
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

May 15, 2023 • 50min
Ania Wysocka from Rootd
Ania Wysocka, founder of Rootd, discusses how she grew the app to millions of users despite being bootstrapped. They also talk about reducing the stigma around anxiety, building the app, important metrics for the business, and effective coping strategies for challenging situations.

May 12, 2023 • 56min
D'Arcy Coolican, angel investor
D'Arcy Coolican is an early-stage investor and was previously investing at Andreessen Horowitz. In this episode, we discuss D'Arcy's founder journey starting Frank, his time spent at Andreessen Horowitz, the nuances of investing in consumer businesses and how he keeps his edge as an investor.
Check out D'Arcy's stuff
Twitter
His personal site
His Substack
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

May 8, 2023 • 48min
Daniel Debow from Shopify
Daniel Debow is the VP of Product focused on Demand at Shopify. In this episode we discuss Daniel’s thoughts on a successful M&A process, what demand means at Shopify, if there is a difference between product market fit at a startup versus a large company like Shopify and Daniel’s love of good music.
Check out Daniels's stuff
Twitter
How to sell your startup article by Daniel and First Round
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

May 5, 2023 • 1h 29min
Benjamin Alarie from Blue J
Benjamin Alarie is the Co-Founder and CEO of Blue J, a Professor & Osler Chair in Business Law at the Faculty of Law at the University of Toronto and co-author of The Legal Singularity. In this episode, we discuss how Blue J started at the U of T, the results of Benjamin letting his students use ChatGPT and the impact of AI on law.
Check out Benjamin's stuff
The Legal Singularity
Twitter
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

May 3, 2023 • 52min
Joshua Goodfield from VC Platform
Joshua Goodfield is the Executive Director of VC Platform. The VC Platform Global Community is the largest dedicated group of platform professionals in the venture capital industry. In this episode, we discuss Joshua’s time at C100, why is the platform function at VCs growing, what it truly means to build community and what KPIs you should track.
Check out Joshua's stuff
2022 Global Compensation Survey we discussed
Twitter
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

May 1, 2023 • 54min
Gui Laliberte from Integral
Gui Laliberte is the CEO and Founder of Integral. Integral empowers web3 organizations in crypto accounting through revenue recognition, NFT collection management, cap gain/loss calculations, audit-compliant reports and more. In this episode, we discuss Gui’s background in founding Setter and its acquisition by Thumbtack, how and why founders should think about markets when building businesses and why he is building a picks and shovels company for web3.
Check out Gui's stuff
Twitter
Integral's site
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

Apr 28, 2023 • 53min
Tobi Oluwole from The3Skills
Tobi Oluwole is the CEO and Co-Founder of The3Skills. In this episode, we discuss how Tobi has gotten millions of impressions on his content, how to create great content and balancing his different business ventures.
Check out Tobi's Stuff
3Skills
Paid in Full newsletter
Check out Evan's Stuff
Cold Start, fractional and advisory sales agency
Cold Start sales newsletter
Personal website
Twitter
LinkedIn

Apr 24, 2023 • 55min
Mark MacLeod, CEO whisperer
Mark MacLeod is a CEO coach and advisor or better yet a CEO whisperer. In this episode we discuss Mark’s time as Shopify’s first CFO, investing at Real Ventures, what he means when CEOs change altitude and Mark’s DJ skills.
Mark's website
Mark's SoundCloud

Apr 21, 2023 • 56min
Chad Bayne from Osler
Chad Bayne is the Co-Chair and Partner of the Emerging and High Growth Companies practice at Osler. Osler is a leading Canadian business law firm with 500 lawyers working together from offices across the country. In this episode, we discuss how Chad built a practice that does 50% of all Canadian tech financings, his journey from Waterloo computer engineering to being a lawyer and the impact of AI on law.

Apr 17, 2023 • 53min
Alex Tong from Information Venture Partners
Alex Tong is a Principal at Information Venture Partners. Information Venture Partners is a Toronto-based venture capital firm focused on early-stage, B2B SaaS applications for the financial services industry. In this episode we discuss Alex’s time spent in corporate development at Hootsuite, what makes a great board member and the importance of founder-led sales.