Shannon Lee Simmons

Founder of the New School of Finance, personal finance expert & media personality

In 2010, Shannon did something unexpected: she quit her job in Toronto’s Financial District to offer financial planning advice in exchange for anything from a pasta dinner to a video game console. Even more unexpected than her wild leap into the unknown was that this year-long experiment was so successful that it’s now a thriving business. Shannon talks with The Prevail Project about profitable risk-taking, using technology to change the way people interact with their finances, and what to do when the internet turns on you.


Combining astrology, numerology, and pure psychic intuition

This book is surprisingly accurate. I believe in the power of the zodiac and it’s application in business.

Using my creativity allows me to push boundaries

Challenging the norm to make finances more fun

My main form of transit, my bike

Her name is Big Red. She is my noble steed.

These are my fav pair of studs. I'm a secret hippie.

These are energy crystals in awesome earring form. I wear them almost every single day.

I feel fully relaxed and happy when playing the piano

So I brought a keyboard to the office because it’s smaller and gives me a chance to step away and reenergize

I love a good game of Euchre!

It’s a lighthearted, competitive way to connect with my team.

My sister gave me this mug at my university graduation.

I use it everyday in the office. It motivates me to keep dreaming big even when things feel impossible.

I have used the same brand of calculator since high school and have always put a dollop of red nail polish on the top right.

It started because I was trying to decipher mine from my classmates but then became a thing. I carry this thing everywhere.

As an entrepreneur, you gotta stay grounded

Yoga helps a lot with that.

Um, the best thing about coming to New School is the tea.

Bengal Spice is a staple here. Sometimes I feel like clients come to hang and drink tea more than nerd out about their finances.


Shannon, what made you decide that financial planning was the career path for you?

Making plans is my hobby; I knew it was something I’m good at, and I’m also really good at math. It’s natural for me to plan with people, and as a numbers geek interested in tackling entrepreneurship – it’s a trifecta of awesome for me!

I don’t think there was a single moment where I decided, “I’m going to run my own financial planning practice – oh, and develop online courses!” It’s been an evolution over time where I’ve created a job for myself out of the things I like. I know that sounds nerdy, but it actually is what I do every day, and I’m super passionate about it.

Money is at the heart of everything that we do – whether we like it or not. It affects whether we take risks, whether we go on vacation, whether we buy a house; helping people figure out their financial plans so that their lives can unfold smoothly is really amazing for me.

In your opinion, what’s the biggest problem millennials are currently facing when it comes to finances?

I think the scarcity of high paying jobs for most people, especially millennials is huge; there’s not a ton of secure work that comes with pensions and that kind of stuff. What the baby boomers had available in terms of employment just isn’t there today, and yet the cost of living has gone up.

We’re in this weird pickle; we still want to buy a house, go on a trip, and not live in a basement suite forever, but the workforce is really challenging. A lot of people are starting their own companies and taking matters into their own hands to combat this. They’re finding the traditional way of working isn’t working for them and asking, “what can I do to make it better?”

What do you think should be taught in schools to prepare young people for managing their finances?

The fundamental thing I would love to see taught is an understanding of when you can and cannot afford something, which comes down to budgeting. It’s boring to talk about budgeting, but just because you study economics and understand what an interest rate is, it doesn’t mean you’re going to make good financial decisions or avoid buying a house you can’t afford. If you don’t have enough money at the end of the day, all of your knowledge is moot. You can be the smartest investor ever, but if you don’t put 50 bucks into your RRSP, you’re done. If we can learn the basics of budgeting at a young age, we’ll start on better footing.

You had a secure, stable job on Bay Street doing investment management for high net worth clients. What prompted you to leave, and how did you end up starting your own business?

I liked my job, and had no hate on for where I was; I worked for a very small, intimate, boutique firm, but when we got bought out by a bank, bank culture weirded me out. I learned a lot about how products are sold to people who aren’t high net worth clients, and it got me thinking, “where are all the people who aren’t millionaires going for financial help?” The answer was basically nowhere, so I wanted to do something addressing that, in an ethical, affordable way.

I saved up enough money to cover my rent and cell phone for one year, then took the plunge and quit my job. For the next year, instead of charging, I bartered my financial planning services to 310 millennial women in exchange for literally anything – a lasagna, a flight to Chicago, a Nintendo Wii gaming system, an iPhone – it was wild! It was probably the smartest/stupidest thing I’ve ever done.

