Earlier this month, I announced the launch of the “My Day” series and invited entrepreneurs from across Canada to participate in an email interview where I sent them questions about what it’s like to be an entrepreneur, how they make themselves stand out, and what an (a)typical day looks like for them.

The first person to respond to my call for action that is from outside of the Bay of Quinte region is Jenny Smith, the President & Creative Director of Ray Creative Agency. Ray’s is a creative shop & ideas company located in St. John’s, Newfoundland. They launched in 2013, and have been racking up awards like crazy (check out Jenny’s bio on their website, WOW). For example, in 2017 they were named the “Leader in Growth and Sales” by the St. John’s Board of Trade and one of Canada Business & PROFIT’s “STARTUP 50 of Canada’s Top New Growth Companies”. To cap that all off, Jenny Smith was named an EY Entrepreneur Ff The Year 2017 Atlantic finalist!

Without further ado, let’s see what Jenny has to say about being an entrepreneur, the importance of sticking to a regular schedule, and how her and her team refuse to see geography as barrier for building relationships with their customers (a philosophy I’m also embracing with BoQ Young Entrepreneurs)!

©David Howells 2013

Question 1: Describe yourself in 3 words only.

  • Driven
  • Generous
  • Fearless

Question 2: Tell me more about your business(es)? What kind are they?

  • Ray is an advertising agency that delivers strategic and creative ideas to help solve business problems.

Question 3: Where does your entrepreneurial drive come from?

  • My drive comes from a strong work ethic that was instilled in me at a very young age. I work my ass off and have a deep desire to lead people and help clients be successful.
  • Above all, I love building something great from nothing. I am never satisfied with something that’s just simply ‘good.’ Mediocrity is the enemy.
  • What are your sources of inspiration? The North Atlantic, the Newfoundland landscape, my children, and vodka martinis :).

Question 4: Considering how fierce competition is among your industry, what are your business(es) competitive advantages?

  • We have a very small, core team who is highly seasoned, nimble, and efficient. We consider ourselves, ‘navy seals’ vs. ‘the army’ (like what you get when you work with a big agency with lots of staff and overhead). We don’t bait and switch… the team who pitches your work, works on your business.
  • We do high quality work without the typical overhead. Our structure of a core senior team that can expand to suit clients’ needs allows us to produce more creative work with a smaller team – reducing costs associated with having everyone on staff. We also take on small and not-for-profit client work that typically means thinking creatively to make a small budget have big impact.
  • At Ray, we’re also free of fluff in the way we work and communicate. We have a flat organizational structure where our clients have access to all players on our team. There’s no pony show – just hardworking people focused on getting clients what they need.
  • Every agency says they have sparkling creative, but ours really does have a special something that we like to think comes from the water in Newfoundland. Our combined talent, industry knowledge, credentials, and awards won by the team make Ray one of the country’s strongest and most experienced shops. But our secret sauce is the different way of looking at the world that’s just part of a Newfoundlander’s soul: ingenuity, resourcefulness, a way with a yarn, and a good dose of wit.
  • Our business model reflects that spirit. We’re entrepreneurial, flexible, and nimble, and the clients we service tend to be that way too.
  • What makes you stand out in the crowd? We don’t follow the rules. We’re always considering different ways of bringing a brand to life.
    • For example, our Freshco client, Mandy Rennehan, is a larger-than-life self-made multi-millionaire who was meant to be a star. So what did Ray do? We created a spin- off content creation production company called Chronic Media as a step to sell her to TV networks. Stay tuned for the new series Mandytown, hitting a small screen in the near future.
    • We’re also big on long distance relationships. In fact, 60% of our clients are out of province. Our business model deliberately refuses to recognize geography as a barrier, and in this day and age, that should be a given. Because we constantly deal in virtual communication with our teams and our clients, we’re singularly equipped to be productive and collaborative in that environment.
    • Fact: for our first two years in business, our team worked virtually (with regular meetings at co-working office space and pubs).

Question 5: No two days are often the same for an entrepreneur, but what does a typical day look like for you?

  • It’s so true – every day is very different. I travel a lot so that throws a big wrench into life in general. All that said, here’s what a ‘typical’ day looks like: I wake up at 6:00am. The first thing I do is put on a giant pot of coffee. Then I check my email (and drink all the coffee). If there’s anything urgent, I address it right away. Then I prep breakfast and make lunches for my kids for school. Breakfast is always eaten together. After the children are gone, I work out (exercise video at home, a hike around Signal Hill or a run around Quidi Vidi lake). This time is precious because it’s my thinking time where I solve problems.
  • Upon return, I get ready to hit the office. I get the daily low down from the team and address any creative or client issues. There are usually two to three meetings a day. I eat lunch at 12:00 every day – I only go out if it’s a client meeting or if I’m taking an employee out. I typically bring my lunch to work. I leave work at 4:00 to spend an hour with my children and to help them with homework or to drive them to their activities. During this time, I’m also answering emails or addressing any work issues. Then comes dinner prep and eating. And there’s always several activities every evening that require driving.
  • After the kids are in bed, I am on email again. I look at what’s in store for the next day and make a big list of to-dos. At around 10:00pm, I like to watch TV/Netflix for about an hour to unwind or chat with my husband. This may include a glass of wine or martini, depending on my mood! Then it’s bed at around 11:30 or 12:00.

Question 6: What do you do daily to grow as a person?

  • Exercise, read the papers (Globe & Mail, New York Times, cnn.com, and local stuff) and learn from the young people I work with. They are full of fresh ideas – I love that! I also spend time with my parents and siblings who are great sounding boards and mentors.

Question 7: What tricks have you discovered to keep you focused, productive and achieve a decent work/life balance?

  • Sweat every day. Exercise is great for your brain and body.
  • I also delegate. I can’t take everything on. I hire talented people whom I trust to handle the things I can’t.
  • During the summer, I garden a lot. It’s very Zen and therapeutic. As is cooking. I love it and especially love to throw massive dinner parties. Doing things outside work to help calm my mind helps me stay focused.
  • Lastly, I write everything I have to on paper. I create my to-do list every night. It helps me get shit done!

Question 8: What popular entrepreneurial advice do you agree/disagree with?

  • I agree with: working really hard, learning from failure and using it as a weapon, and treating people with respect.
  • I disagree with: taking other people down, not admitting to mistakes, and working 24/7.

Question 9: What’s your favourite metaphor to describe entrepreneurship?

  • It’s like jumping out of an airplane and figuring out how to make a parachute on the way down.

Question 10: What was the toughest moment you have experienced in your business practice? How did you succeed to get over it and move forward?

  • Most of my toughest moments are HR issues. It’s so incredibly difficult when you know an employee is at fault or has lied to your face. In these cases, I’ve had to get legal advice and intervention. Getting rid of toxic people is the key to sustaining a great culture.

Lastly, if someone wants more information, what is the best way to contact you?

  • jenny@rayagency.ca


If you would like to be featured in an upcoming “My Day” series post, please send me an email either through the Contact page or directly to boqyoungentrepreneurs@outlook.com