495. Old School Values in a New Age: Oshri Cohen on Family, Tech, and Legacy

What does it mean to balance old school values with the rapid advancements of technology?

In this episode of Better Call Daddy, host Reena Friedman Watts welcomes tech expert Oshri Cohen, who delves into the importance of maintaining traditional values in a world increasingly dominated by AI and digital innovation.

Oshri shares his journey from a young coder to a fractional CTO, discussing how his unconventional beginnings shaped his approach to technology and business. He emphasizes the significance of creativity in an age where AI is often seen as a replacement for human ingenuity.

The conversation touches on the challenges of parenting in the digital age, particularly when it comes to navigating platforms like YouTube, and how his new product, Watchly Player, aims to create a safer viewing experience for children.

Reena and Oshri explore the evolving role of a CTO, the pitfalls of corporate culture, and the necessity of kindness in leadership. Oshri’s insights challenge listeners to rethink their relationship with technology and the impact of family dynamics on personal and professional growth.

Oshri Cohen is an AI-native Chief Product & Technology Officer who helps companies build software the way modern teams actually should. Over 25 years in software — 20 of them in technology leadership — he has made AI-native transformation his focus: rewiring how engineering organizations plan, build, and ship, not just bolting AI features onto old workflows. He leans on cloud-native architecture, DORA metrics, and GitOps to turn slow, siloed teams into fast, measurable product engines.

His range is unusually broad. Since 2018 he has served as fractional and interim CTO to more than 30 companies, almost all US-based, and at his peak directed 12 engineering teams across seven countries. He has shipped more than ten digital products across healthtech, e-commerce, manufacturing, logistics, and finance. A McGill business grad who taught himself to code at 13, Oshri leads business-first — every technical decision starts at the P&L, never the other way around.

🎙️ WHAT'S IN THIS EPISODE: - The importance of old school values in modern society - Oshri's unconventional path to becoming a fractional CTO - The role of AI in creativity and problem-solving - Parenting in the age of YouTube and the creation of Watchly Player - Insights on corporate culture vs. startup mentality - The significance of kindness and respect in leadership

💭 MEMORABLE QUOTES FROM OSHRI: "Don’t lose old school values because if you do, your society can run amok." "Be kind to the person who seems unimportant, because that's the most important person."

⏱️ TIMESTAMPS: (00:00) Introduction to Oshri Cohen (05:15) Balancing old school values with modern technology (15:30) Understanding the role of a fractional CTO (25:00) The challenges of parenting in the digital age (35:45) Insights on corporate culture vs. startup mentality (45:00) The significance of kindness in leadership

🔗 CONNECT WITH OSHRI COHEN: Website | LinkedIn

🔗 CONNECT WITH REENA FRIEDMAN WATTS: Website | LinkedIn | Instagram | YouTube Join us for this thought-provoking conversation that bridges the gap between tradition and innovation, highlighting the essential lessons we can pass on to future generations.