Jacob Cass: From Student Blogger to Disney Designer & Why Sharing Process Matters

In 2007, Jacob Cass was a graphic design student in Sydney documenting his learning journey on a blog. That blog caught the attention of a New York agency launching a digital division, and six months later, Jacob was designing for Disney, Nike, and Red Bull. Nearly 20 years into his career, he’s traveled to 88 countries as a digital nomad, hosted the Just Branding podcast for six years, and founded the Brand Builders Alliance — a thriving membership community serving brand builders across 29 countries.

In this episode of Captn OffScript, Jacob shares the pivotal moments that shaped his career, why he’d give student Jacob the same advice he gives today, and how losing 90% of his traffic became the catalyst for building something better.

The Blog That Changed Everything

Jacob Cass never set out to become a designer for major global brands. He was simply documenting his design studies online in 2007, at a time when blogging was still relatively new and social media platforms like Twitter and Facebook were just emerging. “I was an early adopter in terms of things like social media,” Jacob recalls. “A lot of the big agencies were behind on that at that time.”

His blog wasn’t polished or professional in the way we think of content marketing today. It was a student sharing where he was at in his journey — work-in-progress designs, learning experiments, thoughts on projects. The key distinction: he wasn’t waiting until he had impressive work to show. He was sharing the process of learning itself.

That openness caught the attention of a New York agency starting a digital division. They needed someone who understood the emerging digital landscape, and Jacob’s blog demonstrated both his design skills and his fluency with new platforms. The offer came during his second year of university: move to New York and design for major brands. It was nerve-wracking — he didn’t know anyone in New York, didn’t have a place to stay until the night before he left — but the opportunity was too significant to pass up.

“I went from being a student to designer for Disney and Nike and Red Bull,” Jacob says. “I just had all these amazing opportunities literally land in my lap. And the reason was because of the blog where I was documenting my design studies.”

The Visa Rollercoaster and Learning Not to Get Comfortable

Jacob’s New York journey wasn’t a smooth upward trajectory. After six months at the first agency, he was let go. He needed to get back to the States quickly, so he hired a lawyer and secured a special visa for recent graduates that allowed him to stay for one year. During that year, he moved between different agencies and in-house positions, gaining experience and eventually finding a company he wanted to stay with long-term.

But visa issues continued to plague him. To renew his visa, he had to leave the country, so he went to Canada to file the renewal. It was denied — just after he’d signed a lease and secured a job. “You get two weeks to leave when you’re kicked out of the country,” Jacob explains. He managed to find a new position within those two weeks, but ultimately had to return to Australia and figure out a different path.

The experience taught him a lesson he carries forward: don’t get comfortable. “Things can change at any moment,” Jacob reflects. “When you work for someone else, especially if you have a visa, you’re literally at the mercy of the company. Always stay curious and keep learning, because otherwise you’re just going to plateau.”

This became one of the 10 to 20 lessons Jacob shared at a recent Brand Builders Summit presentation on his 20+ year career. The visa struggles were painful at the time, but they instilled resilience and adaptability — qualities that would prove essential during later career pivots.

From Solo Designer to Digital Nomad

After his time in New York (where he also reconnected with a high school friend who became his wife), Jacob and Emily embarked on a new adventure: traveling the world as digital nomads. Over three to four years, they visited 88 countries while Jacob worked four hours a day as a fully booked logo and visual identity designer.

They documented their travels on a blog called Just Globetrotting, with Emily handling the writing and Jacob managing photos, SEO, and web design. The blog gained traction, leading to influencer opportunities — free stays at luxury resorts in the Maldives, sponsored tours around the world. They ranked their favorite experiences rather than countries, with South Africa’s private game reserves topping the list. They loved it so much they returned for a couple of months, drawn by the people, food, scenery, and overall vibe.

Travel taught Jacob about priorities, experiences, and what truly matters. When asked what changed most about becoming a parent (Jacob and Emily now have four children: Hugo, Mika, Tyler, and four-month-old Kobi), he landed on the word “enrichment.” “Kids enrich your life with more purpose,” he explains. “You don’t have the freedom you used to, but you have so much deeper respect for your parents and life in general.”

The 90% Traffic Loss and the Birth of Brand Builders Alliance

Not every chapter of Jacob’s career has been growth. A couple of years ago, he lost 90% of his blog traffic through a Google algorithm update. For someone who had built a business largely on organic search traffic, this was devastating. “That was a major crash,” Jacob admits. “I lost a lot of my business and had to come to terms with that.”

But as with the visa issues years earlier, this setback became a pivot point. Jacob had been running brand-focused summits, and one event in particular — the Brand Builders Summit — received extraordinary feedback. It was rated 9.7 out of 10, and 100% of attendees said they would recommend it. More importantly, participants didn’t want the event to end. They loved connecting with other brand builders around the world and wanted that community to continue.

