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From Pub Crawls to SaaS: Classy’s journey to $100M with Scot Chisholm

Time: 48:28

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In this episode of The Startup CEO Show, host Mark MacLeod sits down with Scot Chisholm to discuss the multifaceted journey of growing a startup and driving market penetration.

Scot, the CEO and co-founder of Classy, delves deep into topics like forming strategic partnerships with heavyweights like Salesforce, navigating the complexities of fundraising from individuals to institutional investors, and the challenges associated with scaling from SMB to an enterprise-level organization. Scot also reflects on the evolution of Classy and its eventual acquisition by GoFundMe, sharing key insights that all startup CEOs can learn from.

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

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Episode ID: 1000661504030

GUID: 16bb4686-eacf-4ce3-a305-7d88bb33f147

Release Date: 08/07/2024, 09:00:00

Description

The Startup CEO Show hosted by coach and advisor Mark MacLeod, brings you veteran CEOs each week who have collectively had had billion dollar valuations, 9 figure exits, and millions in revenue each week.

Subscribe to join the leading podcast produced exclusively for the CEOs of high-growth startups and the VCs who back them.

This podcast offers concise, yet deep dives into specific themes within each episode, focusing on providing actionable insights for busy leaders. The format includes interviews with CEOs of VC and PE-backed tech companies, their investors, and other key industry figures, ensuring a rich and relevant listening experience for those looking to learn in short, impactful sessions.

About Mark MacLeod

Since 1999, I have sat at the right-hand side of the leaders of high growth technology companies as either a CFO, VC or deal maker. I served as CFO for software companies including Shopify (NYSE: SHOP) and Freshbooks. As a CFO I experienced outright failures, wildly profitable exits, and everything in between.

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I was a General Partner in Real Ventures, Canada's largest and most active seed stage fund. My investments there include the fund's largest cash on cash and highest IRR returns to date. Most recently, I founded SurePath Capital Partners the leading investment bank for SMB SaaS companies where we did hundreds of millions in financing and exit transactions.

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