The Optimist

Ben Sharf is a Division 1 athlete turned founder, creator, and podcast host. But behind his calm confidence is a story of deep insecurity, fear of failure, and the relentless pressure to always do more.In this raw conversation, we dive into:The injury that derailed his hockey career and changed his identityHow one phone call almost made him quit the sport foreverWhy high-achieving men are often the most insecureSocial media, self-worth, and chasing validation in publicWhy success still doesn’t feel like successHis evolving relationship with therapy, presence, and masculinityThis episode is for the guy who feels like he should be happy, but can’t quite figure out why he still feels behind.You don’t have to white-knuckle your way through life. You’re not alone.

If you’ve ever seen someone intriguing at a coffee shop, networking event, or gym, but felt paralyzed about approaching them, this episode is for you.Jake sits down with psychologist and charisma expert Beggie Olafs to crack open the hidden playbook on confidently connecting with anyone, anywhere. They dive into the psychology behind why rejection terrifies us, how simple interactions can dramatically reshape your life, and tactical scripts you can start using immediately to engage with strangers in everyday scenarios.From mastering the gym approach (without being creepy) to breaking the ice at bars, grocery stores, or coffee shops, Beggie reveals practical, proven methods to overcome anxiety and build genuine connections.What if every stranger was a potential new friend, partner, or business collaborator? After listening, you’ll never see an interaction with a stranger the same way again.Listen in to learn:Why fear of rejection is rooted deeply in human evolution—and how to hack it.Simple, actionable conversation starters for everyday situations.How your energy can magnetically draw people to you.Why remembering names and telling compelling stories makes you unforgettable.Turn fear into excitement. Strangers are just connections you haven’t made yet.

Tens of thousands of you made a list. Now it’s time to go deeper.This episode is part two of the bucket list phenomenon, and it answers the questions you’ve been sending me in droves.What if I feel overwhelmed by a list this big?What if I don’t want to cross every item off?How do I know if it’s a goal… or just a distraction?And what if the scariest thing on the list is the most important one?I break down how this project has changed my life, how to think about your own list, and why the poster on my wall might be the single most powerful artifact I’ve ever created.Whether you’ve written your list or you’re still staring at the blank page…this one’s for you.Make the list. Live the life. You only get one.

Men are struggling. And most of us are doing it silently.Welcome to The Optimist; a podcast for people who want to live bolder, deeper, and more emotionally connected lives. Hosted by Jake Hurwitz, this series is part confession, part conversation, and part rebellion against the two extremes of modern masculinity: the hyper-feminine “feel your feelings” camp and the toxic red pill chaos.There’s a third path.One where men can be grounded, vulnerable, funny, messy, ambitious, emotional, disciplined, and wild…all at once.Each week, Jake sits down with world-class thinkers, coaches, athletes, and artists to explore the stuff we don’t talk about enough: heartbreak, identity, fatherhood, freedom, failure, adventure, legacy, emotional intelligence, and how to actually be okay.It’s not therapy. But it’s close.And it’s not just for men. It’s for anyone who gives a damn about the men in their life.Whether you’re in the gym, on a solo hike, rebuilding after a breakup, or just tired of pretending everything’s fine, this is your invitation to start getting real.New episodes weekly. Subscribe and join the movement.

Breakup coach. Philosopher in the woods.Cam King is not your average dude.And this is not your average conversation about masculinity.In this episode, we go deep into:Why so many men are quietly breaking down after heartbreakHow to actually move on (hint: it’s not another rebound)Cam’s rule for turning pain into powerThe real reason modern relationships are falling apartWhy men struggle to define who they want to become—and how to finally figure it outAnd the viral origin story of the “300 Things to Do Before You Die” bucket listWhether you’re navigating a breakup, trying to understand the men in your life, or rebuilding yourself from the ground up, this one hits hard.Cam helped me through one of the most confusing chapters of my life. And in this episode, we’re passing that torch to you.Listen to the full conversation and start rewriting your story.

Think your life isn’t interesting enough for the internet? Think again.In this raw, eye-opening conversation with creator economy expert JT Barnett, we dive headfirst into the biggest lie holding people back: the belief that their lives aren’t worth sharing. JT unpacks how every seemingly “ordinary” life contains extraordinary stories—and why it’s crucial to overcome self-doubt, embrace the cringe, and start creating content anyway.From overcoming panic attacks as a pro hockey player, to launching viral TikTok houses, JT reveals the vulnerable journey behind his success, proving that the only difference between you and the creators you admire is their willingness to put themselves out there.If you’ve ever felt your story wasn’t good enough for the spotlight, this episode might just change everything you believe about yourself—and what’s possible when you stop hiding and start hitting record.

In this episode, Caleb Ulffers joins Jake Hurwitz to explore a powerful mindset shift: Everything is Easy. From embracing rejection and stepping fearlessly into new experiences, to optimizing your life with mindfulness, style, and authentic leadership, Caleb delivers practical insights you can apply immediately. Caleb shares his personal journey of growth, overcoming major setbacks, and building a fulfilling life through intentionality and relentless curiosity. Whether you're starting fresh or seeking deeper clarity, this episode offers tools to optimize your mindset and build a purposeful life.

Danny Cortenraede is a successful investor, former media exec, and founder of InStudio Ventures — but this episode isn’t about business deals or exit valuations.It’s about balance.About fatherhood.About building a wildly ambitious life without sacrificing your health, your kids, or your peace of mind.In this raw and honest conversation, Danny shares the tools, systems, and mindset shifts that helped him move his family across continents, build a venture fund, and stay grounded in what really matters. We talk about marriage, money, kids, burnout, discipline, and how to design a life that’s both powerful and peaceful.

Join James Beshara, a serial entrepreneur and founder of Magic Mind, as he delves into the philosophical underpinnings that influence our actions. He reveals how hidden worldviews dictate our decisions and discusses the pitfalls of ambition without inner peace, which can lead to burnout. James shares his recovery journey after a challenging business collapse and how ancient philosophies shaped his perspectives on true success. Discover the importance of aligning ambition with authentic service and cultivating emotional resilience.

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.