A $2.5B AI IT Success Story | Freshworks CEO Dennis Woodside

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Dennis Woodside, CEO of Freshworks, the $2.5B public software company helping IT and customer support teams use AI to work faster, smarter, and more efficiently. Dennis shares how Freshworks serves more than 75,000 companies around the world, including major names across technology, sports, education, entertainment, manufacturing, and enterprise software. Dennis breaks down how AI is transforming the way com

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Lucas Ngoo, CEO of Cortex AI and co-founder of Carousell, the Southeast Asian marketplace that grew to a $1 billion valuation. Lucas explains why the next major leap in AI may not just be chatbots or software, but general-purpose robotics. While robot hardware is getting cheaper and more powerful, Lucas argues that the biggest bottleneck is still data: the real-world human and robot data needed to train mach

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Rich Diviney, retired Navy SEAL, former SEAL Team Six operator, founder of The Attributes Training Company, and author of The Attributes and Masters of Uncertainty. Rich breaks down the difference between skills and attributes, and why elite performance is not just about what someone knows how to do, but whether they have the internal wiring to perform when pressure, chaos, and uncertainty hit. Drawing from

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with James Henderson, CEO of Exclusive Resorts and The Exclusive Collective, for a fascinating conversation on the future of luxury travel, community, and what it really means to live well. James shares how Exclusive Resorts evolved from a destination club into a luxury lifestyle platform with more than $1 billion in real estate, hundreds of residences, once-in-a-lifetime trips, and a growing family of brands d

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Dan Eberhard, Founder & CEO of Koho, one of Canada’s most exciting fintech companies. Dan shares how Koho grew from a scrappy idea challenging Canada’s powerful banking system into a company with 2 million customers, hundreds of millions raised, and a real shot at building the next great bank in Canada. Dan opens up about his unconventional path from growing up in a small mountain town in British Columbia to

In this episode of The Jess Larsen Show on Innovation & Leadership, Jess sits down with Michael Winn of Chartered Wealth for the first installment in a new mini-series on one of the biggest questions founders face: why do so many exits fail? Michael breaks down the surprising statistic that 75% of founder exits are unsuccessful, and explains why selling a company is not just a transaction, but a deeply personal, financial, and strategic process. Michael shares the three areas every founder mu