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#52 - Season 1 Interview Highlights

May 28, 2024

8 Life-Changing Lessons from Young Entrepreneurs, Models, and Business Leaders

A comprehensive recap of Season One's most impactful moments from the Guyset podcast

The Real Talk Your Career Needs

In a world full of highlight reels and overnight success stories, Season One of Guyset brought you the unfiltered truth about building a career in your twenties. From restaurant industry veterans to tech entrepreneurs, models to finance experts, these conversations revealed the struggles, failures, and hard-won wisdom that actually matter.

Here are the most powerful insights from 8 incredible guests that could change how you think about work, money, relationships, and success.

1. Michael Cechy-Azelina: Breaking Through Addiction and Finding Purpose

The Restaurant Industry Reality Check

Michael shared his raw journey through the restaurant industry's notorious party culture and how he overcame substance abuse through therapy and self-discovery.

His breakthrough moment: "I was really going down a hard road... my girlfriend at the time left me and started going to AA. It got me to stop. I stopped for a good five years and went through massive amounts of therapy."

Key insight: Trauma resides physically in your body. His healing journey included bodywork, talk therapy, craniosacral work, reiki, and even working with shamans in South Dakota. The real breakthrough came when he realized the abuse he'd suffered wasn't his fault.

Actionable tip: If you're struggling with substance abuse or trauma, don't rely on just one type of therapy. Explore multiple modalities including bodywork to release trauma that's stored physically in your muscles.

2. Zach Griff: Master the Credit Card Game for Travel and Rewards

Travel Expert's Financial Strategy

With over 25 credit cards, Zach breaks down the rewards game that most people in their twenties get completely wrong.

The golden rule: "Do not even bother playing the credit card game if you're not paying your bills every month in full. If you're not ready to make that commitment, skip this section entirely."

His top recommendation: Chase Sapphire Preferred for people in their twenties because it bonuses out on dining and travel - the two biggest spending categories for young professionals.

For beginners: Start with the Citi Double Cash Credit Card for simple 2% cash back on everything with no spending category complications.

Actionable tip: Use only 3-5 credit cards maximum (not 25 like Zach). Focus on cards that bonus out on your actual spending categories, and always pay the full balance every month to avoid interest charges.

3. Benjamin Birnbaum: Networking That Actually Gets Responses

The Entrepreneur's Differentiation Strategy

Benjamin revealed why most networking attempts fail and shared the specific approach that lands meetings with executives.

The problem with generic outreach: "Saying 'hey, I want to learn about what you do' or 'I want a job' - neither of those are differentiated points of view."

What works instead: Reach out with specific, valuable insights. His example: "I'm really interested in how technology is being used in the classroom. I thought I was going to work in consulting, but I'm looking for something more unique."

His persistence principle: "If you really want something, writing the email and sending the resume once isn't gonna cut it. We've had people send resumes on pizza boxes, create fan accounts, show up and sing - you have to go as far as possible."

Actionable tip: Before reaching out to anyone, write down what unique perspective or insight you can offer them. Use RocketReach to find contact info, then send a short, specific email that demonstrates genuine value rather than just asking for help.

4. Ryan Winter: Breaking the Silence on Male Body Image

Model's Journey Through Eating Disorders

Ryan opened up about the eating disorders and body dysmorphia that plague men but rarely get discussed openly.

The modeling industry trap: People would see his photos and then 48 hours later say "Oh, was this a long time ago? You look very different." This led to a dangerous cycle of restriction and eventually bulimia.

His breakthrough insight: Understanding that "addiction, depression, anxiety, OCD, eating disorders - they're all basically the same thing: an overactive default mode network" helped him give himself grace.

The recovery principle: "When you fall short of being the person you want to be, that doesn't make you a bad person. It makes you human."

Actionable tip: Give yourself permission to be imperfect. When you fail to live aligned with your values, don't spiral into self-criticism. Acknowledge the disappointment, understand what triggered it, and start again tomorrow with compassion for yourself.

5. Matt (Beard Bar): The Brutal Reality of Building a Business

Startup Founder's Mental Health Journey

Matt shared the reality behind his viral beard care success - the sleepless nights, financial stress, and mental health challenges that nobody talks about.

The hidden costs: "I was burning out physically and mentally. I had no personal time, friendships were out the way, I cut the gym out. I remember thinking 'I'm getting delirious' - I'm just laughing at nothing."

The constant uncertainty: "You're figuring out shipping, taxes, customer service, and you're in charge of all the directions. Your boss isn't telling you what to do - you have to figure it out through Google, YouTube, and books."

His perspective now: "I don't want to be in that position ever again, but now I can kind of joke about it. It's like taking that one math class you hated - I'm glad I learned, but I don't want to do that again."

Actionable tip: If you're starting a business, expect 6-12 months of brutal sacrifice including sleep, social life, and mental health. Plan for this reality and have a support system in place rather than being surprised by the intensity.

6. Erica Ayers Badon: Unfiltered Career Strategy from a Media Executive

Barstool Sports Executive's No-BS Advice

Erica shared hard truths about career advancement based on her journey from $50K to executive leadership.

