Episode 5 of Cocky & Humble is here, and Sean Williams is joined by Anjelica Cirone for a conversation about fitness, relationships, starting over, and what happens when life forces you outside of your comfort zone.

Anjelica’s story has taken her from the University of Louisville and Team USA cheerleading to Dallas, the fitness industry, and eventually back home to Chicago. Along the way, she’s navigated new cities, changing friendships, difficult relationships, career pivots, and the challenge of figuring out who you are when the life you knew no longer looks the same.

Sean and Anjelica get into what it really means to become comfortable with being uncomfortable: from moving somewhere you barely know anyone and building a new community to learning when it’s time to walk away from relationships that are no longer serving you.

They also dive into the world of fitness: Anjelica’s transition from competitive athlete to trainer, the mental side of working out, different fitness cultures between Dallas and Chicago, and the impact trainers can have on the people who walk into their classes.

But this episode goes well beyond fitness.

Sean and Anjelica talk openly about friendships, competition, independence, self-worth, dating, red flags, learning from past relationships, and why you can’t lose yourself trying to make someone else happy.

At the center of the conversation is a simple lesson: don’t settle, stay authentic to who you are, and understand that you’re not going to be everyone’s cup of tea...and you don’t need to be.

Expect plenty of laughs, unfiltered opinions, tequila, fitness talk, relationship stories, and the kind of conversation you’d normally hear between two friends when the cameras aren’t rolling.

🎙️ Cocky & Humble | Episode 5
Featuring Anjelica Cirone
Hosted by Sean Williams

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Sean sits down with Logan Verboomen to talk about what it really means to keep pushing when things get uncomfortable.

From his wrestling background to taking on his first Half Ironman and now training for Ironman Wisconsin, Logan’s story is rooted in competition, discipline, and a willingness to find out just how far he can push himself. All while balancing a 9–5, training, content creation, and everything else life throws at him.

But the conversation goes deeper than training. Logan opens up about the meaning behind “Born to Suffer,” how losing his godmother helped shape his purpose, and why he now sees the hard moments as an opportunity to show other people what they’re capable of.

Sean and Logan get into confidence, competition, mental toughness, knowing when to push and when to recover, and the discipline it takes to keep chasing a better version of yourself.

How bad do you want it when it stops being easy?

In Episode 3 of Cocky & Humble, Sean sits down with Chicago yoga instructor Colton Ksiazek for a conversation that goes far beyond fitness.

Colton shares how he went from working in finance to finding yoga during his time in Dallas, eventually turning that passion into a community built around movement, music, and connection. What started with a handful of friends practicing yoga in a park grew into something much bigger without waiting for the perfect plan, setup, or opportunity.

Sean and Colton also get into the deeper side of the journey: having the courage to take risks, embracing imperfection, finding community, and learning to better understand yourself. They open up about men’s mental health, therapy, vulnerability, and why so many men struggle to step into spaces like yoga and group fitness.

From building confidence on the outside to doing the work on the inside, this episode is about what can happen when you stop worrying about looking stupid, let go of comparison, and give yourself permission to try something new.

Cocky enough to take the leap. Humble enough to know there’s always more to learn.