toast, and OneStream. His insights into workflow gravity, data gravity, and account gravity provide a masterclass in understanding what creates defensible market positions in software.
The discussion takes a provocative turn as Yuan explores AI's dual nature as both opportunity and existential threat for established software companies. He introduces the concept of "integrate surround"—how AI point solutions can gradually subsume control points by becoming the system of action rather than just record—and shares his framework for "fast waters" versus "slow waters" in AI adoption. With characteristic humility and intellectual curiosity, Yuan offers practical advice for navigating today's volatile market while building the Vertical SaaS Knowledge Project community that has become an industry touchstone for founders and investors alike.
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Refounding in the face of AI with Des Traynor of Intercom
Orbit 48 sees Dr Amr Ellabban sit down with Des Traynor, co-founder and CSO of Intercom, to explore how AI requires revolutionary thinking from businesses. Des shares the pivotal moment when ChatGPT emerged in November 2022, spurring Intercom's bold 15-day pivot to develop Fin, their AI customer support agent. The conversation reveals how successful AI transformation demands complete organisational commitment—from reimagining pricing models to restructuring teams—rather than incremental changes: "It's not a cherry on top. It's the only game that matters."
Drawing from his experience at Intercom and as an angel investor, Des outlines the three-phase evolution of AI in business: from augmenting human work to handling portions of jobs to eventually performing entire roles. For leaders navigating similar transformations, he offers unflinching advice on the necessity of decisive action and clear communication, predicting that AI may soon handle 60-80% of support volume in what will be "the largest change in how labour is applied in most businesses." His insights on product boundaries and avoiding "MiniDisc" solutions in rapidly evolving technology landscapes provide a compelling roadmap for organisations embracing this inevitable shift.
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A golden age of software engineering with Russell Kaplan, Founding President of Cognition
What happens when AI can code? In this illuminating conversation with Cognition's Founding President Russell Kaplan, we explore how AI is fundamentally transforming the landscape of software development. Drawing from his journey through Tesla's Autopilot team and Scale AI, Kaplan shares profound insights on leadership in rapid technological change, emphasizing that "talent is everything" and that exceptional outcomes come from "small teams of highly technical people." His perspective challenges conventional thinking about software engineering's future, suggesting we're entering an era of "software abundance" where customer expectations will rise dramatically.
The discussion moves beyond theoretical AI potential to practical implementation, with Kaplan revealing how his philosophy of speed as strategy guides decision-making in a world where AI capabilities in software development are doubling every 70 days. Rather than fearing job displacement, Kaplan envisions a future where "way more people are shaping the creation of software" as the nature of engineering evolves. With refreshing optimism, he suggests we're approaching a time when "software is good by default" and shares his excitement for what may be "the most exciting time to be a software engineer" in history.
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