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20 Unconventional Entrepreneurs Who Will Inspire You

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by David Garland in David's Blog

20 Unconventional Entrepreneurs That Will Inspire YouI only took one entrepreneurship class in college (I was a Women’s Studies major at Washington University in St. Louis…we will skip THAT story for now). It was a solid class, but in many cases it was a parade of traditional entrepreneurship. For example, here were common steps heard throughout the semester:

  1. Come up with an idea.
  2. Research the heck out of the idea, write a massive business plan, raise money, create business.
  3. Wave goodbye to friends and family as now your life is your business. Yay.
  4. After creating business, expand business by hiring one zillion people and move into every market in the world.
  5. Following your massive expansion into a worldwide domination, sell your business for top dollar.
  6. Post-sale, retire to your favorite island or go back to step one and wash, rinse, repeat.

Now, there is nothing wrong with this advice per say. In fact, there was a parade of special guests throughout the semester that shared their story that fit into those steps one way or another.

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

Fact is, there are many types of entrepreneurs.

There are entrepreneurs whose entire goal is to build a company and sell it for as much as possible or take it public. These are the “big exits” we hear about in the tech world.

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

There are entrepreneurs that create factories. Maybe the factory makes cups or hats or something of the like.

There are entrepreneurs that are in more traditional industries who have no aspirations of selling but instead look to make a living brick and mortar style. An example might be the corner bakery or a clothing boutique.

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 is another group all together that I bet you are a part of (I know I am). And that is the unconventional entrepreneurs. Characteristics of this group include:

  • Doing work that matters. Not just work to make a dollar (such as selling weird vitamin supplements online..unless you are ridiculously passionate about vitamins, and in that case rock on). Work that you are passionate about. Work that makes a difference. Work that is art. Money follows passion and not the other way around.
  • Challenging the way it has always been done. Doing it your way. Changing industries that have been stuck for years (or decades or centuries). Creative disrupters.
  • Enjoying the fruits of our labor. No, this doesn’t mean unconventional entrepreneurs don’t work hard. It simply means we understand and live by the philosophy that there is more to life than just work (passions and hobbies outside of work, friends and family, enjoying life the way you want to).

Does this mean as an unconventional entrepreneur that you can’t sell your company or hire a bunch of people? Not at all. It just means that you aren’t conforming to the confines of traditional entrepreneurs.

Since 2008, I’ve had the incredible opportunity to interview over 300 entrepreneurs of all shapes and sizes. Traditional and non-traditional. Huge companies and solopreneurs. People that have sold 50 companies and others that have started one. But I’d have to say, if I was hard-pressed, my favorite ones are the unconventional ones (and that is where most interviews will fall in the immediate future).

Here is a list of 20 of them, in no particular order, that I bet you will pick up insights, ideas and inspiration from. Enjoy!

#1: Andrew Warner –

Why? Successful yet unfulfilled from his previous venture, Andrew has made it his life’s mission to inspire and help startups.

Interview with Andrew

#2: Ishita Gupta – fear.less

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

Interview with Ishita

#3: Tucker Max –

Why? Rejected by everyone in the publishing world, Tucker didn’t give up. Instead, he took his crazy, hilarious stories to the Internet and results have been astounding.

Interview with Tucker

#4: Seth Godin –

Why? The quintessential disrupter and leader, Seth Godin is throwing a wrench into the publishing industry with The Domino Project.

Interview with Seth

#5: Neil Strauss –

Why? Is it possible to make a living by infiltrating and learning from the secret world of celebrities, pick up artists and multiple-passport sneaky world travelers? Neil has done it.

Interview with Neil

#6: Chris Guillebeau –

Why? Moving to Africa? Becoming a professional writer in less than one year? Inspiring others to live unconventional lives? Check, check and check.

Interview with Chris

#7: Matthew Inman –

Why? Matt has created an empire from his unique and hilarious comics by doing it his way.

Interview with Matt

#8: Rob and Kim Murgatroyd – JetSetLife.TV

Why? They created one of the coolest jobs ever for themselves: Traveling to the world’s poshest places and writing unique, insider guidebooks. Sweet.

Interview with Rob and Kim

#9: Jason Sadler –

Why? What does Jason get to do all day? He is paid to wear shirts and create all kinds of fun videos and other goodies online. Sweet.

Interview with Jason

#10: Tim Ferriss –

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

Interview with Tim

#11: Scott Ginsberg –

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

Interview with Scott

#12: Michael Buckley – What The Buck

Why? Michael took a love for pop culture and turned it into his dream career. His show, What The Buck, is one of YouTube’s most popular

Interview with Michael

#13: Adam Baker – Man Vs. Debt

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

Interview with Adam

#14: Chris Ducker – Virtual Business Lifestyle

Why? Chris walks the walk and talks the talk. As I type this, he is probably running his company from a beach somewhere.