On job applications: "We had Dave need a camera guy and we had 18,000 people apply. Your one email, nobody gives a shit, nobody even sees your one email."

What actually works: People who got hired sent resumes on pizza boxes, created fan accounts covering Barstool, showed up and sang their applications, or made movie posters about why they wanted the job.

On knowing when to leave: "You know inside of you when to leave a job. The hard part isn't knowing - it's getting from your gut to actually doing something about it."

Her promotion advice: "Raises and promotions are indications of future work, not recognition for past work. Come prepared with what you've accomplished and your vision for what you want to do next."

Actionable tip: If you really want a specific job, one application won't cut it. Get creative and persistent - show them how much you want it through multiple touchpoints that demonstrate your dedication and creativity.

7. Brian Matthews: Financial Foundation for Your Twenties

Financial Advisor's Money Management Blueprint

Brian broke down the savings and spending strategies that separate financially successful people from those who struggle.

The savings formula: "15-20% of your paycheck needs to go towards retirement, then aim for $1,000-$2,000 per month in additional savings if possible."

The three money drains he sees repeatedly:

Going out and food expenses
Online shopping (especially Amazon)
Travel costs

On social comparison: He shared Steph Curry's wisdom: "Don't count other people's pockets. The fancy car fallacy is real - people buy expensive cars for validation but live in tiny apartments."

His tracking method: "Use apps like Monarch Money for 1-2 months to see where you overspend. It's like counting carbs - you don't need to do it forever, just long enough to identify the problem areas."

Actionable tip: Track every expense for one month using a budgeting app. You'll quickly identify your biggest money drains (usually dining out, shopping, or travel) and can cut back to find an extra $500-700 per month without feeling deprived.

8. Josh Felgoise: The Most Important Conversation You'll Have Today

The Host's Mental Health Mission

Throughout Season One, Josh emphasized that the conversation between your ears - how you talk to yourself - shapes everything else in your life.

The internal dialogue reality: "If you're talking to yourself negatively, you will think more negatively, see yourself more negatively, and see everything more negatively."

The two paths: Negative self-talk ("I'm dumb, bad at my job, unlovable") creates a downward spiral, while growth mindset language ("I'll get that interview, I have what it takes") opens up possibilities.

On being guided by fear: "When your internal conversation becomes 'If I do this, they'll think that,' you've stopped following your authentic path. It doesn't get easier to stop caring what people think - you just get stronger at it."

His call to action: "Find the person you feel like you can tell when you're not feeling like yourself. Have a set of tools available when you're feeling shitty - whether that's writing, walking, talking to someone, or creative outlets."

Actionable tip: Listen to how you talk to yourself today. When you catch negative self-talk, ask yourself: "What's leading to this thinking? Is this something I can address? Do I need to talk to someone about it?" Then consciously work to change that internal channel toward more compassionate, growth-oriented language.

The Bigger Picture: What Really Matters

These eight conversations reveal that success isn't about the metrics we typically chase. The common themes that emerged:

Authentic relationships matter more than achievements: Ryan emphasized that sharing meals and connecting with people matters more than body fat percentage.

Mental health requires active management: Every guest had strategies for dealing with stress, self-doubt, and difficult periods.

Financial literacy is non-negotiable: From credit card strategy to budgeting basics, money management skills determine your options.

Persistence beats perfection: Whether it's networking, job hunting, or building a business, consistent effort over time wins.

Self-awareness is everything: Understanding your triggers, patterns, and reactions allows you to make better decisions.

Your Next Steps

Audit your internal dialogue: Pay attention to how you talk to yourself for one day. Is it helping or hurting your progress?
Master the basics: Set up automatic retirement savings, get a rewards credit card if you pay bills in full, and track your expenses for one month.
Build strategic relationships: Identify 5 people you'd like to connect with and develop unique value propositions for each.
Prepare for challenges: Whether it's job hunting, starting a business, or managing stress, have specific tools and strategies ready.
Define success for yourself: Stop comparing your behind-the-scenes to others' highlight reels and focus on your own growth.

The Bottom Line

Season One of Guyset proved that the most valuable advice doesn't come from success stories - it comes from honest conversations about failure, struggle, and the messy process of figuring it out.

Whether you're dealing with body image issues, trying to break into your dream industry, managing money for the first time, or building a business, these insights provide a roadmap for navigating your twenties with more intention and less anxiety.

The difference between those who thrive and those who stay stuck isn't talent or luck. It's having the right strategies, maintaining the right mindset, and surrounding yourself with people who tell you the truth about what it really takes to build a meaningful life.

Want more unfiltered career advice and real talk about building a life that matters? Listen to new episodes of Guyset every Tuesday, and reach out with your questions at josh@guyset.com or @theguyset on social media.

Here are some of my favorite moments from the guests of Season 1 on Guyset- timestamps below:

1:41 Episode #3 Michael Cecchi-Azzolina

9:10 Episode #5 Zach Griff

21:05 Episode #7 Benjamin Birnbaum

32:55 Episode #13 Ryan Winter

1:00 Episode #25 Mat’s Beard Bar

1:07 Episode #35 Erika Ayers Badan

1:32 Episode #44 Brian Matthews

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