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The Hard Part with Evan McCann

Latest episodes

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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.
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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
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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
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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
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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
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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
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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
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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
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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.
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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.

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