boomerang founder

Definition

An entrepreneur who returns to start another company after their previous venture was acquired or failed. They're either gluttons for punishment or genuinely addicted to the startup lifestyle.

Example Usage

After selling his first company to Google, Jake became a boomerang founder, launching a new AI startup within six months.

Origin

Emerged in Silicon Valley vernacular in the 2010s, referencing the Australian throwing tool that returns

Fun Fact

VCs often prefer boomerang founders because they've learned expensive lessons on someone else's dime.

Source: Startup ecosystem terminology

Related Terms

Intermediate

pirate metrics

The AARRR framework measuring Acquisition, Activation, Retention, Referral, and Revenue—the key metrics for growth-stage startups. Named because AARRR sounds like a pirate, which is somehow still funny to founders.

🚀 Startup / VC

Advanced

shotgun clause

A buyout mechanism where one co-founder can offer to buy out another at a specific price, and the recipient must either sell at that price or buy the offerer's shares at the same price. The nuclear option for irreconcilable founder disputes.

🚀 Startup / VC

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milestone-based funding

Investment structured to release capital in tranches as the company hits specific targets, giving investors control and founders ulcers. Trust, but verify, but mostly don't trust.

🚀 Startup / VC

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deal flow

The rate at which investment opportunities come across a VC's desk. Good deal flow means seeing quality startups before everyone else; bad deal flow means getting pitched by anyone with a Squarespace website and a dream.

🚀 Startup / VC

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graduation round

When a startup raises funding from institutional VCs after initially bootstrapping or taking only angel money. It's like moving from community college to the Ivy League, complete with higher expectations.

🚀 Startup / VC

Advanced

pay-to-play provision

A punitive clause forcing existing investors to participate in future rounds or lose their special privileges—the venture capital equivalent of 'put up or shut up.' Popular after market downturns when companies need to separate real believers from fair-weather friends.

🚀 Startup / VC

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See “boomerang founder” in Corporate Speak, Gen-Z Slang, Pirate Speak, and more.

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