Jack Delosa: Lessons from a Disruptive Entrepreneur

Interviewing Jack Delosa is always an honour. Having followed his journey for years, I’ve been fortunate to sit down with him multiple times, including during a visit to Perth. Jack’s insights on business, resilience, and being a disruptive entrepreneur have dramatically impacted my own business, and his wealth of knowledge is something I’ve always looked up to.

Jack Delosa is the founder of The Entourage, Australia’s largest and most disruptive education institution for entrepreneurs. Known for his impactful leadership, The Entourage was named the 4th Best Place to Work in Australia by BRW Magazine, and Jack himself has been listed in the BRW Young Rich List every year since 2014.

In this episode of LinkedIn Heroes, Jack shares how he transformed personal and professional challenges into monumental success. From his humble beginnings to building one of Australia’s most impactful entrepreneurial communities, his story is a masterclass in overcoming adversity and creating lasting change.

Early Lessons from Breaking the Cycle

Jack’s entrepreneurial mindset was shaped by his parents’ not-for-profit organisation, Breaking the Cycle, which helped at-risk youth transition into meaningful employment. Seeing the impact of their work—and the devastation when government funding was withdrawn—taught Jack the importance of building sustainable models for social impact.

“It doesn’t matter how challenging someone’s background is; they can create a life aligned with their vision.”

From Start-Up to Scale-Up

Jack’s journey into entrepreneurship began with ventures like a marketing agency and an emotional intelligence training company. His first major success, however, was with MBA, a business advisory firm that helped small to medium-sized enterprises raise over $300 million.

In 2010, he founded The Entourage, a business education platform designed to support entrepreneurs at every stage of growth. The company quickly grew, achieving a valuation of $62 million by 2015.

But with rapid growth came unexpected challenges. Four years ago, Jack was faced with the daunting prospect of losing nearly A$1 million every month due to abrupt changes in government funding. The dire circumstances forced him to make drastic changes, cutting staff and rethinking his business model.

“That was an incredibly challenging period for us,” Jack recalls. “We had to go from 90 people down to 40 within a day. We needed to restructure the business and build new products because we didn’t have anything that was going to last longer than a few months.”

Weathering the 2016 Crisis

Despite the turmoil, Jack’s resilience and leadership brought The Entourage through its toughest period. Today, the organisation is more viable than ever, with a thriving network of 350,000 members. Jack’s experience during this time cemented his reputation as a visionary entrepreneur capable of leading through adversity.

“Anyone can lead in good times,” Jack says. “The real test is how you lead through adversity.”

Building a Community of High Performers

A key part of Jack’s mission is fostering a sense of community among entrepreneurs. Through programs like the Elevate Program, The Entourage supports seven-figure business owners, helping them scale sustainably and build systems beyond themselves. The program boasts over $350 million in collective annual revenue among its members.

Jack’s focus on community and education has been transformative for many entrepreneurs. His latest book, Unwritten, captures the unconventional wisdom he’s known for, helping readers live a purposeful life while making the world a better place. Within its first week, Unwritten became a best-seller, further solidifying Jack’s impact on the entrepreneurial world.

Advice for Aspiring Entrepreneurs

Jack’s most important habit for success? Resilience.

“Growth is always hard—whether you’re scaling, plateauing, or navigating challenges. The key is sticking with it, embracing discomfort, and keeping your grit for years to come.”

Jack also emphasises the importance of forging your own path, challenging traditional career expectations, and surrounding yourself with a supportive network of like-minded individuals.

Jack Delosa: A Disruptive Entrepreneur

If Jack could be a superhero, he’d be Iron Man—a fitting choice for a visionary leader navigating uncharted waters. And just like Tony Stark, Jack’s ability to innovate, adapt, and empower others sets him apart.

Check out the video on YouTube – Jack Delosa Interview

What’s your biggest takeaway from Jack’s story? Let me know in the comments!

About LinkedIn Heroes

LinkedIn Heroes was started to deliver the inspiration and strategies you need to accelerate your entrepreneurial journey to success. To ensure you don’t miss an episode of LinkedIn Heroes subscribe to Nathanial’s YouTube Channel.

Also available on Spotify and iTunes.