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

Jul 8, 2024

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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.

Learn More at https://scotchisholm.com/

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.

Connect on LinkedIn: https://www.linkedin.com/in/themarkmacleod/

Contact Mark: https://markmacleod.me/