Guyset

I almost bailed on my first networking event due to anxiety. Instead, I stayed, met a New York Times reporter, and completely bombed my pitch to her. Here's the story of what went wrong and why I'd do it all again.

What You'll Learn:

• How to overcome social anxiety at networking events when you don't know anyone
• Why being "bold" beats being comfortable every time
• My biggest networking mistakes and what I learned from them
• Practical tips for starting conversations at professional events
• How to handle rejection and awkward moments with confidence

Key Takeaways:

✓ Strategies for managing imposter syndrome in professional settings

✓ The power of asking for feedback after difficult conversations

✓ Why taking opportunities matters more than the outcome

✓ How to network authentically without seeming desperate

Whether you're facing your first networking event, dealing with social anxiety, or just trying to be bolder in your career, this episode breaks down exactly how to push through discomfort and grow from every interaction – even the cringeworthy ones.

Perfect for: First-time networkers, anxious introverts, anyone who's ever stood alone at a professional event wondering what the hell they're supposed to do, young professionals ready to take uncomfortable chances on themselves.

Real talk: This isn't about becoming a networking master overnight. It's about showing up scared, making mistakes, and learning that the worst-case scenario (total embarrassment) is actually survivable – and valuable.

Bonus: Behind-the-scenes from my sweaty interview with Phoebe Gates and why I almost asked to pause mid-conversation to towel off.

New episodes every Tuesday.

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• Read my substack: guyset
• Instagram: @theguyset
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Ask Me Anything: guyset.com

In this unfiltered episode, I sit down with Phoebe Gates (Bill Gates' daughter) to discuss her viral "nepo baby" moment on Call Her Daddy, building her shopping app Phia from a Stanford dorm room, and how she handles constant criticism as a young entrepreneur.

What You'll Learn:

• How Phoebe owned her privilege and why authenticity matters more than PR training
• The biggest mistakes she's made building Phia that cost months of wasted work
• Why talking to customers early could have saved her startup thousands of dollars
• Her smart strategy for filtering useful criticism from online trolls
• How she uses ChatGPT to prepare for important business meetings
• The "water pitcher" energy management philosophy from Bumble's CEO that changed her perspective

Key Takeaways:

• Building authentic friendships when you come from privilege
• Why Phoebe focuses on product quality over public perception
• How Phia works as the "Google Flights for fashion" and finds better deals instantly
• Managing ADHD as a founder and the importance of daily prioritization
• Balancing startup life with personal relationships using the "burner" method

About Phoebe Gates: Co-founder of Phia, a revolutionary shopping app that helps users discover better deals and make smarter fashion purchases. Previously interned at Vogue and studied at Stanford University.

About Phia: Download Phia for free on the App Store - the shopping assistant that finds better deals, tracks price drops, and helps you shop smarter across all your favorite sites.

Timestamps:

00:00 - Intro & Nepo Baby Discussion

04:08 - Finding Real Friends Despite Privilege08:27 - Building Phia & Using AI Tools

13:06 - Biggest Startup Mistakes & Lessons

19:41 - Daily Life as a Young Founder

24:08 - Energy Management & Best Advice

Subscribe, give this episode 5 stars, and leave a review!

Watch the full episode on YouTube: @guyset

Connect with me:

• Instagram: @theguyset
• TikTok: @theguyset
• YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Ask Me Anything: guyset.com
• Read my substack: guyset

See you guys next Tuesday!

I'm bringing back the anonymous question box format inspired by my high school sex ed class. This week, I'm pulling random questions from a hat that you guys asked and answering them completely unscripted.

Topics I cover:

• Dating advice: How to know when to end things vs. keep dating someone
• Reading relationship signals: Signs she's actually into you after 5 dates
• Navigating weird conversations: The right way to talk about exclusivity without awkwardness
• Hookup etiquette: Do you have to stay over after hooking up?
• Career advice: What to do when you feel like you can't impress your boss
• Dating app tips: Why Hinge isn't working and how I think you can fix it
• Moving in with your girlfriend: How I think you should split rent fairly
• Life hacks: Products that actually make your life easier
• Dating profile advice: Setting up a dating profile that gets responses

Submit your anonymous questions at Guyset.com - I can't see who sends them, so ask whatever you're really thinking about. No topic is off limits (as you can tell).

New episodes drop every Tuesday with dating advice, relationship tips, career guidance, and honest conversations about what guys in their 20s are actually wondering about.

If something I said helped you out, leave a 5-star review and share it with a friend who needs to hear this advice.

