The online business world has a highlight reel problem. What gets shared is the success, the freedom, the income, the lifestyle. But what often gets overlooked is the messy middle – the part where things get hard, where doubt creeps in, and where most people would walk away.
For anyone sitting in a corporate job right now, weighing up whether to take the leap into building an online business, the polished version of success can actually be more paralysing than helpful. What you really need to hear is the real version – the truth about what it actually takes from someone who’s lived it.
Recently I had the tables turned on me by one of our incredible eBusiness Institute students, Lucy Wood – a former corporate lawyer who successfully transitioned out of her career and now works full-time online. Lucy put me in the hot seat and asked the kind of hard questions most people are too polite to ask. In this article, I want to share what came out of that conversation: the honest truth about the hurdles, the mindset, and the smart strategies that take you from corporate burnout to genuine financial freedom. Make sure you watch the full video below to hear the conversation in Lucy’s own words.
The Hardest Period: When Most People Would Walk Away
When Lucy asked me about the hardest period in building an online business – and our earlier businesses – my mind immediately went to two very different chapters of our journey. The contrast between them is exactly why we teach what we teach today.
The Bricks-and-Mortar Nightmare
Liz and I cut our teeth in bricks-and-mortar businesses – manufacturing, distribution, the works. And I’ll be honest with you, that period was terrifying. We were in our late twenties and early thirties, on the edge of bankruptcy, drowning in bank debt, with every cent of cash flow tied up in physical inventory shipping around Australia.
One year, our combined tax return showed Liz and I earned just $15,000 between us. No super. No safety net. Every dollar was being shovelled back into the business just to keep it alive. The fear was visceral – we couldn’t even afford a taxi without panicking about it.
That’s exactly why today I tell people: don’t go there. You should not be loading up on big debt to start a business. That’s the old model. There’s a much smarter way.
The Online Business Hurdle: The Three-Month Wall
When we transitioned online, the hardest period looked completely different. There was no crushing debt. No payroll panic. But there was a different kind of pain – it wasn’t working as fast as we wanted it to.
Liz, who is an absolute high achiever (and as she’d happily admit – impatient), was building our first ebook business online. After three months, she was ready to quit. She felt like nothing was happening.
Then she had a conversation with a mentor that changed everything. He said: “What are you talking about? The fact that you’ve gotten this to break-even within three months is mind-blowing. Stick at it.”
Three months later, she had it making $5,000 a month net. That single conversation, at that single tipping point, was the catalyst for everything that followed. Without that mentor, we might have walked away from the online space entirely.
“Be careful that you’re not about to give up just as you’re about to succeed.”
Why Online Business Beats Bricks and Mortar Every Single Time
Here’s something I wish someone had hammered into me earlier: not all businesses are created equal. The strategy you choose matters more than almost anything else.
When Liz and I finally got our heads around digital business, it was honestly a walk in the park compared to bricks and mortar. The main thing that held us back was the tech side – but once that clicked, everything went exponential.
Here’s why online wins, especially for someone making the leap from a corporate career:
- Cash flow first, not debt first. No inventory tied up in a warehouse. No bank loans. No payroll tax keeping you up at night.
- Margins that defy logic. Cash-flow positive websites bought the way we teach can net 80–90% profit. Our accountant has said for years he’s never seen businesses like it.
- Digital agency margins of 60–70%. Once you build leverage in, the model just works.
- Monthly data, not yearly. Online, you measure everything monthly. You can spot what’s working – and what isn’t – in 30 days, not 12 months.
- You can walk away. If it isn’t working, you sell the asset and go back to your job. There’s no real downside.
This is exactly why we built the Digital Investors Program – to teach the two highest-cash-flow, lowest-risk strategies we’ve ever found: buying cash-flow positive websites and building websites for local businesses through a digital agency model. If you’re sitting in a corporate role right now wondering how to get out without taking on huge financial risk, this is the pathway we wish we’d been shown 20 years ago.
The Smart Way to Go From Corporate to Entrepreneur
If I could go back and give myself one piece of advice when we were starting out, it would be this: start small, stay scrappy, and don’t quit your job straight away.
We’ve watched this play out over and over again with our students. The ones who quit their jobs too early – before they had proof of concept – were under so much financial pressure that they made bad decisions. They’d rush their due diligence. They’d skip critical questions when buying websites. They were so desperate to replace their income that they couldn’t think clearly.
The ones who kept their day job as a security blanket while they learned the skills? They made far better decisions. They were calmer, more strategic, and more selective. And ironically, they often replaced their income faster as a result.
Here’s the Smart Transition Playbook
- Stay in your job initially. Use it as your security blanket while you build skills on the side.
- Start with a low-cost, high-cash-flow strategy. A digital agency requires only a couple of subscriptions to start. Cash-flow positive websites can be acquired under $20K–$50K.
- Earn your first dollar online. Get proof of concept that the model works for you.
- Carve out time strategically. Many of our students drop to a four-day work week, or get up an hour earlier. As Arnold Schwarzenegger says – sleep less when you’re young.
- Aim for $5,000 a month net. Don’t set the goal at $10K to quit. Five grand a month is the magic tipping point where you suddenly have options.
- Have a 12-month runway. If and when you do leave, make sure you’ve got savings to give the business a proper run.
That $5K-a-month milestone is something I find myself repeating on coaching calls today – the exact same advice our mentor gave Liz 15 years ago. Once you hit it, you know you can make money online. You know the skills work. From there, the world opens up.
