Excessively Obsessed: Find Your Passion, Build Your Business, Learn Your Limits, Love Your Life
A founder's practical guide to turning an obsession into a company: how to test the idea, when to quit your job, how to choose partners, market cheaply and avoid burning out.

Table of Content
1. Introduction
1 min 00 sec
Plenty of people have an idea they cannot stop thinking about, and many of them quit their jobs too early and watch the money run out. In Excessively Obsessed, Natasha Oakley, cofounder of Monday Swimwear and head of the online fitness business The Pilates Class, argues for a slower route: keep your paycheck and build on the side until the business can pay you. At Monday Swimwear, she went four years without a salary so every dollar could go back into the brand.
That patience runs through the whole book. An obsession turns into a lasting company only when it is protected, by honest motives, a steady income, the right partner, dull setup work done well, calm responses to mistakes, marketing built on real customers and a founder who looks after her own health.
The ideas below move from testing an idea to running a team, and they include the three signs Oakley says tell you it is finally time to resign.
2. Test whether your idea deserves years of your life
1 min 49 sec
Being sick of your job feels like a strong reason to start a company. Oakley thinks it is one of the weakest, and she offers a sharper test for knowing whether an idea is worth backing.
3. Keep your paycheck until the business can pay you
1 min 48 sec
Quitting to go all in looks like commitment. Oakley sees it as a trap that makes founders timid with money, and she names three signs that tell you the moment to leave has truly arrived.
4. Pick a partner who covers your blind spots
1 min 46 sec
The person you start a company with can carry it forward or sink it fast. Oakley explains what to look for, what must match and which conversation to have before anything is signed.
5. Get your margins and paperwork right early
1 min 51 sec
The least exciting tasks in a startup lay the foundation that is critical to its success. Oakley lists what to settle before you resign and shows where she lets data decide and where she refuses to.
6. Hold a five-second funeral, then fix it
1 min 43 sec
Thousands of unsold calendars could have shaken a young founder’s confidence for good. Oakley turned the episode into a habit for handling every setback, and it takes less time than reading this sentence.
7. Sell how your product improves a life
1 min 53 sec
A new brand with almost no budget and almost no followers still has to get noticed. Oakley’s approach starts with changing what marketing is for, and then hands much of the work to customers themselves.
8. Protect your health to power your company
1 min 32 sec
The thrill of work you love can hide a slow crash. Oakley found that out through a long illness, and she explains why a founder’s energy shapes decisions, teams and even where good ideas come from.
9. Conclusion
1 min 06 sec
Oakley writes like someone who has made the mistakes and kept the evidence, a stack of unsold calendars among it. Obsession is the fuel in her story, yet most of her advice is about rationing it, so the business grows and the founder does not burn out on the way.
What the book adds up to is a patient kind of ambition. The founder who lasts is the one who builds enough room to take risks: money in the bank, a partner to share the load, a team that stays calm and a body that is allowed to rest.
If an idea keeps you awake, begin by writing down why you want it and whom it helps. Build it beside your job until it pays you a living, you have six to twelve months saved and you can see five years ahead. When something breaks, give it five seconds of panic and then fix it. And keep some quiet time for yourself, since that is where Oakley says the next good idea tends to appear.
Obsession gets a business started. Care is what keeps it, and you, going long enough to see how far it can grow.
About this book
What is this book about?
Many people carry an idea they cannot stop thinking about. Many of the ones who act on it quit their jobs too soon, run short of money and lose control of the venture. Natasha Oakley, who cofounded Monday Swimwear and runs the online fitness business The Pilates Class, argues for a slower and safer route from passion to profit. Her advice follows the life of a young company. She starts with checking your real reasons for starting and choosing between products and services. Then she covers building the business beside a day job, picking a cofounder whose strengths differ from yours and getting names, paperwork and margins right before you resign. She also treats setbacks as lessons, using a quick ritual she calls the five-second funeral, and explains how to market through social media and your own customers on a small budget. The book ends with the founder's health, shaped by Oakley's own struggle with long COVID. Readers get clear signs for when to leave a job, practical habits for a lean launch and a reminder that the business depends on the person running it.
