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  • Writer's pictureCreative Return


Updated: May 18, 2022

In today’s episode, we are joined by Russ Heddleston, Co-Founder and CEO of DocSend.

Whether you are a new startup or a seasoned company ready for expansion, you’re most likely going to need to raise funds to support your business. Tracking investor engagement with your pitch deck is an essential element in fundraising.

DocSend is an application that is increasingly used by the finance industry to sending documents securely like pitch decks. It can also be used to create secure and tracked file sharing spaces, or data rooms. However, this episode is not about DocSend.

Today, Russ shares with us his very interesting Silicone Valley career. Some may even say that Russ has lived the tech dream. From Stanford and Harvard degrees, to selling his first company to Facebook, and now on to launching DocSend, he has been making all of the right moves.

“I approached fundraising in serial as opposed to in parallel. I would go pitch people, a couple a week, as I’d find them, and this is problematic because everyone talks to each other. So, if you’d been fundraising for four or five months, the people you’d pitched three or four months ago, you still haven’t raised the round, it just looks like you don’t have great momentum.” — @rheddleston [0:15:49]

For DocSend, Russ raised venture financing, and is now growing in the high double digits with over 13,000 monthly customers. He has achieved that important stage of not needing to raise more capital. But that doesn’t mean that he is free from the pressures of investor expectations.


Of course, nothing ever goes perfectly. But one has to hand it to Russ for his experience and leadership going through this, as well as for the advice he shares in this episode. He makes the point that raising capital means taking risks and hard work, so don’t let that fall short on you.

A key part of this discussion focuses around the empirical data on raising capital.

“My pitches have never been with a deck in the background. It has always been an informed conversation where they want to push deeper on certain things. And then it makes it a really fun debate. You’ve got to be really concise in the materials you use to get the meeting.” — @rheddleston [0:37:32]

His company’s blog has released a number of reports on how winning pitch decks are composed, the time it takes to raise capital, and other interesting nuances of what makes for a successful capital raise.

Make sure not to miss this episode for all you need to know about using DocSend to apply fundraising best practices.



  • Russ introduces himself and shares a bit about his background in tech.

  • What Russ learned from fundraising for his first tech company and launching a product.

  • Russ explains the process of shopping between companies and the group hiring process.

  • What Russ would have done differently in retrospect – less assumptions and more interviews.

  • What it was like for Russ, bringing order as a product manager at Facebook early on.

  • The authority as a product manager, being able to execute on parts of the business.

  • Russ’s advice for early rounds of fundraising, the mistakes he made, and what he did differently at DocSend.

  • Russ’s strategy for booking meetings with investors – small funds, then more exciting funds.

  • A question Russ got from later-stage investors was, “What is the defensive moat here?”

  • Russ explains why he doesn’t think about exit strategy, and describes his financing strategy.

  • Product-led growth is the way DocSend has scaled – 100% of their revenue is inbound.

  • DocSend’s mission statement is to combine common workflows for documents sent externally into one intuitive solution.

  • Founders that don’t raise funds don’t share their stories – you only hear positive accounts.

  • What was interesting to Russ about the data points they gathered for their pitch deck interest.

  • Characteristics of founders who raise quicker or better rounds than others, like being over 30, or having a diverse founding team.

  • As the number of founders increases, the chances of getting funding decreases.

  • Russ’s tips for using DocSend effectively by sharing tracking engagement on pitch decks.

  • When presenting your pitch deck, you’re not competing for credibility, but competing for time.

  • Final remarks from Russ – work smart, not harder, be open to feedback, and come prepared!


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