
The Hard Part with Evan McCann
The Hard Part, hosted by Evan McCann, uncovers the stories, strategies, and playbooks of Canada’s most influential founders, investors, and leaders. While Canadian innovators often fly under the radar compared to their American peers, The Hard Part shines a spotlight on their impact, redefining Canada’s role in global entrepreneurship.
Latest episodes

Jun 23, 2023 • 49min
Tyler Dyck and Brandon Goode from Outro Health
Tyler Dyck and Brandon Goode are the Co-Founders of Outro Health. Outro is the first digital healthcare solution dedicated to safely discontinuing psychiatric medications, starting with antidepressants. In this episode, we discuss their background at Field Trip Health, why are there so many antidepressants prescribed, why there is a gap in assisting people getting off antidepressants and the strategy behind their business model.
Check out Outro's stuff
The Outro Library
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

Jun 19, 2023 • 54min
Daryl Louie from AntiSocial
Daryl Louie is the Co-Founder of AntiSocial Media Solutions (acquired by Thinkingbox) and a marketing expert. In this episode, we discuss his entrepreneurial roots going back to his great-grandfather, how digital marketing strategies shifted, how to stay on top of marketing trends and would he start an agency today.

Jun 16, 2023 • 1h 6min
Isaac Souweine from Pender Ventures
Isaac Souweine is a Partner at Pender Ventures. In this episode, we discuss Isaac's product roles at Frank and Oak and Sonder, his previous investing roles at FounderFuel, Real Ventures and Front Row Ventures, building tech communities, the impacts of generative AI on B2B SaaS and find out his favourite bagel place which isn't Fairmount or St-Viateur.
Check out Isaac's stuff
His personal site
Front Row Ventures
His Twitter
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

Jun 12, 2023 • 1h 5min
Manica Blain from Top Knot Ventures
Manica Blain is an Investor and Advisor at Top Knot Ventures. Manica has over 15 years of experience in investment banking, private equity and venture capital. She now works directly with passionate founders as they build, grow and scale the iconic consumer brands of the future. In this episode, we discuss Campfire Capital a fund she co-founded with lululemon executives, her learnings there during the wind-down and investments in companies like FIGS and Cotopaxi and nuances to investing in the consumer space.
Check out Manica's stuff
Twitter
Confessions of a pregnant venture capitalist piece in The Globe & Mail
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

Jun 9, 2023 • 52min
Ilya Brotzky from VanHack
Ilya Brotzky is the Founder & CEO of VanHack. VanHack is a network of the world’s top software engineering, design, and digital marketing talent - available on demand to relocate to help companies grow. In this episode, we discuss how VanHack landed its first customers, the complexities of hiring engineers from abroad, trends in hiring and what makes a good hiring process.
Check out Ilya's stuff
Women in Tech event
Twitter
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

Jun 5, 2023 • 57min
Jevon MacDonald from Tier
Jevon MacDonald is the Co-Founder of Tier. Tier is everything a developer needs to create and manage software pricing and billing. In this episode, we discuss how two of his companies were acquired by Salesforce and Snyk, founding StartupNorth and early tech scene days in Toronto, and why the timing is right for Tier.
Check out Jevon's stuff
StartupNorth
Twitter
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

4 snips
Jun 2, 2023 • 50min
Stephanie Wood from Alate Partners
Stephanie Wood is a Vice President at Alate Partners. Alate is a leading proptech investor in Canada. In this episode, we discuss Stephanie's shift from CPP Investments to the venture world, nuances to proptech, strategies for growth in proptech and her work with Proptech Collective.
Check out Stephanie's stuff
Proptech Collective
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

May 29, 2023 • 60min
Michael Kravshik from LumiQ
Michael Kravshik is the Co-Founder and CEO of LumiQ. LumiQ is a native podcast app where engaging conversations with business leaders count as verified CPD/CPE for CPAs. In this episode, we discuss why unlearning is important, how it took Michael and his co-founder 10 ideas to land on their current business, the unique way he got Jim Balsillie (RIM/Blackberry) to do a podcast episode and the balance between entertainment and education in content.
Check out Michael's stuff
Jim Balsillie's rejection piece
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

May 26, 2023 • 55min
Jim Orlando from Wittington Ventures
Jim Orlando is the Managing Partner of Wittington Ventures. Wittington Ventures is a venture capital firm investing in the e-commerce/retail, healthcare and food sectors. They invest in companies throughout North America and at all stages of the start-up lifecycle. In this episode, we discuss Jim's journey through BCE Ventures and OMERS Ventures, Wittington's close ties to brands like Shoppers Drug Mart and Loblaw, what it is like to manage other investors and Jim's musical and game coding talents.
Check out Jim's stuff
Twitter
Jim's musical talents
Jim's old-school games
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

May 22, 2023 • 58min
Eva Lau from Two Small Fish Ventures
Eva Lau is the Founder and General Partner of Two Small Fish Ventures. In this episode, we discuss how she grew Wattpad's community to millions of users, how to not get caught in FOMO as an investor, the nuances of raising capital for a fund versus a startup and areas where we could improve Canadian tech.
Check out Eva's stuff
Twitter
ASSET Framework article and video
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn