She learned Photoshop at 12 on multiple 30-day trials. She got into five art schools and couldn't afford a single one. She moved to New York with no job, no safety net, and no plan B. And then her artwork went around the world on a UPS box.

Sophia Yeshi is a New York-based illustrator whose bold, colourful, inclusive work has appeared in campaigns for Google, Spotify, Adobe, Instagram, and UPS. But this conversation is about the person behind all of it — the mixed-race kid from Baltimore who grew up too fast, taught herself everything, and built a career entirely on her own terms.

What we cover:

• Growing up across multiple identities and being othered from birth
• Teaching herself Photoshop at 12 on repeated 30-day free trials
• Getting into five art schools and not being able to afford any of them
• Moving to New York with no freelance safety net — and figuring it out anyway
• The UPS box campaign that went around the world
• Why she's calling this year "rejection therapy"
• Advice for young illustrators in a shifting industry
• What she'd write in a letter to her eight-year-old self

Connect with Sophia Yeshi:

Website: https://www.yeshidesigns.com/

Instagram: https://www.instagram.com/sophiayeshi/

Listen and subscribe:

Apple Podcasts: https://podcasts.apple.com/us/podcast/captn-offscript/id1837469433

Spotify: https://open.spotify.com/show/7nJ5dKTP2dQN5OwICKjTY5

More from Captn OffScript:

Website: https://captnoffscript.com/

YouTube: https://www.youtube.com/@CAPTNOffScript

Instagram: https://www.instagram.com/captnoffscript

Newsletter: https://captn.myflodesk.com/newsletter

Lettering legend Jessica Hische sat in a room full of ultra-successful entrepreneurs — and realised they all dreamed of doing exactly what she was already doing. Drums, stained glass, creative hobbies, time with their kids, work they actually love. Her life, right now.

In this episode, we go well beyond the portfolio. Jessica opens up about imposter syndrome, building a creative life entirely on her own terms, co-founding StudioWorks, running two retail stores, writing children's books, and why "happy to be here" might be the most powerful career philosophy there is.

What we cover:

• The kindergarten coloring contest that started it all
• Meeting her husband on Match.com before it was socially acceptable
• How she became the Fairy Font Mother at Canva Create
• Drums, stained glass, and giving strangers tattoos from her studio
• Why she released free tools this week — and why you should care
• Imposter syndrome at every stage of success (and why to worry about people who don't have it)
• Parenting as curling — the most accurate analogy we've ever heard
• The one thing she'd tell her younger self

Connect with Jessica Hische:

Website: https://jessicahische.is

StudioWorks: https://studiowork.app

Instagram: https://www.instagram.com/jessicahische/

Listen and subscribe:

Apple Podcasts: https://podcasts.apple.com/us/podcast/captn-offscript/id1837469433

Spotify: https://open.spotify.com/show/7nJ5dKTP2dQN5OwICKjTY5

More from Captn OffScript:

Website: https://captnoffscript.com/

YouTube: https://www.youtube.com/@CAPTNOffScript

Instagram: https://www.instagram.com/captnoffscript

Newsletter: https://captn.myflodesk.com/newsletter

Jacob Cass started a blog in 2007 as a design student in Sydney, documenting his learning journey. That simple act of sharing imperfect work caught the attention of a New York agency and launched a career designing for Disney, Nike, and Red Bull. Nearly 20 years later, Jacob has traveled to 88 countries as a digital nomad, hosted the Just Branding podcast for six years, and founded Brand Builders Alliance — a thriving membership community serving brand builders across 29 countries.

In this conversation, we explore:

• How a student blog documenting imperfect design work landed Jacob a dream job in New York
• The visa rollercoaster: getting denied in Canada, kicked out of the country, and learning never to get comfortable
• Traveling to 88 countries while working four hours a day as a fully booked visual identity designer
• Why South Africa's private game reserves were the top travel experience
• How losing 90% of his blog traffic became the catalyst for building Brand Builders Alliance
• Why he'd give student Jacob the same advice today: keep sharing where you're at, even when work isn't polished
• Taming the "advice monster" and why asking questions beats giving answers
• Running a global community with four young children: work-life integration and boundaries
• Pivotal moments: getting fired, discovering brand strategy, major setbacks, and adapting
• Why sharing process matters more than polished outcomes
• How podcasting gets easier after doing the reps

Jacob's core philosophy: share your process, not just your final work. Don't wait for impressive results before building an online presence. Share the journey of learning itself and let opportunities find you.

ABOUT JACOB CASS: Jacob is an Australian brand designer, community builder, and founder of Brand Builders Alliance. He started his career with a student blog in 2007 that led to designing for major brands in New York. After several years as a digital nomad traveling to 88 countries, he now co-hosts the Just Branding podcast and leads a membership community focused on helping brand builders master branding and build thriving creative businesses.

CONNECT WITH JACOB:

Brand Builders Alliance: https://joinbba.com

Website: https://justcreative.com

Instagram: https://www.instagram.com/justcreative/

Just Branding Podcast: https://justcreative.com/podcast/

LinkedIn: https://linkedin.com/in/jacobcass

WATCH THE FULL VIDEO EPISODE:

YouTube: https://www.youtube.com/@CAPTNOffScript

MORE FROM CAPTN OFFSCRIPT:

Website: https://captnoffscript.com/

Instagram: https://www.instagram.com/captnoffscript

Newsletter: https://captn.myflodesk.com/newsletter