4 Lessons Learned from Running Canada’s Largest Student Entrepreneur Conference

Isabel Gan
7 min readApr 1, 2019

850 attendees. 30+ campuses. 40+ sponsors and community partners. I ran the largest student entrepreneur conference in Canada for 2-years in a row (and 1 year being on the team) and now I’m passing over the baton.

However, after leading a total of 13 different teams and growing the conference in many ways, it was something I couldn’t do on my own.

So here are my thoughts and lessons after a crazy 3-year journey of exponential self-growth:

1. Community is everything

A wise friend once told me: “ Don’t get a job because of your resume. Get a job because of your network.” and I remember thinking that it was so counter-cultural.

I remember when I first arrived in Ottawa, it was such a big, scary city to me- an international student from Singapore. I also remember when Andre Bouzout, Director 2016, was telling me about sending a cold email, I was extremely confused- “who would pay attention to this 19-year-old girl who has no experience and nothing to prove?”

I remember when I received my first email response (who happened to be my biggest mentor to date), I was nervous that she would’ve thought I was wasting her time.

After having over 10+ personal mentors, networking with over 100+ companies and raising over $100k in corporate sponsorship to date, I learned a valuable lesson: people want to invest in you as long as you give them the chance to do so. As a student, there are so many people out there that are willing to help, that are willing to invest in your personal growth. All you have to do is ask.

When I say getting people to invest in you, I don’t mean investment in a selfish way. Investment means getting people to allocate their time/energy because they have an expectation of some benefit in the future. By benefit, that means that they see potential in you becoming something greater than you are now, and that they see your determination to do something bigger than yourself.

Because of the community I have surrounded myself with (p.s. thank you to all of my amazing mentors), I have now grown into someone that I never knew I could grow into. From being a disbeliever in the potential I could achieve, to a woman who is confident of where she can go and what she can accomplish if she puts her mind to it. Why? Because I have a community that believes in me and supports me regardless of how lofty my goals may be.

2. Lead from the back, not the front

Cliche. I know.

But to quote Rob Villeneuve, our emcee and my current CEO, he said that I was “cool as a cucumber” during the week leading up to Legacy and during the weekend. During the weekend, I was reflecting on why I was so relaxed.

Many people said it was due to my 3-year experience, but I think it was definitely something bigger than that: I had the right people on the bus. With a nimble organizing team of 11 people, and a volunteer onsite team consisting of 30 driven students, they were self-driven and quick to think on their feet.

In my last year of leading the Legacy team, I restructured the organization that resulted in me taking a more hands-off approach, and admittedly, that made me extremely nervous. To trust a new hire to run all the marketing campaigns without my supervision? To entrust all my big ideas to someone in the hopes that they will execute it as planned? It was an extremely strange concept of “letting go” all of the control I had.

However, 8 short months later, we ran the biggest and best Legacy conference to date. Because I was willing to let go, everyone on the team took ownership of their roles and were confident to try things out. They were assured that they could fail fast and fail forward because I had their back.

Because I was willing to lead from the back, we were able to launch crazy campaigns like these:

People thought we were crazy in imitating the Fyre festival given that it was one of the biggest, widely-documented failure. It ended up being one of Legacy’s most successful campaigns to date.

We were able to get a few of our biggest speakers to date (i.e. co-founder of Apple Siri, co-founder of Rotten Tomatoes). We were able to set up the biggest, most professionally-run stage we’ve had to date. We were able to have the biggest reach in schools from all-across Canada.

Because I enabled the team to dream big, and to envision the conference as something bigger than myself.

3. Challenge the status quo

In the short span of 3-years in being part of the Legacy team, I was able to start new Legacy ideas and kickstart new campaigns.

It was tradition that the Director of Legacy had to be overworked. Why?

It was tradition that the last two weeks was to be crazy hectic for all teams. Why?

It was known that Legacy only targeted students from Ontario and Quebec. Why?

It was known that Legacy is just a massive conference. Why?

By challenging the status quo and setting crazy, ambitious goals, we were able to make Legacy bigger than it actually was. We launched a pitch competition, coding boot camps, ideation workshops and expanded our reach across provinces. We hired a smaller, intentional team, and we got faculties all-across Canada to provide funding to enable more students to attend our conference.

Now don’t get me wrong- not all of the lofty goals were met. I’ve met some tough failures too. I remember telling one of my mentors that I was going to grow the conference from 700 people to 1,000 in less than a year, with no marketing experience whatsoever. He told me that I was overambitious and that it was “60% growth”, which made me want to prove him even more wrong.

Within the last two weeks prior to the Legacy Conference 2018, I had to humble myself by calling every sponsor that was investing money into our conference and tell them that we were only expecting 750 attendees that year. That we could not meet our goal of 1,000. It was pretty embarrassing for me, but it didn’t stop me from continuing to dream big.

The point? Don’t be afraid to dream big, but know what the steps are in getting to that big dream. I know that I will fall, and I know that I may fail. But through each stumble comes a tactical lesson that I can use on the next bigger goal.

4. Never stop learning

In the summer of 2017, I challenged myself to read a new book a week. I learned a lot of cool ideas and became an extremely fast reader. However, I never knew how those ideas could apply to my life, until I tested it out and understood how those ideas could mean something to me.

活到老,学到老” (translation: live til you’re old, learn til you’re old). That’s what my grandpa told my dad when he was young, and what my dad eventually told me when I was young. I don’t believe that I’ll ever reach the “learning finish line”, because there’s always something new to learn about.

Through the act of journaling and reflecting, I have learned immensely through my experience. From a fixed mindset of only aiming to get good grades, to a growth mindset of wanting to discover new things beyond the classroom. From hating the idea of entrepreneurship as a child, to becoming an active advocate of the entrepreneurs, creators and doers. From being extremely uninterested in the field of STEM, to learning HTML, CSS, UX Design, Photoshop and Premiere Pro on my own. To becoming a massive advocate for women-in-business and women-in-tech. I can’t wait to see what’s next.

So even though the 3-year Legacy journey has come to an end as I pass on the torch to the incoming new team, it also signifies the beginning of a new challenge.

I’m so excited to chase a new goal, become a new person and discover new insights I never thought I would ever encounter.

Thank you, the Legacy Conference, for letting me leave a legacy.

If you liked this article, make sure you give it a 👏.

📝 Read this story later in Journal.

🗞 Wake up every Sunday morning to the week’s most noteworthy Tech stories, opinions, and news waiting in your inbox: Get the noteworthy newsletter >

--

--

Isabel Gan

Growth PM @ Unbounce | writing about all things product & mental models