51: Break Through your Money Ceiling with Dorothy Illson
26th February 2019 • Create Your Own Salary (previously Business Breakthrough) • Estie Starr
00:00:00 01:24:23

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Dorothy Illson was all set for her dream job as an accountant at PwC, when two weeks after graduation, she called them up and informed them that she would not be coming. Instead, she went to work for a meal subscription company, helping to grow it to multiple six figures. She then opened her own marketing agency, Needle’s Eye Media, at the age of 25!
In this episode, Dorothy gives away all the secrets of how to build and run a successful online funnel for webinars, as well as explaining the ins and outs of retargeting campaigns. She also shares her struggle of combining her podcast- Do Well and Do Good with her agency, Needle’s Eye Media, to create a cohesive and memorable personal brand.



My Guest: Dorothy Illson

Dorothy began her career as the 3rd employee at a startup in the meal subscription space which grew from $0 to $6M in annual revenue over the next 3.5 years, giving Dorothy a crash course in what it looks like to successfully scale a business. After that, Dorothy struck out on her own to help entrepreneurs succeed with Digital Marketing, eventually focusing her efforts on paid traffic and founding Needle’s Eye Media at just 25 years old. Needle’s Eye Media became a multiple 6-figure business in its first year and has continued to grow from there.

Dorothy is also the host of Do Well & Do Good, a podcast that helps people bust through their limiting beliefs about money and shows that creating abundance in your own life allows you to do so much more to give back and make a massive impact.


Pivotal Moments:

Studied Finance and Accounting in college and planned to become an accountant at one of the big four accounting firms.
Was introduced to personal development during her senior year of college which made her realize that a career in accounting would give financial success but wouldn’t make her happy.
Had already done an internship and accepted a job offer at PwC (Price Waterhouse Coopers), but two weeks before she informed them that she would not be coming.
Moved to Chicago where she met the co-founder of a start-up’s wife. She got a job at the start-up, eventually becoming addicted to the culture of building something new.
Was taken under the wing of her boss who became her mentor and coach. When he left, she started her own business at the age of 25.
Opened her marketing agency, Needle’s Eye Media, at the age of 25, as well as her podcast show, Do Well & Do Good, that helps people break through their money ceilings and achieve bigger and better.


The Advice:

Mental Ceilings

No matter how much money you are making, everyone has a mental ceiling of what they believe they deserve and are capable of achieving. Until you take deliberate action to raise that ceiling and switch your mindset from “I can’t” to “How can I?”, you will always be bumping your head into your ceiling and limiting what you can and should achieve.


Facebook Ads
Facebook Ads are constantly evolving and changing but there are three important prerequisites that are always important:
  1. Have a great offer
  2. Have great copy and a fabulous message
  3. Tell Facebook exactly what you want
If your ads are not working, you need to go back to your offer and your message and make sure they are compelling, bringing in the right customers and repelling the wrong ones.


Graphics for Ads
Here are five top tips on how to make the perfect graphical ad that will catch peoples’ attention on any platform:
  1. Have people in your ad and make sure they are looking at the camera.
  2. Use diagonal lines in your image. They are a pattern interrupt and make the brain stop and look.
  3. Increase the contrast of your image by 10-30% to make it brighter and “poppier”.
  4. Use a non-standard image size. Instead of building ads through ads manager, create a page post and toggle to dark post (so Facebook knows that it is an ad). You can now upload any image dimension you want so your ad will look a little abnormal and will pop off the page. But, it also won’t have the headline so make sure to put thought into the first line of the ad. An extremely effective opening line is often a question because the brain is wired to close loops and answer questions.
  5. Images should be “native aspirational”. Native means natural to the platform i.e. something that a real person would post and not an obvious stock photo. Aspirational – put subtle psychology to play by using images that speak to your audience’s greatest desires. If their dream would be a vacation with the kids, put an image of yourself on vacation with the kids.


Funnel for Webinars
Webinars are a fantastic tool to sell mid- to high-ticket services. The sales funnel for a webinar can look something like this:


Step 1
A prerequisite for this funnel is that you are selling something that people want and are providing and delivering value for your customers.


Step 2
Create and deploy ads. There are two types of ads:
  1. Long form story ads with a static image with audio. The audio walks the prospect through your journey so they picture themselves inside parts of your story.
  2. Video ads. Here you teach something to your audience and provide value up front.


Step 3
Lead clicks on the ad and is directed to the webinar registration page and hopefully registers for the webinar.


Step 4
At the webinar, you spend 75% of the time providing pure value and spend only the last 25% on your pitch.


Step 5
Webinar participants then have a three-day window to purchase. Be real and stick to the deadline because if you don’t stick to your limited time offer, people won’t trust you anymore


Retargeting Campaign
What about those people who don’t go through the whole funnel and don’t purchase? They are entered into a countdown based retargeting campaign.


Step 1
At the webinar, participants are offered a fast start bonus that is available for 48 hours after attending the webinar.


Step 2
Those who don’t purchase after 48 hours are entered into a non-buyer retargeting ads campaign that has two different ads running:
a. Frequently Asked Questions video, knocking out the main reasons why someone would not buy.
b. Social proof video showing comments from previous customers.


Step 3
Once a lead clicks on a retargeting ad, they are removed from the retargeting campaign (so they don’t keep seeing the ads) and are redirected to the purchase form (without the fast start bonus). They now have 72 hours to buy before they miss their chance completely.


Step 4
If the lead still doesn’t purchase, they are put into a campaign for a different webinar. If they don’t buy on this one, they are put to sleep.
People are naturally very sceptical of online funnels. Most people will check up if something is legitimate by searching on Google. Make sure that you are advertising on your branded keywords on Google so that you show up when people search for you.


The Struggle:

Dorothy is struggling with her personal brand. She currently has her agency, Needle’s Eye Media, and her podcast, Do Well and Do Good, which are two disjointed parts of her personal brand. How does she build content and branding that portrays a clear and cohesive personal brand when she has these two very separate aspects that are only very loosely related?


The Breakthrough:

Dorothy’s essence is her drive to do good for others. She can therefore brand both her agency and her podcast under one personal “Dorothy Illson” brand that focuses on doing good. Her podcast obviously fits in well to this brand, but her agency can also if she markets herself as a Facebook Ads guru who gives back by taking on one struggling client for every ten pro-bono and builds them up to success.



I expect magic in every moment and so I find it. 


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