Last weekend I attended an event called Inspire Toronto, geared towards 18-25 year old Italian Canadians (all were welcome) during the recently established Italian Heritage Month. Before you click away, I’ve highlighted key learnings from 5 incredible Canadians (artists and business people who are all equally passionate and family oriented) that will resonate with you regardless of your heritage, where you love or your life dream.

Nick Di Donato, President & CEO of Liberty Entertainment Group

Growing up to immigrant parents who owned a restaurant, his father warned him to never get into the business. Nick never wanted to work on the restaurant floor, but he always loved clubs, culture and going out (a passion for some). With the business in his blood and early jobs as a waiter, he eventually built an entertainment empire, by diverisfying the location, clientele and concept of his properties. He also chose to invest in historic buildings like the Courthouse (complete with jail cells) to really stand out. His advice:

Get an Education (in anything) and experience in the corporate world first

After getting an engineering degree to please his parents, Nick believes school taught him how to think and adds intrigue and credibilty to his current pursuits (i.e. a surgeon turned painter). I personally don’t think you NEED university to be successful (it isn’t for everyone), but I do think taking something you like or something challenging in school is worth it.

Nick worked as an engineer at Imperial Oil for 6 years, before quitting to pursue his dream (wasn’t feeling fulfilled) and was able to apply similar organizational structures and process efficiencies to his own business, especially as it grew. It feels like a lot of people who leave corporate to pursue their own dream describe it as a quasi prison break (more of a negative spin). If you are going to spend the time at your job, you might as well embrace it to get the most out it (or leave, especially if you hear the whisper urging you to execute your dream).

I sometimes worry that if I spend 3+ years in a corporation, I’ll become complacent, lose drive and never leave.  Nick  proved this theory wrong and showed that everyone is on their own timeline. There is no magic tenure formula to take your leap of faith.   Writing, especially, is about drawing from your life experience – the more you live, the better you write.

Take Planned Risks and start your side hustle before going for broke

Nick didn’t just quit Imperial Oil to start his first restaurant – it was launched one year before quitting and was a huge sacrifice in the short run. If you are like me and need lots of sleep, this strategy may not appeal, but it highlights that it is okay to be pragmatic and take steps slowly in order to build confidence before leaping.

Nick Di Donato: From engineer to Club/Resto Mogul

Enrico Colantoni, Actor (Flash Point, Just Shoot Me, Veronica Mars)

Everything has a lack of stability and there are no guarantees in life so why not risk bigger?

After attending the University of Toronto for one year, Enrico moved to The Big Apple, like many brave souls before him, to study acting formally in the land of  artists. In doing this, he had to withstand the forces of “are you crazy?” and disapproval from his parents, which only made him want to prove himself even more. Enrico basically figured that nothing in life is guaranteed and you have to at least take a shot or live with regret.

I think the recent recession has proven that many “stable” jobs aren’t bullet proof. Also just because you get a university degree and start at a great company doesn’t guarantee success, in the sense of becoming CEO or Executive VP or even starting your own business (if that is what success means to you). The odds are worse if you stick to something you aren’t passionate about = misalignment.

Have faith that the powers that be will continue to carry you forward

I asked Enrico how he dealt with rejection, when there are so many budding actors who pack it in before their big break comes to fruition. He simply said he had faith – he focused on the good things from his journey and believed those would continue (more in front of you than behind you). Perhaps that is the key to tenacity?

Rick the Temp (aka my tween crush) bantering with Enrico Colantoni, TV Star

Rick Campanelli, Entertainment Tonight Host (former Much Music VJ)

Approach any task creatively to stand out / Relish being the gopher

Rick, the gracious Master of Ceremonies, got his start by winning a contest to intern at Much Music, but it took him a year to get on camera, after he zealously fetched coffee and cleaned sets. He also embedded his demo reel inside things like a football and novel in order to get the attention of his boss in a fun, creative, persistent way. When an opening came up, he stepped in and continued to approach his celebrity interviews with a unique spin and the goal to: make this interview memorable for the artist (who does so much press), and unearth new information for the viewer. 16 years later, he is still rocking it.

Anthony Lacavera, Chairman of WindMobile and Chairman/CEO of Global Live

Take on goliath after building credibility & identifying market opportunity. Ignore the haters.

In Business School you study these 5 assessment factors to see if it makes sense to explore entering a business, including barriers of entry, which are high in a monopolistic industry like the Telecomm one in Canada. If Anthony listened to this ideology, he wouldn’t be where he is today – but he saw an opporunity to launch a new mobile brand and persisted to gain financial backing after years of hard work.  Besides, he enjoys being the underdog.

Anthony gained his footing in the communications industry through B2B video conferencing and had years of experience taking on progressively larger loans (from 50k to 200M) while providing a return on investment.

After hearing so many dissatisfied comments re: phone providers, he launched a website that invited all Canadians to give feedback on what they wanted from a wireless service. This was a cheap way to gain valuable market research, while establishing his brand as customer-friendly and fearless.

Ivana Santilli, Juno award winning singer

Fail at being someone else. Be yourself instead.

With presence, tons of soul and intellect, Ivana shared that when she initially started with her now defunct group Bass is Base , she was marketed in the US as a white girl to African Americans and was successful but really felt like she came into her own when she owned herself as a French, Italian Canadian singing in both languages while maintaining her unique sound.  She released her first solo album independently and has maintained true to her vision of mixing the old with the new. For her, it really is all about the craft and not the celebrity.

I was invited to this event by the Chair – Luciano Volpe, who I also happened to TA for. I’m very proud of his initiative and can’t wait to see this event evolve in the years to come.
What message stands out to you the most?