Mark: Your biggest strength at your 9-to-5 job—being reliable, meticulous, and risk-averse—is probably the very thing that will guarantee your failure as an entrepreneur. That's the uncomfortable truth we're unpacking today. Michelle: Wow, that's a bold claim. So you’re telling me my perfect attendance record and my beautifully color-coded spreadsheets are actually a liability? I feel personally attacked, Mark. Mark: It feels like a personal attack, but it’s the central paradox we're diving into with the book Employee to Entrepreneur by Steve Glaveski. He argues that the very wiring that makes you a great employee can sabotage you when you try to build something of your own. Michelle: That’s fascinating. And who is Steve Glaveski? Is he just some guru shouting from a mountaintop? Mark: Not at all, and that’s what makes his perspective so compelling. He’s a first-generation Australian, the son of immigrants from the former Yugoslavia who came to Australia for a better life. He did the "right" thing—climbed the corporate ladder in investment banking and consulting—and then he jumped. Michelle: And I’m guessing it wasn’t a smooth landing? Mark: It was a face-plant. His first big venture, funded with $150,000, was a total failure. But then, he built his next company, Collective Campus, into a seven-figure business. So he has lived this exact paradox. He’s not just theorizing; he’s speaking from the trenches, from his own spectacular failures and successes. Michelle: Okay, I’m in. He’s earned the right to tell me my spreadsheets are holding me back. So, if our corporate skills are a trap, where do we even begin?

Mark: It begins with a complete mental rewiring. Glaveski’s core argument is that the biggest leap isn't financial or logistical; it's psychological. You have to unlearn the habits that made you "safe" in the corporate world. Michelle: What does that unlearning look like in practice? I mean, being careful and planning things out seems like a good thing, no matter what you're doing. Mark: It does, but let's look at his first startup, Hotdesk. The idea was basically an "Airbnb for office space." This was back in the early 2010s, a great idea on paper. He got $150,000 in seed funding and, coming from the corporate world, he did what he knew best: he planned meticulously. He spent months working with developers, perfecting the platform, and getting everything just right before the big launch. Michelle: Sounds like the responsible way to spend investor money. Mark: It sounds responsible, but it was a disaster. He was operating from a corporate mindset: "build the perfect, finished product, then present it." He launched Hotdesk, and… crickets. He had built this beautiful, polished platform that almost nobody actually wanted or was willing to pay for in the way he'd imagined. He found himself in what entrepreneurs call the "trough of sorrow," realizing he'd wasted time and a lot of money building a solution for a problem that didn't really exist. Michelle: Oh, I know that feeling. Not the $150,000 part, thankfully, but the part where you pour your heart into a project and realize you completely misread the room. It’s crushing. Mark: Exactly. And Glaveski's point is that a true entrepreneur would have done the opposite. Instead of building the whole platform, they would have tested the core assumption first. Could he get one person to pay to use one empty desk? He could have tested that with a simple webpage and a phone call, for practically zero dollars. Michelle: But hold on, you can't just wing it entirely, right? There has to be a balance. You can't run a business on pure chaos. Mark: You're right, and the balance he proposes is a shift in mindset. He talks a lot about adopting what Stanford psychologist Carol Dweck calls a "growth mindset." In a corporate, or "fixed," mindset, failure is a verdict on your ability. It's a bad thing. In a growth mindset, failure is just data. It’s feedback. The Hotdesk failure wasn't a sign that he was a failure; it was data telling him his approach was wrong. Michelle: So, failure isn't a stop sign, it's a signpost telling you to turn. Mark: A perfect way to put it. He also leans heavily on Stoic philosophy. The Stoics, like Marcus Aurelius, taught that you should only focus on what you can control. You can't control the market, you can't control investors, you can't control if people like your idea. But you can control your actions, your learning, and your response to the data. The corporate world trains you to try and control everything, to eliminate all risk through analysis. Entrepreneurship is about mitigating risk through action and learning. Michelle: That's a huge mental shift. It's moving from "let me write a 50-page report to prove this won't fail" to "let me run a $50 experiment to see if this will work." Mark: Precisely. You're moving from risk mitigation through analysis to risk mitigation through building and testing. It’s about making friends with discomfort and uncertainty, which is the exact opposite of what a stable 9-to-5 is designed to provide.

