Russ Heddleston, founder of DocSend, shares how nearly going bankrupt forced them to rethink everything—turning a failing startup into a product-led rocket ship that Dropbox bought for $165M. From spreadsheets of startup ideas, to the painful lessons of chasing enterprise sales, to doubling their prices and watching conversions skyrocket, Russ breaks down the hard truths behind building a breakout SaaS company. Plus: why he wishes he hadn’t sold, and what he’s doing differently with his next startup.
(0:00) Introduction of Russ Heddleston
(0:40) Russ Heddleston's early career and founding Docsend
(2:02) Microsoft internships and Maru Networks experience
(4:38) Ideation and approach to selecting startup ideas
(6:54) Docsend's challenges and pivots
(10:11) Struggles with enterprise sales and self-serve model
(13:51) Product positioning, pricing, and packaging evolution
(16:12) Identifying target segments and use cases for Docsend
(19:04) Comprehensive pricing strategy for Docsend
(22:17) Docsend's growth mechanics and viral marketing
(24:30) Utilizing fundraising content for Docsend's marketing
(27:00) Considering and deciding on acquisition offers
(29:42) Reflections on the sale of Docsend
(32:11) Aligning stakeholders and understanding investor perspectives
(34:24) Emotional journey of selling a company
(36:05) Acquisition dynamics: private vs. public company considerations
(38:22) Post-acquisition founder sentiments
(40:27) Founder advice on liquidity options and growth
(45:01) Russ Heddleston’s post-acquisition role at Dropbox
(48:21) The significance of taking a break after company acquisition
(50:59) Planning the next venture and reflecting on motivations
(54:01) Establishing values and principles for a new company
(57:44) Iterating on startup concepts and finding the right idea
(1:00:39) Intrinsic motivations for founders and long-term commitment
(1:02:37) The fulfillment of creating sustainable value
(1:03:27) Founding Distill and the vision behind it
(1:04:21) Distill's concept of people and company profiles
(1:05:03) Innovations in search, information, and indexing with Distill
(1:05:32) Wrap-up and closing remarks
