[S1,E23] Getting acquired by Facebook and raising $8M on a new startup! – How Russ Heddleston, CEO of DocSend, does business in Silicon Valley!

Russ Heddleston, CEO of DocSend – an analytics tool that tracks viewership data after sending documents, is taking Silicon Valley by the storm! His first startup Pursuit – a social referral program – got acquired by Facebook within the first year! He worked for Facebook for over a year as a Product Manager for Pages. It didn’t take him long until he started another business. To keep the ball rolling, he partnered with August Capital and raised 8 million dollars for DocSend!

Sounds like a dream, huh? So how did he do this? What are his strategies? Fortunately for us, Russ speaks about every detail that went into Pursuit and DocSend’s continued success.

– How did his first startup get acquired by Facebook in under a year?
– Does he have any regrets on the acquisition?
– What are his best investment raising strategies?
– What are Russ’s best growth strategies?
– How did it feel to work at Facebook in the acquired team?
– What are the most important startup lessons from comparing the two startups?
– How did Russ and his team get first paying customers for DocSend?

All of this and so much more in our video interview!

A lovely shout out to our sponsor UnStock — mobile first marketplace for authentic video.
Big thank you to our Partner Kamila Dmowska for the fabulous dress and styling!

Check out some highlights of this interview:

  • DocSend was initially started to help founders with their pitch decks; immediately they found a problem base.

    “People send around their pitch decks. The problem there is that you don’t know which investor actually cares. You don’t want them forwarding documents to your competition and you want to be able to update or retract it at any time.”

  • It’s really difficult to do a full-time job and build a startup. It’s either all in or not.

    “Another thing that can be a big problem is having co-founders that are committed as you are, and if people have jobs it’s really hard to know. Especially if you’re splitting equity and you’re making big decisions. So when Dave, Tony, and I started DocSend, we did it full-time.”

  • Russ and his co-founders made it through the initial period with around $40k to start.

    “It was mostly just our own labor. I did all of our first design. We were cheap about everything. The MVP is the thing that just needed to work. It just needed to be a solid product, from an engineering perspective. So I think we got the rest put up for 40k. Which is nothing, our own labor would’ve been much more expensive.”

  • Oh yes… it’s hard to fundraise money at first.

    “For Pursuit when we tried to raise money, it took me forever. It took me four or five months running around and I felt I wasn’t making a lot of progress. Even though we got a small seed round together, I kind of felt that people were just giving it to me because they liked me and I seemed like a smart guy.”

  • DocSend’s seed round and Series A investment was much more strategically planned and executed.

    “I don’t want to go spend four months fundraising if it’s not going to work. I set up as many meetings as I could in a two week window. I basically told everyone the same thing… ‘we are looking for a lead investor, if you’re interested please give us terms.’”

  • In terms of acquisitions, there are small and large scale forms.

    “The lowest acquisition you can get is a talent acquisition, which is still a really big compliment to you. For some of these companies, it’s hard to find people who are really passionate and knowledgeable about certain specific problems that you are trying to solve. So in those situations, talent acquisitions happen.”

  • Sometimes big companies let you explore a much, much larger audience scale.

    “Being a Product Manager for the Pages team, I’m responsible for making sense of the product. Because Facebook is a global company, and it was 2011, I realized I didn’t know what users in other countries are doing. So I said I’m going to fly around the world and talk to different customers on Facebook to see why are they using Pages and what do they want out of it.”

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