Michelle: That makes sense. If your old mindset is wrong, you need a new way of thinking. But that brings up the next big question. After a failure like Hotdesk, how do you even know what to build next? This 'find your passion' advice that gets thrown around feels so hollow. Mark: It is hollow, and Glaveski directly attacks it. He says you can't follow a passion you haven't found yet. He argues that most people haven't found their passion because their lives are too narrow. They haven't collected enough "dots." Michelle: "Collecting dots." That’s a bit abstract. What does he mean by that? Can you give me a concrete example of a 'dot' he collected that paid off? Mark: Absolutely. This is the core of his discovery process. He’s a huge proponent of what Steve Jobs famously described in his Stanford commencement speech: "You can't connect the dots looking forward; you can only connect them looking backward." So, Glaveski's advice is to proactively collect as many diverse dots as possible. For him, this meant getting a master's degree, but also running a heavy metal nightclub. It meant working in investment banking, but also learning to surf and ride a motorcycle. Michelle: A heavy metal nightclub? Okay, that's definitely a diverse dot. Mark: Right? And he tells a powerful story about a trip to Hanoi, Vietnam. He was out for a jog in the sweltering heat and humidity, feeling miserable. And he saw these local workers paving a walkway, doing backbreaking labor in the same heat, but they were laughing and cheerful. It was a "dot." It gave him a profound sense of perspective on hardship and attitude. That dot, that experience, wasn't about a business idea, but it rewired his perspective on what "hard" really means. Michelle: I can see how that would stick with you. But again, most people listening have a mortgage, maybe kids. They can't just quit their job and fly to Vietnam to collect dots. What's a dot a regular person can collect this week? Mark: That's the beauty of his approach. A dot doesn't have to be expensive or exotic. He says a dot can be reading a book on a topic you know nothing about, like Roman history or quantum physics. It can be listening to a podcast from a completely different industry. It can be taking a $20 online course in something random, like calligraphy—which, by the way, was the dot Steve Jobs collected that led to the beautiful typography on the first Macintosh. Michelle: The calligraphy class! I remember that story. So a 'dot' is really just any new input that breaks your routine and expands your frame of reference. Mark: Exactly. It's about building a library of experiences and knowledge in your head. You don't know how they'll connect, but you have to trust that they will. By collecting these dots, you start to see patterns. You might read about a problem in biology and realize the same pattern applies to a problem in finance. That's where innovation comes from. That's how you stumble upon a "why"—a purpose or a problem you genuinely care about solving. Passion isn't a lightning strike; it's the fire you build by rubbing enough interesting sticks together.

Mark: And once you have a potential idea from all that dot-collecting, a little spark from rubbing those sticks together, Glaveski's final piece of the puzzle is to not repeat the Hotdesk mistake. You don't build the whole bonfire. You make a small, smart bet to see if it will even light. Michelle: You test it. This is where we get really practical. Mark: This is where it gets brilliant. And the best story in the book, the one that perfectly illustrates this, is how he started his children's entrepreneurship program, Lemonade Stand. He and his team had the idea, but after the Hotdesk disaster, he was not about to spend thousands building a curriculum and a website. Michelle: So what did he do? Mark: He made a tiny bet. He created a simple event page on Eventbrite for a "Kids School Holiday Business Workshop." It was a hypothetical product. It didn't exist yet. Then, he spent just $100 on Facebook ads, targeting parent groups in Melbourne. Michelle: A hundred bucks. That's it? Mark: That's it. He was testing one single, crucial assumption: would parents pay for this? He wasn't testing the curriculum or the venue or the brand. Just the core demand. And the result was staggering. Within two weeks, he had sold 12 tickets at just under $500 each. Michelle: Wait, let me do the math. He validated a nearly $6,000 business idea for a hundred bucks. That is the polar opposite of the $150,000 Hotdesk failure. Mark: It's the perfect case study in lean execution. He calls it maximizing "Learning on Investment," or LOI. For a tiny investment of time and money, he got the most valuable data possible: people were willing to open their wallets. Only after he had their money did he actually go and build the workshop. Michelle: That's a powerful concept. It flips the entire corporate model of "plan, approve, build, launch" on its head. It's "sell, then build." Are there other examples of this kind of small-bet thinking? Mark: Tons. It's the foundation of the whole lean startup movement. Dropbox famously started with a simple explainer video. Before they wrote a single line of code for the complex product, they made a video showing how it would work and put it online. It got tens of thousands of sign-ups overnight. Zappos, the shoe company, started by its founder taking pictures of shoes at a local mall, posting them online, and then physically buying the shoes and shipping them himself whenever he got an order. He didn't own a single shoe. Michelle: He was a concierge, not a warehouse. Mark: Exactly. All these are examples of small, smart bets designed to test the riskiest assumption first. For Zappos, the assumption was: "Will people buy shoes online without trying them on?" For Dropbox: "Is file-syncing a big enough pain point for people?" For Glaveski's workshop: "Will parents pay for this?" Find the one question that could kill your entire idea, and find the cheapest, fastest way to get a real-world answer.

Mark: When you put it all together, you see this clear, three-stage journey. First, you have to rewire your mind to embrace uncertainty and see failure as learning. Second, you have to proactively go out and collect dots to build a foundation for a purpose you can believe in. And third, you test that purpose with small, smart, scientific bets. Michelle: It’s a process of personal reinvention that happens to result in a business. You’re not just building a product; you’re building a new version of yourself. Mark: That’s the deep insight. Entrepreneurship, in Glaveski's view, isn't a single, terrifying jump off a cliff. It's a series of small, calculated steps away from the edge. It's about building a new identity, not just a new company. And that’s why it’s accessible to anyone, not just the stereotypical risk-loving maverick. Michelle: So for someone listening right now, feeling stuck in their cubicle and inspired by this, what's the one thing they should do after this episode ends? What's the first, tiniest step? Mark: I think Glaveski would say to forget about the grand plan for a moment. Don't try to find your ultimate 'why' today. Just pick one 'what.' One small, curious action. Michelle: Like what? Mark: Subscribe to one podcast that's completely outside your field. Go to a bookstore and read the first chapter of a book from a section you would never, ever visit. Sign up for a free online lecture on a topic you know nothing about. Take one tiny, deliberate step to collect one new dot. Because the path only reveals itself once you start walking. Michelle: I love that. It’s not about having the answers. It’s about starting the search. Mark: It’s about starting the search. The world needs more people who are alive with purpose, not just busy with tasks.