In this episode, Drew and Zane talk about what it really takes to build a service business from scratch, why he chose to sit in the first chair instead of hiding in the back, and how he built a team where everyone can cut every type of hair. They get into the hiring struggles every business owner faces, why respect has to be the foundation of any team, and how the service industry lost its way after Covid.

Zane also shares the moment he stopped holding onto lies and anger, why he tells every new hire exactly what to expect from day one, and how three of his barbers have become six figure earners under his roof.

This conversation is for anyone building a service business or trying to figure out how to lead a team that actually gives a damn.

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 contact@wemakecoolshit.co.

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

In this episode, Drew and Adil talk about how a random networking dinner led to partnerships with David Meltzer, Alex Machuca, and a pivot into the data center world. They break down what data centers actually are, why AI is creating the biggest infrastructure boom in history, and how the cloud isn't invisible. It's a warehouse full of supercomputers in the middle of Oklahoma.

They also get into the mindset of saying yes and figuring it out after, why most networking events are bullshit, and the emotional rollercoaster of entrepreneurship. From feeling like a fraud to closing a deal and feeling like the man.

This conversation is for anyone who wants to understand where business is going and how to position yourself in the right rooms.

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 contact@wemakecoolshit.co.

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

In this episode, Drew and Sam talk about what it really means to run events the right way, why the lacrosse showcase world has a credibility problem, and how building a real brand overnight changed the value of his company before he made a single sale. Sam also breaks down why branding is the only cheat code for new business owners who have the knowledge but not the time.

This conversation is for anyone building something in youth sports, or any founder who wants to understand the difference between ROI and real value.

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 contact@wemakecoolshit.co.

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

In this episode, Drew and Anthony talk about what it really takes to build a business while working a full time job. They get into rock bottom moments, the discipline required to wake up at 3:50am every day, why most side hustles never become real businesses, and how surviving as a touring musician prepared him for entrepreneurship. Anthony also shares his journey from sleeping in a candle warehouse in Manhattan to launching a skincare brand that actually helps people.

This conversation is for anyone who knows they’re meant for something more but hasn’t figured out how to make the leap yet.

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 contact@wemakecoolshit.co.

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

In this episode, Drew and Genea talk about what it really looks like to build a business when you’re operating from unprocessed emotions. They get into trauma, decision-making, why most business owners are stuck in prevention mode instead of creation mode, and how the invisible cages we build for ourselves dictate everything from our pricing to our client relationships.

This conversation is exactly what Make Cool Sh*t is about. It’s about long-term thinking, clarity, and understanding that real business growth is built through self-awareness, not just spreadsheets. If you’re a founder, creative, or operator trying to scale without burning out, 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 contact@wemakecoolshit.co.

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

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 contact@wemakecoolshit.co.

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

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 contact@wemakecoolshit.co.

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

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 contact@wemakecoolshit.co.

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

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 contact@wemakecoolshit.co.

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

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 contact@wemakecoolshit.co.

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

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 contact@wemakecoolshit.co.

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

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 contact@wemakecoolshit.co.

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

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 contact@wemakecoolshit.co.

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