Freeing Dreamers & Transforming Lives

One Entrepreneur At A Time


Our Mission

It's our mission to make entrepreneurship simple & accessible to everyone. We aim to change the future of business by spreading a culture of generosity, collaboration, inclusivity, & optimism to every business we touch. Let's revolutionize the way business is done, together. 


You're In The Right Place If You're...

  • Wondering how to build a business that will allow you to have location and financial freedom.
  • An open-minded, adventurous, & creative entrepreneur who's ready to take control of your future.
  • Someone who's inspired and excited by the idea of continuous learning and growth.
  • Looking for a supportive community to connect & grow with that educates and inspires you.
  • Interested in building a business that not only fills your wallet, but nourishes your soul.
  • Tired of the status quo, and ready to be the change the world needs & create success on your own terms.

Founder's Story

Cassidy...

  • At 16 she graduated high school.
  • After two years of college, she dropped out.
  • She took her first management position at 19, and quickly realized she had no interest in having a 9-5.
  • She discovered her passion for travel and wanted to backpack the world but couldn't afford it.  That year, she built her first website, a travel blog called "Destination Pending" to record her adventures, and started her journey as an entrepreneur. 
  • After years of mistakes, failures, traveling, and learning - she decided to launch Hippie On Holiday in 2019 with the goal of making entrepreneurship easier, clearer, and more accessible so that anyone with a dream could put it in action.


Who We Work With

No matter your size or industry, we can help

In our time getting to know and support entrepreneurs, coaches, dreamers, freelancers, and digital nomads across the globe we've learned that while you and your business are unique, your problems are not.

Our strategies and solutions help you take back your time, so you can run a business that frees you instead of consumes you.




Every single thing we do,

is driven by our values.

Love

Because freedom, curiosity, & integrity mean nothing without love. Love is community, understanding, friendship, respect, purpose. Love is the true north that allows us to connect and value differences.

Freedom

We believe in freedom for all in all forms. The freedom to discover, grow, try, fail, think, create, change - freedom from anxiety, fear, hate, expectations, constraints. Our goal is to set the WORLD fucking free. 

Integrity

Without Integrity, what's the point? Integrity is is being true to yourself, true to your values, & authentic AF.  We believe everything should be done with integrity. Integrity is the only path to your highest self.

Curiosity

Curiosity is the seed of growth, courage, creativity, & adventure. It inspires us to question the world around us & to dream bigger dreams. We try to bring the spirit of curiosity & wonder into every day. 

Growth

Growth is what drives us to strive to be better, to re-think assumptions, to brave change &  break past barriers. What the world needs more than anything is for everyone to take the time to grow.

Courage

We aim to do everything we do with boldness, confidence, and courage. We aren't afraid to stand up for what we believe, and we hope to inspire others to take chances, even when in doubt.

Want To Be A Part Of It?

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