Jacob spent the next month interviewing attendees and people who filled out surveys, trying to understand what they truly wanted. From those conversations, the Brand Builders Alliance was born — a paid membership community focused on two things most communities separate: mastering branding and building a thriving creative business.

“People come for the content and stay for the community,” Jacob explains. The Alliance now serves over 100 members across 29 countries with mentorship, resources (over 150 hours of video content), eight resident coaches, regular live events, accelerators, action plans, roadmaps, and master classes. The community’s mantra is “no one builds alone,” directly addressing the isolation many solo designers and creatives feel.

The ROI is visible in member transformations. Jacob recently posted about the community’s first birthday, and members commented that they couldn’t even fully utilize all the resources anymore — because they were now fully booked with client work, had hired teams, and opened new studios. They’d gone from slow and struggling to thriving. “The proof is in the pudding,” Jacob says.

Why Sharing Process Still Matters (Even After 20 Years)

When asked what advice he’d give to student Jacob at university, his answer was immediate: “Keep doing what you’re doing. Keep sharing.” The blog that launched his career wasn’t the result of having impressive work to showcase. It was about sharing where he was at in his journey, being open about being a student, and connecting with others through that vulnerability.

“As a student, you’re not going to have the best work, and it’s okay to share that,” Jacob explains. “You share what you learn by sharing, and through that mechanism you connect with other people — other students, other designers — and you may even get feedback.”

This philosophy extends beyond student work. Even today, Jacob emphasizes sharing the process, the journey, the behind-the-scenes thinking. “It’s not just the final result. It shows the thinking, it shows the human behind the work.” In an era where social media often showcases only polished outcomes and highlight reels, showing the messy middle — the iterations, the challenges, the learning — builds genuine connection.

Jacob’s six-year podcasting journey with Just Branding illustrates this evolution. His early episodes were, in his own words, “so cringe.” He was nervous, over-prepared yet under-prepared at the same time, buried in pages of notes. But through doing the reps — recording episode after episode, interviewing different guests, getting more confident in the craft — podcasting became natural. Now he and co-host Matt show up with minimal prep, let conversations flow organically, and trust the process.

The lesson applies beyond podcasting. Growth happens through repetition, through showing up imperfectly, through learning in public. Jacob’s career didn’t take off because he waited until he was ready. It took off because he shared his journey while he was still figuring it out.

Taming the Advice Monster: Coaching Over Telling

One of the more nuanced insights Jacob shares is about the “advice monster” — a concept from Michael Bungay Stanier’s book The Coaching Habit. People naturally want to help, so when they hear a problem, they immediately jump in with solutions. But this approach often misses the mark because the advice-giver doesn’t truly understand the problem’s root cause.

“You don’t know enough about the problem to give proper advice,” Jacob explains. “That’s why coaching is about listening, asking the right questions, and getting deeper to the root cause before jumping in with advice. And sometimes we don’t even need to give advice — we just ask questions to help the other person come to their own conclusions.”

This philosophy shapes how Jacob runs mentorship and coaching in the Brand Builders Alliance. There’s a balance between offering resources based on experience (“In my experience, this is how I tackled this challenge — I’m not saying it’s right for you”) and asking questions that help members discover their own solutions. It’s being clear and transparent about perspective while resisting the urge to prescribe answers.

Jacob admits this took work. Before reading The Coaching Habit, he would immediately give advice. Only after studying coaching principles did he shift his approach. Taming the advice monster is an ongoing practice, especially for someone who has accumulated 20+ years of design and business experience and genuinely wants to help others succeed.

Work-Life Integration with Four Kids and a Global Community

Work-life balance is a myth, according to Jacob — and he’s not alone in this perspective. What he practices instead is work-life integration with clear boundaries. He doesn’t work weekends. Sunday is family time. He has regular work hours that can flex for calls but generally maintains a consistent routine. In summer, he does “summer Fridays” — a four-and-a-half-day workweek.

The key is communication and sticking to the boundaries you set. “It’s about setting boundaries and knowing what lifestyle you want to live,” Jacob says. His wife Emily manages the household (which Jacob readily admits is the much harder job), and they function as a team. He has a home office separate from the house, which allows him to focus during work hours while remaining available when needed.

The setup works because of intentionality. Jacob doesn’t have a perfectly balanced life where work and family get equal time every day. Instead, he has an integrated life where both have their place, and neither is sacrificed for the other. He acknowledges the mental load of managing a household with four young children — something that “doesn’t get spoken about enough” — and credits Emily’s extreme organization and partnership for making it all function.

Running a global community while parenting four kids (including a four-month-old) requires focus and efficiency. Jacob works in intense bursts: deep research, full immersion in a project, then rest. Repeat. This pattern applies whether he’s buying a car (full research, decision, done — no test drives) or working on a brand project (research, get in the zone, execute). Understanding his own work style and honoring it has been crucial for sustainable productivity.