『Jason Smith: 5 Companies, 30 Years, and One Unshakable Love for the Build』のカバーアート

Jason Smith: 5 Companies, 30 Years, and One Unshakable Love for the Build

Jason Smith: 5 Companies, 30 Years, and One Unshakable Love for the Build

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Jason Smith has built five companies, led teams from a handful of employees to hundreds, celebrated an early exit, endured a very public startup failure, and started over with Klue, a leading competitive enablement platform.In this episode of Giants, host Nejeed Kassam sits down with his longtime friend to trace that journey, from mowing lawns and reselling clothes as a teenager to launching his first company after UBC, selling it to TELUS, navigating a failed startup, and gaining valuable lessons at EA and Vision Critical before founding Klue.Jason shares the emotional highs and lows of entrepreneurship, including the confidence that comes with success, the identity crisis that follows failure, and the persistence needed to keep building. He reflects on the toughest decision of his career, leading Klue through a major AI-driven transformation, and explains why he believes data, not software, will define the next generation of winning companies.Tune in for an honest conversation about resilience, timing, leadership, fatherhood, and what it takes to build and rebuild over a lifetime.In This Episode:[00:00] Welcome to Giants[00:52] Passion and balance[02:08] Early hustles[04:11] Fearless building mindset[05:38] Teaching kids the grind[06:58] Columbus breakthrough[09:02] Riding the rollercoaster[10:52] Youthful confidence[13:11] Exit and money reality[16:30] Second startup failure[19:57] Timing postmortem[21:09] Learning inside companies[24:54] Ownership mindset[26:32] Family year of travel[28:46] Forcing functions to leap[29:31] Volunteering and culture shock[30:05] Off-grid family connection[30:48] Emotional inflection points[31:10] Seventeen ideas and an energy refill[33:40] 500 coffee shop meetings[35:24] Finding the right co-founder[37:04] What Klue actually does[37:27] When co-founder trust breaks[40:55] Finding the right second co-founder[42:41] ChatGPT changes the game[45:42] Data moats and enterprise LLMs[47:45] Refounding through layoffs[54:12] Lessons from the build[56:37] Earned luck and judgment[58:27] Beyond growth metrics[01:01:18] Rapid fire Notable Quotes[00:09:27] "It's never up and to the right. It's always a jagged line." — Jason Smith[00:17:19] "Your identity does get attached to your startup... So look, when it fails, there's a piece of you that fails." — Jason Smith[00:39:06] "Founding relationships are based on trust." — Jason Smith[00:56:40] "There truly is this concept of earned luck. I think you have to put yourself in the position to be lucky, and it's not just random." — Jason Smith[01:01:05] "I hope that my legacy is demystifying what entrepreneurialism is and inspiring more people to be entrepreneurs." — Jason Smith[00:27:31] “Think like owners. And what that means is you're really trying to see around corners, not just within your own job. You're trying to look at the whole picture, not just your specific slice of it. and then anticipate what some of the problems are and try and proactively solve those.”- Jason SmithOur GuestJason Smith is a Vancouver-based serial entrepreneur who has founded or helped scale five companies over nearly 30 years. He co-founded his first web company right after graduating from UBC, and it was acquired by TELUS while he was still in his twenties. After launching a group-buying venture and taking on leadership roles at EA and Vision Critical, where he helped grow the company from 8 employees to about 500 and nearly $100 million in revenue, Jason took a year off to travel the world with his family. That experience inspired him to found Klue, a competitive enablement and buyer intelligence platform that has raised $80 million in venture funding.GiantsLinkJason SmithLinkedInKlueNejeed KassamLinkedIn
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