56: From Miserable and $100,000 in Debt to Self-Employed Author, Speaker, and Coach

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This edition of The Side Hustle Show is probably one of the most inspiring yet. I’m joined by Kimanzi Constable, who shares his story about the struggle of entrepreneurship and his dream of becoming a writer.

We talk about the specific steps he took to get out of debt and build an audience of buyers for his books. This is a powerful one because Kimanzi opens up about how seriously he needed to make some changes in his life.

And because of the compound effect of those changes, it added up to a real side hustle success story.

When we recorded this, he had just moved from Milwaukee to Maui where he runs his successful blog, speaking and coaching businesses, as well as works on his upcoming book projects.

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  • How Kimanzi was an entrepreneur from age 19, but built himself into a business that made him miserable.
  • Kimanzi’s wake up call that made him transition from existing to living.
  • The hustle he had to invest in himself to produce his first book and website ($1200).
  • How his first book sold 5 copies in 6 months (and 2 of those were his own orders).
  • The specific actions he took to build his audience and subscriber base (and earned 6000 new subscribers in a day, without even having an opt-in bribe).
  • How his first attempts at guest blogging were immediately rejected, and his unique strategy to get a “yes” from big sites.
  • The life of a side-hustling author and blogger, and how you can do the same with some discipline and an hour a day.
  • The other revenue streams that resulted from the books and the blog.
  • Kimanzi’s #1 tip for Side Hustle Nation.


What do you think of Kimanzi’s journey? Can his success be replicated? Would you have made the same kind of commitment he made to his dream?

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Nick Loper

About the Author

Nick Loper is a side hustle expert who loves helping people earn more money and start businesses they care about. He hosts the award-winning Side Hustle Show, where he's interviewed over 500 successful entrepreneurs, and is the bestselling author of Buy Buttons, The Side Hustle, and $1,000 100 Ways.

His work has been featured in The New York Times, Entrepreneur, Forbes, TIME, Newsweek, Business Insider, MSN, Yahoo Finance, The Los Angeles Times, The San Francisco Chronicle, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, The Penny Hoarder, GoBankingRates, and more.

18 thoughts on “56: From Miserable and $100,000 in Debt to Self-Employed Author, Speaker, and Coach”

  1. This was a great episode, thanks Nick and Kimanzi! I’ve been listening since the Nick Reese cold showers episode, and every week I’m inspired to keep hustling. I especially love this week’s links.

  2. Oh my gosh this story hit me to my core…mainly because I am know I should be speaking. Kimanzi was so transparent, passionate and funny I really felt where he coming from. Thank you for sharing your obstacles, mistakes and outline a strategy that would work for today.

  3. I’d love to share this podcast on DNN if I may. I checked out the share button, but no embedding ability? I want to inspire people to take the side hustle seriously and share this on DNN sometime if I may. Thank you.

  4. Another great episode Nick. I have learned so much from listening to your podcast. Thank you Kimanzi for the detailed strategy you shared.

    I don’t like guest posting. I am so possessive about my own material, but I have found out that one great way to connect with other people is by podcasting. I started a podcast this January 2018 and I am having a very positive experience.

    If ever anyone of you two would like to be a guest on my podcast, I would love to have you.


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