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:
And much more.
Shownotes:
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:
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:
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:
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.
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
When Dani Alger was 13 years old, her dad died of a heart attack. He was only 41 years old. This catapulted her into a lifelong journey to become the healthiest version of herself while helping others do the same.
Dani calls herself a Foundational Health Consultant and is the creator of the DIGmethod, a science-backed system designed to help people align with their biology and unlock their full potential. The DIGmethod simplifies the Human Operating System into four actionable lifestyle factors—THINK, EAT, MOVE, SLEEP.
Dani works with individuals, teams, and organizations creating measurable improvements in health, energy, and performance. She believes that real success in business and life begins with foundational health— when your biology works for you, Everything Improves: Health, Energy, Performance, and Life!
In this episode, expect to lear:
And much more.
I had the privilege of working with Dani as a coaching client and she is one of my favorite people. The world needs to hear Dani's message and if you're looking to improve your health, Dani is your woman!
Shownotes:
Connect with Dani on Linkedin: https://www.linkedin.com/in/dani-alger-374b5512/
For more Dare to Dream content find us on:
Apple Podcasts: https://podcasts.apple.com/us/podcast...
Spotify: https://open.spotify.com/show/599zlwe...
Join Gregory’s Newsletter - Live a Story Worth Telling: https://liveastoryworthtelling.gregor...
If you’re ready to take bold action and live a story worth telling, book a discovery call with Gregory: https://calendly.com/gregoryrussellbe...
Join Vincent’s Newsletter - Vinny's Field Notes: https://vincentvanpatten.substack.com/
Vinny's book: https://www.amazon.com/When-Sky-Opens...
For Vincent's writing, travel photography, and more, check out: https://vincentvanpatten.com/
From her college radio station to NPR, and now the travel media brand Afar, Cat Sposato has let her curiosity and intuition guide her to both foreign shores and renowned newsrooms.
With her finger on the pulse of travel trends and cultural insights, Cat fosters a keen understanding of the media world and where it’s heading.
She’s written for a variety of prestigious media outlets and has paved her own path in the industry through self-belief, persistence, and by continually embracing uncertainty, making her a dreamer we all can learn from.
Expect to learn:
- How Cat went from being Glamour Woman of the Year to being a writer and editorial assistant for the travel media brand Afar
- The importance of trusting your intuition when navigating the professional world
- How the ones who are persistent eventually separate themselves
- Why the people with power often have no idea what they’re doing
- Why it’s crucial to define what success means to you
- And cultural and travel trends to look out for
Connect with Cat: https://www.catsposato.com/
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
I spent 2 days living at a Buddhist Monastery. Here are 3 things I learned:
1. How wonderful silence is
At the monastery, we practiced "Noble Silence." This is a period of complete silence that starts after dinner and lasts until after breakfast the next day. Being silent at night helped me fall asleep faster. And not having to make small talk at breakfast That was a blessing I never realized I needed.
2. I've been eating wrong
Every meal was enjoyed in complete silence. This was awkward at first & amazing once I got used to it. It made my food taste better, and I never realized how distracted I usually was at mealtimes. I ate slower and got full a lost faster.
This habit came home with me without me realizing it. I found myself eating breakfast today in silence, with my phone in a different room. Like most people, I used to always catch up on texts/podcasts while eating. But after experiencing how pleasant a fully present meal is, I can't go back.
3. Do everything with 100% focus
When you are breathing, know that you are breathing. When you are eating, know that you are eating. Thích Nhất Hạnh founded the monastery I was at and he was BIG on doing one single thing at a time. When you give 100% of your focus to ONE task...You show up with a powerful presence that's rare.
Shownotes:
Visit Deerpark Monastery in San Diego:
https://deerparkmonastery.org/visit/
Born in Egypt, Bishoy Tadros was diagnosed with cancer at age three. His family moved to the U.S. and for the next 10 years he battled acute lymphoblastic leukemia, culminating with a life-saving brain surgery on his 13th birthday.
After a decade of medical challenges, he was finally granted a clean bill of health—an experience that shaped his relentless drive and perspective on life.
Denied the chance to fully pursue athletics as a child, Bishoy returned to fitness as an adult with a renewed sense of purpose. He is now an Ironman and a dedicated marathon runner, and is going to become the first Egyptian to complete all seven World Major Marathons. Along the way, Bishoy has led charitable campaigns and raised over $150,000 for causes close to his heart, using his story to inspire others facing their own battles.
In this inspiring episode expect to learn:
And much more.
Bishoy's story is incredibly inspiring and he is someone who is living a story worth telling. This is an episode you do NOT want to miss!
Shownotes:
Learn more about Bishoy on his Website: https://www.bishoytadros.com/
Read his book: Break Barriers: https://www.amazon.com/Break-Barriers-Setbacks-Rather-Define/dp/1086196627
Listen to the Mile 40 Podcast: https://podcasts.apple.com/us/podcast/mile-40-podcast/id1622896615
For more Dare to Dream content find us on:
Apple Podcasts: https://podcasts.apple.com/us/podcast...
