Mark: Alright Michelle, I'm going to say a book title, and you give me your gut reaction. Excessively Obsessed. Michelle: Excessively Obsessed? Sounds like my relationship with my morning coffee, or maybe the official handbook for Silicon Valley burnout. Is this a 'how-to' or a 'how-not-to'? Mark: That is the million-dollar question, isn't it? And in this case, it’s a $63 million dollar question. We're talking about Excessively Obsessed: Find Your Passion, Build Your Business, Learn Your Limits, Love Your Life by Natasha Oakley. Michelle: Ah, Natasha Oakley. The name rings a bell. She's the one behind that massive swimwear brand, right? Mark: Exactly. For anyone who doesn't know, she's the Australian entrepreneur who co-founded the A Bikini A Day blog and built it into the global swimwear brand, Monday Swimwear, and several other successful companies. This isn't theory from an academic; it's a playbook from someone who has lived and breathed this stuff. Michelle: Okay, that changes things. So this 'obsession' is the secret sauce, not the poison? I'm intrigued. Where do we even start with a concept that feels so... intense? Mark: We start where she did, with the obsession itself. The book’s first big idea is that to survive the brutal early days of a startup, you don't just need passion. You need to be, in her words, "excessively obsessed."

Michelle: I have to be honest, Mark, that phrase makes my shoulders tense up. It sounds like a recipe for disaster, a rebranding of hustle culture that we're all trying to escape. Mark: I get that, and the book actually tackles that head-on. Oakley argues that this obsession isn't about working yourself to death for the sake of it. It's about a deep, almost irrational belief in your idea. She talks about how this drive was in her from a young age. We're talking about a six-year-old collecting and selling rocks to her neighbors. Michelle: Selling rocks? Okay, that's some serious early-stage-CEO energy right there. Mark: It gets better. At age ten, she was making custom Christmas cards—which were basically just a single scribble—and selling them to family friends for twenty bucks a pop. She says, "I felt like I was in my purpose when I was ‘doing business’." The obsession was with the act of creation and commerce itself. Michelle: Okay, but lots of people are 'obsessed' with their jobs and just end up miserable and burnt out. What's the difference between her version of obsession and just being a workaholic? Mark: That's the critical distinction she makes. She lists all the wrong reasons to start a business: because you hate your job, you want to be famous, or you want more 'freedom'—which is the biggest myth of all. Her point is that the obsession has to be with the idea and the value it provides, not with the escape it offers. Michelle: So it’s a focused obsession. It has to be pointed at something meaningful. Mark: Precisely. Look at how she and her partner, Devin Brugman, started A Bikini A Day. They were posting bikini photos and getting mixed reactions, some of it negative. Instead of backing down, they leaned in. They created a dedicated platform, a home for swimwear lovers. They were obsessed with serving that niche community. Michelle: I remember that! It felt like they were everywhere. Mark: They were. But for years, they reinvested every single dollar they made back into the business. They were traveling the world, but it was to take photos of themselves in bikinis, day in and day out. The obsession wasn't with the glamorous lifestyle; it was with building the best possible platform for their audience. Michelle: Okay, that reframes it for me. The obsession is the engine, but it needs a steering wheel. It has to be directed by purpose, not just fueled by a desire to work hard. It’s about being obsessed with the what, not just the doing. Mark: Exactly. And that focused obsession is what gives you the courage to actually execute on your idea, which is the book's second major theme. It’s one thing to have a great idea; it’s another to bet your life on it.

