Libsyn Directory

#107 - Dear Guyset: Ask Me Anything (Part 3)

Release Date: 06/17/2025

#111 - How to Talk About Your Value at Work (Without Sounding Arrogant)

Guyset

I used to freeze up every time my boss asked how things were going. I'd ramble about how "things are good, things are moving" without actually saying anything meaningful about my work or impact. Recently, my boss left and I had to have THE conversation with our CEO about my role and future. I was terrified. But this time, I came prepared with a framework that completely transformed how I present myself at work. What I cover in this episode: The 3-example method that helped me showcase real impact instead of just listing tasks How to attach concrete numbers to your accomplishments (even if...

#110 - The End of an Era with Reid Becker

Guyset

My roommate Reid is back! After living together for three years in our East Village apartment, we're moving out. This is his second time on the podcast and it’s the perfect time because we're both going through some major life changes right now. Reid is moving out to live with his girlfriend and I'm going to live on my own for the first time. Reid also just finished a pretty long job search - 50+ interviews across 10+ companies over several months. After dealing with lots of rejection, he landed a great new role and learned a lot along the way. He talks about working with an interview...

#109 - Why Being Bold Beats Being Comfortable

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...

#108 - Phoebe Gates: Turning Privilege Into Purpose

Guyset

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...

#107 - Dear Guyset: Ask Me Anything (Part 3)

Guyset

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...

#106 - How To Find Your Style with Simon Goldman

Guyset

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...

#105 - The What's Next Anxiety

Guyset

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...

#104- What Brain Surgery Teaches You About Living with Dr. Randy D'Amico

Guyset

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...

#103 - What They Don't Tell You About Life After College

Guyset

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...

#102 - How to Write Your Story with Robert Bailey

Guyset

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...

More Episodes

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.

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