☕ Coffee Playdate Podcast

Guest: Jack Shukman, CEO & Co-Founder of The Way - a groundbreaking meditation app.

Episode Description: What if the secret to deeper meditation wasn’t more choices… but fewer? In this inspiring episode of Coffee Playdate, Dr. Olga Deengar sits down with Jack Shukman who cofounded the groundbreaking meditation app featuring a single, progressive path of 1000 sessions guided solely by his uncle and Zen teacher, Henry Shukman.

Jack shares how they defied 3000 competing apps with a “no-choice” philosophy, his journey going cold turkey off caffeine, working with family, building a joyful remote team culture, and why focusing on the process (not just outcomes) is essential for entrepreneurs. Packed with practical wisdom on mindfulness, leadership, and staying grounded as a parent and founder.

Whether you’re a busy professional, new meditator, or entrepreneur, this conversation will leave you inspired to simplify, commit, and find stillness in the chaos.

👉 Click here to get 30 meditation sessions on The Way Meditation App for FREE: https://www.thewayapp.com/coacholgamd
It is a unique single-path meditation experience with 1000 guided sessions rooted in authentic Zen tradition.

Timestamps / Chapters:

• 00:00 – Welcome, Coffee Chat (Jack’s caffeine-free journey) & Games
• 02:46 – Introducing Jack Shukman & The Way App
• 03:48 – Working with Uncle Henry Shukman (Family + Zen Mastery)
• 05:35 – Heartwarming wedding meditation story
• 06:33 – Facing competition from 3000+ meditation apps
• 07:46 – The “No Choice” philosophy
• 08:55 – Mindset tools for entrepreneurs
• 10:27 – Building a playful, meditation-centered company culture
• 11:27 – Team experiences at Mountain Cloud Zen Center
• 13:57 – Connecting with real users through live retreats
• 14:42 – Advice for founders
• 16:12 – 200,000 users & the mission behind the app
• 17:09 – Book Recommendation: Original Love by Henry Shukman
• 18:39 – Closing thoughts

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💬 Subscribe & Share! If this conversation touched you, please subscribe on YouTube, Apple Podcasts, Spotify, Amazon Music, iHeartRadio, or Deezer and share it with a fellow doctor or healthcare friend who might need to hear it. One intentional step at a time ✨ — Dr. Olga Deengar, Coach Olga MD © 2026 Coach Olga MD. All rights reserved.