Spotify: https://open.spotify.com/show/599zlwe...
YouTube: https://www.youtube.com/channel/UCoim...
Instagram: https://www.instagram.com/thedaretodreampodcast
Join Gregory’s Newsletter - Live a Story Worth Telling: https://liveastoryworthtelling.gregor... If you want to transform your life through BOLD action, book a discovery call with Gregory: https://calendly.com/gregoryrussellbe...
Join Vincent’s Newsletter - Vinny's Field Notes: https://vincentvanpatten.substack.com/
Vinny's book: https://www.amazon.com/When-Sky-Opens...
For Vincent's writing, travel photography, and more, check out: https://vincentvanpatten.com/
Everything has happened for a reason, and that reason is to bring you to this moment.
With what you’ve experienced and what you know, what will you decide to change?
How do you want your future to look?
Who do you want to become?
You are exactly where you’re meant to be.
Do you believe that?
If you want to change, it’s up to you to create it.
So take what you’ve been given, start where you are, and, like us, go forth into the unknown with purpose and a vision.
It only takes a single step to begin the journey.
Be brave.
You can reach the future of your dreams.
But it won’t just happen on its own.
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
Our great friend Santana is a man who embodies the entrepreneurial spirit. Daring. Adventurous. A lifelong student. Passionate. Big-hearted.
He's creating something very special in the world, putting himself and his communications coaching business on the line again and again in his everlasting pursuit of excellence.
Because anything less just won't do.
What's great about talking to Santana is he doesn't shy away from sharing his missteps, stumbles, sacrifices.
He's right there in the pit with us, following his dream and traversing the earth to achieve what he knows in his heart is possible.
This conversation is sure to get you one step closer to emerging from the pit, the valley, and one step closer to that mountaintop. We're in this thing together. So let's keep climbing, one foot after the other, in pursuit of something that actually matters.
Connect with Santana on Instagram
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
Matt Mosich is an Executive Communication & Speaker Coach, fancy speak for “he helps CEOs, founders, and keynote speakers speak good.”
He never imagined he’d end up here, doing work that defies everything he once believed he was capable of. As a recovering perfectionist and amateur philosopher, he channels that hard-won self-awareness into every client session and conversation.
In this episode, expect to learn:
And much more.
Shownotes:
Are we supposed to have our lives together by thirty?
It can certainly feel that way—especially when we’re comparing ourselves to friends, coworkers, and, of course, people on Instagram.
Our thirties carry a certain weight. They mark the shift between the freewheeling twenties and the decade where we're supposed to start families, plant roots, and finally figure it all out.
But maybe that’s all just a facade. The truth? Nobody really has their sh*t together—we’re all just figuring it out as we go.
In this episode, Vinny dives into the complexities of turning thirty, and why it’s not a decade to fear, but one to embrace.
He also reflects on his weekend at the Pretty Lights music festival in Colorado, and the importance of saying yes to the once-in-a-lifetime experiences we share with our friends.
Life is short. Life is for living. Enjoy every season of it.
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
In March of 2023, Gregory took bold action and gave his number to a cute girl he met at a cafe. Two years later, his TEDx talk chronicling this experience has over 60K views and the internet wants to know more about this mysterious wonder woman.
My guest today is Mikah Leggo. Mikah is a paralegal, a lover of philosophy, yoga, and sour candy, and for the past 2.5 years she's been putting up with Gregory's illustrious mustache.
In this episode expect to learn:
And much more.
Shownotes:
In this conversation, we delve into the spiritual teachings of Michael Singer, whose booksThe Untethered Soul and The Surrender Experiment have greatly enhanced both of our lives.
Yet it’s his cheerfully free lectures on Youtube that we come back to daily. His lessons focus on enjoying the journey of life rather than fixating on outcomes; fostering a profound sense of gratitude for life on earth; and surrendering to the flow of nature, rather than fighting it.
Perhaps most helpful is the recognition that external achievements will not fix what’s happening inside of us, and that’s okay.
We had a lot to explore on this expansive episode, and we hope it brings a little more peace, understanding, and beauty into your world.
Show notes:
Michael Singer's lectures: https://www.youtube.com/@SeatsofContemplation
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
Emily Gibbens is former D1 tennis player turned Holistic Performance Coach. On this episode, she shares the untold story behind her athletic journey from the moment things fell apart to how that breakdown sparked a powerful transformation.
We dive into embodiment, identity shifts, and why bold, aligned choices paired with deep self-trust are the ultimate competitive edge. Now based in Bali, Emily helps athletes stop outsourcing their performance and start owning their game.
Through her 12-week Aligned Athlete program, she teaches high performers how to bridge the invisible gap between talent and consistent execution by working with their bodies - not against them - and cultivating intuition to unlock flow, focus, and sustainable success on and off the court.
Shownotes:
Spiritual practices that are changing my life, and my first day in a new town.
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