What If Your Worldview Is What’s Holding You Back? With James Beshara, Founder & Executive Chairman at Magic Mind
In this episode of The Optimist, I sit down with James Beshara; serial entrepreneur, investor, founder of Magic Mind, and host of Daily Vedanta, for a powerful conversation about what really drives us.We explore:- The hidden worldviews that shape every decision we make- Why ambition without peace leads to burnout- How ancient philosophy helped James recover after selling his company in a fire sale- The dangers of chasing success to prove your worth- And what it means to truly find your dharma — and build a life around itTimestamps00:00 – Intro & how this episode came together03:00 – James’ story of building Magic Mind & going caffeine-free05:00 – The intersection of masculinity, entrepreneurship, and philosophy06:30 – What is Vedanta? The philosophy of non-duality explained08:00 – How your worldview shapes everything (even if you don’t know it)12:00 – Peace vs. Prosperity: the two things we’re all chasing15:15 – Growing up with meditation, Descartes, and entrepreneurship19:00 – Building a $400M company—and what happened after it collapsed21:00 – The breaking point: depression, identity crisis, and ego death23:00 – Discovering Alan Watts and the philosophy that changed everything28:00 – Why most of us never articulate our worldview31:00 – Vedanta’s 3 internal tools: body, mind, and intellect34:30 – The “virus” of attachment — and how to overcome it36:10 – The one book James recommends to every founder38:00 – How to build emotional resilience through daily practice40:00 – Exposure therapy, knowing your level, and startup lessons44:00 – Don’t chase excitement — how to stay grounded47:00 – The danger of building from a place of proving yourself50:00 – How to find your dharma: what the world is asking of you53:00 – Why life really begins at 40 (and everything before is just research)57:00 – Dharma, individuation, and the key to real belonging1:00:00 – Your talent is what feels *easy* to you — don’t overlook it1:02:00 – Albatrosses, surfers, and the beauty of doing what comes naturally1:03:00 – Where to find James and what he’s building now---✨ Whether you’re building a company, rebuilding yourself, or just trying to stay present, this episode will move you.
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1:03:05
Why You Need a List of 300 Things to Do Before You Die
I used to think bucket lists were kind of cheesy… until I made one.Then I printed it on a four-foot poster and hung it in my house.That one exercise completely changed how I see my life.In this solo episode of The Optimist, I break down how a simple homework assignment from a coach turned into the most profound and energizing thing I’ve ever done:creating a list of 300 things to do before I die.I’ll share:How I came up with the list (with a little help from ChatGPT)Why 300 is the magic numberHow I designed the poster and what happened when strangers at Kinko’s read itThe sniper rifle story (yes, really)And why this list has become my favorite tool for staying inspired, grounded, and excited about the future🎁 Want your own poster?The first 5 people who DM me their list — even if it’s messy or unfinished — I’ll design and ship you your very own version for free.No fluff. No coaching funnel. Just a gift from me to you.Make your list. Hang it up. Watch your life change.👉 Subscribe to The Optimist for more honest, human conversations on identity, ambition, and becoming who you’re here to be.
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Why You Can’t Get Over Your Ex, with Breakup & Relationship Coach Niki Van Houten
Why do breakups hit men and women so differently? And what does real healing actually look like?In this episode, Jake sits down with relationship coach Niki Van Houten for a raw, revealing conversation about heartbreak, emotional maturity, and the evolution of modern masculinity. They dive deep into the science and soul of breakups—why women often grieve earlier, why men stay distracted longer, and how both can learn to process pain without shame.Together, they unpack:- Why most men avoid feeling their grief (and what to do instead)- How to support your friends through breakups (without giving terrible advice)- Why it’s okay to not be “fully healed” before dating again- The difference between masculine & feminine energy—and how to balance them- How to consciously uncouple with love, respect, and growth- What every man should ask himself before trying to “glow up” post-breakupIf you’re navigating the end of a relationship, or supporting someone who is, this one’s for you. It’s not just about getting through heartbreak—it’s about becoming who you’re meant to be on the other side of it.
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1:29:02
The Hidden Cost of Heartbreak & Loneliness: How It Affects Your Mind, Body, and Life, with Naz Perez
This week, Jake welcomed Naz Perez, the first woman on his podcast, for a candid conversation about heartbreak, loneliness, and meaningful connections. As founder of Heartbroken Anonymous, Naz shares insights on why so many Americans feel disconnected despite being more "connected" than ever. They discuss the physical and emotional toll of heartbreak, how men and women process pain differently, and practical advice for creating safe spaces to be vulnerable.TIMESTAMPS:0:00 Introduction & Getting to Know Naz 14:38 The Loneliness Epidemic in America25:21 Heartbroken Anonymous Origin Story35:05 The Universal Experience of Pain41:42 How Men and Women Experience Heartbreak Differently51:00 "Open Heart vs. Closed Heart": Creating Vulnerability59:03 Dating Advice & Communication Between Men and Women1:05:42 Why Men Need Non-Judgmental Spaces1:15:20 Final Thoughts on Modern Masculinity
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1:20:41
How To Navigate Today’s Chaos And Find Peace, with Executive Coach, Kenny Borg
In this episode of The Optimist, Jake sits down with Kenny Borg, a coach and entrepreneur, to discuss the "meta crisis" - the overlapping series of crises affecting our modern world and mental health. They explore how men can navigate feeling overwhelmed, the importance of finding connection, and practical ways to maintain balance. Kenny shares his journey from D1 college football player to entrepreneur to coach, offering insights on masculinity, fatherhood, and finding stillness in chaotic times.Timestamps:0:00 Introduction and defining the meta crisis5:48 The physiological effects of being overwhelmed14:40 Three essential practices: time alone, time in nature, time with men20:39 The importance of personal retreats and creating space31:42 Effectively communicating needs in relationships38:34 The value of male connection and friendship46:30 Kenny's transformation from athlete to entrepreneur54:15 Finding happiness beyond financial success1:02:46 What it means to be a man today1:04:30 The power of meditation and controlling your attention
In an era of unprecedented success and isolation, The Optimist tackles the silent crisis facing ambitious men. Through powerful conversations with leaders and visionaries, we're creating more than just another podcast—we're building a blueprint for modern masculine wellbeing. Each week, we explore raw, honest truths about identity, connection, and what it truly means to thrive. Whether you're a founder, veteran, or someone seeking deeper meaning beyond achievement, join us in forging a new path that embraces both strength and vulnerability. Welcome to the future of modern masculinity.
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