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Meet the Investor: Jason Drummond, Angel Investor and Entrepreneur

Jason Drummond, Broad Street Bulls
Jason Drummond, Broad Street Bulls

Jason Drummond is an active entrepreneur, investor, and business owner. He’s a founder in a multitude of sectors, with a track record in technology, hospitality, cannabis, retail and energy—and passionate about supporting and promoting Saskatchewan. He has formed numerous local companies and brands such as Leo’s Hospitality Group which owns and operates 13 Leopold’s Tavern restaurants across the prairies, Victoria’s Tavern restaurant in downtown Regina, two Gud Eats plant-based restaurants, Path CoWork in downtown Regina, Farmer Jane Cannabis in Regina, as well as two venture funds with Sask roots—Broad Street Bulls and Green Acre Capital. Broad Street Bulls was founded as an extension of Jason’s passion and apt to grow the local innovation economy in Saskatchewan. He is currently serving his fourth year as a board member of Economic Development Regina and his third year serving as Chair of the Council for Entrepreneurship Growth.

Industry West caught up with Jason to ask a few questions about how he became an entrepreneur and investor.

  1. How did you become an entrepreneur?

“I learned what an entrepreneur was at an early age as my father became a successful businessperson and entrepreneur while I was a teenager. From that point on I knew I wanted to eventually run a business. But I really didn’t become an entrepreneur until about eight to 10 years ago after gaining a bunch of work and investment experience.”

  1. How did you become an angel investor?

“There used to be a Sask Angel network located in Regina and a guy named Don Black was very involved in the network. He brought a tech deal our way and that was really my first interaction with angel investing.”

  1. What is your investing philosophy?

“Invest in people, especially those with some sort of edge in their industry or in their approach.”

  1. What do you look for in a startup investment?

“People. Most startups aren’t going to work out, though it’s a great process for founders as they learn a ton and can use those learnings in their next venture. However, in a startup, I really look for founders you can believe in; they need to really be able to sell you on their idea. Although they may not have all the answers, they should know their business and industry inside and out, so you can trust that they will do everything they can to find the answers.”

  1. What advice would you give a startup preparing their pitch?

“Practice the pitch over and over. Get comfortable and make sure to get feedback from family, friends or peers and then make sure you cover all angles. Go through the (sometimes painful) process of building the pitch because by doing that you can learn something about yourself, your team, your product, your sales strategy, or your pitch. The process is everything so don’t try to skip it or find a hack.”

  1. What advice would you give someone considering angel investing?

“Interact with fellow angels who have more experience than you and be patient. Don’t fall for the first pitch, make sure to see a whole bunch of deals before placing your first cheque.”

  1. What have been some highlights in your time as an angel investor?

“Meeting founders and people in the network and learning about new ways to do business. But really, it’s about the people and seeing them have success.”

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