Darren Magarro is the founder of DSM, an independent agency built through nearly two decades of growth, hard lessons, and real relationships. His work centers on leadership, trust, and building teams that last beyond any single phase of a business.

In this episode, Drew and Darren talk about what it looks like to grow up as a leader. They get into mentorship, imposter syndrome, learning when to step back, and why building the right relationships matters more than control or ego. Darren opens up about the realities of running a business through different seasons of life, becoming a parent, and learning how to lead people with patience, humility, and perspective.

This conversation is exactly what Make Cool Sh*t is about. It is about long-term thinking, accountability, and understanding that real leadership is built through trust, not authority. If you are a founder, creative, or operator navigating growth, responsibility, and change, this episode will resonate.

For more from Make Cool Sh*t, follow us:

Instagram → @wemakecoolshit

TikTok → @wemakecoolshit

YouTube → @wemakecoolshit

LinkedIn → Make Cool Sh*t Studio

Drew O’Brien → @drewobrien

Make Cool Sh*t is a design and strategy studio for the mavericks and misfits. Want to work with us? Email us directly at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Mike Ham is a New Jersey–based storyteller and the creator of Local Originals, a project dedicated to documenting the people and places that still mean something. His work focuses on real conversations captured on location, in the spaces where culture is actually built.

In this episode, Drew and Mike talk about why the best stories do not happen in studios, the importance of showing up where real life happens, and what it means to preserve culture through conversation. Mike shares his approach to storytelling, building trust with the people he interviews, and why authenticity always matters more than polish.

This conversation is exactly what Make Cool Sh*t is about. It is about paying attention, respecting the work, and creating space for voices that often go unheard. If you are a creator, founder, or anyone who cares about culture, community, and meaningful storytelling, this episode will resonate.

For more from Make Cool Sh*t, follow us:

Instagram → @wemakecoolshit

TikTok → @wemakecoolshit

YouTube → @wemakecoolshit

LinkedIn → Make Cool Sh*t Studio

Drew O’Brien → @drewobrien

Make Cool Sh*t is a design and strategy studio for the mavericks and misfits. Want to work with us? Email us directly at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Alexandra Cimino is the founder of SōlMedia, a social media agency built around community, integrity, and long-term growth. Her work focuses on helping brands build real relationships online without chasing trends, virality, or empty metrics.

In this episode, Drew and Alexandra unpack what it actually takes to build a sustainable business in the social media space. They talk about consistency over hype, why community always outperforms exposure, and the difference between being visible and being trusted. Alexandra opens up about scaling responsibly, saying no to the wrong clients, and building a business rooted in integrity rather than quick wins.

This conversation is exactly what Make Cool Sh*t is about. It is about playing the long game. It is about doing work that aligns with your values, building relationships that last, and understanding that real growth comes from showing up consistently, not selling your soul for attention. If you are a founder, creative, or operator navigating growth in a noisy digital world, this episode will resonate.

For more from Make Cool Sh*t, follow us:

Instagram → @wemakecoolshit

TikTok → @wemakecoolshit

YouTube → @wemakecoolshit

LinkedIn → Make Cool Sh*t Studio

Drew O’Brien → @drewobrien

Make Cool Sh*t is a design and strategy studio for the mavericks and misfits. Want to work with us? Email us directly at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Leia Gaccione is a chef and partner at The Saint Clair, where she leads the kitchen while helping shape the vision, culture, and long-term direction of the restaurant. Her work sits at the intersection of hospitality, leadership, and creative discipline, balancing craft, consistency, and ownership in an industry that demands everything.

In this episode, Drew and Leia talk about what it actually takes to build and sustain a restaurant, the pressure that comes with ownership, and the reality of committing fully to your work when there is no off switch. Leia opens up about leadership in the kitchen, earning trust over time, and the difference between loving the craft and carrying the responsibility of the business. They get into discipline, decision-making under pressure, and what it means to stay grounded while building something that lasts.

This conversation is exactly what Make Cool Sh*t is about. It is about commitment, accountability, and respecting the work enough to show up every day. If you are a founder, creative, or operator navigating high standards, long hours, and real responsibility, this episode will resonate.

For more from Make Cool Sh*t, follow us:

Instagram → @wemakecoolshit

TikTok → @wemakecoolshit

YouTube → @wemakecoolshit

LinkedIn → Make Cool Sh*t Studio

Drew O’Brien → @drewobrien

Make Cool Sh*t is a design and strategy studio for the mavericks and misfits. Want to work with us? Email us directly at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Andrew Stadelberger is the Managing Director at Player Coach Advertising Agency, where he focuses on building long-term partnerships, strategic collaboration, and relationship-driven growth. His work sits at the intersection of agency leadership, trust, and navigating risk inside the creative industry.

