TLS #78: 27 Ways To Make Money Online with Hilary Rushford (Part 1)


After seeing friends and online business owners, Hilary Rushford (Dean Street Society) and Jessie Artigue (Style & Pepper) rock out a packed session at Alt Summit on 27 Ways to Make Money Online, I knew I needed to bring their great content to you through The Lively Show!

To start, we’ll be discussing all of the ways that Hilary has made money online during her web-based career. This lady is crushing it with her style and business offerings. In the show, she’s dishing on the ways she’s done things in the past, doling out advice based on what she’s learned, and giving us a peek into what she’s focusing on right now.

Next week, Jessie will come on the show and share her income streams over the years and her advice for people just starting out, as well as more seasoned business owners.

Plus, we’ve made a free printable (below) that outlines the 27 money making methods below so you can follow along and take notes!

This (two-part) episode is perfect for anyone looking to get advice on making money online, or anyone simply curious about how two web-based business owners optimize their income streams. 





Free Printable






  • The aha moment that lead Hilary to discover what she wanted to do with the next chapter of her life.
  • The difficulties she has faced in collaboration and what she had to do to remain true to her message.
  • How to tell the difference between “faking it until you make it” and just faking it.
  • The importance of looking to others for feedback and wisdom.
  • How Hilary made $2,000 dollars in a week by teaching a last minute online course.
  • Hilary gives us a huge tip for what we can be doing right now to improve our Instagram feeds and encourage more following.
  • The advice Hilary received that has lead her to focus, simplify and improve the services she offers.
  • How to strike a balance between making money and doing work that brings you joy.
  • The pros and cons of monetizing your blog and the ways that have been most effective for Hilary.
  • Hilary’s advice to anyone who doesn’t know where to start.
  • Why she believes it is important to develop relationships with people who have your desired career and see what their lives are really like behind the scenes.
  • How she is currently struggling with slowing down and simplifying her business.
  • What Hilary would tell someone just starting out on this journey.



The 4-Part Entrepreneur Cocktail

Hilary’s Free One Hour Instagram Class

Making Things Happen


The Lean Startup

Jessie’s blog

Squarespace Mini Interview:







PS – Don’t forget to print out the free printable to take notes on this two part episode (above)!


This Post Has 47 Comments

  1. Not sure if anyone else is having this problem, but the free printable isn’t working for me – it just downloads as garbled text!

    1. I’m sorry you’re having trouble clicking the yellow button in the email to download. Would you mind trying to right click the yellow download button on the email and then pick “Copy link in new tab” to see if that allows it to show up?

      Fingers crossed it works that way. : )

      1. Thanks for the reply and the suggestion! Unfortunately no luck on my end – I’m on a Macbook using Safari, if that info is of any use. I’m not overly technological so have no clue what is up or what else to try!

        1. Gotcha, please reply to that email that’s not working and Grace will help you out. : )

  2. F

    Me too. The link sent by leadpages didn’t work.

    1. I’m sorry you’re having trouble clicking the yellow button in the email to download. Would you mind trying to right click the yellow download button on the email and then pick “Copy link in new tab” to see if that allows it to show up?

      Fingers crossed it works that way. And if it doesn’t feel free to email us at jess(at) : )

      1. F

        No worries. This sort of thing is to be expected with mercury in retrograde :). I was on my phone so I will try the desktop when I can.

        1. Amen! Only one more day of MR!!

          Yes, try it on desktop and do the right click thing if it’s still giving you trouble. : )

  3. THIS HAS BEEN THE MOST HELPFUL PODCAST EVER!!!!! I learned so much and it inspired me to be more entrepreneur-like!!!!! Thank you for this! I can’t wait for the next one!!!

    1. I’m so glad this episode and Hilary’s advice resonated with you so much, Ina!

      I hope you enjoy this week’s second part as well. : )

    2. That she talked so openly, honestly and authentically about the behind the scenes stuff has won my trust and confidence completely.

