Valuable lessons from a laptop lifestyle Gen Z entrepreneur who skipped university and found freedom working with AI and websites
The world is changing fast. With artificial intelligence growing stronger every day, many parents are asking:
“Will my child be left behind? Is university still the best option? How can they build a secure future in such uncertain times?”
At the same time, Gen Z is feeling the pressure too—stuck between outdated career advice and a fast-moving digital world that doesn’t follow the old rules.
In this real and inspiring interview, you’ll meet Jack Smart, a digital entrepreneur who didn’t follow the traditional path. Instead of going to university, he learned how to build websites, use AI tools, and create a business he can run from anywhere.
Now, he has freedom, confidence, and a future that’s fully in his hands.
If you were born between 1997 and 2012—or you’re a parent looking for real answers about the future—this interview is for you.
Grab a cuppa, sit down with your teen or young adult, and spend 20 minutes watching it together. It could spark one of the most important conversations you’ll have about their future.
Choosing Entrepreneurship Over Traditional Education
At just 17 years old, Jack made a decision that would shape his future in ways he couldn’t have imagined. Standing at a crossroads familiar to many young Australians—university or an alternative path—he chose to follow his passion for business by starting a digital agency, Smarter Web Solutions and joining a mentorship program at the eBusiness Institute Australia.
“I was always interested in business, had a passion for it and read Robert Kiyosaki books since I was 12 or 13 and immersed in all of that,” Jack explains. “It was always a pathway I wanted to go down, but I didn’t see how I was going to do that, the vehicle that I was going to use to get into business until I came along to a business showcase event.”
This decision wasn’t made lightly. Jack carefully weighed the benefits of university against the practical, hands-on training offered through industry mentorship. “It was a big decision to look at the benefits that university had or doing what I could do with [mentors],” he reflects. “For me, it was a no-brainer to join up with the team and learn from the best from people who are out there making a living from this stuff.”
Now 27, Jack has spent a decade building and buying websites, creating digital assets for local businesses, and developing a portfolio of online investments. His journey demonstrates that success doesn’t always require following conventional educational paths—especially in the digital space.
The AI Revolution: Disruption and Opportunity
The conversation around careers has become increasingly complex with the rapid advancement of AI tools. For Gen Z, this technological revolution presents both threats and unprecedented opportunities.
“I mean, I wasn’t there for the dot com boom, but from hearing from people who’ve been in the dot com boom and now in the AI era, it sounds like it’s the same wave of opportunity passing through this space,” Jack observes. “It is going to disrupt this industry and a lot of industries as much as the internet did. It’s just revolutionizing a whole bunch of stuff and it’s making a whole heap of things a hell of a lot easier.”
The disruption is happening at lightning speed. Tasks that once required teams of people working for weeks can now be accomplished in minutes using AI tools. This efficiency comes with implications for traditional entry-level positions—particularly concerning for those just entering the workforce.
“If you’re listening to this, where it looks like AI is really going to hit hard is that beginner entry level into a lot of organizations. Typically that was those low-level white-collar roles, menial roles were given to the intern. Guess what AI does now? It replaces all that within seconds,” notes Matt, Jack’s mentor.
Developing Future-Proof Skills in the AI Age
Rather than viewing AI as a threat, Jack suggests embracing it as a complementary skill set—regardless of your chosen field. This multi-skilling approach offers protection against disruption while creating unique value in the marketplace.
“While it might be very scary to be someone studying in the medical or the legal field at the moment, if you can also learn AI skills to leverage what you’re learning there and then bring that package to an employer, suddenly you’re worth three, four or five people at your level because of the leverage that you can get on your skills by knowing how to use AI,” Jack explains.
The practical experience gained through entrepreneurship has also developed Jack’s “soft skills”—those human elements that AI cannot easily replicate. Through building websites for local businesses, he gained confidence in communication, sales, and interpersonal interactions.
“I’m on camera today. I’m a very different person to how I used to be when I started this journey,” Jack reflects. “The idea of getting onto a podcast or even picking up the phone to call a business about talking about how their online marketing is going used to scare the hell out of me. But these days, it’s just part of the journey. I’ve done it enough that it’s, you know, you put in the reps and you feel confident doing it.”