Interview with Chris

#15: Gregory Ng – Freezer Burns

Why? Two words: Frozen food. That is exactly the subject matter of this unconventional entrepreneur’s web show.

Interview with Greg

#16: Elizabeth Marshall – Author Telesminars

Why? She found her passion for books and turned it into an amazing career. The best part might be she gets the pick of the litter when it comes to her clients.

Interview with Elizabeth

#17: Vanessa Van Petten –

Why? Vanessa didn’t wait to be picked. She wrote a parenting book from a teen’s perspective when she was a teen. Her empire has incredible expanded since then and she gets to do what she loves every day.

Interview with Vanessa

#18: Jonathan Coulton –

Why? The entrepreneurial musician. His business model allows him to create (and make money from) the music he wants without the confines of a label.

Interview with Jonathan

#19: Scott Kurtz – PvP

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

Interview with Scott Kurtz

#20: Nate Houghteling and Kai Hasson – White Collar Brawler

Why? Quitting their day jobs to become amateur boxers and create an online web series and movement? This stuff is just awesome.

Interview with Nate and Kai

Who else do you think should be on the list? Who inspires you?

Image Credit: caniodica

  1. Red from MyBusinessOwnsMe .com says:

    Great job David! 

  2. Ashley says:

    Well David we should add you to the list too you know 🙂 It’s very true though you have to go against the flow sometimes with what you’re doing even if others don’t agree with it. Being in the small business audience like we are with BB (like the brick and mortar you mentioned) they are very conventional with things and we had to figure out how to break that barrier and not to mention we are literally the only ones saying “hey, you have to fire your bad customers as business owners and entrepreneurs.” Someone has to stand up and say right? 😉

    Great post!

    1. David Siteman Garland says:

      Too kind, Ashley, too find 🙂

  3. Cory Shanes says:

    Great post David.  Love the list, lots of great entrepreneurs. Would love to be interviewed by you in the near future!

  4. Anonymous says:

    Great post! I liked that I have a bunch new sites and resources to check out. I agree with Ashley that you should make the list. Also what about Gary Vaynerchuk?

    1. David Siteman Garland says:

      Thanks! I’m not sure why I didn’t put Gary on the list. Definitely unconventional. And on the other hand works 24/7 lol.

      1. Anonymous says:

        He does work a lot!! Maybe he can benefit from your new book with the section on how you streamlined??

  5. Whatever says:

    Can’t get past the headline… It should read “20 Unconventional Entrepreneurs WhoWill Inspire You”. People are not objects… who, who, who… apparently they don’t teach grammar in Women’s Studies?

    1. Lanih says:

      no, they teach grammar in 8th grade…

  6. Excellent list – can’t wait to dig in later tonight! Thanks for keeping me inspired, David. 🙂

    1. David Siteman Garland says:

      Happy to help 🙂

  7. SharelOmer says:

    Once again… a set of inspirational leaders…. who did it in their own special way 🙂

    10x 4 sharing David…

    I would add Max Levchin and Chris Brogan two inspirational ppl that did it in their own way… 🙂

  8. Thanks for including me in this list, David.

    It’s a real honor to be listed with the rest of these guys.

    Much appreciated!Chris

    1. David Siteman Garland says:

      My pleasure buddy!

  9. Happy to see some fellow entrepreneur friends on here-especially written by a WashU Alumn!! fight on as the Trojans say!

    1. David Siteman Garland says:

      Go Bears!

  10. Rob Simovic says:

    I would add Oren Klaff in there just to add another dimension. You should definitely interview him. His interview on Mixergy was awesome.

    1. David Siteman Garland says:

      Rob – Thanks for the rec, I’ll take a look.

  11. Mauricio says:

    I want to thank from the mind. I was really inspired form you. You helped me so much.

    1. David Siteman Garland says:

      glad to hear it!

  12. Michael Cranston says:

    Good list.

    I have to give an extra personal endorsement to Andrew Warner. As someone who knew literally nothing about tech entrepreneurship 8 months ago, his Mixergy podcast is among the few that excitedly introduced that world to me. Now that I’m more experienced, can design & develop, and indeed have more knowledge in the field than I did 8 months, can say his Mixergy podcast is still as invigorating and helpful as ever.

    All of you should yourselves a favor and check it out

  13. Martin says:

    Nice list and important to not buy the usual narratives about what an entrepreneur is as you say. There are other ways than the ‘individual first’ list here. Godin, Ferris, Strauss etc…are all ‘personal brands’ in themselves and rely on the heroic individual doing creative / disruptive / ideas narratives. Many entrepreneurs aren’t all about themselves and their insights into the modern world but are building companies focused on providing services or products that matter to people, that actively solve social, environmental or economic problems. They are doing this with teams, groups and sometimes movements of people who have similar goals or intentions.

  14. Shubhendu Singh says:

    Just wow!!!!!

  15. The Gringocua says:

    Just curious… Women’s major but your name is David. Was this ghostwritten?

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