Podcast Category: Taxes and Accounting

  • Episode 11: {Interview} Freelancing and Finances with Shannon Simmons

    Shannon is a Certified Financial Planner (CFP), Chartered Investment Manager (CIM), media personality, personal finance expert, financial literacy advocate and founder of the New School of Finance. Shannon is a best-selling author of the two books:
    — Worry Free Money
    — Living Debt Free

    0:18 — Intro with Shannon Simmons

    2:15 — What is your money history story? We explore how money is talked about within the household, and how families can reflect shame and secrecy around finances. It’s time to get open about your finances!

    5:40 — Do you talk about how your business is doing, whether it’s good or bad? We talk about all the feelings that people have when talking about and handling money.

    8:35 — Are you passionate about what you do, but scared to see if it’s actually profitable? We dig into the emotional layer of taking a hard look at whether your business is actually profitable.

    9:55 — Why Shannon chose to work Freelancers and how she made a niche for herself.

    11:48 — TAXES! This is what you’ve been waiting for. How to organize your taxes and what you need to do when you’re just starting off. How to wrap your head around income tax.

    15:50 — EXPENSES! What are they? What’s a write-off, and how to organize the money that is  going OUT of your business. How do you know if something is a an expense? Find out here.

    23:25 — What are some things that are not allowed to be expensed, and what in Shannon’s experience has been the most bizarre expense attempts.

    26:00 — How do media personalities and influencers determine expenses? We discuss how the landscape has changed since the emergence of all these new careers.

    27:20 — We talk CRA and how they are a great resource for entrepreneurs. It’s not a big bad agency who’s out to get your money. We talk all about the role of Revenue Canada.

    31:30 — What is the difference between income tax and sales tax? Let’s clear up some muddy waters about GST/HST, sales tax and income tax.

    37:25 — Where can you find Shannon, and what resources she has to offer.


    Here’s where you can find Shannon

    Financial Services:



  • Episode 5: Accounting 101 for Freelancers

     Today I’m super stoked to be joined by my accountant Susan. Susan Watkin is a recognized and sought-after accounting educator, small business advisor, and start-up strategist.   Working closely with business owners in all phases of their business life-cycle, Susan strives to help those owners take their businesses to whatever level they want to reach.

    In her approachable style, she’s upfront and pulls no punches when it comes to the reality of small business finance and all that it entails so that those she works with are given the tools for their future success.  Susan is proud to be recognized as a leader in digital accounting technology, as well as holding a position as a trainer and writer for Intuit Canada, and part-time professor at both Mohawk and Canadore College in Ontario.

    Welcome Susan!

    PD: Please note that all the information we are covering in this episode relates to Canadian Freelancers. Some of the major concepts can be translated to the US and beyond, but just keep in mind where our area of focus is.

    Here’s the following topics we dive into, and questions we have answers for:

    Interview Questions Susan Watkin The State of Finance Questions:

    2:23 — About Susan, what she does, who she serves and the services she offers.

    Interview Q’s

    4:30 — When you work with Freelancers and small business owners, what is their typical level of knowledge on finances, and do you think the school system is lacking in that area, given the rise of the “gig economy”?

    Specific Freelancing Questions: 

    6:55 — SALES TAX: In Canada, when a person first starts out as a sole prop, do they need charge pay tax? If not, should they opt in to paying right away, and what are the advantages of that?

    12:35 — REMOTE WORK: Since many people are working remotely, we often work with people in different provinces and across borders. Who do we charge tax to, and how much?

    19:17 — INTERNATIONAL CLIENTS: Being remote, there are many times that we deal with US customers. Is it ok to charge in another currency?

    23:22 — EXPENSES: Let’s talk about “write-offs”. Can you clarify what a “write off” is? Because many people believe that it’s free money that you get back from the government. What are some major misconceptions about expenses?

    27:45 — CRAZY EXPENSES & AUDIT POTENTIAL: What are the allowances of expenses when just starting out, and what’s the craziest thing someone has tried to justify expensing?

    31:50 — INCOME TAX: As a general rule, do you have a guideline of how much of your sales you should put aside in the expectation of paying it for tax?

    37:05 — INCORPORATE VS SOLE PROP: People most will start off as a sole prop, but as they grow will consider incorporation. Is there a general guideline on when you should start to consider that? I know each case is different, but when should you start the conversation?

    44:55 — COMBATTING FINANCIAL OVERWHELM: For people who are overwhelmed by finances and stressed out about numbers, what advice would you give to help them stay on top of their cashflow?

    50:58 — STARTING OUT: What’s the 2 major pieces of advice you would give to someone starting from scratch (I’ll also add a couple of my experiences from a Freelance perspective)

    53:46 — INVOICING SOFTWARE: Finally, for a Canadian solo-preneur, is there a bookkeeping/online invoicing program  you would recommend, also do you need one right out of the gate? (you can add referral links if you have them)

    Susan has also given us a wealth of resources. Here is everything mentioned in the episode:

    Free webinars/tutorials for small businesses

    For accounting/invoicing software:
    GST/HST Rulings: