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Case study: From $17/hour to $65/hour. How did she do it?

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We’re in the final week of my 3-week course on earning more money. After this week, I’ll be releasing an additional week of private content on earning more.

And then I’ll be releasing a step-by-step program to help you earn your first $1,000 on the side.

Sign up for free.

* * *

Today, a case study to show you how even the weirdest skills can be very, very profitable.

This is one of my favorite case studies because you’ll learn how to take your skills — even if they’re unusual or seemingly not in demand — and turn them into significant income.

Cassie Phillipps realized that she was working too hard for too little money .She was a theatre stage manager, and as you know, I usually make fun of weirdo drama/artsy types because they revel in their poor financial skills and complain that the world is against them.

But Cassie realized how to carve out a specialized niche using her existing skills. Now, she produces exclusive events for the tech industry. She went from $17/hour to $75/hour and works fewer hours than her old job. What if you could do the same?

In this 35-minute interview you’ll learn:

  • How Cassie managed to turn specialized skills from her stage manager job into a profitable and high-profile freelance business
  • Where she chose to invest in her business, and where she’s chosen to save (if you’re wary about spending money to make money, listen to this section)
  • Her marketing strategy, where every engagement is a secondary marketing channel
  • How she’s developed multiple pricing plans to fit an unusual niche
  • How she cultivates repeat business, even with big-budget, infrequent conferences

Listen to the interview here:

Audio clip: Adobe Flash Player (version 9 or above) is required to play this audio clip. Download the latest version here. You also need to have JavaScript enabled in your browser.

* * *


  • 0:24 How do you earn money on the side?
  • 1:05 Why Cassie’s unusual skills turned out to be perfect for freelancing
  • 2:40 Cassie’s old job as a stage manager — lots of hours, little pay
  • 3:45 A friend sees her transferable skills, and asks for her help with events
  • 4:35 Getting started working a little on the side, and realizing she’s already making more money


  • 5:01 It’s not about the technical specifics. It’s about what the client wants.
  • 7:59 “We have $5,000 for you, can you make it happen?” Cassie is offered money for something she can do in less than 10 hours
  • 8:06 Getting over fears: “What if I’m not the right person?”
  • 9:45 Cassie goes from $200 a WEEK to $100 an HOUR
  • 15:02 Addressing startup costs and getting over initial barriers
  • 16:33 How she spends for value, and invests in her own business
  • 16:41 “If you don’t have the confidence to invest $2000-$4000 in something you’re going to be doing for the next 5 years, then you’re not ready to do it yet”


  • 11:16 Understanding her clients’ worst fears
  • 11:24 How Cassie negotiates rates with vendors, and pays for herself
  • 12:35 Specific phrases to communicate her unique value proposition
  • 13:35 Cassie cuts her hours, and triples her income

Marketing her niche business

  • 19:17 How Cassie gets new clients, and attracts only big names
  • 20:41 Cassie’s marketing strategy: work with influencers, and don’t hide in the background
  • 22:08 “Niche it down!!” What this means for freelance event production
  • 23:57 “By specializing in the startup industry, I can pretty much beat out any other events person”
  • 27:15 How Cassie screens clients, diagnoses her client’s real problems and needs, and eliminates the need for hard sells
  • 29:38 Creative rate plans
  • 31:35 How Cassie guarantees repeat business
  • 34:47 Her work does its own marketing

* * *

Get advanced strategies to earn more: You’ll find more case studies — including someone who turned down over $100,000 of side income — plus an MP3 download of this interview with Cassie. And lots more unannounced techniques to help you earn more on my private Earn1K insider’s list:

(Can’t see the form? Click here.)

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  1. Hey Ramit,

    I’m lovin’ these case studies (the one with Elizabeth rocked).

    Nothing proves that something works better than a personal story. And the real-world examples flesh out the practical steps we ourselves can be taking with our stuff.

    Looking forward to downloading this (I’m a Earn1k subscriber),

  2. I agree with Oleg. These case studies are probably one of my favorite things on this blog. Keep them coming!

  3. Great interview and very interesting niche…it’s something I’m interested in and see value in as well for what we’re doing here in the Midwest…

    Can’t wait for the additional information Ramit and keep up the great work!

  4. Ramit, this is awesome. I come from the theatre world and I know a ton of stage managers. I’m going to share this with every single one of them.

    Great stuff.

  5. Wow, this was an awesome interview! There were so many poignant moments throughout the interview, don’t even think she realized how truly significant they were lol. Loved it, very inspiring and gives me hope for my niche market :)

  6. Enjoying the case studies Ramit- the highest complement I can give is that this blog is one of the few that continually stays interesting and applicable enough for me to stay a subscriber.

    On another note, would like to see more of your stuff on investing. I am of the same philosophy that more “intelligent” risk needs to be taken in our younger years.

  7. Argh! Ramit! I’m so excited for the Earn 1K course. All these previous weeks of teaser blog posts (albeit full of awesome and inspiring content) have gotten me really geared up for your course.

