The Dare to Dream Podcast

Vincent Van Patten and Gregory Benedikt
  • 5.0 (38)
  • SELF-IMPROVEMENT
  • UPDATED WEEKLY

The Dare to Dream Podcast is where Vincent Van Patten and Gregory Russell Benedikt challenge you to embark on the adventure of your life. This podcast is for those who crave meaning and fulfillment and are willing to step into the unknown to find it. Vincent and Gregory draw wisdom from their own journey and from guests who exemplify what is possible when you have the courage to live a life that is truly yours. Dare to Dream represents what it's like—not just reflecting upon one's trial by fire—but dancing in the flames. When you feel lost. Inspired. Alone. Called to be different.

  1. NOV 5

    #236 - Alana Ruoso - How to Ditch The Struggle and Live a More Enjoyable Life

    Alana Ruoso is a Career & Success Coach for those who deep down know that they can do better but keep falling short of where they want to go. With humor & honesty, Alana shows them how to ditch the struggle, own their value and move their career (and life) from vanilla success to spectacular triumph. In this episode, expect to learn: Why Alana was addicted to strugglingHow struggle is often linked to worthinessHow to know if you are burnt outThe first step Alana takes when she realizes she's in struggle mode and wants to get out And much more. Shownotes: The Big LeapRemarkably Bright Creatures

    1h 1m

  2. OCT 24

    #235 - Paige Wilhide - How to Use Improv to Increase Your Confidence & Accelerate Your Career

    Paige Wilhide is a trained improvisor, award-winning playwright and performer, and Play Facilitator for organizations looking to build trust and encourage bold creativity, all while having more fun than anyone should have at work. Trusted by clients like Morgan Stanley, Wix, and Columbia University, Paige’s signature improv-inspired trainings give teams a permission slip to play, leaving them inspired and invigorated to tackle any challenge they may face, both professionally and personally. In this episode, expect to learn: How Paige started a successful media company by following her passion and posting on CraigslistHow learning improv up-leveled her business skillsHow Paige healed herself from heartbreak by creating a one-woman showHow Paige is bringing play into the corporate world Shownotes: https://www.yesnco.com/ https://www.breakupaddict.com/ https://www.linkedin.com/in/paigewilhide/ https://www.instagram.com/paigewilhide/?hl=en

    1h 4m

  3. OCT 16

    #234 - Episode Swap from Rejection Rehab - Gregory Benedikt on Bold Action, Rejection Reps & The Terrifying 10-Second Rule

    This is an episode swap from the amazing Rejection Rehab podcast. Fortune favors the bold. Gregory Benedikt left private equity, delivered a TEDx talk, and—thanks to 10 seconds of terrifying action—met the love of his life by sliding his number across a café receipt… in front of two people. In this episode, EMMY winner Dr. Tom unpacks Gregory’s Bold Action formula and his 100-Day Rejection Challenge: door knocks, pool jumps, and a USPS “mustache discount.”We cover:🚪 Why the pain of staying beat the fear of leaving (“Finance Greg” → purpose)⏱️ The Terrifying 10-Second Rule: stand up, walk over, say the line🏋️ Rejection reps: how creative asks build durable confidence🧭 Identity → Dream design → Daily bold acts (behavior-change stack)🎯 The surprising upside of facing rejection with specific asks + being in motion👉 If you’ve felt stuck—at work, in love, or in your head—this conversation is your call to action.Host: Dr. Tom | ‪@rejectionrehab‬ (IG/TikTok/YouTube) | @TomFlaherty (IG)Guest: Gregory Benedikt — @gregoryrussellbenedikt (IG) | https://gregoryrussellbenedikt.com/  / gregoryrussellbenedikt

    33 min

  4. OCT 10

    #233 - A Dramatic Reading of Gregory's TEDx Hate Comments

    My TEDx talk just crossed 300,000 views! That's wild, and to celebrate, here is me reading my favorite hate comments. Enjoy!

    11 min

  5. OCT 1

    #232 - Shane Pope - Building a Human-Centric AI Company

    Shane Pope is the founder of Reflect Technology, a company dedicated to transforming mental wellness. After a long, intense journey through trauma and healing, he emerged with a deep curiosity and drive to help others. Shane specializes in deconstructing complex ideas, translating them into accessible insights, and building bridges that make mental wellness tools approachable for everyone. He believes that in today’s world, where we are constantly overwhelmed with inputs, what people need most are safe spaces to let thoughts and emotions out, creating clarity, resilience, and growth. Expect to learn: - Why Shane created an AI app that's intentionally designed to feel "not-human" - Why Taylor Swift has been a big inspiration in building Remi - What the human revolution is and how AI can enrich our human experiences - How the Disney movie Cars highlights the danger of optimization And much more. This was one of the best conversations I've had all year. I learned A TON from hanging out with Shane and you will too by listening to this. Enjoy! Shownotes: Remi Website Download the app Connect with Shane For more Dare to Dream content find us on: Apple Podcasts:⁠ ⁠https://podcasts.apple.com/us/podcast/the-dare-to-dream-podcast/id1522983890⁠⁠ Spotify:⁠ ⁠https://open.spotify.com/show/599zlweDDcmXP5YhOX6TFw⁠⁠ Instagram:⁠ ⁠⁠⁠https://www.instagram.com/thedaretodreampodcast/⁠⁠ If you want to Live a Story Worth Telling, join Gregory’s Newsletter :⁠ ⁠⁠https://liveastoryworthtelling.gregoryrussellbenedikt.com/laswt⁠ If you’re ready to achieve your dreams without quitting your job or losing your ability to provide for you family, book a discovery call with Gregory: https://calendly.com/gregoryrussellbenedikt-1/discovery-call

