Employee to entrepreneur: the multifaceted career of Jonathan Pease

Jonathan Pease (M Bus ’10) knew exactly what he was meant to do with his life from the age of 12. A criminologist told him everything he needed to know.

“My dad was friends with a criminologist who could read handwriting,” he says, laughing gently. “And when I was about 12, Dad got him to analyse my handwriting. He told me I was an inventor, and a creative, and a Renaissance man.”

“I’m a bit of a romantic and I always held onto that in the back of my mind.” Did the prediction become a self-fulfilling prophecy? Maybe - but no matter, says Pease, “Whether it’s the tail wagging the dog or not doesn’t matter - I love what I do.”

Pease is exactly the Renaissance man he was predicted to be, wearing many hats. He’s currently the co-owner of Delorean, a creative consultancy that operates in three ways: investing in new businesses, building brands and consulting to other brands on their strategies, products and marketing. Put simply, Pease says Delorean, “bridges the gap between creativity and commerce.”

“Often the value we add is simply that we are one degree removed from the business,” he says. “People who are in the business every day - it's hard for them to be disruptive when they’re dealing with profit and loss and quarterly targets. When you’re an outsider you have the privilege of playfulness.”

Pease is also the co-owner of Oyster Media Investments — an entertainment investment group with interests ranging from a hard-seltzer brand, a boutique hotel development, and iconic international pop-culture magazine, Oyster. He’s also the founding creative director at Sohn Hearts and Minds, Australia’s leading investment conference.

From his experiences in all of this, he developed an executive coaching program over the last 15 years called Winning The Room, and authored a book of the same name that was published globally last year.

Juggling everything can be a challenge, he says, but he’s learned to seek out projects that complement one another. “I look for things that link, so I can make one plus one equal three,” he says. “And I tell clients to do that, too - you might be doing more than one thing at a time, but if they feed into one another, they will add up to more than the sum of their parts, propel you forward and be beneficial to each other.”

Pease credits taking the leap from “employee to entrepreneur” to his Master’s of Business degree at the University of Sydney. He’d been working in the advertising world for more than a decade before he took the plunge, knowing that he would need a solid business education to launch his own agency (Tongue, which he went on to sell to STW in 2017).

“I was getting to a point in my career where I was being asked for strategic advice, finding myself in boardrooms and C-suite meetings,” he says. “I knew I wanted to start my own agency; it was my plan from day one and I knew I’d need my Master’s to get there. As I progressed through the creative chain I realised I needed the other skills to take me from employee to entrepreneur.”

At the University, Pease particularly connected with marketing professor Donnel Briley, who taught the class real-world case studies that Pease found illuminating. “It was amazing to study business stories in class that were unfolding in the media live,” he says. The partnership has evolved, and now Pease teaches Briley’s students the art of communication through his Winning the Room workshops, a practise he says is “so enriching and rewarding.”

Completing his Master’s allowed Pease, who was already well-established in his field, to take “the leap of faith” he needed to start his own business.

“Stepping away from a monthly salary is so risky,” he says. “I needed the systems to work. Doing my master’s helped me have my eyes wide open about the realities of business. I’m no mathematical genius but my master’s helped me understand numbers so much more; I can be dangerous (in a good way) now.” Pease says that, coupled with his own creative thinking, this combination has proven enormously valuable.

Pease’s experience as a graduate student was, he says, markedly different to how he started his first degree (at a different institution). Though he knew he wanted to be in advertising and marketing, he struggled to enjoy school and imagined university would be the same.

“I went to amazing schools but hated it,” he says. “And I feel really guilty now because my parents spent every dollar they had on educating me. I scraped through.” Thinking university would present the same monotony, Pease planned a two-week ski holiday that coincided with the start of his first semester and got his mother to sit in on lectures for him. “That should give you an indication of how not present I was,” he says drily. “To say I was disinterested was an understatement.” His mother, he said, “took probably the best notes of my university career.”

But when he made it off the ski fields and into the lecture theatre, Pease suddenly found his calling. “I can’t even remember what we were studying,” he says. “I just knew that I immediately felt connected and that this stuff - all of it - was so fascinating to me. I went from barely getting by to getting high distinctions.”

Pease’s career has been defined by diversity. He’s done everything from run a small fashion label to appear on five seasons of Australia’s Next Top Model (as a judge), and says he relishes trying different things. The key that links all of his projects is “creative problem solving,” and it’s what gets him out of bed each morning.

“Without sounding too cheesy, I get that 'highlight feeling' most days,” he says. “I get to solve tricky problems and work with people who stretch me daily. I see my job more like an obsessive hobby than anything else.”

Jonathan Pease recently shared his insights with the Sydney Alumni Community on LinkedIn as part of the 'Ask Me Anything' alumni series. Join today to connect with fellow alumni.