Sheila Dwyer
Founder, Iron & Adventure
Seasonal Lifestyle Strategist & Business Mentor

Where My Journey Began

My journey didn’t start online or with a polished business plan. It started decades ago in the real world, working in tourism, hospitality, and outdoor recreation, long before those paths were trendy or automated. I learned early what seasonal work really looks like. Busy months, quiet months, and the constant pressure of making it all stretch. Hosting, cooking, managing properties, running operations, and figuring things out when there was no playbook taught me how to survive and eventually how to build something sustainable.

The Path That Shaped Me

Over 30 years, I’ve hosted guests, run a bed and breakfast near Yellowstone, cooked in the backcountry, and built businesses that had to work in real conditions, not ideal ones. I’ve seen firsthand how relying on bookings alone creates stress, burnout, and financial whiplash. That experience shaped how I think about business. Not as hustle, not as hope, but as systems, structure, and ownership. I’ve rebuilt more than once, and every rebuild made the systems sharper and the strategy clearer.

My Beliefs and Values

I believe a vacation rental is an asset, not a complete business. I believe clarity beats chaos, systems beat scrambling, and integrity always matters more than fast growth. I don’t believe in shortcuts, passive income myths, or selling people dreams that fall apart under pressure. I believe in earned authority, honest conversations, and building income that supports your life instead of running it.

Milestones That Matter

• 30+ years in tourism, hospitality, and outdoor recreation
• Founder of Iron & Adventure and host of The Chicory House Bed & Breakfast
• Built multiple income streams beyond bookings using backend systems
• Mentored vacation rental hosts and seasonal entrepreneurs into stability and control
• Created systems that support year-round income, not platform dependence

What Drives Me

What drives me is helping people stop living at the mercy of the calendar. I want hosts and seasonal entrepreneurs to feel steady, clear, and confident even when bookings slow. A well-built backend creates peace of mind, better decisions, and a business that lasts. My goal is simple. Help people build something they own, something stable, and something that supports the life they actually want to live.