

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

Oct 10, 2023 • 47min
Jonathan Hershon from Pathway Medical
Jonathan Hershon is the Co-Founder and CEO of Pathway Medical. Pathway is a health tech company working on helping clinicians and patients access important medical information more effectively throughout the care journey. They leverage AI and big data to create a medical knowledge platform and software solutions that drive evidence-based medicine into clinical practice.
Jonathan's Twitter
Pathway's Twitter
In this episode, we discuss...
Building an end-to-end encrypted social network in 2013 called Syme
Jonathan's mindset when Syme had to be wound down
Launching a digital agency called MILE END
Building a health tech company and navigating the regulatory environment
Why they initially bootstrapped and then decided to raise capital
His thoughts on product market fit
The impact of AI and LLMs on Pathway's product and healthcare industry
How Jonathan thinks about product-led growth, specifically in health tech
His favourite bagel place in Montreal
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!

Oct 6, 2023 • 1h 5min
Bertrand Nembot from Billdr
Bertrand Nembot is the Co-Founder & CEO of Billdr. Billdr is a vertically integrated home renovation marketplace operating in Montreal, Toronto, and Chicago. They facilitate renovation projects by providing turnkey solutions for homeowners supported by a digital back-office platform for general contractors. Their mission is to make home renovation simple, transparent, and efficient for everyone.
In this episode, we discuss...
Bert's first foray into renovations
launching Uber in Uganda in 3 weeks
existing challenges that homeowners and general contractors had with the renovation process
how Billdr increases general contractors' win rates
building an operating system/back office for general contractors
launching a managed marketplace in new markets like Toronto and Chicago
pivoting from a managed marketplace to a B2B offering
why he prefers croissants to bagels
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!

6 snips
Sep 25, 2023 • 1h 9min
Jonathan Becker from Thrive Digital
Jonathan Becker, Founder and President of Thrive Digital and a General Partner at Occasional Ventures, discusses founding Thrive, landing Lululemon and Uber as clients, misconceptions around paid growth, running marketing experiments, keeping up with different platforms, his investing style, and transitioning from CEO to chairman.

Sep 22, 2023 • 43min
Kevin Stadnyk from Obruta Space Solutions
Kevin Stadnyk is the Co-Founder and CEO of Obruta Space Solutions. Obruta Space Solutions is enabling the space economy through reimagined, autonomous, and safe spacecraft docking systems. Obruta's turnkey Docking Kit combines the necessary hardware and software for virtually any spacecraft to perform on-orbit servicing and logistics. In this episode, we discuss Kevin's time at Carleton's Aerospace Engineering program, where Obruta plays in the ever-growing space industry, what the testing process looks like for a space company, why the satellite servicing space will be $14B by 2031, why is the space industry opportunity growing so rapidly, the regulatory environment around space and the nuances to raising capital in the space industry.
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!

Sep 18, 2023 • 53min
Randy Garg from Vistara Growth
Randy Garg is the Founder & Managing Partner of Vistara Growth. Vistara provides highly flexible Growth Debt and Growth Equity financing solutions to mid to later-stage technology companies across North America. Vistara's typical investment size ranges from $10M to $30M per investment for companies that have scaled or are scaling past $10M+ in revenues. In this episode, we discuss his time at Discovery Capital Corporation a Vancouver-based venture capital firm with investments like Sierra Wireless, working at Beedie Capital and uncovering a gap in the tech space, misconceptions people have about debt, common mistakes growth stage companies make, how debt and equity deals differ and what makes a great board member.
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!

Sep 11, 2023 • 55min
Chris O'Neill, technology leader, board member and advisor
Chris O'Neill is a technology leader, board member and advisor. His resume is extensive, currently, he is the Chief Growth Officer at Xero, a Board Member at Gap Inc., a GP and Advisor at Portage and an angel investor. Previously he was Chairman and CEO of Evernote, Managing Director of Google Canada with a stint at Google X (now X), Board Member at Tim Hortons and much more.
In this episode, we discuss Chris's upbringing in his family's Canadian Tire business, learnings from launching Google Glass with Sergey Brin and Astro Teller at Google X, being on the board of Tim Hortons during the 3G Capital acquisition, leading a turnaround of Evernote, why the perception that Canadians don't take risks is BS and his passion for cleantech.
Chris's Twitter
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!

Sep 5, 2023 • 46min
Scott Stevenson from Spellbook
Scott Stevenson is the CEO and Co-Founder of Spellbook. Spellbook uses GPT-4 and other large language models to review and suggest terms for lawyers' contracts, right in Microsoft Word. In this episode, we discuss Scott co-inventing a new instrument, how to run experiments when building product, how they are converting their waitlist to raving customers, nuances to building a co-pilot product, utilizing GPT versus creating your own LLM and his blog post "Lego Mindset versus Woodworking Mindset".
Follow Scott on Twitter, he is an excellent follow
His blog post "Lego Mindset versus Woodworking Mindset" and other writings
His instrument creation the Mune
A written interview with Scott by Ben Yoskovitz (previous podcast guest)
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!

16 snips
Aug 18, 2023 • 53min
Chris Neumann from Panache Ventures
Chris Neumann, Partner at Panache Ventures and founder of DataHero, dives into his entrepreneurial journey and insights into the venture capital landscape. He shares the challenges he faced while building DataHero, the nuances of effective startup accelerators, and the pressing need for more venture funds in Canada. Chris emphasizes the importance of mentorship and a supportive network for startups. He also discusses the evolving Canadian startup scene, the potential of AI innovations, and why Canadian cities should focus on their unique strengths rather than comparisons with Silicon Valley.

Aug 14, 2023 • 51min
Patrick Monnot from Pod
Patrick Monnot is the Founder and CEO of Pod. Pod is the ultimate AI copilot for B2B sellers. In this episode, we discuss Patrick's time at Fuel by McKinsey, how Pod competes in a busy sales tech market, what it is like to sell to salespeople, solo versus multi-player user experience, how to have focus when building product and the strategy behind their last raise from Bling Capital and GTM angels.
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!

Aug 11, 2023 • 56min
Hamza J Alamtab from Tamba
Hamza J Alamtab is the Co-Founder of Tamba. Tamba is a product and digital solutions studio specializing in outstanding user interface & user experience. In this episode, we discuss Hamza's business acquired by Tiny, companies that are AI proof, what makes Victoria's tech community so great, meeting Andrew Huberman which led to the start of his new business Routines and the best advice Hamza got from Andrew Wilkinson.
Tamba's website
Routine's website
Hamza's Twitter
Tamba's Ambassador Program
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!