Book Information
Who it's for
Deciding when to quit
Employees with a business idea who want to know exactly when it is safe to quit.
Starting a company cheaply
New founders choosing a cofounder, setting up paperwork and marketing on almost no budget.
Entrepreneurs close to burnout
Entrepreneurs who love their work but feel close to burning out.
About the Author
Natasha Oakley
Natasha Oakley started A Bikini A Day with Devin Brugman in 2012, and it grew into a marketing platform. The pair launched Monday Swimwear in 2014 and Monday Body, an activewear and everyday essentials line, in 2023. She is a CEO, model, presenter and designer, and she leads The Pilates Class, an online fitness business set up in 2020 and described as multi-million-dollar.
Ratings & Reviews
Ratings at a glance
What people think
Listeners describe *Excessively Obsessed* as a transparent and motivating guide for people starting their own businesses, especially if they lack traditional business training. Though views differ regarding how technical the advice is—since some listeners find the material a little simplified for seasoned experts—many enjoy the genuine glimpses into the author’s professional life and her private stories. Furthermore, people highlight that the work offers a useful combination of psychological adjustments and practical steps for starting a company. On top of that, listeners appreciate the direct style of the prose, with one listener describing it as a "perfect mix" of overarching strategy and practical knowledge.
Top reviews
Natasha Oakley has been a massive inspiration to me since her early blog days, so seeing her business logic laid out like this was incredible. The way she describes her journey from the 'A Bikini A Day' era to running multiple global ventures is both humble and empowering. This book helped me tap into my inner boss babe and realize that my unique perspective is actually my greatest asset. I loved the mix of mindset shifts and actionable tactics, especially regarding burnout and maintaining momentum. Why are there not more books like this that actually speak to young women in a language we understand? A true gem for any entrepreneur’s bookshelf.
Show moreFinally got around to reading this, and it’s easily one of the most straightforward business guides I’ve encountered lately. It's honest. She shares the good and the bad of running a company without the usual gatekeeping you see in this industry. For those of us without a formal business degree, this is an absolute godsend of a roadmap. I loved that she advocates for bootstrapping and staying lean, as that’s exactly where I am in my journey. The chapters are perfectly sized and the tone is incredibly encouraging without being cheesy. If you have an idea but feel paralyzed by the 'how,' just buy this book and get moving. It’s the kick in the pants I needed.
Show moreWow, Tash really delivered a gem that feels less like a dry textbook and more like a mentor chat over coffee. I’ve been following her since I was a teenager, and seeing her evolve into this powerhouse business owner is so inspiring. The book is a perfect mix of tactical advice and emotional intelligence. She doesn't sugarcoat how hard the hustle can be, but she makes it feel possible with the right mindset. The roadmap she provides is clear and actionable, covering everything from the initial spark of an idea to long-term growth. It is easily the first business book I’ve actually finished and enjoyed. Every aspiring founder needs this on their desk immediately.
Show moreThis book serves as a fantastic entry point for anyone looking to ditch the 9-5 and build something of their own. Natasha provides a solid roadmap that balances the 'why' with the 'how,' focusing heavily on the power of authenticity in a crowded market. I particularly appreciated the sections on bootstrapping versus seeking outside investors, as it’s an honest look at maintaining control over your vision. Some parts felt a little light on specific data, but the overall message is incredibly motivating for aspiring founders. It’s not a dense textbook. It is a heartfelt guide from someone who has actually done the work and stayed true to herself throughout the process.
Show morePicked this up on a whim after seeing some chatter on social media, and I have to say the advice on mindset is where it truly shines. Natasha’s perspective on the 'hustle' is refreshed by her compassion for the process and her focus on avoiding total burnout. Not gonna lie, I was worried it would be another influencer vanity project, but she really delivers some honest, straightforward lessons. Hearing the behind-the-scenes stories about her partnership with Devon added a nice personal touch that made the business advice feel more grounded. It’s perfect for those in the pre-launch phase of their brand. You won’t find complex financial modeling here, but you will find the courage to actually start.
