What if leaving your dream job was the way to discover your true self? Jon de la Motte failed his first Stripe interview, but he didn't give up. It was his dream job, a company that connected with his father's work in finance with his software ambitions. At Stripe, Jon faced challenges. He joined a risky JavaScript infrastructure team and struggled to find his footing. Eventually he found his way, built a great team and then it all started to fall apart again. Discover how Jon's journey reshaped his life and what it means to balance personal and professional priorities. Episode Page Support The Show Subscribe To The Podcast Join The Newsletter
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51:45
Story: Inside Shopify's Layoffs
What if you had to break life-changing news to your team—could you handle the weight of their futures? Allison's journey from software engineer to compassionate leader at Shopify is filled with challenges and growth. It all started when her mentor was suddenly laid off, leaving her with uncertainty and guilt. This turning point taught her the importance of adaptability in the tech industry's ups and downs. When Allison faced her own layoff, she found the strength to move on to new roles, including a position at Shopify. There, she had to announce layoffs to her team, learning to lead with empathy and prioritize their well-being. Her story highlights the power of empathy and resilience in leadership. She shares how to end employment on good terms and create a supportive environment for those affected. While layoffs are tough, they can also be a place to show strength. Episode Page Support The Show Subscribe To The Podcast Join The Newsletter
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43:04
Story: ReiserFS
Have you ever known someone who's technical brilliance was overshadowed by personal failings? This is the story of Hans Reiser, a software developer driven to create a superior Linux filesystem, but whose difficult personality got in the way. Then came the disappearance of his wife, Nina, in 2006. The investigation pointed to Reiser, ending with a murder conviction that shocked the tech world. Reiser's story is a reminder of how technical skills and personal integrity need to go hand in hand. From prison, he reflects on his mistakes, realizing the need for empathy and collaboration. His legacy, once about innovation, now serves as a cautionary tale. Episode Page Support The Show Subscribe To The Podcast Join The Newsletter
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52:36
Story: From Everest to Startups: Yoshio's Journey of Resilience and Coding
How do you know what matters? What if training to climb Everest left you certain you were on the wrong career path? Join us as we explore Yoshio's incredible journey from the heights of Everest, to coding bootcamps, to finding his true calling in start-ups and communication skills training. Episode Page Support The Show Subscribe To The Podcast Join The Newsletter
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50:21
Story: From Code to Capital - Tim Chen's Journey from Engineer to VC
What if your corporate job left you feeling empty, and you decided to leap into venture capital? Tim Chen, a software engineer, was disillusioned with corporate life at Microsoft. The 2008 market crash and layoffs deepened his dissatisfaction. Seeking more impactful work, Tim joined startups and contributed to open-source projects, like Kafka and Docker. Then after his own start-up, Tim found a niche bridging the gap between technical founders and venture capital. But could get into Venture Capital himself? Join me and Tim to hear his journey from a disillusioned software engineer to a successful venture capitalist, exploring the highs and lows of his unusual career move. Episode Page Support The Show Subscribe To The Podcast Join The Newsletter
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