Digital Investors

He had no experience, no audience, and no roadmap. Today, Owen Rask runs one of Australia’s largest financial education businesses, with 750,000 podcast listens a month, over 35,000 students, and $50 million in funds under management. In this episode of the Digital Investor Podcast, Owen shares how he went from working in corporate and starting with zero experience to building a multi-million-doll...

Everyone is talking about starting an AI business - zero code, zero employees, and a $1M outcome. And while that can be true, it usually assumes you have 40+ hours a week to learn AI from the ground up. But what if you don’t? What if you’re working a full-time job, have kids and family commitments, and only have 8-12 hours a week to work on a side hustle? In this episode, we talk about why a digit...

If you want to sell your online business or digital agency one day, you have to understand 3 things: 1) How big buyers actually think 2) What buyers look for in a digital agency  And 3) how to increase your agency valuation  ... so it's not just an asset that brings in cash flow but one that pay you 2-3x your annual profit if you do decide to exit in the future. That's why in this episod...

How do you run an entire business in 42 minutes a day? By using international Virtual Assistants. But not in the way you think. In fact, everything you know about hiring and working with VAs is wrong. In this episode, Matt Raad interviews Josh Thomas, who built four seven-figure businesses using a simple VA system. Learn the Online Income Skills That Can Make $10k/mo from your laptop? You don’t ne...

What if your hobby or passion blog could sell for seven figures? Most people laugh at that idea. "Passion blogs don't scale," they say. "They're just hobbies." What if they're wrong? I've brought in someone who's proven it over and over again. Fiona Laidlaw, Regional Director for Asia Pacific at Flippa, senior M&A broker, and absolute legend at selling seven-figure online businesses. She's bee...

What if you could turn $8,000 into $130,000 in just three months? That's exactly what today's guest, Chelsea Clarke, accomplished with a single website flip - and she made an additional $25,000 in revenue while she owned it. Chelsea is the founder of Niche Investor, a boutique website marketplace that rejects 50% of submissions to maintain quality. She's also the founder of Her Paper Route and has...

My guest today is short on time and didn't have the cash to invest in real estate, so what did he do? After listening to the Robert Kiyosaki Rich Dad podcast with Matt Raad, he decided to go the route of digital real estate and make small investments there, and gain some passive income. In less than 10 months, my guest's initial investment has paid for itself and while he's at his day job, with hi...

16-hour shifts. 3 kids. And no tech skills. That was Josh's reality. Yet, he still turned his spare time and days off into a nice $5,000 per month. Today, you'll hear how he did it and what you can do today if you want to start a side business without quitting your full-time job. Learn the Online Income Skills That Can Make $10k/mo from your laptop? You don’t need tech skills or prior experience,...

Twelve months ago, Steph knew nothing about buying businesses. Today? She owns one - purchased for an amazing price - and she’s on track to pay off the investment in just a few months. In this episode of the Digital Investors Podcast, Steph breaks down exactly how she found the deal, handled negotiations, and made her first acquisition happen. She also shares her ambitious plan to hit $30k/month a...

From gruelling 70+ hour police shifts to earning $60K in his first year building websites, working just 15 hours a week! Rhys walked away from the force to reclaim family time, launching a local digital agency that quickly ranked #1 through SEO and attracted 20+ clients. In this episode of the Digital Investors Podcast, Rhys reveals how focusing on regional areas and face-to-face connections lead...

The next great gold rush isn’t in crypto, AI, or NFTs… It’s in small, high-margin digital agencies and the smart operators are quietly cashing in. In this episode of the Digital Investors Podcast, Matt Raad interviews Fiona Laidlaw, senior M&A broker at Flippa, to reveal why digital agencies are fast becoming the hottest acquisition targets online. Hear: • How a 23-year-old turned walked away...

What if you could quit your job, work from home, and build a million-dollar business in just two years? Derek and Courtney did exactly that, while raising two kids and starting from scratch with zero capital. In this episode, you'll hear how they left high-pressure corporate roles to launch a digital agency that hit $160K in its first year, scaled to $50K months in year two, and is now valued at s...