  4. Weezie Boiles

    This was such an informative podcast! I can’t wait for part 2! This will definitely be one I’ll listen to multiple times! Thank you! A question I have that Hilary mentioned and has been mentioned before on yours shows is about finding a life coach or strategist. What is the best way to find one? And where do you find master mind groups? I thought they were more organic and didn’t realize until this podcast that you could find paid ones (Unless the paid ones are parts of Facebook groups or something like that). Thanks again!

    1. Great question about finding a coach, I’d suggest looking around online through the channels you currently enjoy, ask friends you respect in person or online that may have a coach for recommendations, or for masterminds, might be a place to try starting with as well. : )

      1. Weezie Boiles

        Thanks! Currently I don’t have a “tribe” that’s doing what I am doing but I may look into or try to expand my online tribe by reaching out!

        1. Perfect!! You can also try forming a tribe by reaching out to other fellow bloggers you know online and have some relationship as well. Also, you’re in LWIO, too, right?!

          You should check the message boards there once we get started this fall with a new crew in the class to form relationships with others as well. : )

          1. Weezie Boiles

            That’s a great idea! I’ll try to reach out more with the LWIO group next session! Thank you! And I am still considering Fizzle. That episode was one of my favorites. Thanks again!

  5. ShannDuff

    I loved this podcast so much, I’ve listened to it twice!

    1. That’s great to hear! I hope you enjoy the second part coming out this week as much as the first. : )

  6. Jess, this is absolutely a great episode! My brain is bursting!! You are one of my very favourite podcasts – I’ve listened to a lot of your episodes twice! Thanks for doing what you do 🙂

    1. Adanna Thompson

      ME TOO! Mind…BLOWN! I took almost of full page of notes and thought up a few product ideas etc while listening to this! Priceless info here!

    2. : ) That’s so wonderful to hear! It’s wonderful to hear you’re getting so much useful content from the show!!!

  7. This is by far the best most brilliant Podcast you ever published Jess – and I’ve listened to pretty much all of them. I recently discovered Hilary on Instagram so was excited to see you’d interviewed her here. What I wasn’t expecting was this – this is SO MUCH MORE informative, honest, raw and authentic than I was expecting. Brilliant. So much I could relate too – I was nodding all the way through. I really want you to know I’ve taken a lot from this that I intend to use to make improvements in my own situation. Thank you SO much Hilary. BIG new fan here.

    1. Jess Lively

      That’s awesome to hear, Annabel! It’s wonderful to know that you got so much from the interview – I agree – Hilary rocked it! : )

  8. Laura Murphy

    Hey Jess, where can we find the blog post that was mentioned in this podcast from Lara Casey?

    1. Jess Lively

      I’ve never read that post by Lara (which Hilary mentioned in this episode) before, so I’m not sure where it is. Maybe a quick google search will help you spot it if it’s still on her site. : )

      Also, Lara has been on TLS, if you haven’t heard it yet, it might be an interview you’d enjoy. : )


  9. Ché Dyer

    LOVED this post! I also have a question (similar to Weezie Below!) Does Hilary mention the name of her business coach? How do you find one?!

    1. Jess Lively

      I do not believe Hilary mentioned the name of her coach in the show, so I can’t help you there. But when it comes to finding a coach, I’d try searching biz resources like Smart Passive Income Podcast, biz blogs you enjoy, and listen to other podcasts that focus primarily on biz to see if any coaches that strike your interest pop up. Also, conferences are a great place to meet people, including coaches if you are at the right even for that kind of thing. : )

      1. Ché Dyer

        thanks so much Jess – love your podcast and all the business advice! Will take a look at those other podcasts you’ve mentioned! x

  10. Jenna Meow

    I’ve just discovered your blog and am binge listening to so many podcasts. Super relevant and useful content. A huge thank you!

  11. This podcast was so helpful to me. After I listened to it, I was like, “Duh! There’s so much you can do online”…it was great because it helped me brainstorm and get un-stuck. Thanks for a great interview 🙂

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