Success Story with Scott D. Clary
Lessons - The Brutal Truth About Fundraising | Russ Heddleston - Built & Sold DocSend for $165M
Published on Nov 6, 2025, 9:24:03 PM
Total time: 00:10:12
Success Story with Scott D. Clary
Published on Nov 6, 2025, 9:24:03 PM
Total time: 00:10:12
➡️ Like The Podcast? Leave A Rating: https://ratethispodcast.com/successstory
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
Welcome to the Success Story Podcast, hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary (@scottdclary). On this podcast, you'll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups and entrepreneurship. Scott will discuss some of the lessons he's learned over his own career, as well as have candid interviews with execs, celebrities, notable figures and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas and insights. He sits down with leaders and mentors and unpacks their story to help pass those lessons onto others through both experiences and tactical strategy for business professionals, entrepreneurs and everyone in between. To get more of the Success Story podcast, go to www.successstorypodcast.com.