20 Unconventional Entrepreneurs That Will Inspire You9297164

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I only took one entrepreneurship class in school (I was a Women's Studies major at Washington University in St. Louis...we will cut THAT narrative for now). It turned out to be a course that is strong, but in many cases it was a parade of traditional entrepreneurship. For example, here were common steps heard throughout the session:

Think of an idea.

Research the heck out from the thought, write a gigantic business plan, raise money, create business.

As your life is the business, tide goodbye to family and friends. Yay.

After creating business, expand business by hiring one zillion folks and move into every market in the world.

Following your huge expansion into a global domination, sell your business for top dollar.

Post-sale, wash, rinse, repeat and retire to your own favorite island or return to step one.

Now, there is nothing wrong with this guidance per say. The truth is, there was a parade of special guests throughout the session that shared their story that fit into those steps one way or another.


There are entrepreneurs who create a company to franchise it (the E-Myth doctrine). Examples where I'm from in St. Louis include a chain of tanning salons and massage parlors.

There are. Perhaps the factory makes something of the like or hats or cups.

There are entrepreneurs that are in more traditional sectors that have no aspirations of selling but instead look to earn a living brick and mortar design. A good example could be a clothing boutique or the corner bakery.

There are Internet entrepreneurs focused on creative passive income by any means necessary to make a living (and perhaps enjoy life on the beach or something). Example might be someone who sells vitamin supplements online.

But, there's another group all together that I bet you are a part of (I understand I am). And that's the entrepreneurs that are non-traditional. Features of this group comprise:

Doing work that questions. Not just work to make a dollar (such as selling strange vitamin nutritional supplements online..unless you are ridiculously enthusiastic about vitamins, and in that case stone on). Work that you're passionate about. Work that makes a difference. Work which is artwork. Cash follows fire and never the other way around.

Challenging the manner it has been done. Altering industries which have been stayed for years (or decades or centuries).

Enjoying the fruits of our labor. No, this does not mean unconventional entrepreneurs don't work hard. It only means we understand and live by the philosophy that there is a lot more to life than just work (fires and hobbies beyond work, friends and family, enjoying life just how you want to).

Does this mean as an unusual entrepreneur that your company can't be sold by you or hire a bunch of folks? Not at all. It simply means that you aren't conforming to the boundaries of conventional entrepreneurs.

Since 2008, I've had the unbelievable chance to interview over 300 entrepreneurs of shapes and sizes. Conventional and non-conventional. Huge companies and solopreneurs. People that have sold 50 companies and others that have started one. But I'd need to state, if I was hard pressed, my favorite ones will be the non-traditional ones (and that's where most interviews will fall in the immediate future).

The problem, as I see it, is less instead more and in validity of the guidance in the limitations of it. Significance, entrepreneurship certainly doesn't have to look like, feel like, be like or follow most of those steps. It is like offering a class but the only real sport covered is baseball.

Fact is, there are many kinds of entrepreneurs.

There are entrepreneurs whose entire aim is really to build a business and sell it for as much as possible or take it public. These are the "enormous exits" we hear about in the tech world. Tom Caufmann Here is a list of 20 of them, in no particular order, that I bet you'll pick up insights, thoughts and inspiration from. Love!

  1. 1: Andrew Warner - Mixergy.com

Why? Successful not yet fulfilled from his previous venture, Andrew has made it his life's mission to inspire and help startups.

  1. 2: Ishita Gupta - panic.less

Why? Who says magazines have to be in print? Always a disrupter, Ishita is changing the publishing world through her exceptional magazine anxiety.less.

Interview with Ishita

  1. 3: Tucker Max - TuckerMax.com

Why? Rejected by everyone in the publishing world, Tucker didn't give up. Rather, he took his wild, hilarious stories to the World Wide Web and results have been astounding.

  1. 4: Seth Godin - SethGodin.com

Why? The quintessential disrupter and leader, a wrench is throwing into the publishing business with all The Domino Project.

Why? How is it possible to earn a living by learning and infiltrating in the secret world of celebrities, pick up multiple and artists -passport sneaky world travelers? It has been done by Neil.

Why? Becoming a professional writer in significantly less than one year? Inspiring others to live unconventional lives?

Why? By doing it his way, Matt has established an empire from his hilarious and unique comics.

  1. 8: Rob and Kim Murgatroyd - JetSetLife.TV

Why? They created one of the coolest jobs ever writing unique, insider guidebooks and Traveling to the poshest areas in the world. Sweet.

Interview with Rob and Kim

Why? Exactly what does Jason get to do all day? He's paid to wear tops and create all kinds of entertaining videos as well as other goodies online. Sweet.

  1. 10: Tim Ferriss - FourHourWorkWeek.com

Why? Yes, we all know Tim has inspired an incredible amount of visitors to work less, live more (and more recently, get in great shape), but there's a whole lot to understand from how Tim has created his own business and lifestyle. He is a walking model of entrepreneurship that is unconventional.

  1. 11: Scott Ginsberg - HelloMyNameIsScott.com

Why? The guy that has built an empire around counting and wearing a name tag regular for the previous 10 years. You have to see it to believe it.

  1. 12: Michael Buckley - What The Dollar

Why? Michael took a love for pop culture and turned it into his dream profession. His show, What The Dollar, is one among YouTube's most popular

  1. 13: Adam Baker - Man Vs. Debt

Why? Can the act of sharing the insights become a business and getting yourself out of debt? Leave it to Adam Baker to turn it.

  1. 14: Chris Ducker - Virtual Company Lifestyle

Why? Chris walks the walk and talks the talk. His company is probably running from a beach somewhere as I type this.

Interview with Chris

  1. 15: Gregory Ng - Deep Freezer Burns

Why? Two words: Frozen food. That is just the subject matter of the non-traditional entrepreneur's web show.

Interview with Greg

  1. 16: Elizabeth Marshall - Author Telesminars

Why? She found her passion for books and turned it into an incredible profession. The very best part might be she gets the pick of the litter in regards to her customers.

Interview with Elizabeth

  1. 17: Vanessa Van Petten - RadicalParenting.com

Why? Vanessa did not wait to be picked. When she was a teen, she composed a parenting publication from a teen's view. Her empire has incredible expanded since then and she gets to do what she loves every day.

Interview with Vanessa

  1. 18: Jonathan Coulton - JonathanCoulton.com

Why? The entrepreneurial musician. His business model permits him to create (and generate income from) the music he desires without the bounds of a label.

Interview with Jonathan

  1. 19: Scott Kurtz - PvP

Why? The guy who's redefining the world of cartooning. And he is doing it on his terms.

Interview with Scott Kurtz

  1. 20: Nate Houghteling and Kai Hasson - White Collar Brawler

Why? Quitting their day jobs make movement and an online web series and to become recreational boxers? This stuff is just amazing.