Excessively Obsessed summary

Ready to take the leap and launch your dream business? Not so fast! Quitting your day job too soon could turn out to be a huge mistake. Instead, start your business as a side hustle and keep your steady paycheck until you gain traction.

Yes, working two jobs is exhausting. But without a financial safety net, you’ll be tempted to pinch pennies in your new venture instead of taking the risks needed to grow. When Oakley started Monday Swimwear, she didn’t take a salary for 4 years! This allowed her to pour every dollar back into the business.

No entrepreneur is an island. Behind every successful business is a dedicated team working together toward a shared vision. But building that dream team starts with finding the right partner.

When Oakley launched Monday Swimwear and later The Pilates Class, having a cofounder whose skills complemented her own was essential. Be selective about who you go into business with – the right partnership can propel you forward, but the wrong one can tank a venture fast.

Before you rush to quit your job, make sure you’ve got the nitty-gritty details squared away. This means logistics, finances, and all other administrative work. It’s not glamorous, but laying a strong foundation is critical for success.

First up, choose a name for your business that’s memorable, expandable, and, importantly, not already taken. Secure the trademark and buy the URL. Then get your paperwork in order: register the business, get a tax ID number, open a bank account, and consider hiring an accountant and lawyer to ensure you’re doing it all correctly.

Buckle up, aspiring entrepreneur–- your business journey will be filled with ups and downs. But here’s the secret: even the “downs” are opportunities in disguise. Every mistake is a master class in what to do differently next time.

When Oakley started out, she once ordered way too much inventory for a swimsuit calendar. She was left with thousands of unsold copies. It wasn’t a total disaster, but she learned her lesson about accurate ordering.

Finding the right marketing mix is essential for any new business looking to make a splash. While traditional channels like print ads and billboards still have their place, embracing digital platforms is non-negotiable in today’s landscape. Here’s how to craft a killer strategy on a startup budget:

First, shift your mindset. Marketing isn’t about hyping your brand anymore – it’s about communicating how your product will improve your customers’ lives. Be crystal clear on your unique value and infuse it into all your messaging. 

When you first launch a company, that business becomes your baby, demanding all your love and attention. You eat, sleep, and breathe work, especially in the early days of your entrepreneurial journey. But just as parents on an airplane are advised to put their oxygen masks on first, so too must you prioritize your own well-being.

Burnout is a very real threat. The exhilaration of jumping out of bed on a Monday morning, driven by purpose and fulfillment, can be addictive. But constantly working without downtime has extreme negative effects that often sneak up unexpectedly. Oakley’s personal encounter with long COVID, which left her debilitated with tension headaches, fatigue, and brain fog, was a stark reminder of this reality.