Affiliate Marketing, Early Retirement, and Side Hustle Shifts Over 8 Years of Podcasting: 20 Questions with Nick

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20 questions round 12

It’s time to dive into the ol’ listener mailbag and answer a few questions in this week’s edition of The Side Hustle Show.

I’ve had quite a few interesting questions come in since the last Q&A episode, and picked 20 to talk through in today’s show.

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Like this format?

This is the 12th installment of “20 Questions” so feel free to go back and binge on the older ones too:

A common piece of advice you’ll hear is to take audience questions and turn them into content, so here’s a meta example of that in action.

This episode covers overcoming the fear of selling, combatting shiny object syndrome, passive income motivation, podcasting, protecting your ideas, and more.


The Questions

  1. How I can use my knowledge for a blog or a podcast or affiliate marketing? (0:34)
  2. How have your attitudes about side hustling changed over the last 8 years in the space? (2:35)
  3. How do bundle sales work? Why would these product creators give their work away for so little? (4:39)
  4. What’s the table of contents plugin you’re using on your site? (6:53)
  5. How is the “You Might Also Like” box in your newsletter working for you in terms of boosting clicks, pageviews, etc.? (7:45)
  6. I noticed that you are using Teachable — any particular reason? (9:50)
  7. Which WordPress theme should I use? (12:13)
  8. How much do podcasters get paid by sponsors? (12:50)
  9. What made you “jump” [from your day job]? How did failure not become an option for you? (16:03)
  10. Should you build a review site around a single product or service, or broaden it a bit to the whole family of products of services? (18:30)
  11. What are some good potential side hustles for retirees? (20:03)
  12. How can you protect yourself from legal liability related to online content? (23:40)
  13. What’s your take on services like Skimlinks? (25:00)
  14. Do you still recommend putting your books in Kindle Unlimited / KDP Select? (26:21)
  15. When registering a business, can I be my own registered agent? (28:20)
  16. I have 11 separate websites for the local towns where we operate. Should I consolidate domains? (29:12)
  17. I’m just getting started. Should I write and publish a book or start a service business? (30:51)
  18. How much is enough to retire at 35? (31:54)
  19. What side hustles or gigs grew the most in the last year? (34:26)
  20. How would you speed up the process of growing a community? (36:11)

Links and Resources


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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, The Financial Times, Bankrate, Hubspot, Ahrefs, Shopify, Investopedia, VICE, Vox, Mashable, ChooseFI, Bigger Pockets, The Penny Hoarder, GoBankingRates, and more.

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