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I Make a Living

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I Make a Living I Make a Living is a podcast for people who work for themselves. Whether you are a freelancer, small business owner or entrepreneur, our mission is to provide a space for insightful and candid conversations about what “making a living” means to you.

I Make a Living I Make a Living is a podcast for people who work for themselves. Whether you are a freelancer, small business owner or entrepreneur, our mission is to provide a space for insightful and candid conversations about what “making a living” means to you.
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Toronto, Ontario


I Make a Living I Make a Living is a podcast for people who work for themselves. Whether you are a freelancer, small business owner or entrepreneur, our mission is to provide a space for insightful and candid conversations about what “making a living” means to you.








Success and Unique Businesses- Season Finale

The idea of success has many faces and iterations, most of us relate success to financial freedom or fame, but when you are an entrepreneur, success can mean much more than that. Who knew that waiting in line for hours on end could turn into full fledge operation, that someone could find joy in dressing up as Batman just to bring joy to tourists or that selling finger-painting art on Facebook for $50 could turn into a million dollar business or that anyone would pay for literally garbage...


Failure- Sam Rosen- Michelle Horton

The statistics aren’t too friendly when it comes to the longevity of small businesses. Nearly 50% fail at the five year mark. But, how does knowing this statistic help you? Most people can talk about failure ethereally—hardships builds character, you can’t succeed without failing, you know, those kinds of phrases. But, when it comes to us, you, specifically failing, you don’t want to and often times we do everything in our power to avoid thinking about the possibility of it. But, accepting...


How To Start a Start-Up- Seth Radman

Coming up with problems without immediately trying to fix them is a lot harder than you’d think. Our minds really are trained to find solutions. But, throughout this episode we focus the most on the beginning two steps— The biggest take away from this whole conversation is to start at the beginning, with the problem—and spend a lot of time there. The last thing you want to do is create a solution that no one wants or is willing to buy into. We also discover that starting a startup is not...


Branding and Social Media- Beverley Cheng

Episode Guests Beverley Cheng- Born To Sweat Zoey Masters- Instagram Jeremy Bailey- LinkedIn Center Stage Christopher Jones- SeeJonesWork “To be featured on Center Stage, send us a voice message!” Disclaimer: The views and opinions expressed on this podcast are those of the guests and production team and do not necessarily reflect the official policy or position of '2ndSite.INC dba FreshBooks, its employees or affiliates.'


Growing Your Business- Kristen Pumphrey

Every business starts somewhere before it's a well-oiled machine. Sometimes it's at your kitchen counter in-between your part-time jobs. The whole concept of growing your business means it was small at some point. This season, we've seen that it takes a lot to start a business from the ground up. Not everyone is cut out to be an entrepreneur. It takes a lot of diligence and hard work to get any business off the ground. It's not for the faint of heart. There are a lot of ups, downs,...


Developing Your Business

For a while now, we have been planning an episode on diversifying your business. We wanted to document the story of an individual who had just started their business and what it looked like to establish diversification in the initial steps of development. But, the story we ended up capturing was much more specific; someone who was forced to diversify due to external issues out of their control. So, we briefly discuss the general idea of diversification and offer a few tips on starting your...


Work-Life Balance

Productivity is important as an entrepreneur but so is the balance between your personal life and your work life. If you’re not careful you can easily burn yourself out, harm personal relationships, and actually become less productive because you’re not giving yourself the space to rejuvenate—which is often times why people are most productive. It’s a balance. The Western world is in a bit of an epidemic these days. Some of the leading organizations in today’s world give their employees...



Episode 05“It’s all about the money....and taxes.” Today’s episode is about one of the most dreaded yet necessary pains every entrepreneur has to endure...tax season. No matter how big or small your business is, taxes are always going to be somewhat complicated, confusing and could create a lot of troubles if not dealt with appropriately. We are here to help! Our featured guest, Paco de Leon is a self-proclaimed ‘money nerd,’ she founded “The Hell Yeah Group” to help small creative...


Being a Female Entrepreneur PT. 2

Episode 04 "Being a Female Entrepreneur PT. 2" Welcome to the second episode of our 2-part series in honor of “Women’s History Month.” On this episode, we explore the role of equity in the female entrepreneurial world. We hear from 2 female business owners who share their experiences and journies to success. Equality. This is the conversation we’re having during women’s history month. However, to give this topic justice, we need also to consider what part equity plays. Equity is the...


Being a Female Entrepreneur PT. 1

Episode 03- "Being a Female Entrepreneur PT1" Welcome to a special 2-part series in honour of Women's History Month. We take a look at the entrepreneurship world from a female perspective. Being a woman in the small business world isn’t easy. Even if you don’t self-identify as a woman, because of recent media movements, you can probably gather that it’s not exactly a walk in the park for females. There’s been a shift, on a large scale, in society recently. The #metoo and #timesup...


How I Work- Productivity and Workspace

The average entrepreneur works over 60 hours a week. That’s 20 plus hours more than the traditional 9-5er. Are you using your time wisely? Explore how other self-employed folks choose to approach their productivity. Hal Elrod, best-selling author of the Miracle Morning book shares with us why morning routines can boost your productivity throughout the day. Hal is a wealth of knowledge when it comes to morning routines and jumpstarting your day in the best way possible. If you want to read...


A New World of Work

Episode 01- Present and Future of Entrepreneurship Why are people turning to self-employment in the current economy? Alex, a freelancer who thought jumping ship and starting her journey would be a lot simpler than it turned out to be. A whole new set of challenges arise once someone decides to venture into entrepreneurship and a lot of times, those challenges are not-so-common knowledge. We talk to some FreshBooks folks who share some interesting numbers and data on the present and...


Coming Soon!

The #imakealiving Podcast powered by FreshBooks is back! Our new host Darbi Masters will dig deep into the fascinating and ever-growing world of entrepreneurship. Join us every other Monday starting February 11th for honest conversations on success, failure and what it is to make a living as a self-employed individual in today's world. Don't forget to subscribe to get the latest episodes as soon as we release them!