The best idea with the worst reputation

The best idea with the worst reputation

While Caddie is excited to use this platform to start sharing announcements, news and updates about our business; we wanted to first take some time to tell our story so far and share our company’s humble beginnings.


The old adage goes that you shouldn’t mix the personal and the professional with the implication being that doing so would somehow spoil one or both. The repetition of this saying has shaped many a company’s culture and cultivated a mindset that these two aspects mix like oil and water. Caddie was founded with a drive to innovate and challenge such status quo and it all began with rejecting this notion entirely. Once the team agreed that we wouldn’t let anyone but ourselves set the tone of what the company would be it came as easily as riding a bicycle. Mike went to work chasing leads and showcasing just what we could do for prospective clients, Calvin engineered the deliverables that Mike put to work wowing our clients with, Tom kept the ship on a steady course by coordinating the projects and Paddy did what he does best by packaging it all into digestible communication.


Caddie’s start wasn’t when the company was founded in the twilight of 2022 though, nor was it when we signed our first client only a short time later. Caddie began in the small conversations had in between projects as our co-founders worked together at ClickPay or offered advice to one another in their separate ventures. It began with the success the current team saw as it overcame problems and innovated solutions together on projects working for those same companies. It grew as an idea as we maintained contact even after going our separate ways, sharing in failures and successes both professional and personal as we developed our skills apart. Caddie began in a hundred small conversations over years of friendship about a shared dream of coming back together one day to use those years of skill and experience to create a trailblazing company with a powerhouse team dedicated to delivering first class service. Even at weddings as we would reminisce and talk about the good times to come, those conversations would always inevitably turn toward ways we could realize this shared idea.


Caddie is the culmination of a group of friends’ dreams. Our story began with the camaraderie of our founding members working hard to realize a vision of someday creating a world class business. A business that would bind us together and that we could all feel pride in. More than anything we wanted to show the difference it makes in this business when friends who have worked together for years, who can anticipate the needs and compliment the skills of one another, assemble to create a company that puts the client’s needs first. ?As we launch on this maiden voyage together, we’re looking forward to forming new friendships with our partners and clients so that they can reap these benefits as well. We’re looking forward to showing our clients just what we’re capable of through prompt responsiveness and a level of consultancy service that makes you feel like one of our friends too. We can’t wait to carry your cloud!

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