The Hard Part with Evan McCann

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 Jo...

Naman Budhdeo is a General Partner at Antler Canada . Antler is the investor backing the world’s most driven founders, from day zero to greatness. In this episode, we discuss Naman's background founding businesses in the travel tech space, what makes Antler unique, what Antler looks for in founders, and how Antler attracts founders to their platform.

Robert Price is the Founder and CEO of Bōde. Bōde is a radical shift in how real estate is bought and sold. It finally empowers everyone to buy and sell their own home. Making the process simple, transparent, and more economical. In this episode, we discuss the dynamics of the current home-buying process, myths around buying real estate, the importance of data and the importance of neighbourhood p...

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 stra...

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.

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 perso...

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 durin...

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'...

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 Col...

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 advi...

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 bala...

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 Sho...

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...

Ania Wysocka is the founder of Rootd . Rootd is an app for individuals suffering from panic attacks and anxiety. It offers a refreshingly engaging design, interactive exercises, tools, and lessons focused on helping people manage panic and anxiety attacks as they occur and a guided process toward lifelong relief. In this episode, we discuss how Ania grew Rootd to millions of users, and has remaine...

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...

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 Rou...

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...

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 Compensat...

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 an...

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 Tw...

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

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...

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.

Pablo Srugo is a Partner at Mistral . Mistral is a seed-stage venture capital firm and typically is the first institutional investor in their portfolio companies. In this episode, we discuss Pablo’s time as a founder, his thoughts on VCs being money managers, not company builders and we break down one of Mistral’s latest investments. Pablo is also the host of a great podcast called The Product Mar...

Alex Norman is a partner at N49P Ventures and co-founder of TechTO . N49P is an early-stage venture capital firm focused on Canadian start-ups and Canadian founders. In this episode, we discuss his first business in collectibles, how to build a strong tech ecosystem and advice to founders on how to think about raising capital.