Success Series: Taking Chances ft. Tyler Winder 

He is one of those people who you know of before you actually meet him in person. 

One of those people who feels confident and comfortable in his own skin.

He is one of those people that everyone can befriend…the kind of guy that everyone cheers on from the sidelines.

He is too funny for his own good. Kind. Smart. And he is killing it in his career. 

Drum roll please! May I introduce you to the one! The only! The ever awesome and relentlessly driven Tyler Winder!

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Winder graduated from Colorado Mesa University in 2015 with a major in Sports Management and a minor in Business Management.

Winder is currently a realtor in the Greater Boston area – but he’s not your typical run of the mill realtor. He’s got big plans. Winder recently partnered with two individuals in the spirit of entrepreneurship to open a new brokerage and development company.

Basically, they buy vacant land in affluent towns outside of Boston and build luxury homes on the lot. Winder works with investors, finance companies and venture capitalists to help fund the projects. AND he helps sell the finished houses on the back end.

It’s no surprise that Winder is at the humble beginnings of a brilliant career. He has always been one of those people that stand out of a crowd.

With fondness I recall when Winder was trying out to be Ellen DeGeneres’s “New Gardener.”

His hilarious 2 minute video appeared on DeGeneres’s daily show and has over 20k views.

Winder wasn’t selected as the winner in that contest…But he didn’t stop there.

When DeGeneres called for a “New Handyman” Winder submitted himself back into the running with another widely popular YouTube video capping out with over 40k views.

Those videos (be them silly as all get out) clearly exemplify a few of his traits that I believe contribute to his limitless potential.

First, Winder is not afraid to take risks.

After he graduated, Winder moved from Colorado to Las Vegas to make a career out of selling gym memberships. After demonstrating his abilities, the company offered to move Winder to Boston to help with the grand opening of one of their newest clubs.

And so, believing in himself and in his company, Winder took another leap and moved to Boston. Was selling gym memberships his ultimate life-long goal? Perhaps not. But he moved to Boston anyway.  Winder knew he had to take the opportunity when it presented itself. 

Successful people are willing to do anything for a good opportunity. Not only that, but they recognize a good opportunity when they find one. 


Furthermore, Winder has this powerful sense of self, which directly relates to his to-die-for confidence.

It’s that sense of self and confidence that guided him to hang up his cleats midway through his final season of college football in 2015. He loved his team and the sport and said that being part of collegiate athletics “kept him more focused” and “kept his head on straight.”

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But, when his love for the sport became overshadowed by this and that, Winder was able to take a step back from the situation and clearly analyze what would be best for him. It couldn’t have been easy for him to make that decision, but at the time, it was what he knew he needed.

Successful people are willing to make hard decisions and personal sacrifices to ensure they do what is right for themselves. They don’t get caught up in overthinking about the”what ifs.” They make decisions and they stick with them. 


Not to mention, it’s impossible to ignore Winder’s use of Facebook and LinkedIn. He has integrated his hilarious show-stopping personality with his professional pursuits, and is packaging it in a way that is deeply authentic and captivating.

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That captivating authenticity is a HUGE ingredient in success in ANY field, but I could argue that it’s essential in his role as a realtor, where trust and legitimate connection are highly valued.

Here’s a perfect example of his creativity used to connect with his audience in a modern and catchy way:

Successful people innovate, create and are forward thinkers. They get with the times rather than going against them. They use their resources.


In my opinion, Winder is positioning himself perfectly to set massive personal and professional goals and then smash them. The recipe for success is all there.

captureI was curious then, what he would say when I asked if he had any advice for other people starting out a career (or even changing careers)…? This is what he said:

“The human psyche wants to feel successful but that definition is 100% different from person to person. If you do not feel like your current position is giving you that successful glow, then find something new. Ignore the money and the belief that you have to slave an 8-5 and get benefits and prep for retirement now… it will all work out in the end. But if you don’t take any chances and play it safe, you’ll never get that career buzz you’re looking for. Take a chance. Chances are, if you go with your gut and pursue something new for your own desire, that some better opportunity will “out of the blue” pop up for you.”

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Thanks to Tyler Winder for taking the time to chat with me about his experiences.

For business inquires, message Winder on LinkedIn.


Do you know someone (or are you someone) who is finding a bit of success after graduating University? I want to hear from you! Email leahjanedavidson@gmail.com to submit your story ideas. 

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Being Bohemia Business Casual is a collection juxtaposing the unconventional and professional. It’s an exploration of art and imagination peppered with the ordinary and routine. It’s more than surviving the 9 to 5 – it’s about thriving the 9 to 5. Join me as I navigate a budding career and the world around me as best as I know how.

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