This 'Dream' Side Hustle Out-Earned Her Corporate Salary in 2 Years — Now It's a $2 Million Business Here's the exact blueprint she used to leave her W2 job behind and step fully into entrepreneurship.

By Katie Cline Edited by Mark Klekas

Key Takeaways

  • This as-told-to story is based on a conversation with entrepreneur and author Stacey St. John, who outlines her approach to replacing her corporate salary in her new book, LIVE BIG.

Opinions expressed by Entrepreneur contributors are their own.

Two years. That's how long it took me to build a short-term rental business that replaced my six-figure corporate salary and gave me the freedom I craved. But let's be clear — this wasn't some lucky break or overnight win. This was a journey of intentional action. I started with one property, stacked my wins and leaned in every time an opportunity whispered, "Let's go."

When I started, I didn't have it all figured out. I didn't have a five-year plan, a business degree or a crystal-clear vision. What I did have, though, was a gut-deep knowing that I wasn't meant to be stuck in a job that drained me. I wanted freedom — real freedom — and was willing to take small, smart steps to create it. That journey led me to write LIVE BIG, where I share the exact blueprint I used to leave my W2 job behind and step fully into entrepreneurship. And here's the truth: If I can do it, so can you.

Related: Her Dorm Room Side Hustle Put a New Spin on a Closet Staple. It Led to $60,000 in Sales Overnight — Then Over $1 Million.

The framework that changed my life

I was stuck on a hamster wheel, feeling like I was going nowhere. My lucrative job (which was once a source of pride) felt like a ball and chain, weighing me down. I was working 14+ hour days, crashing into bed every night utterly exhausted and lacking inspiration. I didn't want to keep living this way, so I decided to start investing in real estate.

I pulled together all the savings I could: $50,000. I used that nest egg to buy my first three properties, small condos each purchased for $90,000 (or less) with a mortgage. Once I got started, the idea of living off my real estate, side hustle income sparked excitement in me. To combat the self-doubt monster, I knew I needed to build my business using a clear framework, and this is what I developed:

1. Boss2 Up: Develop the behaviors to achieve the outcome you want, and leverage strategy, skills and systems to get there faster.

I took lessons I learned from my corporate career and applied them to my business. For example, we'd have weekly meetings to review our quarterly goals and break them down into clear, actionable tasks. The following week, we'd repeat the process, always refining and executing the roadmap.

Fast forward a few years, and this same philosophy became the cornerstone of my vacation rental management business. I started holding weekly leadership team meetings — even though I was the only one on the team. I set time aside to review my goals, measure my progress and create action steps to build the infrastructure, systems and processes needed to support a million-dollar operation (even though I didn't have one yet). It wasn't just about checking off tasks — it was about laying the foundation for a scalable, sustainable business from the ground up.

2. Show Up: Master your mindset so you can operate with clarity and confidence.

I started waking up at 4 a.m. to build my dream before clocking in for someone else's. I got myself into rooms with people who were further along than me. I devoured books, articles and podcasts, desperate to understand the intricate workings of my mind and how to rewire it for success.

3. Step Up: Take aligned action, even when it feels stretchy or scary.

Before I left my W2, my schedule was tight — but I made it work. I time-blocked early mornings, evenings and weekends to focus on revenue-generating activities and personal development. No fluff. No scrolling. Just focused execution. I also reinvested any profit into automation and a dream team.

I didn't have all the answers, but I had drive and commitment. And that was enough to turn that initial $50,000 into a real estate portfolio worth more than $2 million.

Related: Time Blocking Tips Top Experts and Scientists Use to Increase Productivity

You don't need a master plan, but you do need a financial runway

Let me save you from one of the biggest mistakes people make: waiting for the perfect plan. If I had waited until I had everything mapped out, I'd still be stuck in that cubicle. Instead, I focused on the next right step. That one property led to purchasing another. Then, managing other people's vacation rentals. Then, coaching and hosting masterminds. Then podcasting. And now, building an empire. Each step allowed me to gain exposure to new audiences. Even better, now my largest revenue stream comes from simply helping others.