Connect with me:

• Instagram: @theguyset
• TikTok: @theguyset
• Watch the full episode on YouTube: @guyset
• Website: guyset.com
• Email: [email protected]
• Read my substack: guyset
• Ask Me Anything: guyset.com

See you guys next Tuesday.

Simon Goldman, a 24-year-old menswear designer and content creator, is here to share his style advice, brand recommendations, and summer fashion tips. He talks about his journey from sneaking into NYC fashion events as a student to building a massive following of over 500k across social media. He reveals the biggest mistake guys make when getting dressed (hint: it's all about fit), breaks down his essential 5-piece wardrobe formula, and explains his "buy once, buy well" philosophy.

From sending 40 cold emails daily to networking with fashion legends, Simon discusses the hustle required to break into any industry. He also covers practical style advice, the best brands for different budgets, why thrift shopping is a goldmine, and seasonal fashion tips.

Whether you're looking to upgrade your style or learn how to put yourself out there professionally, this conversation is packed with actionable insights.

Topics discussed:

• The 5 essential wardrobe pieces every man needs
• How to find your perfect fit
• Best brands for any budget
• Networking and cold outreach strategies
• Building confidence through style

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Find Simon on Instagram and TikTok @Simon__Gold

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Ask me anything HERE

Check out Guyset Magazine HERE

See you guys next Tuesday.

I've been asking myself "what's next?" constantly lately, and I'm pretty sure you have too. In this episode, I talk about the anxiety that comes with being 25 and feeling like life is one giant transition period that never ends.

I'm moving out of my apartment in less than two months which is my first move in three years and it's got me thinking about how we're always looking ahead instead of appreciating what we have right now. Whether it's wondering what's next for your job, your relationship, your friendships, or where you're going to live, these questions never seem to stop.

If you're feeling overwhelmed by constant change or caught up in always thinking about what's coming next, or what I call the "what's next?" anxiety that defines our twenties, this one's for you. Sometimes the best thing we can do is just look around at what we have today.

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See you guys next Tuesday.

Renowned neurosurgeon at Lenox Hill Hospital Dr. Randy D'Amico is here to talk about one of the most high-pressure careers on the planet. After going viral on TikTok with his "day in the life of a neurosurgeon" videos, Dr. D'Amico opens up about what it's really like to perform brain surgery and how years of working on the human brain have shaped his perspective on life.

What You'll Learn:

Brain Health & Nutrition:

• The neurosurgeon's daily diet for optimal brain function (avocado toast, Greek yogurt with chia seeds, and why he limits coffee)
• Which supplements actually work (hint: only one made his list)
• How alcohol really affects your brain and readiness scores
• Natural ways to protect and strengthen your brain

Life & Career Insights:

• How Dr. D'Amico went from punk rock musician to brain surgeon
• What it's like to perform 15-hour surgeries and awake brain operations
• His philosophy on handling pressure when lives are literally in your hands
• Why "your brain is just mushy yellow tofu" - and what that means for how we experience reality

Practical Advice for Young Guys:

• The "check your own pulse first" technique for staying calm under pressure
• How to process difficult conversations and setbacks
• Why reading books expands your beliefs and experiences
• His controversial advice to his younger self

Key Takeaways:

Dr. D'Amico reveals how witnessing mortality daily has taught him that "life is a gift and none of us are owed anything." He shares intimate stories from the operating room, explains why he wakes up at 4:30 AM everyday, and discusses how he balances being a father of two while literally saving lives.

From his curated Spotify playlist "Great Songs" (featuring everything from Dead Kennedys to Taylor Swift) that he listens to during surgery, to his thoughts on social media's impact on young people's happiness, this conversation covers the intersection of medicine, mindset, and modern life.

Guest: Dr. Randy D'Amico - Neurosurgeon at Lenox Hill Hospital, TikTok creator, and author of the Spotify playlist "Great Songs"

Recorded live at Lenox Hill Hospital in New York City

Subscribe to Guyset for weekly conversations about what should be talked about for guys in their 20s. Available on all podcast platforms.

Subscribe, give this episode 5 stars, and leave a review!

Connect on Instagram HERE and HERE

Check out Guyset.com!

Watch on YouTube HERE

Watch on TikTok HERE

Read my Substack HERE

Ask me anything HERE

Check out Guyset Magazine HERE

See you guys next Tuesday.

Graduating this year? Already in your twenties and feeling lost? This episode is your brutally honest guide to navigating life after college when everything feels contradictory and confusing.