    1h 8m

  6. SEP 12

    #231 - I'm Tired of Trying to Achieve

    I’m tired of racing. Of feeling like there’s somewhere I need to go in life, and that I won’t get there unless I fix, do, solve, more, more. I’m tired of it. Tired of trying to achieve. Believing that’s what’ll make me happy, secure, free. I’m tired of this game. I wanna live life the way I want to live. And be free now. For more Dare to Dream content find us on: Apple Podcasts:⁠ ⁠https://podcasts.apple.com/us/podcast/the-dare-to-dream-podcast/id1522983890⁠⁠ Spotify:⁠ ⁠https://open.spotify.com/show/599zlweDDcmXP5YhOX6TFw⁠⁠ YouTube:⁠ ⁠⁠⁠https://www.youtube.com/channel/UCoimyPFCjO_qrJhH4ALafcA⁠⁠ Instagram:⁠ ⁠⁠⁠https://www.instagram.com/thedaretodreampodcast/⁠⁠ Vincent's Book, When the Sky Opens and the Answers Shimmer: https://www.amazon.com/When-Sky-Opens-Answers-Shimmer/dp/B0DSQ7MYRZ?ref_=ast_author_dp Join Vincent’s Newsletter - Vinny's Field Notes:⁠ https://vincentvanpatten.substack.com/⁠ Join Gregory’s Newsletter - Live a Story Worth Telling:⁠ ⁠⁠https://liveastoryworthtelling.gregoryrussellbenedikt.com/laswt⁠ If you’re feeling empty despite your “success”, book a discovery call with Gregory:⁠ https://calendly.com/gregoryrussellbenedikt-1/discovery-call⁠

    26 min

  7. SEP 3

    #230 - Eric Bowen - Building a Human Connection Social Club, Raising Resilient Kids, & Letting Go of Identity

    Eric Bowen is a husband, dad, entrepreneur, and recovering corporate executive who spent two decades leading in the corporate world before deciding to challenge himself and build something of his own. Now the co-founder of Bermuda Club, he’s focused on creating spaces where connection, wellness, and business collide—without the country club pretension or big-box gym vibe. Beyond the club, Eric invests in real estate and business ventures while teaching his kids that money is a tool for freedom, not a treadmill for trading time. When he’s not working, he’s happiest near the ocean or on the golf course, chasing balance over busyness. Expect to learn: Why Eric left the corporate world as a Vice President to become an entrepreneur Why his 13-year old son just attended a resilience and mental toughness bootcamp What the Bermuda Club is and why you should joinWhy Eric thinks that responsibility and purpose are connected And much more. You guys are going to love this one. Eric is an absolute legend and someone that I look up to immensely. Enjoy! Shownotes: Bermuda Club on Instgram: https://www.instagram.com/bermudaclubs/?hl=en

    1h 12m

  8. AUG 26

    #229 - Matt Lillywhite - The Challenges, Rewards, and Mental Health Struggles of Being a Digital Nomad

    This week’s guest is Matt Lillywhite, a writer and digital nomad whose vulnerable stories on Medium have made him one of the most influential writers on the platform. I was drawn to his work because of his honesty regarding the realities of being a digital nomad, a lifestyle many believe we want, yet don’t truly understand the ramifications of.  In this conversation, we discuss how Matt went from being a writer in the music industry to traveling the world as a digital nomad, the challenges and rewards that come from working remotely around the world, the mental and physical health struggles he’s dealt with, how his experiences have made him cherish home and community, and much more.  Matt Lillywhite on Medium Matt on Substack For more Dare to Dream content find us on: Apple Podcasts:⁠ ⁠https://podcasts.apple.com/us/podcast/the-dare-to-dream-podcast/id1522983890⁠⁠ Spotify:⁠ ⁠https://open.spotify.com/show/599zlweDDcmXP5YhOX6TFw⁠⁠ YouTube:⁠ ⁠⁠⁠https://www.youtube.com/channel/UCoimyPFCjO_qrJhH4ALafcA⁠⁠ Instagram:⁠ ⁠⁠⁠https://www.instagram.com/thedaretodreampodcast/⁠⁠ Vincent's Book, When the Sky Opens and the Answers Shimmer: https://www.amazon.com/When-Sky-Opens-Answers-Shimmer/dp/B0DSQ7MYRZ?ref_=ast_author_dp Join Vincent’s Newsletter - Vinny's Field Notes:⁠ https://vincentvanpatten.substack.com/⁠ Join Gregory’s Newsletter - Live a Story Worth Telling:⁠ ⁠⁠https://liveastoryworthtelling.gregoryrussellbenedikt.com/laswt⁠ If you’re feeling empty despite your “success”, book a discovery call with Gregory:⁠ https://calendly.com/gregoryrussellbenedikt-1/discovery-call⁠

    58 min
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5
out of 5
38 Ratings

About

The Dare to Dream Podcast is where Vincent Van Patten and Gregory Russell Benedikt challenge you to embark on the adventure of your life. This podcast is for those who crave meaning and fulfillment and are willing to step into the unknown to find it. Vincent and Gregory draw wisdom from their own journey and from guests who exemplify what is possible when you have the courage to live a life that is truly yours. Dare to Dream represents what it's like—not just reflecting upon one's trial by fire—but dancing in the flames. When you feel lost. Inspired. Alone. Called to be different.

Information

  • Creator
    Vincent Van Patten and Gregory Benedikt
  • Years Active
    2020 - 2025
  • Episodes
    236
  • Rating
    Explicit
  • Copyright
    © Vincent Van Patten and Gregory Benedikt
  • Show Website
    The Dare to Dream Podcast

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