Docsend revenue hit $9.2M in 2024

Founder / CEO

Russ Heddleston

Russ Heddleston – Co-founder & CEO, DocSend Russ Heddleston (excerpt) I think it’s important to not have like that hero streak where you try to do everything. I think it also helps that this is my second startup. I think if you’ve been through it once before, it helps you pace yourself a little bit better because everything is critical and you do have to move really fast. You also have to continue to live your life.” Stephen Cummins Welcome to 14 minutes of SaaS, the show where you can listen to the stories and opinions of founders of the world’s most remarkable SaaS ScaleUps. 0:42 This episode is part 1 of a 3 part mini-series with Russ Huddleston, CEO and Co-founder of DocSend, a content management and tracking system – recorded in Collision New Orleans. Russ talks about his career which he kickstarted by interning for a string of superstar software companies. He discusses the pros and cons of starting a company with friends, says mobile-first strategies can be overrated and touches on how people interact with content, their attention spans, and brings in even a little bit of deep learning. 1:20 How are you doing Russ? Russ Heddelston Great, thanks for having me on Stephen. Stephen Cummins Brilliant. Could tell us a little bit about yourself and your life history? Russ Heddelston I’ll try to describe it in a concise manner. My family was in the military – so I was an army brat growing up. Lived in Berlin for 5 years, lived in Denver, grew up mostly in South Dakota. I had the very good fortune to go to Stanford for undergrad and grad in computer science. And, I had no idea what I was getting into coming from South Dakota. I certainly wasn’t prepared for it. That’s basically how I got into tech. Spent some time building robots. Decided software was a little bit better suited to me … much faster paced. After leaving Stanford I worked at a company called Graystripe and ended up being their director of engineering and it was a wonderful ride for a few years. They ended up selling the business to ValueClick – that was like my first taste of like, you know, like a startup just kinda doing it from the beginning. I also interned at Trulia as their first intern back in 2006 … back in the day. There were 5 people there and then interned at Microsoft. I left Graystripe and went back to Harvard business school. A lot of people who were in HBS with me had a consulting background or a business background. But for me it was entirely new information. I hadn’t taken any business classes before. And it was really fascinating to see – probably the only business classes I’d taken before was doing this thing called the Mayfield program at Stanford – which is … for anyone in Stanford they should definitely apply to this. It’s an amazing 9 month work study / entrepreneurship program. HBS – a great experience.

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