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From the Operators

Hiten Shah of Quick Sprout dives into monetizing free users, product feature roadmaps, and building a product for multiple markets in an analysis of “Why Trello Failed to Build a $1 Billion+ Business”

Paul Rosania of Slack recalls the hardest decisions made while working on product at Twitter and Slack, emphasizing that there’s no room for doubt when you believe something about the world in “Make Product Decisions Without Doubt — My Lessons from Twitter and Slack”

Anne K. Halsall of Winnie shares the lessons, with an emphasis on uncertainty and an entrepreneur’s “unique relationship with reality,” that she uses every day as a founder in “Six Impossible Things Before Breakfast”

Steve Blank (of MIPS, Ardent, SuperMac, Convergent, and more) recounts being skewered by a former boss over a lack of marketing strategy to demonstrate that marketing leadership isn’t just about tactics in “Strategy Is Not A To Do List”

From the Investors

Fred Wilson of Union Square Ventures shares a quick note about receiving more initial pitches that don’t have a deck - and notes how much he likes “more conversation and less presentation” - in “The Conversational Pitch”

Semil Shah of Haystack summarizes a podcast with Harry Stebbings and Michael Dearing of Harrison Metal, with Semil focusing on VC price sensitivity, recycling LP funds, the Bay Area seed market, and more in “Brief Thoughts On VC Fund Management”

Seth Levine of Foundry Group writes about the challenges an idea faces as it starts as a feature, possibly becomes a product, and even more unlikely becomes a company, in “The Feature -> Product -> Company Continuum”

Jason Lemkin of SaaStr points out that in order to successfully sell to a specific market (especially enterprise), products may need to include features that no one will ever use in “Want to Go Upmarket? You Need a Great Dashboard”

Bryce Roberts of Indie.vc points out that “Venture Scale” is a misnomer, since it turns out that 99.86% of venture funded software/internet startups fail to achieve it.

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