Now, just because I didn't have a master plan doesn't mean I leapt without a parachute. I made sure I had six months of savings before walking away from my corporate paycheck. That gave me breathing room to make smart decisions, not desperate ones. If you're serious about building a business, start by mapping your monthly expenses and creating a financial cushion. It'll give you the freedom to build from peace instead of panic.

Give yourself a shortcut

One of the most powerful things I do is what I call "knowledge hacking". It means I constantly ask: Who's already done this — and how can I learn from them?

I was instantly hooked on my new "Airbnb biz," but the reality of running a 24/7 hospitality operation hit me hard, even with just two properties. As a newbie, I didn't have the know-how to thrive. So, I did what any resourceful person would do: I followed Dan Sullivan's Who Not How approach and went searching for my "Who" — someone with the time, experience and expertise I didn't have. I hired my first employee, who took charge of revenue management, guest screening and pretty much everything related to guests. My role? When a repair popped up, I just coordinated with our maintenance guy. Easy-peasy — I could handle that! And I paid her through a revenue share, meaning she got paid when we got bookings, which meant I could afford her from the beginning.

I also invest in books, podcasts, masterminds, coaching, courses and reading excellent publications. The best way to fast-track results is to tap into someone else's experience. Every dollar I've ever spent on education has paid me back tenfold. Success isn't about doing it all yourself. It's about being smart enough to leverage other people's wisdom.

The bottom line

I didn't build a freedom-based business by chance. I built it by getting clear on what I wanted, taking aligned action, and refusing to give up. If you're sitting there wondering if you're meant for more — you are. You don't need all the answers. You just need the courage to start.

Katie Cline

Public Relations Professional

Katie Cline is an award-winning public relations professional who has led global communications for world-renowned brands such as The Ritz-Carlton, W Hotels, St. Regis, The Luxury Collection, JW Marriott, Le Méridien, Michael Kors, and more, in both New York City and London. An obsessive traveler, Katie is a dual citizen of the US and Ireland who applies her love of hospitality to her two short-term rentals in upstate New York: Trout Landing (near Lake George) and Gallant Fox (in Saratoga Springs). She’s the host of the soon-to-launch Hospitality.FM Original podcast, Suite Success, where she interviews hotel executives, hospitality leaders, and industry innovators to uncover the strategies and techniques that make hotels and short-term rentals stand out. Her writing has been featured on Entrepreneur, Business Insider, Yahoo!, MSN, The Everymom, and more.

When she’s not busy planning her next trip, Katie can be found trying a new restaurant in Astoria (her NYC neighborhood) with her husband, Joe; schooling her British-born toddler, Nora, on the magnificence of New York bagels; or refilling the Prozac prescription for her anxious, asthmatic rescue pup, Jack Daniels.

Want to be an Entrepreneur Leadership Network contributor? Apply now to join.

Science & Technology

101 Small Business Ideas to Match Your Personality, Investment, Skills & Goals

Still stuck on what biz to start? Use AI to uncover 101 custom ideas aligned with your skills, values & lifestyle—plus a 90-day roadmap to launch with clarity.

Business Ideas

70 Small Business Ideas to Start in 2025

We put together a list of the best, most profitable small business ideas for entrepreneurs to pursue in 2025.

Side Hustle

She and Her Sister Started a Side Hustle to Help People Elevate Their Homes — Now Their Brand Pulls In Hundreds of Millions: 'Get to Work'

When Lee Mayer moved from New York City to Denver, Colorado, she wanted to find an affordable, fun way to decorate her home.

Growing a Business

Why Storytelling (Not Selling) Is Your Most Powerful Branding Tool

A thought leader is a sum of their stories. Learn why sharing your unique thoughts, feelings and perspectives can help you stand apart from other experts in your field.

Business Solutions

Access 25 Hours of AI Training for Less Than $20

This e-degree gives you hands-on AI training that's perfect for entrepreneurs wearing many hats.

Business News

'One of the Most Consequential Bills Ever': Here's How the 'Big, Beautiful Bill' Will Affect Small Businesses

President Donald Trump is expected to sign the multi-trillion-dollar bill on July 4.