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From 9-to-5 to $300K Success: The Emily McDermott Story

Written by:

Esther is a business strategist with over 20 years of experience as an entrepreneur, executive, educator, and management advisor.

From 9-to-5 to $300K Success: The Emily McDermott Story

In this inspiring interview, we meet Emily McDermott, a Canadian entrepreneur who turned her passion for budgeting into a thriving online business, Pretty Arrow™ Inc. Starting with a simple yet unique idea — a pink budget spreadsheet catered to women — Emily harnessed the power of Etsy and her keen sense for market demands, catapulting her business to $300,000 in sales within just two years.

With a background in business and a former 9-to-5 in insurance, Emily’s entrepreneurial journey began with a leap of faith, quitting her job to pursue her dream. Her story unfolds from humble beginnings, learning spreadsheet design through online tutorials, to rebranding her business with a focus on trademarking and expanding her product line. Emily’s strategic use of digital platforms like Etsy, Pinterest, and Facebook ads, coupled with her mastery of email marketing, illustrates a roadmap for aspiring entrepreneurs.

Today, Pretty Arrow stands not just as a budget spreadsheet shop but also as a beacon of entrepreneurial success, pivoting towards offering mini-courses and expanding its digital footprint. Emily’s journey is a testament to the power of a well-executed idea, relentless learning, and the art of connecting with customers on a personal level.

Meet Emily McDermott

SBS – Hi there! Can you introduce yourself and the venture you embarked on?

Emily – I’m Emily McDermott, a 30-year-old Canadian entrepreneur who founded Pretty Arrow™ Inc., a budget blog and budget spreadsheet shop. 

When I first launched my first pink budget spreadsheet targeted to women, it resonated with customers almost immediately. I loved creating a colorful, simple-to-understand budget planner — because, at the time, I wasn’t able to find anything like it elsewhere. 

By launching these spreadsheets on Etsy (a marketplace with predominantly female shoppers) and creating products with high demand and low competition, I was able to reach $30k in sales in the first two years on Etsy.  

This was a great launching pad for continued growth in my business outside of Etsy, and it certainly validated my business idea.

The Birth of a Unique Budgeting Solution

SBS – Share with us your journey leading up to this idea. What inspired it?

Emily – I have a degree in business and started out my working career in an insurance office (I worked there for about five years).

In 2020, I had a 9-to-5 job in insurance and was inspired by stories I read online about people starting online businesses and making their own schedules. I was feeling burnt out in my career and ready for something new. I made the decision to quit my job and start an online business. I told myself that if I didn’t make enough to get by in three months, I would just get another job.

I was always really interested in budgeting (my friends and family often asked me to help them with their budgets), and at the time, I was also paying off my $35,000 student loan debt. My dream was to start a blog where I could share my story with other people who wanted to manage their money better. 

I wanted to monetize my new blog quickly, so I could earn just enough income to get by. But I was still figuring out how to get traffic, and I knew it would take me some time to build my audience.

I stumbled upon budget spreadsheets on Etsy and realized that people were selling them every day. I was so excited and wanted to use Etsy as both a traffic source for my blog and a way to earn an income by selling my own budget planners. 

I researched product keywords on Etsy using a tool called eRank, and it became clear that there were lots of searches each month for budget spreadsheets but not a lot of people selling them. This solidified my idea to get started ASAP.

I knew I needed to take it a step further and make my products really attractive to shoppers on Etsy. This is where I got the idea to make budget spreadsheets that would be fun and exciting for women to use. I wanted to fill a gap in the market. 

I had little to no experience with spreadsheets (other than using them a couple of times in university and at my 9-to-5), so I was actually quite intimidated when I started. I felt like an imposter among the “pro” spreadsheet sellers online. 

I just started to design, and each time I wanted to add something new to my spreadsheet, I watched online tutorials on how to do it. It wasn’t a quick process, but I was really having fun with it and grew a lot of confidence in my skills. 

My first spreadsheet was a simple monthly budget in Google Sheets. It made its first sale on day one! I felt confident in my idea and started to make more spreadsheets with the same design. 

By month two I was making enough to pay my bills, which was so cool!

From Girls Who Budget to Pretty Arrow

SBS – Walk us through the journey of conceptualizing, creating a prototype, and bringing your first product/service to life.

Emily – When I first started, I named my business “Girls Who Budget.” I learned that if I wanted to trademark my business name, it needed to be unique and not literally describe my product or service.

I hired a branding agency to help me walk through the process of rebranding, and I chose the new name, “Pretty Arrow.” I wanted the name to really reflect how pretty yet impactful my product was. It is nice to look at, but it also provides direction and clarity. The branding agency also made me a pretty logo to go along with this. This was great because it can really be a long process to figure all of this out on your own.

I also learned that giving your business a “trademarkable” name helps you to pivot easily in the future, if you decide to sell different products. 

Leveraging Digital Platforms for Business Growth

SBS – What was your strategy for putting your business on the map?

