It is with heavy hearts that we bring you the last episode of The Dare to Dream Podcast, possibly ever.

We started this podcast over 5 years ago and after 238 episodes, we are ready to close this chapter.

This episode is a final reflection and celebration of the journey we embarked on and who we become along the way. Thank you so much for listening, supporting, and encouraging us over the last 5 years. We couldn't have done this without you all.

Expect to learn:

• Why Vinny and Greg have decided to put The Dare to Dream Podcast into hibernation
• Why we started the podcast in the first place
• Why Vinny is moving to New York
• Why Greg's word for 2026 is "enjoyment"
• About the retreat Greg's hosting in Sedona

And much more.

Goodbye for now, but please know that this is just the beginning of what is coming next for both Vinny and Greg.

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/⁠⁠Join Gregory’s Newsletter - Live a Story Worth Telling:⁠ ⁠⁠https://liveastoryworthtelling.gregoryrussellbenedikt.com/laswt⁠ If you’re ready to create your dream life, book a discovery call with Gregory:⁠ https://calendly.com/gregoryrussellbenedikt-1/discovery-call Join Vincent’s Newsletter - Vinny's Field Notes:⁠ ⁠⁠⁠https://vincentvanpatten.substack.com/Vinny's book: https://www.amazon.com/When-Sky-Opens-Answers-Shimmer/dp/B0DSQ7MYRZ?ref_=ast_author_dp For Vincent's writing, travel photography, and more, check out:⁠ ⁠⁠⁠https://vincentvanpatten.com/⁠⁠

Melissa Aarskaug is the founder of Executive Connect, a purpose-driven platform that unites high-level leaders to explore transformation, reinvention, and the future of modern leadership.

With a background in civil engineering and an 18-year career spanning highly regulated and fast-moving industries, Melissa brings a rare blend of strategic rigor and emotional intelligence to every endeavor. She has helped businesses grow, teams transform, and individuals reconnect with their purpose all while navigating complexity with vision and resilience.

Beyond the mic and the stage, Melissa is a mentor, nonprofit founder, and community builder dedicated to elevating others through access, storytelling, and bold connection. Her mission is simple: to help people lead themselves first so they can lead others better and build lives of purpose, integrity, and freedom.

In this episode, expect to learn:

• Why Melissa's 3-year-old is son is both her mentor and fashion consultant
• How to build ride-or-die relationships
• How to use your emotions to make great decisions
• Why fear is evidence you're on the edge of growth

And much more.

Shownotes:

Melissa's Website

Connect with Melissa on Linkedin

Connect with Melissa on Instagram

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 struggling
• How struggle is often linked to worthiness
• How to know if you are burnt out
• The first step Alana takes when she realizes she's in struggle mode and wants to get out

And much more.

Shownotes:

• The Big Leap
• Remarkably Bright Creatures

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 Craigslist
• How learning improv up-leveled her business skills
• How Paige healed herself from heartbreak by creating a one-woman show
• How 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

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  

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

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

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

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 join
• Why 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

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