CAPTN OffScript

35. The Monday Break(Through) 023 - Launch Before You’re Ready

In this episode of Monday Break(Through), I take you behind the scenes of a major milestone — the launch of my new Type Foundry website. But this isn’t just about celebrating a website going live; it’s about a deeper lesson I’ve learned over years of building creative projects: launch before you feel ready.I share why I decided to publish the site even though it wasn’t finished — with missing product uploads, unfinished mobile layouts, and without a polished freebie section or newsletter signup in place. I explain why choosing progress over perfection has made all the difference not just in this launch, but across my entire creative career.Through stories about my unexpected journey building both a design agency and a successful type foundry — neither of which were part of my original “plans” — I reveal how simply putting work into the world, even when it feels messy and incomplete, leads to real opportunities, growth, and surprising success.You’ll hear practical insights on why endless tweaking behind closed doors doesn’t serve you, how feedback (not fear) drives real improvement, and why being visible — even imperfectly — matters far more than being flawless in hiding.Whether you’re working on a portfolio, launching a side project, starting a freelance career, or simply battling perfectionism, this episode is a reminder that the bravest (and smartest) thing you can do is to show up — as you are, where you are.If you’ve been waiting for the “perfect” moment to hit publish, this episode might just be the push you need.Stay creative. Stay curious. Keep going.

34. The Monday Break(Through) 022 - Feel the Fear. Start Anyway.

In this unscripted Monday Break(Through), I finally take a leap I’ve avoided since the start of this podcast—recording solo without a script. It’s raw, imperfect, and real.I talk about pushing through fear, showing up even when you’re unsure, and the underestimated power of side projects. From recording in a noisy apartment to learning new skills outside of font design, this episode is a love letter to doing the thing—even when it’s scary.Plus, I share a major lesson from ⁠Elliot Jay Stocks⁠ about why side projects matter more than we think, and how they can actually help us avoid burnout, spark new ideas, and reignite passion for our main work.If you’ve been waiting for a sign to start something on the side—this is it. Let’s talk fear, creativity, and why the messy beginning is often the most powerful part.

33. The Monday Break(Through) 021 - How Many Tries Does It Take to Make a Masterpiece?

We live in a world obsessed with the highlight reel — the bestselling book, the viral moment, the overnight success. But what if the real magic is in the volume of work no one ever sees?In this Monday Break(Through), I reflect on a single post by ⁠@mattgottesman⁠ that hit me hard — and how it led me to discover a feed full of wisdom, perspective, and quiet truth. From Frank Sinatra’s 1,300 songs to Picasso’s 150,000 artworks, this episode is about the unseen effort behind every masterpiece… and what that means for the rest of us who are still creating in the quiet.—👀 Takeaway: The ratio doesn’t matter as much as the rhythm.💡 Quote to keep: “Create. Swing. Share. Repeat.”

32. The Monday Break(Through) 020 - The Clichés That Actually Matter

In this episode, I’m talking about the one thing that keeps coming up in almost every Type Convo I’ve done so far—the so-called cliché of “loving what you do” and “having fun with it.” It might sound overused, but there’s a reason it keeps showing up. In just a few minutes, I explore why joy, curiosity, and play are often the real secret to creative longevity. A soft reminder to bring the fun back into your work—especially when things start to feel heavy.

31. From Surf Life to Type Boss: Creative Hustle & Font Fame w/ Tom Cunningham

In this inspiring and laid-back conversation, I sit down with Tom Cunningham, the founder of Tropical Type, to talk about his seven-year journey from surf-loving freelancer to building one of the most recognizable font foundries on the internet. We explore how Tom’s “fast font” philosophy democratized high-impact typography for everyday designers, why he ditched clients for creative freedom, and how he stays grounded in a rapidly evolving design world.Tom shares personal stories about launching his business with zero formal training, watching his fonts end up in Billie Eilish & Ed Sheeran videos, designing a typeface with his 5-year-old son, and how he’s navigating the rise of AI. If you’re a creative tired of design elitism or just someone trying to balance creativity with life, this one’s for you.Find more about Tom and Tropical Type:Intagram: https://www.instagram.com/tropical_type/Website: https://tropicaltype.com/

30. The Monday Break(Through) 019 - Copying Won’t Take You There

In this episode, I talk about something we don’t address enough: creative copying. After Jen Wagner shared a recent example of font theft, I reflected on my own experiences with people releasing work that feels too close to mine—and others, like Sam Parrett or Tropical Type.Copying might feel like a shortcut, but it leads nowhere meaningful. It’s not just unfair to the original creator—it’s empty. True success comes from putting in the work, finding your voice, and staying honest with your process.Whether you’ve ever been copied—or felt tempted to copy—this episode is a reminder of where the real creative power lives.

29. The Monday Break(Through) 018 - Build First, Perfect Later

In today’s Monday Break(Through), I’m sharing a simple principle that has shaped my entire creative journey: Build first, perfect later. Whether you’re designing fonts, launching a product, building a website, or creating anything from scratch—waiting for perfection will only slow you down. I’m sharing personal stories from my own path as a type designer, lessons from guests on The Type Convo, and a gentle push to get your work out there, even if it’s not “ready.”If you’ve been stuck in planning mode, this episode is your sign to start messy, learn fast, and refine as you go. Because momentum beats perfection every time.

28. The Art Of Learning by Doing w/ WILL PATERSON

In this episode of The Type Convo, I had the pleasure of chatting with Will Paterson—a logo & brand designer, lettering artist, and YouTube educator with nearly a million followers. 🎙️We dived deep into:🔥 The power of backengineering in design – how Will deconstructed work to teach himself design from scratch.🎨 Why failing more makes you a better designer – embracing mistakes as part of the process.💡 The art of branding & typography – why Will creates fonts for clients and how it transforms brand identity.📣 Communication & creativity – the secret skill that separates good designers from great ones.👥 Working with his wife in design – the real challenges & benefits of building a business together.😈 Imposter syndrome & self-doubt – why it never fully goes away and how to use it as a superpower.Will’s journey from struggling in school to running his own agency and building a massive online presence is packed with insights for any designer, creative, or entrepreneur.📺 Watch Will on YouTube: https://www.youtube.com/@WillPatersonDesign📸 Follow him on Instagram: https://www.instagram.com/willpat/🌐 Check out his work & agency: https://www.willpaterson.designLet me know your biggest takeaway from this conversation! 💬🔥 #TheTypeConvo #Branding #Typography #SelfTaughtDesigner #CreativeProcess

27. The Monday Break(Through) 017 - One Conversation Can Change Everything

In this episode of Monday Breakthrough, I’m talking about the power of conversations—how they shape careers, relationships, and unexpected opportunities. Inspired by my chat with James Martin on The Type Convo, this is a reminder that every big moment starts with a simple conversation.So, what’s stopping you from starting the convo that could change everything? This week, I challenge you to reach out, speak up, and open doors—because the best things in life don’t happen in silence.🎙️ Listen now and take that first step!

26. The Monday Break(Through) 016 - Time Is Running—Are You in Control?

In this episode of Monday Break(Through), I reflect on a simple but crucial question: Are you truly in control of your time, or is it slipping away unnoticed? A recent conversation with Martina Flor left me thinking—time is the only resource we all have in equal measure, yet how we spend it defines everything.I dive into the quiet moments when I catch myself asking, ‘Is this really the best use of my time?’—not in a productivity-obsessed way, but in a deeper, more intentional sense. Are we investing our time in what matters, or just moving on autopilot? If time is the one thing we can never get back, maybe it’s time to start spending it differently. Tune in for this quick shift in perspective to start your week with clarity and purpose.