Michelle: Oh, I love a good 'bet on yourself' story. This is where it gets messy and interesting, right? Mark: It’s the heart of the entrepreneurial journey. Oakley tells this incredible story about their first attempt to launch Monday Swimwear. In 2013, a manufacturer approached them to create a swimwear line. It seemed like a dream deal—they design, and this established company handles production and sales. Michelle: Sounds like a golden ticket. What went wrong? Mark: They poured their hearts into designing a ten-piece collection. They flew to Australia on Christmas Day to shoot the campaign. They did everything right. But then, the company's buyer decided she only wanted to purchase a few of the pieces, leaving them with a broken collection and inventory they couldn't sell. Michelle: Oh, that's brutal. All that work, and someone else holds all the power. Mark: And this is the turning point. Natasha scheduled a meeting to confront them. She describes this tense moment where she just looked at them and said, "Maybe this isn’t working." She and Devin walked out on the deal. They had no manufacturer, no backup plan, nothing. Just their designs and their belief in themselves. Michelle: That's terrifying. And it brings up a huge point from the book: funding. She talks about how women-led startups receive a tiny fraction of venture capital funding, less than 3%. So for two young women to walk away from a seemingly secure deal is an even bigger risk. How on earth did they afford to start over? Mark: This is where the book gets really practical and, frankly, inspiring. Oakley is a huge advocate for self-funding and avoiding VC money if you can, because it means you keep control. Her advice is to not quit your day job. She worked multiple jobs simultaneously for years. Michelle: The classic side hustle. Mark: But she frames it differently. She says, "There is no job that you’re too good for, and no work that won’t teach you something." She uses her teenage retail experience to inform customer service at her pop-up shops today. The side job isn't just for money; it's for intel. Michelle: I love that. It’s market research you get paid for. But what about the big costs, like building a website? You can't pay for that with a weekend retail job. Mark: This is where her scrappiness shines. She talks about the power of bartering. In the early days of A Bikini A Day, they needed a professional website but had no money. So, she found a friend whose father was a web designer launching a clothing line. She offered to shoot his entire launch campaign in exchange for him building their website. Michelle: That is brilliant. Trading skill for skill. It’s such an old-school concept, but it's perfect for the digital age. It’s about building a network of mutual support, not just transactions. Mark: And that’s the essence of her execution strategy. It’s not about having a huge bank account. It’s about having resourcefulness, a strong work ethic, and the guts to bet on yourself when no one else will. But, as the book makes very clear, that hustle and obsession comes with a very real, very high price.

Michelle: Okay, so they hustle, they build this incredible empire... but the title also says 'learn your limits.' This is where the story has to turn, right? The obsession can't be sustainable forever. Mark: This is the most powerful and, I think, the most important part of the book. It’s where she moves from business advice to life advice, and it's grounded in a deeply personal story. In 2022, at the height of her success running multiple businesses, Oakley contracted Covid. Michelle: Like so many of us. Mark: But for her, it turned into long Covid. She describes this terrifying period of debilitating fatigue, dizziness, joint pain, and severe brain fog. She was a CEO who prided herself on her energy and drive, and suddenly she could barely walk. She even had to be taken off a flight because of severe muscle pain and an irregular heartbeat. Michelle: Wow. That's a brutal reality check. It's one thing to hear a guru say 'prioritize wellness,' but it's another to hear it from a high-performer who was physically forced to a complete stop by her own body. Mark: It completely reframes the conversation. It makes you realize that self-care isn't a luxury or a reward for hard work. She argues it's a non-negotiable business asset. Your health is your company's biggest asset. Without it, the entire empire is at risk. Michelle: That experience must have changed her entire approach to work and life. Mark: Absolutely. It’s where she introduces practical strategies for avoiding burnout. One of my favorites is her concept of the "5-second funeral." When something goes wrong—a bad shipment, a key employee quits—the team is allowed five seconds to be angry, frustrated, to mourn the problem. Michelle: A 5-second funeral? That's less time than it takes me to mourn a dropped ice cream cone. How does that actually work in a crisis? Mark: After those five seconds, the conversation must immediately pivot to: "Okay, what's the solution?" It's a mental trick to stop the team from spiraling into negativity and to train them to be relentlessly solution-oriented. It keeps perspective. Most business problems, she says, are not life-or-death. Michelle: I can see how that would build incredible resilience in a team. It acknowledges the emotion but doesn't let it derail the mission. It’s about managing energy. Mark: And that’s the final, profound message of the book. She quotes, "If you are truly excessively obsessed, perhaps the hardest thing I will ask of you in this whole book is to slow down, breathe and take a moment for yourself. It is also the most important." The ultimate challenge for the obsessed is to learn the discipline of rest.

Mark: So when you put it all together, the book isn't just a guide to being obsessed. It's a guide to a sustainable obsession. It’s about building a fire hot enough to forge a business, but also building the fireplace to contain it so it doesn't burn your whole house down. Michelle: I love that analogy. It’s not about choosing between ambition and well-being, but about integrating them. The real success story isn't just the $63 million valuation; it's learning how to run the empire without it running you into the ground. What's one thing you think our listeners should take away from this? Mark: That your biggest business risk isn't a market crash or a failed product launch; it's your own burnout. And the best way to mitigate that risk is to treat your own well-being with the same 'excessive obsession' you give your business idea. Your energy is your most valuable, non-renewable resource. Michelle: A perfect place to end. It really makes you think. We'd love to hear from our listeners on this. What's one small thing you do to protect your own 'human asset,' to keep that fire contained? Find us on our socials and let us know. We read all the comments. Mark: This is Aibrary, signing off.