Steph was living the dream, or so it looked on paper. A secure teaching job. Two beautiful kids. A loving husband. But behind the scenes? She was drowning, exhausted and stuck... wondering if this was really it. Then her brother took the Digital Investors Program, and told her to do the same. The rest was history. In just 12 months, Steph walked away from her teaching job, built a $70K digital age...

Bill Gallagher has coached 11+ companies to $100M+ exits in 12 years. Three of those hit $1 billion in value. But in this exclusive interview, he shares his most painful business mistake - one that cost him $2 million out of pocket and a potential $250 million exit. Tune in to hear: - The #1 exit mistake that destroys business value - Why you should sell BEFORE hitting your vision (not after) - Ho...

Ashlene was working 60-80 hours a week and thought "I can't keep doing this, there must be a better way to make money." Then she heard us on The Rich Dad Poor Dad podcast, signed up for our free masterclass, bought a small website, then grew from there. Today she has 4 websites that makes her $8,000/mo. And instead of working 60-80 hours weeks like before, she works a maximum of 2 hours a wee...

Where are the biggest opportunities in buying and selling online businesses right now? In this interview, Matt Raad interviews Greg Elfrink, head of marketing at Empire Flippers who’s helped create over 100 millionaires, to share what’s working, what’s changed, and how to buy profitable online businesses in 2025. Greg reveals million dollar lessons, stories, and actionable strategies for both begi...

In this episode of the Digital Investor Podcast, we sit down with Captain FI , a former military pilot who reached financial independence and retired at age 30 . But here’s the twist…It wasn’t just index funds and frugal living that got him there. It was a passion blog that turned into a six-figure income stream , accelerating his FIRE (Financial Independence, Retire Early) journey faster than tra...

A few months ago, Alyssa was working two part-time jobs (retail and lifeguarding) making $18/hour. 6 months after quitting university, she made almost $12,000 in just one month. Here are the lessons she learned. Learn the Online Income Skills That Can Make $10k/mo from your laptop? You don’t need tech skills or prior experience, just the right strategy and a proven plan. Learn how 6-figure earners...

In this episode, we sit down with Greg O’Rourke... jazz guitarist, digital entrepreneur, and graduate of the eBusiness Institute... to unpack how he built financial freedom through multiple online strategies. Greg shares how he: Grew his passion project, Fret Dojo, into a $10K/month semi-passive income machine Built a boutique agency with just 5 clients generating $25K/month Landed his first clien...

What would you do if a sudden health crisis forced you to shut down your business, quit your job, and move in with your parents… with two young kids to support? That’s exactly what happened to Lucy and Reefe w hen illness struck and Doctors couldn’t figure out what’s wrong. In short, they had to shut down their solar business and move back in with family just to get by. But within 12 months, they...

In a world where anyone can list a website for sale, Empire Flippers accepts only 5% of submissions. Why? Because their marketplace has become the gold standard for serious buyers. Every listing undergoes rigorous verification through APIs, financial checks, and seller background screening. In this interview, CEO Andy Allaway shares what’s really happening in today’s market. And what separates mil...

How do you go from flying planes to quietly building one of Australia’s most successful FIRE blogs, all without revealing your identity? In this exclusive episode, Captain FI joins Matt at eBusiness Institute for the very first time on camera to reveal his identity and the real story behind his six-figure finance blog and how he achieved financial independence years ahead of schedule. Tune in now...

How do you walk away from a $160K-a-year corporate job, take a gap year with your young family, travel around Australia… and then, within six months, build a high six-figure freedom business? In this inspiring episode, we sit down with Luke, a former engineer turned digital entrepreneur, who did exactly that. You'll hear: ✅ The burnout that led to a life-changing decision ✅ How a $100K gap year...

Imagine quitting your job, buying a bus and travelling full time, all whilst still earning a 6 figure income. Chris and Bec have been paid to travel the world for the last 5 years, earning remote income and literally living the laptop lifestyle. Today we are going to find out what that journey has been like for them. You'll hear: How they are making money online and how they're AI proofing it What...

If your child was born between 1997 and 2012, this could be the most important conversation you have together. In this powerful episode, you’ll meet Jack Smart—a Gen Z entrepreneur who skipped university and built a successful business using AI and digital skills. No degree. No debt. No waiting for permission. Instead of following the old playbook, Jack chose a smarter path—one that gave him freed...