Show moreThe chapter on authentic brand building alone made this worth the purchase for my small side-hustle. Natasha explains how to conceive of an idea and actually bring it to life in a way that feels achievable rather than intimidating. I really valued her take on the importance of staying true to your values while navigating the complexities of scaling. While I would have loved a few more technical details on the logistics of manufacturing, the big-picture strategy is excellent. It’s a very honest look at what it takes to be an entrepreneur today. I’ve already recommended it to several friends who are currently in the thick of launching their own ventures.
Show moreAfter hearing Natasha speak on a podcast, I wanted to see if her book offered more than just the usual influencer platitudes. Gotta say, I was pleasantly surprised by the level of real-life experience she shares regarding her multiple ventures. The focus on bootstrapping and staying authentic in the face of pressure from investors was particularly insightful for me. It’s not necessarily a deep dive into advanced economics, but it is a very practical guide for the modern entrepreneur. I enjoyed the blend of personal anecdotes and actionable steps. It feels like a genuine effort to help others succeed. It’s exactly the kind of honest, straightforward advice that most business books are missing these days.
Show moreEver wonder what really happens behind those glossy Instagram filters? Natasha Oakley gives a decent peek behind the curtain, but the content sometimes lacks the grit I was hoping for. The advice feels primarily geared toward total beginners who haven't even registered a business name yet. Truth is, if you have spent any time in a corporate environment, you might find the tactical sections a bit elementary and repetitive. However, her personal anecdotes about the early days of her swimwear brand are genuinely engaging and provide some great context to her success. It’s an okay read for a weekend, though it didn’t quite teach me how to spark a deep obsession with my own professional goals.
Show moreAs someone who has spent years following the author's career, I found the first half of the book a bit repetitive compared to her social media content. In my experience, the 'mindset' portions could have been condensed to make more room for the tactical 'how-to' sections. I was really looking for more detail on the interim stages of growth, rather than just the start and the current success. That being said, her transparency regarding the struggles of the industry is refreshing for the genre. It's a quick, easy read that works well as a motivational tool, even if the business advice is a little thin for seasoned professionals. Good, but not revolutionary.
Show moreTo be fair, I expected a much deeper dive into the actual mechanics of scaling a multi-million dollar brand than what was offered here. Most of the chapters felt like a very basic business school report that summarized concepts you could find in a short article online. I zoomed through it because the prose is quite light, but I left feeling like I missed the 'meat' of the strategy. It’s more of a memoir with a few tips sprinkled in rather than a robust roadmap for serious entrepreneurs. Frankly, if you already have a business background or have launched a company before, you’re likely to find this repetitive and far too surface-level for your needs.
Show moreQuestions about this book
What is the main idea of Excessively Obsessed?
Natasha Oakley argues that passion can become a profitable business, but only if the founder protects it. That means starting as a side project while keeping a salary, choosing a partner with different strengths, settling paperwork and margins early, treating mistakes as lessons, marketing through social media and customers, and guarding your own health. She draws on her experience building Monday Swimwear and The Pilates Class.
When should you quit your job to run your business, according to Natasha Oakley?
Oakley names three signs. The business should already pay you a livable wage, with stable revenue and a growing customer base. You should have an emergency fund that covers six to twelve months. And you should have a growth plan for the next five years. Until then, she advises keeping your paycheck, as she did by going four years without a salary at Monday Swimwear.
What is the five-second funeral in Excessively Obsessed?
It is Oakley’s ritual for handling setbacks. When something goes wrong, such as a late shipment or a failed launch, everyone gets five seconds to panic, and then the team turns to solutions. Because people take their cue from the leader’s reaction, she sees staying calm as part of the job. Over-ordering a swimsuit calendar early on taught her a lesson about ordering accurately.
How does Natasha Oakley recommend marketing a new business?
She focuses on showing how the product improves customers’ lives and on social media, where reaching people costs little. Early steps include claiming account names, posting regularly and asking friends and family to share. She values content made by customers, quick replies to feedback, small paid ads aimed at people like your best buyers, genuine influencer support and using polls and messages to learn what customers want.
Who should read Excessively Obsessed?
It suits people who want to turn a passion into a business but are unsure how to start safely, especially those still in a job. Early founders will find advice on partners, paperwork, margins and low-budget marketing. Entrepreneurs already running a business may value its chapter on burnout, shaped by Oakley’s experience with long COVID.
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