Russ Heddleston

Russ Heddleston, founder of DocSend, shares his incredible journey from the brink of bankruptcy to a $165M acquisition by Dropbox. He dives into the painful lessons learned from chasing enterprise sales and the surprising success of a self-serve model. Russ also discusses strategic pricing changes that skyrocketed conversions, the emotional complexities of selling his company, and what he wishes he had done differently. Now, he's focused on his new venture, Distill, with a fresh perspective on innovation and growth.

Russ Heddleston, former CEO of DocSend and a seasoned pro in tech acquisitions, shares his journey from VC funding to selling his company to Dropbox. He discusses the art of building relationships with potential buyers and competitors. The conversation explores product-led growth and capital efficiency. Russ also dives into the challenges faced during the acquisition process, emphasizing the importance of trust and adaptability in the tech landscape. Plus, he unveils a new initiative aimed at revolutionizing professional online identities.

Russ Heddleston, Co-founder & former CEO of DocSend, shares insights on sell-side M&A. Topics include considerations for selling a startup, balancing stakeholder interests, managing relationships in negotiations, key factors for a successful exit, challenges of sell-side M&A, and efficiently managing diligence.