    I’m a college student looking to earn money freelancing with the skills I’ve learned in my courses along with the skills I’ve picked up through hobbies. I know how you feel about Web Designers and high barriers to entry so I’m looking towards niche markets which still need those interactive marketing touches (the field in which I’m studying).

  8. Cassie’s brilliant! I liked how she invested money and time in a project even when it still wasn’t really off the ground yet. She was willing to think long-term and it paid off for her.

  9. Well said about the upfront money to starting a biz. Do you feel that you are worth $2000? You are putting the startup costs into YOURSELF. You never really lose it, only the number in your back account decreases.

  10. Great interview, case study interviews are incredibly valuable because it shows the interviewee’s problem solving thought process. Learning to fish instead of just handing us a fish–much more effective. Thanks.

  11. This is some badass content. The landscape is changing. Thank God there are a few people left with the intelligence and chutzpa to move forward.

  12. just FYI… I signed up for Earn1K and also RSS via email for the IWTYTBR blog — This is first post I did NOT receive an email for — , You’re doing great, Ramit!! Looking forward to Earn1K unleashed :)P

  13. Oh man, I talk too much sometimes. >_<

    Thanks for the great interview, Ramit! I had a blast talking with you, and glad folks do seem to be getting some inspiration out of it. I try to tell my friends at home (Minneapolis) that it is SO much easier than it seems, seriously easier.

  14. Hi Ramit,

    I love these “real life posts”, possibly the best thing on your site as they add authority to the lessons. Great stuff.

  15. Well done Cassie. Some great pointers, both for the business aspect and the hosting an event aspect as well.

  16. Love it. This is really great stuff here.

    This girls attitude says everything about what it takes to be successful. Everything else is just tools and tactics.

    I also signed up for the Earn1k. I’m looking forward to use the techniques in my full time job though instead of a side job.

  17. This is fascinating stuff. Keep the interviews coming, they are great! The business end of freelancing is daunting for many, these are inspirational guides.

  18. Ramit,
    these Q&A sessions are fantastic! Here’s what I appreciate most:
    1. How you dig into the speakers’ motivation for freelancing: (was it financial? was it following a hobby or childhood passion). Everyone is different in why they want to freelance so it’s nice to see the impact of the motivation on the outcome.

    2. Deconstructing first sale/deal/encounter with a client and why it worked.

    3. Deconstructing into (if relevant) the first failure the enterepreneur had – even more interesting because we can see how the learning is applied later.

    4. Understanding choices taken to get to the entrepreneur’s niche approach (and understanding why they chose to NOT to take a different niche approach).

    5. How the entrepreneurs applied their specific skill set to the market place.

    Keep ’em coming! Many thanks!

  19. I love the detailed and practical information in this interview.

    I wonder if Startup conferences are a good business opportunity outside of the valley?

  20. Fantastic. My favorite part was how she could convey her own value proposition clearly, concisely and honestly–not as some sort of skeazy pitch.

  21. Awesome interview, high quality audio.

    Ramit, did you by chance get your twitter link from that blog post that showed percentage increases based on the strongness of language in the link? I think it was something like

    I’m on Twitter
    Follow me on Twitter
    You should follow me on Twitter
    You should follow me on Twitter here

    with each step down having higher click through rates. Just curious if you noticed a similar effect as the published results…

    • Thanks for the kind words.

      Yep, we saw that. Fascinating experiment. We’re testing stuff on iwillteach all the time (including the Twitter messages).

  22. loved the case study; got my brain going…..

  23. Fantastic interview, and it’s great that Cassie is so confident and willing to share this information.

    I think Cassie has the right idea with being able to turn away clients that aren’t always a good fit instead of just taking on work that’s there.

    Walking away from paid work is really hard to do when you’re just starting out. It’s good to see Cassie’s combating that urge by using the tactic of charging appropriately and not undervaluing her talent and contacts – it seems to be paying off.

  24. Btw Ramit, what plugin are you using for redirecting commenters after posting a comment to the thank you page? I’ve been looking all over for a good one.

  25. […] step is to niche down your market. Do not try to find every person who uses a computer between the ages of 18-34, lives in the USA, […]

  26. […] be fun – find a new job that you enjoy more.  Not the right time to change  jobs?  Start a side job using your skills and abilities.  By empowering yourself to control your situation as much as […]

  27. I completely agree with her statement about investing in your company/idea.

    I recently hired a web developer who quoted me around 4k for my e-commerce idea. At first I was hesitant and started to doubt my idea. But after doing the math, it only came out to $333.00/month over 12 months. Over 5 years, that’s 66.00 a month. When I think about the business a well designed site will bring, the trade off is a no brainer.

  28. Great case study on successful entrepreneurship. Cassie was a great example. Her constant brainstorming and and creativity has led her to higher pay and better hours. Her business has a great foundation, and it’s sure to continue onwards in the future! Keep the case studies coming!

  29. […] Case study: From $17/hour to $65/hour. How did she do it? […]

  30. Can you tell us more about this? I’d like to find out more details.