

The Hard Part with Evan McCann
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.
Episodes
Mentioned books

Aug 8, 2023 • 49min
Arsham Ghahramani from Ribbon
Arsham Ghahramani is the Co-Founder and Co-CEO of Ribbon. Ribbon is a professional social platform centred around verified achievements and ownership. They empower managers, leaders, and HR teams to effortlessly and publicly celebrate their team’s work by sending lasting verifiable awards and credentials. In this episode, we discuss his background in machine learning and data during his Ph.D. and working at companies like Amazon, how social networks should think about verification, the hack LinkedIn used to kickstart their network and how Ribbon is looking to shake up the professional social space.
My podcast supporter!
Fasken's Emerging Tech and Venture Capital practice is comprised of 80+ dedicated legal professionals across the Canadian market. We're deeply involved in the startup ecosystem and have worked closely with founders from startup to scale-up to exit. Our team is a leading Canadian law firm for VC financings and tech M&A and act for many of the best-in-class startup and scale-up innovation-based companies and entrepreneurs in Canada.
Given this experience we understand market trends and can assist in guiding your company forward as you scale – we take a holistic and strategic approach to helping our clients achieve their goals and provide the full suite of services including corporate, corporate finance, M&A, commercial, IP, data and compliance, employment, tax and beyond. We are excited to help the next generation of unicorns!

12 snips
Aug 4, 2023 • 53min
Ben Yoskovitz from Highline Beta
Ben Yoskovitz, Founding Partner of Highline Beta, shares his expertise in the hybrid corporate venture landscape. He dives into the significance of collaboration between startups and large corporations, emphasizing how innovative strategies can be tailored for both solo and multi-founder teams. Ben discusses the journey of transitioning from tech to entrepreneurship, the unique dynamics of a venture studio, and the importance of community in fostering growth. His insights into building successful companies and the challenges of fundraising add depth to the conversation.

Jul 31, 2023 • 51min
Rami Alhamad from PUSH (acquired by WHOOP)
Rami Alhamad is the Founder of PUSH which was acquired by WHOOP in 2021. PUSH was a leader in the wearable sports tech space with a focus on biomechanics and movement analytics. Founded in 2013 with the goal of revolutionizing the way athletes train, PUSH grew to support over 150 professional sports organizations as well as thousands of athletes across the college and high school markets. In this episode, we discuss Rami's unique mechatronics degree at Waterloo, PUSH's acquisition by WHOOP, the importance of reducing the footprint of hardware while increasing the footprint of software, what it was like to work with pro sports teams and how Canada can bridge the gap between researchers and entrepreneurs.
Rami's article "Bridging the Gap: Connecting Researchers and Entrepreneurs in Canada's Innovation Ecosystem"!

Jul 28, 2023 • 50min
Cato Pastoll from Loop
Cato Pastoll is the CEO and Co-Founder of Loop. Loop offers tailor-made products including CAD/USD corporate cards, interest-free spending, corporate-level purchasing power, no-fee global payments, accessible growth capital and real US dollar accounts to help businesses grow. In this episode, we discuss the pivot from Lending Loop to Loop today, why word of mouth is one of their fastest growth channels, why caring about your customer is the ultimate flywheel and where we need changes in our banking regulations.
Loop's new site!!!!

Jul 24, 2023 • 37min
Nadia Ladak from Marlow
Nadia Ladak is the Co-Founder and CEO of Marlow. Marlow is a menstrual health brand that has created the first-ever lubricated tampon. In this episode, we discuss how Marlow originally started as a university project, why there is a stigma in the menstrual health space, their DTC and new retail strategy, how they got 50M+ views on TikTok and their micro-influencer strategy.

Jul 21, 2023 • 49min
Arun Iyengar from Untether AI
Arun Iyengar is the CEO of Untether AI. Untether AI provides ultra-efficient, high-performance AI chips to enable new frontiers in AI applications. In this episode, we discuss why chip companies need to raise close to $400M, what part of the AI market they are targeting, Untether's chips versus GPUs, the cost and importance of manufacturing and the importance of IP remaining in Canada.

Jul 17, 2023 • 53min
Boris Wertz from Version One Ventures
Boris Wertz is the Founder and General Partner of Version One Ventures. Version One invests in mission-driven founders at the earliest stages. Founded in 2012 and with $250M+ in AUM across 6 funds, they have backed over 100 start-ups. They invest in SaaS and marketplaces as well as emerging technologies and industries such as crypto/Web3, bio/healthcare, energy/climate, AI and robotics. In this episode, we discuss why your fund size is your strategy, why branded categories are too late to invest in, his Coinbase investment, and his anti-portfolio.
Boris's Twitter
Version One's anti-portfolio

Jul 14, 2023 • 56min
Jason Silver, startup trainer and author
Jason Silver is a startup trainer and author. In this episode, we discuss what the term startup trainer actually means, his time at Airbnb, decision-making frameworks for individuals and startups and why scaling doesn't mean a startup slows down.
Go preorder Jason's book "Quietly Crushing It" at www.quietlycrushingitbook.com or www.qcibook.com and get 40% off.

Jul 10, 2023 • 47min
Ty Wilson from Tab Commerce
Ty Wilson is the Co-Founder & CEO of Tab Commerce. Tab is reinventing expense control for the restaurant industry. Tab is building a suite of data-driven products to help restaurant groups maximize profitability, optimize cash flow, and always have complete control over every dollar they spend. In this episode, we discuss Ty's upbringing in the restaurant world, the gap he saw in the restaurant tech space, how he thinks about growth and sales, and how he keeps his edge as a first-time founder.

Jul 7, 2023 • 45min
Josh O'Kane, author and reporter at The Globe and Mail
Josh O'Kane is a reporter at The Globe and Mail covering the Business of Arts and Entertainment and is an author of Sideways: The City Google Couldn't Buy. In this episode, we discuss what it takes to be a great reporter, what it is like to write a book, how he uncovered the real story about Sidewalk Labs and our mutual love for Fred Again.
Josh's Twitter
Josh's personal website
Josh's book Sideways: The City Google Couldn't Buy
Josh's book Nowhere with You: The East Coast Anthems of Joel Plaskett