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Community Highlights: Meet Cameron Caldwell of Purchase Your Freedom

Today we’d like to introduce you to Cameron Caldwell

Cameron, we appreciate you taking the time to share your story with us today. Where does your story begin?
My name is Cameron Caldwell, and I’m the founder of Purchase Your Freedom (PYF). What started as a small blog in 2020, fueled by my deep-seated passion for entrepreneurship, has blossomed into a community of entrepreneurs seeking to live life on their own terms.

I previously worked as a Project Manager at Teachable, an ed-tech company that empowers creators to monetize their audience through digital products. After helping to build their creator launch initiative as one of its early employees, I saw first-hand how everyday people could leverage the internet and its vast suite of tools to generate income that rivaled their normal 9-5. They could also do so by utilizing skills they already had. So, I set out to remove barriers to this life-changing information in the form of a blog during the pandemic.

In 2022, I took a bold step and transformed PYF into an in-person weekly meetup series– originally designed to guide beginner entrepreneurs in unlocking new streams of income online. My vision was clear: to give people the information and tools to design their own destinies and live life on their terms. But I didn’t stop there. I envisioned a thriving community in Dallas where builders could meet face-to-face, exchange networks, and invest in one another. And so, every single week, without fail, we’ve gathered to turn ideas into action and dreams into reality. PYF is more than just an entrepreneur meetup—it’s an accountability community.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I’m not familiar with the term smooth road. The road has been ambiguous and full of bumps the entire way. My very first meetup only had one attendee, despite me having about a dozen registrations. It was a humbling start, and I almost decided not to show up the next week. I tried expanding to a Fort Worth chapter and even launched another niche meetup for creators, but neither gained the traction I hoped for. In the beginning, I kept the flow of the meetup low-key to avoid burnout, but that approach soon made the meetups feel stagnant. I’ve also had to deal with people trying to sell things to my community that they didn’t ask for, which was disheartening.

Just the logistics of attending the meetup every week have required sacrifices. Anyone who lives in Dallas knows that the city shuts down at the slightest sign of ice on the ground. I’ve driven through a freeze storm to make sure we never missed a week. I distinctly remember being on a family trip in Oklahoma, and I drove back to Dallas alone early Saturday morning just to ensure I could still host the meetup. I’m thankful that I made the drive because it was that week where we had two people who visited from Austin, TX attend and have a great experience.

Showing up for my people every single week is no small feat, but through all the challenges, I’ve learned that true growth often comes from overcoming adversity and keeping the promises you make.

Thanks – so what else should our readers know about Purchase Your Freedom?
Purchase Your Freedom (PYF) is the experiential arm of my creative agency, Tayper Branding. PYF is dedicated to educating and empowering individuals to create additional streams of income online. My focus is on helping beginner entrepreneurs, in Dallas and abroad, take those first crucial steps towards financial independence. What sets PYF apart is the community-driven approach to entrepreneur development. I’m not just offering information, I’m fostering a space where like-minded individuals can connect in real life, share networks, and grow in tandem. I’m most proud of the consistency and commitment behind the PYF brand. We’ve held weekly meetups without fail since 2022, creating a dependable and supportive environment for our members.

What I want readers to know about PYF is that it’s more than just a series of events; it’s a movement. Our offerings go beyond the typical advice—you’ll find practical strategies, genuine connections, and a community that truly wants to see each other succeed. Whether you’re just starting out or looking to expand your network, PYF is here to help you build the life you’ve always wanted. We’re about real, actionable steps towards freedom, not just in business, but in life.

Where we are in life is often partly because of others. Who/what else deserves credit for how your story turned out?
I want to give credit to the Kauffman Foundation for their 1 Million Cups event series. As an attendee and previous organizer, I learned that it was possible to bring interesting people together under one roof, consistently, and in a non-competitive environment. We were all there to grow, indulge our curiosities, and meet other people on the same journey. I adopted a lot of their model in the early stages of building out the weekly meetup.

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Purchase Your Freedom

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