Lessons - The Brutal Truth About Fundraising | Russ Heddleston - Built & Sold DocSend for $165M
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In this "Lessons" episode, Russ Heddleston, founder of DocSend, breaks down the harsh realities of startup fundraising and what truly separates successful founders from the rest. Drawing from his experience building and selling DocSend for $165M, he reveals why timing a raise is less about fixed milestones and more about credibility, vision, and momentum. Learn how simplicity in your pitch deck earns investor trust, why clarity always beats complexity, and how to approach different fundraising stages with confidence. This conversation cuts through the noise to deliver practical, data-backed insights every founder needs before their next investor meeting.
➡️ Show Links
https://successstorypodcast.com
YouTube: https://youtu.be/HwEWy24UDWs
Spotify: https://open.spotify.com/episode/7MY2iI39B6OlywWV7b5CX3
➡️ Watch the Podcast on YouTube
https://www.youtube.com/c/scottdclary