After I decided this was for me, it was what I wanted to do, and I could make a business work out of it, I launched the New School of Finance instead of returning to Bay St. I had minimal startup money, a very tight budget, and in the beginning I was working out of my house. It’s definitely scary starting your own thing, but the smartest thing I did was ensure that I had my bills covered for long enough that I didn’t have to worry about getting evicted or being unreachable, even if I didn’t make a single dollar getting my new business going.

What is an average day like for you?

A day in the life of the New School of Finance is a pretty wild one. Most of the time, I’m seeing clients one on one, creating new courses, or I’m behind the camera doing a video shoot. It’s usually one of those three things, plus of course answering hours and hours of email!

What do you consider the pros and cons of being a financial planner?

I’m a financial planner and an entrepreneur. As an entrepreneur, sometimes wearing all the hats is pretty exhausting; I have never worked harder than I have in the last five years. The perks of being an entrepreneur outweigh the administrative tasks though; I don’t have to get approval for business decisions, I’m handling things on my own terms, and I’m fully self-expressed every single day. I’m really appreciative of that.

I love my job as a financial planner, but sometimes you have to get real with people who don’t want to hear it. In the past I’ve had to give hard news or a reality check to people who might be in a little bit of denial about their finances.

In such a competitive industry, how do you differentiate yourself?

One of the keys of entrepreneurship is to always be watching for and forecasting trends. If you don’t stay relevant, there’s a potential you’ll sink your business. I always think about how are people going to get financial advice five or ten years from now and try to align myself with what I think that may look like. My use of technology and online courses are unique in an industry that’s relatively old school.
In addition, I keep it real: I am who I am, all the time. My personality is disarming, I’m not intimidating, I wear jeans to the office, and I don’t put on airs. I try to give funny and fresh advice and not patronize anyone. Lastly, I take risks instead of always trying to play it safe, which also makes me stand out.

What exactly do you mean by ‘play it safe’? And how has risk-taking paid off for you?

To play it safe in finance would be to sell products; it’s a way easier business model to run. You give advice and sell a product, and it’s a way to make money increasingly over time.

I’m really passionate about giving unbiased advice though – and that means not selling products. Traditionally that could be considered risky, but it’s paid off in spades because I book out two to three months at a time. People love that my approach is affordable and unbiased, and definitely different than the norm.

Was there ever a big business risk you took that didn't pay off?

I got cyber-bullied once! I have an online video show where I gave a financial tip and advice on how to carry it out. In the financial industry it’s fairly common for advisers to avoid giving a strong opinion on something; you can open yourself up to being ridiculed if someone else disagrees, so it’s a risk. A well-known personal finance expert in the industry did not like what I said, copied me on a nasty tweet, and that person’s online community internet-hated me for 24 hours – it was horrific! I cried, and I called my mom. Because I was quite young at the time, I was pretty afraid for a while to take more risks.

The lesson was that if you are going to post something, stand by it, which I totally did. I took a risk and I lost, but I don’t regret anything about it, and I learned that it’s OK if people disagree with you. I still think it was smart advice – it just went against another person’s ethos; they happened to subscribe to a different way of financial planning. I really believe you shouldn’t be afraid to put something out there that you think has value to a specific type of person – it’s not necessary to always try to be everything to everyone.

How did you go about finding your audience, who are mostly female millennial entrepreneurs? Are they just the group who can naturally most relate to what you’re doing?

I think so; it started there because the people I understand the most started listening to what I was saying. I was talking from a personal point of view about things I wanted, and so giving tips for that exact demographic naturally helped create a following.

People tend to like what I’m about and tell their friends, who pass it on to their friends. That’s how the community got going – it started with me just being totally authentic, and because I am also a millennial female entrepreneur trying to figure my own shit out, that’s exactly who I ended up targeting as clients.

You were trailblazing the online lifestyle space with your own web series way before online video became a common marketing tool for businesses. Could you speak about that?

The web series Money Awesomeness was actually my first online adventure. A production company was interested in having me host a television show for regular tv programming, and we shot a pilot but it didn’t end up getting greenlit. The woman who leads that production company has such great vision, and thought that an online web series featuring me was maybe the way to go instead. This was back in 2012, before it was really popular to be doing something like that.

