Five Things Friday: Evan Carmichael | FreshGigs.ca

Five Things Friday: Evan Carmichael

Evan-Carmichael-Interview-Fresh-Gigs

Five Things Friday is a departure from the interviews and features we typically post. Part conversation, Part Proust Questionnaire – but with just five questions, Five Things Friday (hashtag alert! #5TF) shows the lighter (and sometimes sillier) side of our interviewees. We’ll be talking to everyone we can get our grubby little hands on; it’s our way of introducing you to the communications, marketing and creative cognoscenti who rock their respective industries. This week, Joanne M. Brathwaite chats via Google Hangout with entrepreneur Evan Carmichael.

What was your first business idea and what did you do with it?

My first business idea was when I was five years old. I convinced my 3-year-old little sister to make paintings with me and go sell them door-to-door. We sold one to our next-door neighbor for ten cents, I think. But this is interesting: I had a whole bunch of ideas growing up, but I never thought I was going to be an entrepreneur, mostly because of my environment; I didn’t have entrepreneurs in my family – my parents had normal, safe jobs (although, they did always encourage me to do whatever I wanted).

So I had lemonade stands…I once tried to turn raisins into grapes and tried to sell them (not realizing it goes the other way around!). I tried selling baseball cards at garage sales and I’d make more money than anyone in my family. Then there were a bunch of ideas that I tried that never really took off.

The first adult idea that I had, that ended up doing well was a biotech software company. I didn’t come up with the idea; I met two people at U of T who had a piece of software, and they wanted to get it out there more. I came on to help market it and grow the business, and then became an owner in the company. So it was the three of us owners, helping researchers find cures for cancer and diabetes and AIDS and all sorts of important issues.

What made you want to be an entrepreneur? Was it actually a choice – or did entrepreneurship find you?

I was in my third year university when I connected with the entrepreneurs, but we’re sucking at it. I’d kind of taken it on as a challenge, sort of like, “Well, why not? I’ve got nothing else to do and school’s kind of boring, so sure, I’d be willing to help!”

I wasn’t making any money – like 300 bucks a month – massively below poverty line – and then when I was coming into fourth year, I had and opportunity to work for Merrill Lynch. A year prior, that were like, my dream job. So here they were, offering $80-100k starting salary, and they flew me to New York and put me up at the Waldorf Astoria for the weekend…with promises to fly around the world and do deals – something I thought I always wanted!

But coming out of that, I felt like I could go take this job, but what if this business takes off and I’m not a part of it, or I didn’t give it my fullest? That helped me to make a decision. I told myself I would give it a year to try to make my business happen, and if it didn’t I could always go back and get the safe job that I always wanted.

And now it all makes sense, but at the time it was super scary because all my friends wanted those jobs but I just didn’t want to have to live with regret…and I use that framework with what I’m doing now. When I’m thinking about any really big decisions, I try to fast forward to age 80 – and when I look back on my life am I going to regret not taking a particular action?

I’m super grateful that I made that choice, because a couple years later I met up with some of my friends who were all asking, “Evan, how do I become an entrepreneur, because I hate this job that I’m in!” and I’m like Oh, man! That could have been me!

What habits helped make you successful?

I think your environment and your habits hold you where you are. Any time you change and break through and make it to that next level it’s because you’ve changed your environment or your habits somehow.

When I wake up and jot down three things that I’m grateful for – just quickly on a notepad beside me. I find starting the day with a little bit of gratitude really helps me. Then I’ll put on some music; I find it’s a really great way to change your state. I have what I call the #Believe Playlist, and it’s a mix of stuff. Some of it’s salsa, some of it’s Eminem, it’s all over the place.

My other secrets:

I don’t use a cell phone, and I don’t use the phone.
I usually do Skype calling. I don’t use a phone, because its’ really other people’s agenda for your time. I hate being interrupted when I’m in the flow on something

Chunking my time.
Every day I do something differently.

  • Mondays are for business; I’m in the midst of an acquisition, so I spend Monday working on that.
  • Tuesday is my writing day; I’m writing a book with Penguin Random House and I have to get it done by January, so I walk to Whole Foods and I write.
  • Wednesday’s my video day so I’ll record videos…I do three videos for every day that come out on the channels – so that’s 20 videos plus that I have to record.
  • All of my public-facing stuff is on a Thursday: Google Hangouts, the radio show, interviews…Skype calls… they’re always on a Thursday.
  • Friday is CEO/Big Picture day.

I have different days for different things. Public-facing, energetic Evan is different from introverted, let-me-get-this-stuff-done-don’t-talk-to-me Evan. I do this because I have a hard time switching; I couldn’t write for half the day and then be communicative and outgoing the other half.

Chunking my time really helps my productivity.

So, you’re an avid salsa dancer – can you make the connection between salsa and business? Is there one?

You know, I believe in people. I encourage people when others don’t and I often see greatness in people when they don’t see it in themselves. And the way that most makes sense to me is through entrepreneurship. I can see someone with great communication skills, or writing skills, or artistic skills and say to them, “you’d make a great entrepreneur” when they may not have anyone in their environment telling them that.

Your environment and your habits hold you where you are. Any time you change and break through and make it to that next level it’s because you’ve changed your environment or your habits somehow.

So the #Believe mentality works mostly through entrepreneurship but it definitely applies to salsa in that a lot of people come to learn, but doubting themselves, saying, “I can’t be a great dance.” It’s anywhere from helping students who are trying to pick up steps to helping out the instructors/potential instructors get better and believe in themselves and push themselves – it’s basically seeing a brighter future in someone than they see in themselves.

What‘s next for you? Where do you go from here?

That’s a great question. My bigger term life ambition is to help a billion entrepreneurs, and so I am all-in on two projects: one is my YouTube channel, and the other is my book. And since I’ve shifted towards thinking about having a global impact, it changes the type of projects that I want to get involved with and work on.

So while I love working one-on-one with entrepreneurs, I don’t do nearly as much as I used to because it doesn’t scale as much. I’ve got YouTube on the brain, and everything is seen through a YouTube filter. I love the platform. My next goal is to hit a million subscribers; we’ll close out the month at around a hundred and fifty thousand.

And then my book! I’ve never written one before, and I don’t’ know if I’m going to continue on as a writer or if it’s a one-off thing.

But really, I’m still young…I’m 35-and-a-half (am I even allowed to do half-ages, anymore?) all of my longer-term goals have changed so much. I know people have ten-year goals and five-year goals but I can’t do it. For me, if I see a five-year goal I want to make it happen in one. I don’t have five-year goals. It’s now! Go! Attack!


Toronto-based Evan Carmichael #Believes in entrepreneurs. At 19, he built then sold a biotech software company. At 22, he was a VC helping raise $500k to $15mil. He now runs EvanCarmichael.com, a popular website for entrepreneurs. He has set two world records, uses a stand-up desk, rides a Vespa, raises funds for Kiva, wears five-toe shoes and created Entrepreneur trading cards. He loves being married, his son, salsa dancing, DJing, League of Legends, and the Toronto Blue Jays.

This edition of #FiveThingsFriday was actually done live via GoogleHangout and posted to Evan’s Youtube Channel. View the full interview here.


Know anyone who would be a great fit for #5TF? We want to hear from you. Drop us a line, or leave a comment below.


  • Thanks for the love – great article and was lots of fun to participate in 🙂

    • Great article Evan and FreshGigs.ca team!

    • You’re welcome, Evan! And thank YOU for giving us a moment (or two) of your time.