Entrepreneurs That Push Boundaries

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The journey of an entrepreneur is not always about the best strategies and tactics. Having control and discipline can indeed get you to the starting line, but it’s not everything.

What you need is that spark. You know? The one that people are always talking about. That lit fire inside of you that allows you to go beyond what is normal. The one that nudges you towards a journey of pushing boundaries in the name of success.

Some people say that this spark only comes ‘naturally.’ That if you don’t have it, then you’re out of luck. But that’s just quitter’s talk! And the entrepreneurs we’ve got lined up for you below should prove that you can find your ‘spark’. You just have to open yourself up to it!

What’s the best way to do that? Continue reading to find out!


Dave Gilboa and Neil Blumenthal, the co-founders of the exclusive direct-to-consumer eyewear company Warby Parker are the first two entrepreneurs to make it on our list! They established their brand back in 2010 as classmates, and now, their business has sold over 1 million glasses worldwide and is reported to be worth $1.75 billion! 

How did it all begin? With problem-solving! A decade ago, back when they were still just students, backpacking across the nation, Dave & Neil experienced an epiphany!

During their trip, one of the two had lost their glasses, and as many glasses-wearing grad students will probably sympathize with, they had no spare, and thus, were forced to continue the trip without. Squinting at the harsh sun, the pair could only sigh as they commiserate at just how ridiculously overpriced glasses were, especially when one considered just how easy they were to break.

This sparked an idea to create an alternative. One that ignored traditional practices to create higher-quality (and better looking!) prescription glasses that they could sell at a price that even a broke grad student would be able to afford.

And, from then on, the idea sparked many others as the two jumpstarted their business journey.

One of their many stand-out marketing decisions occurred in 2012. This was just two years after they founded their company, and they pushed themselves even further by repurposing an old school bus and taking it across a total of nine cities, attracting not only media attention but a consumer base that was left in awe at their ingenuity and their down-to-earth business model!


Next up is Luke Battiloro, the founder and CEO of Vavoom Vodka, an exclusive, direct-to-consumer vodka brand! This entrepreneur faced his long-lived fear of sharks in order to hack his brain and build it up for making bigger and better business decisions!

In an interview, Luke Battiloro said, “I’ve always been a risk-taker. I was the guy those big companies went to when they were looking for strong leads, after all. And to do that, I had to be able to be always innovative, always pushing boundaries, and always breaking barriers.”

Luke Battiloro

And for this, he went above and beyond what most people would be willing to risk! Going as far as to discipline his body and mind so that he could literally swim with sharks. An activity that would have been scary for anyone, never mind Luke Battiloro himself, who professed that he has had a fear of them since he was a kid. But still, he pushed through! He describes the results of this gut-wrenching and yet enlightening experience as follows…

“With this training, I’ve taken control of my subconscious. I’ve pushed aside the anxiety that we’re all naturally riddled with. I’ve faced my fears head-on and developed a strong belief in myself. And with that belief, I can do just about anything. Now, I’m much closer to my ultimate state — where no fear is too scary, and no problems can’t be turned into positives.”

And with that, you can’t deny that it wasn’t worth it! Especially for Luke’s Vavoom Vodka, which experienced over 300% growth since the global pandemic began. Beating out even their biggest competitors when it comes to leading the charge on the online distribution of alcohol.


Casey Mongoven, born in La Jolla, California, is a lover of music and an inventor at heart. He took his ‘first jump’ at the age of 33 with Jeremy McGrew at Skydive Santa Barbara.

This first heart-stopping jump ended up being the thing that propelled him towards the sky diving industry. He took his own experiences and translated them into something people could love.

In an interview, Casey stated that one of his favorite things to talk about are “-people’s opinions about my company’s products and other companies’ products in the industry.”

He went on to say that, “I’m interested to know what people are looking for, as it seems there haven’t been many significant developments in terms of skydiving altimeters in a long time, and only recently has there started to be more movement on this front. I’ve been lucky to have talked to hundreds of skydivers at the various boogies I have been to this year, so it has given me a good general picture of where this part of the skydiving industry is in this regard.”

Suffice to say! If he hadn’t picked up the courage to take that first crazy jump, he wouldn’t have been able to create the flexible and dependable skydiving products that his company, Free Fall Data Systems LLC, is prized for.


Our fourth trailblazing entrepreneur is none other than Scott Keys, the founder of Scott’s Cheap Flights. Which is an email newsletter that offers both FREE and subscription-based options for those looking to get cheap flight deals in real-time!

According to Keyes, this venture of his had started completely as a hobby! Keyes was an avid traveler, and after expending effort into seeking out the best deals for his own traveling adventures, he began doing it for his friends and family.

Keyes spent up to 18 months cultivating this skill, searching for the cheapest deals, and setting up a system to make sure that all his friends were kept alerted via email before realizing that, wait! He could actually make money out of this!

And, after finally deciding to make the shift from hobby to business, Keyes spent the better part of mid-2015 trying to figure out how to turn his love for travel into profit!

Now, his email newsletter has over 2 million subscribers! All of whom are able to benefit from the $550, on average, that they are saved on flight tickets!


Sometimes that ‘spark’ doesn’t come from the present, but the past! At least, that was the case for Jake Kalick and Chip Malt, the founders of Made In Cookware, a direct-to-consumer kitchen cookware brand that is quite proud of its rich family history!  

According to Made In Cookware’s founders, Chip and Malt, they had founded their business in 2016 to bring a little bit of their history into the cookware industry of the present. Putting forth a variety of high-quality products that were manufactured from “raw material providers” and the best “multi-generational, family-owned manufacturers in the U.S., France, and Italy.”

Jake Kalick, specifically, describes his childhood as “entirely rooted in the kitchen.” Having told of a grandfather that had owned a kitchen designer and supply company back in 1929. A business that his father had inherited, and one that Jake had grown up knowing. Now, Jake and Chip are the co-founders of the world’s first direct-to-consumer cookware brand, cultivating their already rich family history for the many generations to come!


What did the stories of these entrepreneurs have in common? They all have different backgrounds, different interests, and they all belong to different industries.

BUT! One thing is for certain. Each of them had that ‘spark.’

They just so happened to have discovered it in their own unique ways.

Luke Battiloro was born as a natural challenger, but by facing his fears, he enriched his natural-born talents to become the best version of himself possible. Scott Keyes found an answer in a hobby that ended up being his proverbial winning lottery ticket. And, Jack Kalick cultivated his pre-existing love and history for the kitchen space into a business that his family could be proud of.

By finding their ‘spark’ or the thing that motivated them to keep working, the thing that pushes them to do better, to be constantly improving, they found success! And the best thing is? You can do the same thing!