In this episode, Drew and Andrew talk about what it actually takes to build a career without chasing attention or shortcuts. Andrew breaks down the risks behind betting on yourself, the realities of agency life, and why meaningful growth almost always comes from relationships, not exposure. They get into whitelabeling, trust-driven collaboration, and the difference between being visible and being valuable.

This conversation is exactly what Make Cool Sh*t is about. It is about playing the long game. It is about credibility, patience, and creating opportunities through consistency instead of noise. If you are a founder, creative, or operator trying to build something that lasts, this episode will hit home.

For more from Make Cool Sh*t, follow us:

Instagram → @wemakecoolshit

TikTok → @wemakecoolshit

YouTube → @wemakecoolshit

LinkedIn → Make Cool Sh*t Studio

Drew O’Brien → @drewobrien

Make Cool Sh*t is a design and strategy studio for the mavericks and misfits. Want to work with us? Email us directly at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Eric Maury is an entrepreneur and the owner of Marcel Bakery & Kitchen, Drip Coffee, and Aligned Creative. He is a creative director turned operator who has built multiple businesses out of pure conviction, strategy, and an ability to see opportunity before everyone else. His work spans hospitality, branding, catering, and systems design, and he brings a unique perspective on what it takes to scale something from nothing.

In this episode we get into what it really takes to build and rebrand a business. Eric opens up about leaving the agency world, the pressure of buying Marcel, the risks behind Drip Coffee, and the lessons he learned building Aligned Creative. We talk about the realities of entrepreneurship, why branding is often misunderstood, how AI is changing the creative landscape, and what happens when you stop chasing validation and start running your own race.

We also dig into the discipline required to build systems, develop teams, and stay patient as a founder. This conversation is honest and grounded and exactly what Make Cool Sh*t stands for. It is about clarity. It is about growth. It is about the work behind the work. If you are a creator an entrepreneur or someone building something real this episode will hit home.

For more from Make Cool Sh*t, follow us:

Instagram → @wemakecoolshit

TikTok → @wemakecoolshit

YouTube → @wemakecoolshit

LinkedIn → Make Cool Sh*t Studio

Drew O’Brien → @drewobrien

Make Cool Sh*t is a design and strategy studio for the mavericks and misfits. Want to work with us? Email us directly at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Ryan Mack is the founder of Kill The Headlights, a creative agency built on an anti-agency philosophy. Make Cool Sh*t collaborates with KTH on select projects, and Ryan is someone Drew turns to for honest, grounded conversations about the industry and the future of creative work.

In this episode, Ryan and Drew talk about meaningful work, fulfillment, identity, and the uncomfortable truth that most people feel disconnected from the work they do. They break down why four out of five people are unhappy at work, how AI is exposing talent gaps, and what it actually takes to build a life you believe in.

They also get into the mindset behind decision making, the value of clarity, and how to become someone you can trust in difficult moments.

This conversation is raw, honest, and aligned with what Make Cool Sh*t stands for. It is about purpose. It is about clarity. It is about the work behind the work. And it is about showing up every day with intention, even when it feels uncomfortable.

If you are a creator, an entrepreneur, or someone trying to build a meaningful life, this episode will hit home.

For more from Make Cool Sh*t, follow us:

Instagram → @wemakecoolshit

TikTok → @wemakecoolshit

YouTube → @wemakecoolshit

LinkedIn → Make Cool Sh*t Studio

Drew O’Brien → @drewobrien

Make Cool Sh*t is a design and strategy studio for the mavericks and misfits. Want to work with us? Email us directly at [email protected].

Hosted on Acast. See acast.com/privacy for more information.

Jamie Knott is a chef entrepreneur and one of the sharpest creative minds in New Jersey hospitality. He is the owner and partner behind The Saddle River Inn, Saddle River Cafe, Cellar 335 and MADAME. He is also a partner with host Drew O"Brien in their luxury streetwear brand Sunday Sauce.

In this first episode we get into what it really takes to build a brand that people remember. Jamie opens up about the early years the fear the pressure and the strange mix of confidence and doubt that every creator carries. We talk about finding your voice as an entrepreneur why imposter syndrome never fully goes away and how the hospitality world forces you to grow up fast.

We also get into the discipline it takes to build a streetwear brand and why designing clothing teaches you lessons that restaurants never will. This conversation is raw honest and exactly what Make Cool Sh*t stands for. It is about the work behind the work. It is about staying true to who you are when things get loud. It is about the moments when you have to bet on yourself before anyone else does.

If you are a creator an entrepreneur or someone obsessed with how ideas become real this is the perfect place to start.

For more from Make Cool Sh*t, follow us:

Instagram → @wemakecoolshit

TikTok → @wemakecoolshit

YouTube → @wemakecoolshit

LinkedIn → Make Cool Sh*t Studio

Drew O’Brien → @drewobrien

Make Cool Sh*t is a design and strategy studio for the mavericks and misfits. Want to work with us? Email us directly at [email protected].

Hosted on Acast. See acast.com/privacy for more information.