019: A Campaign Against Email Attachments with Dave Koslow

The SaaS (Software as a Service) Business Podcast

In this episode of the SaaS Business Podcast, Ron Gaver’s guest is Dave Koslow, co-founder of DocSend. Dave and Ron discuss how Dave and his co-founders discovered the problem that led to the creation of DocSend, a document sharing and monitoring tool. Dave details the various ways DocSend provides users with seamless, real-time feedback, listing its advantages over tools like email attachments and screen-sharing programs. This, in turn, opens a conversation about promoting asynchronous communication for business success and how businesses can use DocSend to bridge the communication divide separating them from their clients.

Along the way, Dave discusses opportunities and pitfalls for early-phase startups doing product research and design.

The full show notes contain a thorough listing of all resources mentioned in the episode and a full transcript of the entire episode.

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Episode Outline

Click any timestamp on the website to start listening at the noted time.

• [00:00] Intro
• [02:24] Attachments and the Failure of Transparent Communication
• [05:15] Purpose-Built Platform for Data Sharing
• [06:11] External Communication Beyond Shared Content
• [08:39] Using DocSend to Study the Effectiveness of Pitch Deck Slides
• [09:08] Using DocSend with Your Existing Documents
• [10:11] Raising Funds with DocSend
• [11:53] Investors Value a Solid Startup Team
• [12:43] DocSend’s Study of Sequoia Capital’s Recommended Pitch Deck Slides
• [13:19] Using DocSend for Lead Capture
• [14:55] Using Lead Capture for Organizational Mapping and Networking
• [16:35] What Happens to Your Documents after You Hit Send?
• [17:36] How Are Attachments Performing?
• [18:17] Using DocSend to Evaluate Page Engagement
• [19:16] The Importance of Asynchronous Communication to Business Success
• [21:20] Getting User Feedback from DocSend
• [21:57] What Feedback Are You Missing with Email Attachments?
• [23:40] DocSend’s Feedback Is Easier Than PDFs
• [24:24] Using DocSend for Remote Live Presentations
• [25:55] DocSend’s Live Present Advantages over Screen Sharing Apps
• [27:35] DocSend’s Highlighting and Cursor Tools
• [28:00] DocSend’s Advantages over WebEx
• [28:42] DocSend’s Origin Story
• [29:33] How DocSend’s Team of Founders Met
• [31:55] How DocSend’s Founders Entered the Industry
• [34:20] The Character of DocSend’s CEO – Russ Heddleston
• [35:20] The “Perfect Co-Founding Team” According to Dave McClure
• [35:48] Brainstorming the Idea of DocSend
• [36:14] Finding the Need
• [37:06] The Need-Finding Hustle
• [39:16] DocSend’s Dachshund Delivery Service Marketing Campaign
• [40:28] Building with Heroku
• [41:07] Scaling with Heroku
• [42:25] Real-Time Messaging with Off-the-Shelf Components
• [43:09] DocSend and User Privacy
• [43:40] DocSend’s Experience Working with Ruby on Rails
• [44:30] DocSend’s Experience Creating a Website with Bootstrap
• [44:57] Funding: Seed Round and Series A
• [45:42] The Future of DocSend – Upcoming Developments
• [46:36] DocSend’s First Conference Experience
• [47:19] Dave Koslow’s Personal Influences
• [51:18] Conclusion