Legit – everything you need to know to cover your butt as a CDN sole-proprietor and run your business like a boss.


Wanna get a handle on your biz finances?

Taxes, HST, GST, Revenue, Expenses, and business viability…

Sole-Prop School is the first of its kind. Ever. This is where you learn how to run your sole-proprietorship finances. Entrepreneurship is the future. Sole-proprietors/freelancers/solopreneurs are hustling hard in the self-employment world, making our own way, doing it our way. These days – our self-employment finances ARE our personal finances, cuz we are all hustling. But, like, wtf do we do at tax time? How can I afford to work less and go on vacation… for reals though. As your business scales you start making that money, you’re gonna have one helluva tax bill. 



  • Can you work less?
  • How much do you charge?
  • What do you need to make?
  • How much do you need to sell/work?
  • Can you ever go on vacation?

MAKE THAT MONEY  has got you covered in Sole-Prop School!



  • How much do you need to save for tax time?
  • What expenses can you deduct at tax time?
  • What receipts you need to keep?
  • When do you need to start charging GST/HST?
  • What do you do with it and how does it work at tax time?
  • What rates do you need to be charging if you’re selling outside your province.

Don’t Get Eff’d At Tax Time & GST/HST – The Good, The Bad & The Ugly  have got you covered in Sole-Prop School!



  • Separate your business from your personal life (with banking plan)
  • Learn how to track your revenue and expenses so you don’t have to count receipts at tax time
  • Understand what records you need to keep (beside just receipts)
  • How to prepare for an audit/review from the CRA (dun dun dunnnnnnn) so that you’d be like “oh, no big deal yo.”

Track That Shiz has got you covered in Sole-Prop School!



BONUS: All Sole-Prop School Students are invited to be a part of the legendary Sole-Prop School Facebook Group! An amazing place to get customized answers from New School of Finance financial planners to your biz and tax questions when you need them throughout the year!

Whether you’ve been in biz for a long time or you’re just starting your adventure, Sole-Prop SchoolTM is your one-stop-shop to help you get your business finances organized (so you can sleep at night!).

Sole Prop School includes one year access to all 4 New School business courses and the online Facebook Community Group:


“I was charged late fees when I got my notice of assessment because I was supposed to pay my taxes in installments? No one told me this”



“Can I afford to take time off or hire someone? I am burnt out.”



“I literally have a bag of receipts at home. Please help.”



“I owe $2000 in back dated HST/GST because I went over the threshold without knowing it and now I have to pay it back out of pocket… fml”



“ credit card statement doesn't count as a record for tax-time?”

Get immediate access to all 4 courses for $397 (Save $141!)

“The courses are amazing and carefully laid out which made learning simple. After doing the courses,

I now know that tax season is not the end of the world.”

Jason Gordon, Photographer, Sole-Propper


“It was mind blowing. I found all of them [the modules] fun. They’re fun because your energy is fun. I LOVE that you can make the most difficult and “boring” really entertaining and fun to watch.  The way that you present taxes made me actually WANT to tackle that part of my business instead of leaving it to the last minute. You’re super motivating.”

Carol Dano, Web Designer, Sole-Propper

“I’m so happy I did it. I just did my 30 mins of bookkeeping for the month before answering this email and it feels damn good to be on top of my shit now. I get what I’m supposed to do! I feel lucky that you had this program out when you did, just in time for my first tax season as a sole prop. I’m a lucky lady. You’re great!”

Emily Bennet, ND, Doula & Sole-Propper

“Thank YOU so so much for making me feel like I am not: a) incredibly unaware of how to run my business and b) not running a shoddy back alley flower shop. So glad to have your help and guidance ( huge sigh of relief)”

Rebecca De Oliveira, Blush and Bloom, Sole-Propper

“Taking my business to the next level was stunted by my lack of confidence and knowledge in financials. Having a clear separation between my personal and business finances has made me take the business more seriously; transforming it from a weekend craft into an empire that supports me full time. I’m living the dream, and never have to count a receipt again thanks to Sole-Prop School!”

Jordana Halpert, Simple Studs, Sole-Propper


Don't Get Effed at Tax Time



Make That Money



Track That Shiz



GST/HST - The Good, Bad, + Ugly



Office Hours With Shannon



Get Organized.


Feel Legit.


Sleep at night.


Understand your taxes.

Meet Your Teacher

Shannon Lee Simmons

Shannon is a Certified Financial Planner (CFP), Chartered Investment Manager (CIM), media personality, personal finance expert and founder of the New School of FinanceTM. She loves helping everyday people survive the new economic climate through personal finance, ethical investing and small business advice. Simmons is widely recognized as a trailblazer in the Canadian financial planning industry and an expert in Millennial personal finances and the digital world and it’s relationship to our money. She was named one of Canada’s Top 30 Under 30 and she recently won the 2014 Notable Award for Best In Finance. She is a regular financial expert on CTV News and also appears as a financial expert in the media, a regular contributor for Toronto Star’s Money Makeover and BBC Capital and host of Coral TV’s Money Awesomeness. Shannon travels across the country speaking for some of Canada’s largest corporations and universities including IBM Canada, The Canadian Women’s Foundation, University of Toronto, Ryerson University and Bishops University to name a few.

Sole-Prop School is everything you need to know to run a legit small Canadian business.

Legit, practical info—in human speak—from a Certified Financial Planner, so you don’t get eff’d at tax time. NO MORE FEAR of the brown envelope (or online alert from your MYCRA account) from the CRA. If you’ve dotted your i’s and crossed your t’s – those brown envelopes become more of an administrative duty than a terrifying nightmare.

Shannon Lee Simmons


  • Please ensure you have read the Pre-Requisites and Course Restrictions for this course before signing up
  • This course is not financial or tax advice. The information in this course is for educational purposes only.
  • The information in this course does NOT replace the information in the Income tax act or its Regulations.
  • For all Quebec residents, the information given in this course is federally oriented and may not take specific tax differences for Quebec into account as Quebec residents may be subject to specific rules that are outside the scope of this course. We invite you to get in touch with us at for more information before you purchase to confirm whether this course will suit your needs.
  • Les renseignements fournis dans le cadre de ce cours concernent surtout le palier fédéral et peuvent ne pas tenir compte des différentes règles fiscales auxquelles sont soumis les résidents du Québec. Nous vous encourageons à communiquer avec nous à l’adresse pour obtenir de plus amples renseignements avant votre inscription, afin de vérifier si ce cours vous convient.
  • All courses will be charged in USD (based on that day’s USD equivalent to the CAD course price). Your credit card may charge you a different exchange rate or additional fees for foreign transactions.

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