How 25 Side Hustlers Made Their First Entrepreneurial Income

What’s the story of your first job-free income?

To celebrate the 4-year anniversary of The Side Hustle Show, I asked the Side Hustle Nation community to join me in creating a really fun episode.

I asked people to tell me how they first started making money on the side, and got 25 different voicemails!

In this episode, you’ll hear first-hand the steps your fellow listeners took to put themselves back in the driver seat of their own financial well-being. If you’re still looking for a side hustle idea, listen in for some of the simple and creative ways people made extra money.

And no matter how you shake it, that first sale is a powerful one.


  1. Rich Jones – (1:30) – Career consulting.
  2. Julie Morgenlender – (3:46) – Job search consultant.
  3. Matt Tran – (6:17) – YouTube channel (Engineered Truth).
  4. Shane Labs – (7:00) – Built and sold a joke website, which led to freelance work.
  5. Dr. Caitlin Faas – (8:33) – Freelancing on Upwork.
  6. Michael Alder – (10:45) – Carpet re-selling and installation. 
  7. Elle Martinez – (12:27) – Freelance SEO writing.
  8. Stefanie O’Connell – (13:04) – Babysitting, personal assisting, hosting; now freelance writing and brand representation.
  9. Christi Johnson – (15:52) – Freelance copywriting.
  10. Ozeal Debastos – (17:11) – Selling break-dancing tapes on VHS.
  11. Tyler Basu – (19:15) – A book on sales published on Amazon.
  12. Dennis Smith – (20:50) – A book on how to use social media; now teaching courses on Udemy.
  13. Julia Tunstall – (22:20) – Rental real estate; now a website for bartenders and cocktail enthusiasts.
  14. Jalpan Dave – (23:43) – Stock market investing w/ options.
  15. Tracey Minutolo – (24:45) – Virtual assistant for podcasters; now a side hustle coach.
  16. Yann Ilunga – (25:56) – Freelance writing and web design.
  17. Kim Anderson – (28:02) – Sock monkeys, used educational electronics, and “boho” dresses on consignment.
  18. Sally Miller – (29:16) – Kids consignment event business; now self-publishing books and courses.
  19. Mike Riscica – (30:33) – Blogging and affiliate marketing. “If you can make $200, you can make $2000.”
  20. Priest Willis, Sr. – (32:15) -Affiliate marketing, dropshipping, and freelance web development.
  21. Aja McClanahan – (34:22) – Kool-Aid stand, database consulting, and blogging.
  22. Danielle Isbell – (35:56) – Photography; now digital marketing while traveling the world.
  23. Morgan Gist MacDonald – (37:30) – Freelance editing.
  24. Andy McCabe – (40:56) – Ebook and course sales in the insurance restoration niche. 
  25. Scott Carlson – (42:40) – Building computers and selling them on ebay.

Links and Resources

Your Turn

How would YOU answer? Be sure to leave a comment below.

Did you like this episode? It was my first attempt at a round-up style episode so definitely curious to hear your thoughts.

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