I break down the impossible expectations placed on twenty-somethings: You're supposed to save money AND travel, take risks AND stay stable, find your purpose AND stick with your first job for two years. Sound contradictory? That's because it is.

In this episode, you'll learn:

• Why feeling lost in your twenties is completely normal (and necessary)
• The "connect the dots" philosophy that will change how you view uncertainty
• How your twenties are like building muscle - through breakdown comes strength
• Why the only constant in your twenties is change (and how to embrace it)
• How to find magic in the mundane when life feels repetitive
• The superpower our generation has that previous ones didn't

Whether you're job hunting, dealing with rejection, questioning your path, or just trying to figure out what the hell you're doing - this episode will make you feel less alone and more equipped to handle whatever comes next.

Subscribe, give this episode 5 stars, and leave a review!

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Watch on YouTube HERE

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Read my Substack HERE

Ask me anything HERE

See you guys next Tuesday.

Thriller author Robert Bailey is here to talk about his new novel "The Boomerang" a page-turner that will have you guessing until the very last chapter. Whether you're a thriller fan, looking for your next summer read, or just love books that keep you hooked from page one, this episode has something for you.

We dive deep into Robert's writing journey, from his early aspirations to getting his first book published, and what a typical day looks like for him as an author. Get an exclusive behind-the-scenes look at his writing process, how he sits down to create these nail-biting stories, his daily writing habits, and the rituals that keep him motivated.

Robert opens up about the inspiration behind "The Boomerang," sharing how this particular story hits close to home and what he hopes readers will take away from it. We explore the highs and lows of the writing life, his favorite aspects of the creative process, and the challenges that come with writer's block.

Robert discusses how to separate yourself emotionally from your work, the bittersweet moment of finishing a book, and how his life has changed since becoming a published author. Plus, he shares his favorite books, career-changing advice he's received, and his best tips for aspiring writers.

This episode is perfect for anyone interested in writing or just wants to hear an engaging story about pursuing your passion. Tune in for practical writing advice, honest insights into the author's life, and discover your next favorite book.

What You'll Learn From Robert Bailey:

• The daily habits and rituals of a successful thriller writer
• How to push through writer's block and creative challenges
• The story behind "The Boomerang" and its personal significance
• Practical tips for aspiring authors
• Book recommendations from a master of the genre

Book: "The Boomerang" by Robert Bailey, available everywhere now

Subscribe to Guyset for weekly episodes featuring inspiring guests and conversations on what should be talked about. Available on Apple Podcasts, Spotify, and wherever you get your podcasts.

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Watch on YouTube HERE

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Read my Substack HERE

Ask me anything HERE

Check out Guyset Magazine HERE

See you guys next Tuesday.

Jordan Litz who is currently playing Fiyero in Wicked on Broadway is here! Wicked is also his Broadway debut and he is now the longest-running guy to ever play the role. He has such an interesting story of how he got here from competing against Michael Phelps in the 2012 Olympic trials to completely changing his career and chasing a new dream to play Fiyero in Wicked. This is one of my favorites and reminded me that it's never too late to change your life, change your career, find your passion, and chase a new dream. Watch the full interview on YouTube HERE

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Check out Jordan Litz as Fiyero in Wicked and Instagram

Connect on Instagram HERE and HERE

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Check out Guyset Magazine HERE

See you guys next Tuesday.

When I started Guyset almost 2 years ago, I had no idea what I was getting myself into. What I did know was how much I wanted to see something like this in the world, a place for guys to hear real advice and different perspectives on the things they're thinking about, wondering about, anxious about, or feel weird about for not knowing and since I couldn't find that, I created it. Because I was that guy, and I am that guy. I created a place where I could hear advice that applies to me and the guys my age in every aspect of my life from dating and relationships to career, success, confidence, insecurity, style, health, wellness, fitness, appearance, and so much more. What I didn't know was how much this would change me, how much I'd learn, and how much I'd grow.

Thank you so much for being here and for sticking with me through 100 episodes... WHAT! 100 episodes?!?!

I'm really grateful to do this, that you're here with me, and that I took a chance on myself. And the best part is, we're just getting started.

Subscribe, give this episode 5 stars, and leave a review!

Connect on Instagram HERE and HERE

Check out Guyset.com!

Watch on YouTube HERE

Watch on TikTok HERE

Read my Substack HERE

Ask me anything HERE

Check out Guyset Magazine HERE

See you guys next Tuesday.