The Solo Squad
Your Crew for Building a Business That Feels Like Freedom
Being your own boss doesn’t mean going it alone. The biggest struggle solopreneurs face isn’t the work — it’s the isolation. The Solo Squad is your space to stay motivated, share wins, swap referrals, and get support from people who actually get it.
Join the Solo SquadWhat’s Inside
The Solo Squad gives you the perfect mix of coaching, community, and accountability so you can stop second-guessing and start making real progress. Here’s what you get when you join:
Monthly group coaching call
Bring your questions, get feedback, and walk away with a clear plan.
Weekly goal-setting prompts
Simple nudges that keep you focused, consistent, and moving forward.
The Free-Way Forum
A private space to share wins, ask questions, and find your business besties.
Real Wins from the Squad
You don’t have to take my word for it. Here’s what solopreneurs inside the community are saying about finding support, clarity, and momentum with the Solo Squad.
Drew is my "biz bestie". Since day one, Drew has been someone I can count on for a non-judgmental and fun listening ear. He's incredibly wise and thoughtful when dealing with people and situations. When I have a difficult client or employee, or l'm at a crossroads in my business, I go to Drew. He's the perfect mixture of kind, business savvy, and empathetic. I've never brought him a problem he couldn't solve!
Audrey
Owner of Freebird
"Freelance Your Way to the Top gave me the tools and confidence I needed to kick start my freelance career. I had known for some time that I wanted to work for myself, but struggled with knowing where to start. This course was the roadmap I needed to really dive in head first. The personalized recommendations paired with experience to back it up was crucial – Drew was answering questions before I even knew I had the question! I would recommend this course to anyone on the fence of diving into a freelance career. Before even completing the course, I had signed my first client + shot my first wedding as a content creator! The investment is well worth it and you'll be paying yourself back in no time."
Sarah
Wedding Content Creator
About Drew
Hey, I’m Drew Henry, solopreneur coach and founder of The Free-Way. After leaving the 9 to 5 grind and building my own freelance business, I realized the hardest part was not the work. It was the loneliness. That’s why I created the Solo Squad.
I have coached and connected with hundreds of solopreneurs who all wanted the same thing: clarity, support, and a crew that gets it. My goal is simple. To help you build a business that fuels your freedom while giving you the community to make the journey lighter, smarter, and more fun.
