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.🎙️ Plus — a little behind-the-scenes: Matt Gottesman will be joining me for an Instagram Live this Friday on The Type Convo. Don’t miss it.—👀 Takeaway: The ratio doesn’t matter as much as the rhythm.💡 Quote to keep: “Create. Swing. Share. Repeat.”
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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.
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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/
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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.
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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.
The Type Convo is a podcast that dives into the world of typography, design, and creative journeys. Each episode brings you behind the scenes with top designers and type experts who share insights, challenges, and inspiration from their work. Hosted by SilverStag Type Foundry, this series is perfect for creatives eager to learn from the industry’s most innovative minds. Join us for real conversations that go beyond the surface of design.
Ireland