Stage · 5 of 84 articles

Bridge / Extension fundraising, from people who have done it

Bridges are raised in the gap between milestones, and they are harder than they look. These pieces cover when an extension makes sense, how insiders and new investors read one, and how to raise it without signaling distress.

Medium·September 2013 ·15 min read

Postmortem of a Venture-backed Startup

The CEO of Sonar (millions of downloads, ~$2M raised) explains the company's death: chasing engagement over growth, a failed nine-month attempt to sell rather than cut costs, and how investor incentives shaped the endgame. Read by over a million people.

Failed RaiseFundraising PsychologySeedPostmortem
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paulgraham.com·December 2014 ·8 min read

The Fatal Pinch

Defines the default-dead trap: moderate growth, months of runway, and an assumption investors will save you. Explains why bridge rounds usually don't come and what to do instead (cut costs or grow into default-alive).

Raise ReadinessFailed RaiseBridge / ExtensionHow-To
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tomtunguz.com·2019 ·5 min read

Second Seed Rounds: How They Impact a Startup's Ability to Raise a Series A

Quantifies the second-seed phenomenon: how common repeat seed rounds are and what they do, statistically, to a company's Series A odds and terms.

Bridge / ExtensionMomentum & SignalingSeedData & Benchmarks
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The Verge·November 2013 ·20 min read

Out of the picture: why the world's best photo startup is going out of business (Everpix)

The definitive reported account of Everpix's death: a beloved product with paying users that ran out of runway mid-raise; the founders later open-sourced their pitch decks, metrics, and investor pipeline. A masterclass in how good products die from failed fundraises.

Failed RaiseFundraising PsychologySeedPostmortem
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Medium·June 2014 ·10 min read

Mattermark Has Raised $2M in Our Second Seed Round

Morrill explains publicly why Mattermark took a $2M second seed instead of the Series A she'd been pitching: two years of nonstop fundraising, a bridge from a customer-investor, and the honest math of raising below your hopes.

Bridge / ExtensionFundraising PsychologySeedFirsthand Story
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