We experimented and played in the web space, and it became huge. Online commenting grew into online communities and naturally branched throughout social media. People share what they care about, and if you can get people to genuinely care – if you’ve had a real impact on someone’s life – the community that organically emerges can become the most amazing breeding ground for success, as well as the best conduit for growing your business.

Do you have a mentor?

I do. She was my boss on Bay Street, and she’s a formidable woman. I looked around the firm and thought: “Who do I want to be most like? Where do I want to go?” I’ve found having a mentor to be important – she’s definitely helped me navigate my career path.

In the beginning it was really intense coaching every quarter, but now we’re friends and I call her when I’m freaking out or excited about something; it’s a lot less formal at this point.

I’m also part of a mastermind group with other female entrepreneurs at the same level of business as I am. We’re not just starting out, but we’re not running Fortune 500 companies – we’re in the middle somewhere. All four of us jump on a monthly call, and we each get a 15-minute hot seat. You get to say, “Here’s what’s up in my life, in my business. I need help.” Then everybody chimes in with their advice or resources. Because we all work in different industries, I find the different approaches and opinions really valuable. Aside from me, one is in online business, one is a coach, one is a copywriter and one’s a web developer. I can chime in on some financial stuff, while other people have more to offer in areas like sales and marketing; it’s a really great sounding board.

When you’re running your own business, it’s often difficult to find balance. How do you maintain healthy levels of both work and play?

Sometimes I lose sight of how important balance is; when I am unbalanced, that’s when things start to slip in both my business and in my personal life. I try to shut my phone or laptop off so I can be fully present with friends and family, and alternately make sure that those things get the full attention they need when I’m focusing on work.

There are times when I have to say no to friends and family because it’s tax season, and it’s crazy, and I have to make a living. Then there are times I say no to clients because it’s the holidays, and my personal relationships take precedence.

Instead of trying to find balance in daily life–because some days are just insane–I try to find balance overall. At the end of the year, I sit down and say, “What do I want out of the next year that’s going to give me balance?” Maybe I want to travel with friends, I want to go to the cottage with my family a certain number of times; and what are my business goals? If at the end of the year I have accomplished the things I wrote, then I feel like I achieved balance, even though there are days I have no balance whatsoever.

Speaking of goal setting, how do you set your goals? And what do you do if things aren’t quite going to plan?

I do a vision board every single January 1st with a group I call my entrepreneur soul mates. We get together, we recover from New Year’s Eve, and we literally have arts and crafts; we cut pictures out from magazines and paint – it’s a really fun way to set goals.

I also map out a realistic plan: how many clients do I need, how many programs do I need to sell, how many meetings do I need to take? I make an actual to-do list. I print it month by month, and check to see if I’m on target or below target. It breaks down something that seems massive into manageable, clear steps so I don’t get overwhelmed. If things are not on track, I reorganize and reprioritize what’s happening; I’m always open to adjusting the plan – ALWAYS.

It’s all about setting intentions, right? You’re putting the intent out there, and you keep on strategizing and evolving the idea. I call it doing business on purpose, and I find it helps make sure I don’t end up spinning my wheels and saying yes to everything. I learned – the hard way – that I can’t do everything, and sometimes people will be upset with me, and that’s okay.

What qualifications would you suggest people interested in becoming financial planners seek out?

If you want to be in the financial industry you need to get accreditation. A CFP [Certified Financial Planner designation] is non-negotiable for financial planning; it will open all the doors, and it can help block out some of the noise. There are a lot of people who are financial experts, but that doesn’t mean they’re actually a CFP. There’s a big variance out there in terms of what clients are willing to pay for, and also in who they trust.

It’s worth it to invest in accreditation, even though the major learning in your business and in your life will come from actually sitting down with people. It’s a huge first step on your journey to make sure that you’re considered legit; whether you join a firm or strike it out on your own, you’ve got that designation to back you up.

Looking ahead, what upcoming trends do you see for the way people receive financial planning advice?

The whole mentality is shifting; as we millennials start to invest and learn more about finances we’re going to be wise and savvy to the fees we’re paying [for product-based financial planning] and we’re not going to stand for it. I think that what I do, unbiased fee-only financial planning is the future, and a lot of e-learning as well. The online trend is here already, and I think it will continue to grow as more and more people get excited about e-learning and are comfortable doing online courses.