A New Wave Podcast

Afraj Gill: Health , Wealth and Happiness

portrait of Afraj Gill
Afraj Gill Currently, Afraj Gill is a Partner at On Deck and was previously a Director / GM at the Royal Bank of Canada's ventures arm. Recently, he also co-founded Drop Mobility, one of the first micro-mobility companies in North America that was backed by top Silicon Valley investors.

Season 5 — September 14, 2022

What advice would you tell your 18-year-old self? 

  1. Pursue your curiosity. People are not fearful of failure, but they’re afraid of success. 
  2. Immigrants grow up in an environment where they must stay within their lane. Stay out of trouble, go to school, and get good grades. It’s something some of us have to grow out of, and I would suggest not being fearful of taking those big swings, and don’t be afraid to succeed, especially with things outside of your comfort zone.
  3. A second method is meditation. To my younger self, I would recommend trying it out. 
  4. The third piece of advice would be around being grounded and pragmatic. I experimented a lot when I was in university, built a lot of products, worked on a lot of projects, and tinkered around a lot. Throughout those times, I  got turned down by many investors but still kept going. So just try things and see where it takes you.

Do you think part of fostering resilience is detaching oneself a little bit from the outcome?

  1. The most important thing is taking a swing. The worst thing you can do is not keep taking swings, pick up the bat. You never know as you just might hit a home run. 
  2. There’s a difference between experimental failures and operational failures. A lot of it also comes down to unlearning everything you’ve learned. Especially, given the nature of our education system. 
  3. To achieve the success you desire, you will fail. However, when you fail, you should just take a moment, pause, and ask yourself what have you earned, and what can you improve on. What will I do differently next time?

What’s the biggest challenge of scaling a community, like on-deck?

  1. As you scale, you’re trying to bring and keep a high-quality group of people. On Deck is very big on making sure that the CEOs that are brought in, are the highest quality CEOs, and equally important, making sure they’re a good community fit.
  2. This could be like, does the CEO find value in peer-to-peer learning? On Deck has noticed that most of the people in that camp building, and are winning companies,  really do appreciate and respect the need for peer-to-peer learning and being part of a network.
  3. There are things that an entrepreneur, board member or even manager cannot bring up. Sometimes people just need to share with a group of peers who understand where they’re  coming from. And that’s part of the reason I think like we’re building such a thriving ecosystem, and community.
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