These human skills combined with technical knowledge create a powerful combination that remains valuable even as AI continues to advance.
The Real Estate Dilemma: Why Gen Z Seeks Alternatives
One of the most significant challenges facing young Australians today is the seemingly impossible goal of home ownership. With property prices soaring, many Gen Z individuals find themselves priced out of the traditional real estate market.
“I know a lot of people these days who just feel like they don’t have a chance, starting side hustles, getting second jobs, working their butts off to even be able to consider it. And a lot of people are just renting until an opportunity comes up. And who knows when that’s going to be,” Jack shares.
This financial reality has forced many in his generation to reconsider conventional wisdom about investing. The massive debt required to enter the real estate market appears increasingly risky to a generation that values flexibility and lifestyle.
“For me, I’ve got a pretty unique situation where I can work anywhere, anytime. And the freedom of being able to pack up and move and go wherever as part of that takes a lot of stress off my shoulders,” Jack explains.
Online Businesses as Alternative Investment Assets
This desire for flexibility, combined with the prohibitive cost of real estate, has led Jack and many of his peers to explore online businesses as alternative investment vehicles. These digital assets offer advantages that traditional property investment cannot match.
“We had a really good discussion about it recently when you and I were talking about investment properties, and looking at the numbers,” Jack says. “To be lumped with that debt, to put that amount of capital in, when with the skills that I’ve got, I can look at buying online businesses that are way more leveraged… It’s a whole different asset class. It’s a much easier buying point.”
The economics of online business acquisition can be remarkably favorable compared to property investments. “These days, there’s awesome deals out there. We can buy these online assets that are making… We might buy them for 20 to 30 times their monthly profit now. So they’re assets that pay themselves off in two to three years, even if we don’t make any improvements,” Jack explains.
This approach allows for starting small with a side hustle that requires minimal initial investment. With skill development and reinvestment of profits, these digital assets can grow into substantial income sources without the massive debt burden associated with property investment.
The Power of Community and Mentorship
Throughout Jack’s journey, one factor stands out as particularly crucial to his success: being part of a supportive community of like-minded entrepreneurs.
“I think that all the knowledge is already out there. There’s so much that you can learn about this space, any space really, to get the skills you need to be able to deliver a really good service to create something awesome,” Jack acknowledges. “But what I think helps a lot on top of that is the accountability and support of having a network of like-minded people. That has been the number one difference for me along the way, is having a support group that I can go to when I’m feeling stuck or have a question and be able to get real-world advice from people who’ve done it.”
This community aspect provides both practical guidance and emotional support during the inevitable challenges of entrepreneurship. It accelerates learning and helps avoid common pitfalls—something particularly valuable for those taking non-traditional paths.
Navigating the Future: Advice for Gen Z
For Gen Z individuals contemplating their future careers in this rapidly changing landscape, Jack’s journey offers several valuable insights:
First, consider complementing traditional education with practical skills—particularly AI literacy. The ability to leverage artificial intelligence tools will be essential regardless of your chosen field.
Second, don’t underestimate the value of developing “soft skills” through real-world experience. The ability to communicate effectively and build relationships remains invaluable even as technology advances.
Third, explore starting a side hustle alongside your primary career path. This provides both additional income and alternative options should your main field face disruption.
Finally, consider online businesses as legitimate alternatives to traditional real estate investing. The lower entry point, faster return on investment, and lifestyle flexibility make digital assets particularly attractive to younger generations.
Most importantly, connect with communities and mentors who can provide guidance, accountability, and support along your journey.
Taking the First Step
The rapidly evolving landscape of work and investment may seem daunting, but it also presents unprecedented opportunities for those willing to explore alternative paths. Whether you’re a Gen Z individual planning your future or a parent guiding the next generation, understanding these emerging options is crucial. That’s why we’ve put together a masterclass on how you can build a career in the AI age – without needing a degree, or going into debt. Register and watch the masterclass.
