DocSend's Roadmap: From VC Funding to Dropbox Acquisition with Russ Heddleston

The Startup CEO Show

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In this episode of The Startup CEO Show, host Mark MacLeod interviews Russ Heddleston, former CEO of DocSend, to explore the nuances of startup acquisitions and creating market value. Russ shares his experience selling to Dropbox, navigating competition, and making strategic business decisions. Discover how building relationships with potential buyers and competitors can influence acquisition outcomes. Russ also discusses product-led growth, capital efficiency, and his new ventures focused on leveraging LLMs.

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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/

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Contact Mark: https://markmacleod.me/