Side Hustle Hero

How To Buy Websites For Cash Flow, with Matt Raad

Matt Raad · August 29, 2023

Entrepreneur · Finance · Leadership · Artificial Intelligencein

Interview with Matt Raad

How To Buy Websites For Cash Flow, with Matt Raad

Podcast: Side Hustle Hero

August 29, 2023

Want to skip the start-up phase and jump right into a business that cash flows? Today’s Side Hustle Hero guest Matt Raad will tell us how. With the help of mentors, he and his wife Liz became rock stars in Australia, analyzing the value of bricks and mortar businesses for…

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Key topicsNo Followers, No Problem: How Millennials Are Building A Successful Future-Proof IncomeMost online income advice tells millennials the same thing: start a YouTube channel, grow an audience, post every day, build a personal brand. For a lot of people, that advice is exhausting before it even begins. Matt Raad offers a fundamentally different model, one where you don't need followers, a camera, or a content calendar to build real online income. Drawing on decades of buying and growing websites that already have traffic and revenue, he talks about why buying digital assets is the smarter, quieter alternative to the creator grind, and why more millennials who hate the idea of "going viral" are building serious cash flow without ever putting themselves on camera. Digital real estate is the asset class priced out millennials can still enter Real estate has become the wealth-building default, but for younger investors the numbers often do not stack up without huge debt and years of pressure. Matt introduces a different asset lens: websites and online businesses can be bought, improved, monetised, and sold without needing a million-dollar mortgage. Because he and Liz have spent 18 years applying business renovation principles to websites, he can explain the mechanics in plain language rather than hype. This gives investing and FIRE audiences a fresh conversation about ownership when property feels increasingly out of reach. The new burnout is earning good money and still feeling trapped Many burnt-out professionals are not failing financially on paper, yet they still cannot see a path to freedom because the mortgage, rent, commute, childcare, and career pressure consume everything they earn. Matt sees this pattern in millennials, vets, engineers, FIFO workers, teachers, and professionals who look successful but feel boxed in. He can speak to the moment when someone realises a pay rise will not solve the deeper problem because they still do not own the engine producing their income. That makes this a strong fit for lifestyle, career-change, and freedom-focused podcasts. View all topics →

About Matt Raad

Matt Raad, podcast guest

Digital Investor and Educator on Building Online Income for Life on Your Terms

30 Years Entrepreneur & business investorSince 2008 Website investing pioneer100–800 Live & online event audienceseBusiness Institute CEO & Co-Founder

Matt Raad is a 30-year entrepreneur, digital investor, and CEO & Co-Founder of eBusiness Institute, Australia’s leading digital skills training organisation. After starting his career as a zoologist studying kangaroos in the Australian outback, Matt rejected the conventional path and built wealth with his wife Liz by buying, growing, and selling businesses instead of relying on property, a corporate career, or the traditional wealth playbook.

Eighteen years ago, Matt and Liz took that same business-buying approach online and became pioneers in buying, renovating, and selling websites as digital real estate. Today, Matt is one of the leading voices helping millennials, burnt-out professionals, and aspiring entrepreneurs build AI-leveraged digital businesses they own, control, and can one day sell as 6–7 figure assets.

Matt’s message is especially timely for a generation that has been sold a path that no longer works: expensive degrees, insecure careers, unaffordable property, and income that disappears the moment they stop working. Through eBusiness Institute and the Digital Investors Podcast, he teaches people how to earn while they learn, use practical digital and AI skills, create cashflow from home, and build real future security through ownership.

A regular guest on major business and wealth podcasts including Rich Dad Radio, Entrepreneurs on Fire, and RASK, Matt brings a rare mix of contrarian thinking, practical strategy, and lived experience.

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About this episode

Want to skip the start-up phase and jump right into a business that cash flows?

Today’s Side Hustle Hero guestMatt Raadwill tell us how.

With the help of mentors, he and his wife Liz became rock stars in Australia, analyzing the value of bricks and mortar businesses for potential buyers.

But then they realized the world was changing, and they could pivot and apply their knowledge and skill to online businesses.

Fast forward some years, and today they have an extensive portfolio of “website” businesses and earnings well into 7-figures.

And here’s a fun fact…having expertise or knowledge of the industry in which you’re buying the website business, is not a prerequisite.

Matt explains why.

You’ll also discover,

how to test the waters in a relatively inexpensive way, to see if this side hustle is for you, what to look for when buying a website business, red flags to look out for, how to gain access to a website’s Google Analytics the importance of keyword research best niches to go after, and the “Fallen Angel Strategy”

What You’ll Hear:

03:07 Matt’s income is from a portfolio of investments and website businesses

05:00 First business was a small manufacturing company

06:05 Coming from a science background trained them to be curious

07:30 Rich Dad Poor Dad - a thought provoking book

07:50 Has only owned one retail business…and never again

08:19 Buying and selling businesses for high net-worth individuals and private equity firms

09:45 First website business they bought on eBay - and what they did to increase its income

12:35  “Passion” niches are Matt’s favourite - crafting, pets, golfing sites, etc

13:05 You don’t need to be an expert in the industry

14:38 Three good ways to monetize a golfing site

19:00 With “passion” sites, sometimes the seller will stay on to contribute content

19:44 How to determine if a website is a good buy

20:16 If you want to start, buy a “starter” site under $1,000

20:42 Flippa.com is a main site for beginners

22:12 This is not a “get rich quick scheme”...there is a learning curve

23:00 Look at a website’s profit and traffic. Not sales!

23:29 How to know the numbers a seller is stating is accurate

24.41 Google Analytics is the #1 tool Matt uses for due diligence and to analyze sites

25:01 The things that look “bad” to people, are often the best opportunities

26:01 How you gain access to a website’s Google Analytics

27:47 The importance of SEO in website businesses, and selling out to deep-pocket buyers

29:22 Red flags to look out for when buying a website business

31:06 A main thing to look at is keyword research

31:54 If you stick to these main big industries -  health, wealth, happiness - they’ll always be around

32:25 People come online to look up answers - that’s why keyword research is important

34:36 A primary component of what you need to do for due diligence

36:55 The “Fallen Angel Strategy”

40:31 You can do this part-time and learn

41:33 Matt’s best tip to start or grow your side hustle

Pro Tip:

42:51 “The things that look bad to people, are often the best opportunities.”

Platform for buying and selling online businesses:

https://flippa.com/

Google Analytics:

https://marketingplatform.google.com/about/analytics/

Connect with Matt:

https://www.ebusinessinstitute.com.au/

Connect with Joan:

https://www.instagram.com/joanposivy/

https://www.facebook.com/posivy/

https://www.sidehustlehero.com/about/

Be on the show!

https://www.sidehustlehero.com/guests/intake/

Guest: Matt Raad

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