Failure Is Just Data: The Mindset Shift That Changes Everything
One of the biggest hurdles for anyone going from corporate to entrepreneur isn’t the tech, the strategy, or the money. It’s the relationship with failure.
In a corporate job, failure is something to be avoided at all costs. It threatens your performance review, your bonus, your standing. In business – especially online business – failure is just information. It’s data. It’s part of the process.
When we first got online, Liz and I were hand-coding websites. We had endless technical failures. But here’s what we learned: every failure online is small, fast, and fixable. You can fail in 30 days online – in bricks and mortar, you can be failing for two years before your accountant even spots the problem.
I’ve got a poster I’ve kept on my wall for over 20 years that reads:
“You must always push the limits, because if you never fail, you’ll never succeed.”
I now put a version of that mantra on the mousepads of every one of our members: Don’t think, just do. Stop overthinking. Make the move. Make the mistake. Learn the lesson. Move on.
How to Tell If Failure Is a Signal to Pivot or Push Through
Lucy asked me a great question: how do you know if you should keep going or change direction?
Here’s my honest answer:
- If you’re doing this as a side hustle and you’re not making money in 12 months – welcome to the journey. That’s normal. It just takes longer when you’re also holding down a job. Keep going.
- If you’ve quit your job and gone full-time and you’re still not making money after 12 months – something is wrong. Either your execution, your strategy, or your mindset needs to change.
Liz and I have a rule we’ve lived by in every business we’ve been in: we can put up with the difficulty for a year or two – but after that, we’re the problem. If you’re still banging your head against the wall after a year of full-time effort, the issue isn’t the market. It’s your strategy.
The Hurdles Nobody Warns You About
If you’re exploring online business for beginners for the first time, here are the realities I wish someone had laid out for me clearly:
1. There’s a Knowledge Gap You Have to Push Through
Building websites isn’t technical the way it used to be 15 years ago – but it’s still tricky for beginners. There’s a learning curve, and you have to be willing to be a beginner for a while. The good news? Once you sort it out, it gets dramatically easier than anything in the bricks-and-mortar world.
2. Change Is Constant – And That’s Actually a Good Thing
Online, something is changing every single month. Google updates. AI is rewriting the rules. New tools appear. New opportunities open up. You have to make peace with change – but here’s the truth: the change is almost always to your benefit if you’re paying attention. Online entrepreneurs end up addicted to the pace of change because it creates new opportunities constantly.
3. The Pressure From People Around You
When Liz and I went all-in online back in 2008, family and friends thought we’d lost our minds. “How are you going to make money on the internet?” Online business was still considered borderline scammy back then. The pressure from people who didn’t understand what we were doing was one of the biggest hurdles we faced – bigger than the tech, in some ways.
If you’re facing the same scepticism from people around you today, just know: you don’t need them to understand. You just need to earn that first dollar online and let the results speak.
Why Cash Flow Is the Secret Weapon (And Why We Picked These Strategies)
I want to come back to this point because it’s the point that separates online businesses that thrive from those that bleed their owners dry.
When you pick a high cash flow strategy with no debt, you completely change the psychology of being in business. You feel freer. You make better decisions. You can experiment without fear. You can walk away if you need to.
Compare that to a bricks-and-mortar business where you’re constantly reactive, in survival mode, just chasing the next sale to make payroll. We’ve lived both. We know the difference.
That’s why everything we teach at the eBusiness Institute is built around two principles:
- Start small and stay lean. No big debts. No big risks.
- Pick high-cash-flow strategies. Cash flow first – always.
The two pathways we teach in our Digital Investors Program – buying cash-flow positive websites and building a digital agency – both tick those boxes. The agency model in particular, with AI accelerating what’s possible today, is what I’d choose if I were starting over from scratch right now. Almost no money down. Just your skills, time, and effort.
The Real Takeaway: Mindset Beats Strategy Every Time
If there’s one thread that ran through my entire conversation with Lucy, it’s this: the more we talked about strategy, the more we ended up talking about mindset.
- Getting comfortable with failure as a normal part of the process.
- Getting comfortable with change as the only constant.
- Believing that your skills are always transferable – that no time is ever wasted.
- Knowing that the hurdles in business are better hurdles than the hurdles of being trapped in a job you don’t want.
Lucy put it beautifully when she said: “No matter the hurdles I’ve faced since being in an online business, I would pick those hurdles any day of the week.” Because they’re hurdles in service of your vision – not someone else’s.
The Bottom Line for Aspiring Digital Investors
If you’re sitting in a corporate job right now reading this, here’s what I want you to take away about building an online business the smart way:
- You don’t need to quit your job to start. In fact, please don’t.
- Pick a smart strategy. High cash flow. Low debt. Lean and scrappy.
- Aim for $5,000 a month net. That’s the tipping point that gives you options.
- Get a mentor or community. Liz almost quit three months in. One conversation changed our life. Don’t try to do this alone.
- Embrace the messy middle. The micro-failures are the path. Don’t think – just do.
The journey from corporate to entrepreneur isn’t a single heroic leap. It’s a series of small, smart, calculated steps. When you pick the right strategy – one with high cash flow and low risk – you give yourself the best possible chance of breaking through the three-month wall, hitting that $5K-a-month milestone, and stepping into the kind of freedom that Liz and I have built our life around for over 15 years.
If you’re ready to take those first small steps and learn the exact strategies our community of successful Digital Investors are using right now, you can learn more about our Digital Investors Program here. We’d love to help you write your own version of the story.
Remember – you must always push the limits. Because if you never fail, you’ll never succeed.