Emily – The launch of my business started with a WordPress blog that is hosted on Bluehost (this was relatively inexpensive and was a low monthly fee). I started by posting a few SEO-optimized posts that were related to my niche, so I could eventually grow my Google traffic while also building trust with new customers. 

I did keyword research on eRank and identified the first spreadsheet I wanted to make (because it was high demand and low competition). 

I then launched my Etsy shop (this only took a couple of hours) and listed my first product for sale. I made sure to let customers know everywhere that I could that I had an email newsletter they could sign up for, so I could capture customers/leads from Etsy. It is very important to have an email list, as you have no control over what will happen to a social media algorithm or any external platform. You don’t want to lose your audience!

Since I started with a digital product, I only invested my own time in creating it. This helped me to launch my business without any loans or funding.

Mastering Social Media

SBS – After your initial launch, which tactics stood out in attracting and retaining your clientele?

Emily – To attract customers, I really focused on Etsy and Pinterest. The reason for this is that both of these platforms are really like search engines, which would help me to get product sales. My goal was to retain as many of these customers/potential customers as I could on my email list. 

Although I did get some traction using Instagram and TikTok, I really wanted a sustainable business that worked best for me as a solopreneur. I find that daily social media posting is really time-consuming. I like to focus on marketing “sticky” content, like on Pinterest — where something I post today will get me traffic in the months and years to come (whereas an Instagram post stops being shown to my audience much sooner). Blog posts on Google are also an example of “sticky” content that can get you long-term traffic. It just takes some time for this to pay off in the beginning. 

One thing I wish that I had done from the beginning (and only started recently) is using Facebook ads. Even though I like focusing on “sticky” content, Facebook ads are a great way to reach more buyers without multiple social media posts a day. Jana Bishop has an incredible course for beginners on this that I recommend.

Expanding Horizons and New Ventures

SBS – Give us a snapshot of your business today, and share a glimpse of your future plans.

Emily – Nowadays, I’m focusing fully on moving products to our own Shopify store and gaining more control over our daily traffic (through email marketing to my list, Pinterest, Facebook ads, and Google SEO). I’m not really including social media in this strategy as I really don’t have the time, and I don’t want to spread myself too thin.

I’m also working on mini-courses to help people create or customize their own spreadsheets and grow their spreadsheet confidence! 

I spend my days replying to customer emails, making new products (whether that’s a spreadsheet course or a spreadsheet), and marketing these products. 

Valuable Lessons Learned

SBS – What key takeaways or beneficial lessons have emerged as you’ve built your business?

Emily – I made so many mistakes with email marketing in the beginning! Looking back, I felt like mastering email marketing was really a mystery that I couldn’t crack. I focused a lot on this skill, and I learned a few non-negotiables for selling a digital product over email:

  1. When you write an email to your list, don’t try to be “all business.” Be personable and friendly. When you are too focused on sounding professional, people will view you solely as a business trying to sell them something and will put walls up. They want to get to know you and what makes you different! Focus on really providing value and helping them. Write the email like you’re writing to one person, not a crowd.
  2. Pre-launch your offer the day before. Get them excited to open tomorrow’s email from you!
  3. Make an irresistible offer, not one that’s “meh.” Give your email list an incredible deal that they don’t want to miss out on. 
  4. Give them a deadline to take action. You can’t just send out a discount and hope everyone will take action today. Give them a deadline, and remind them about it before time runs out. 

Essential Resources for Running an Online Business

SBS – Which tools or platforms have been of great value for running your business?

Emily – Convertkit is absolutely indispensable to my business! I’ve used it for my email marketing since day one. It is so easy to use and helps fuel many of my sales.

If you want to sell digital products on Shopify, I love the Honeycomb app! It lets you add automated upsells and cross-sells to related products when a customer buys from you. It added an additional 15% in sales when I added it to my store. 

I also use the Digital Downloads app to attach my digital product files instantly to each order. You will need an app like this to sell your digital products on Shopify.

Book That Shaped the Journey

SBS – Are there books, podcasts, or other mediums that greatly influenced or motivated you?

Emily – I love the book Building a Story Brand by Donald Miller. It provides so much clarity when you’re a new entrepreneur looking to start a brand but don’t know what to build. 

Advice for Aspiring Entrepreneurs:

SBS – What advice can you offer entrepreneurs gearing up to launch their first business?

Emily – Knowing what brand to start can be so confusing. You’ve heard that it’s important to pick a niche, but you don’t know how specific to go. It can be helpful to look at it like this: 

Your target customer has a burning, but perhaps common, problem that, in and of itself, might not be very “niche”: i.e., they want to make money, they want to save money, they want to save time. 

What gives you a competitive edge and your “niche” is your approach to solving this problem for them. 

So instead of saying, “I help people with budgeting,” you could say, “I help people budget in a faster, automated way: A budget spreadsheet.” 

You want to stand out and be memorable while also solving one of the burning problems that keep them up at night. 


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From 9-to-5 to $300K Success: The Emily McDermott Story