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Amazon’s Reported $1B Ring Deal: O’Leary Calls It “Probably the Biggest Miss” in Shark Tank History

Jamie Siminoff turned down Kevin O’Leary’s offer for DoorBot. Amazon later acquired the renamed Ring in a reported billion-dollar deal whose exact terms were never disclosed.
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Amazon acquired Ring in 2018 in a deal reported at around or above $1 billion, but the exact price was never disclosed. Five years earlier, Ring founder Jamie Siminoff—then pitching his Wi-Fi video doorbell as DoorBot—turned down Kevin O’Leary’s offer on Shark Tank. O’Leary later called the missed investment “probably the biggest miss” in the show’s history. That is his retrospective judgment, not an official ranking.

What happened when Jamie Siminoff pitched DoorBot?

In 2013, Siminoff asked the Sharks for $700,000 in exchange for 10% of DoorBot, implying a $7 million company valuation. DoorBot was a Wi-Fi video doorbell that let homeowners see visitors remotely. The company would later be renamed Ring.

The Sharks other than O’Leary declined to invest. O’Leary made the sole offer, but Siminoff rejected it and left without a deal. GeekWire reported that DoorBot had $1 million in annual sales at the time; Fortune’s 2026 account describes about $1 million in business during the first nine months. Those are differently framed reports, not interchangeable measurements.

What was Kevin O’Leary’s offer—and why did Siminoff say no?

The accounts describe the offer in related but not identical terms. GeekWire’s 2018 report characterized it as a $700,000 loan plus 5% equity. Babson’s 2025 account gives more detail: $700,000, 5% equity, and a royalty that started at 10% and fell to 7% after O’Leary recouped his initial amount.

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Term Babson’s 2025 account GeekWire’s 2018 account
Cash $700,000 $700,000
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Royalty or loan structure 10% royalty, declining to 7% after recoupment Described as a loan; royalty schedule not stated

Siminoff objected to the royalty because he believed it would leave the early-stage business with too little profit to keep making the product. At a Babson fireside chat, he explained: “You can’t make the product if you have a royalty,” he said. “There’s no way a small company could make it. You couldn’t make enough profit to do it.”

O’Leary defended the size of the offer, telling GeekWire: “I think giving anybody $700,000 is a full offer, and there’s a reason they call me Mr. Wonderful.” The disagreement reflects the risks each side was weighing: O’Leary proposed capital in exchange for a share of the business and payments tied to sales, while Siminoff feared the royalty would constrain the company’s ability to grow.

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How did DoorBot become Ring?

Siminoff said the television appearance brought exposure to the fledgling business even though he did not accept a deal. He later attracted investors and expanded beyond the initial doorbell into home security. Fortune reports that DoorBot was renamed Ring in 2014. Ring video doorbells remain associated with that product category, though today’s products should not be assumed to be identical to the 2013 DoorBot.

How much did Amazon pay for Ring?

Amazon announced its acquisition of Ring in 2018, but the companies did not disclose the financial terms. News coverage reported a value around or above $1 billion; GeekWire cited a reported $1.1 billion figure. That figure is a reported estimate, not a confirmed purchase price.

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In a 2019 GeekWire interview, Siminoff said, “We can’t confirm those numbers, but they sound pretty close.” His comment did not confirm the reported valuation. The public information therefore supports describing the transaction as a reported billion-dollar deal, not stating an exact price or estimating Siminoff’s personal proceeds.

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Why did O’Leary call it “probably the biggest miss”?

After Amazon’s agreement to acquire Ring, O’Leary looked back on the offer he had made and described the decision as “probably the biggest miss” in Shark Tank history, as reported by GeekWire. The qualifier matters: this was O’Leary’s own assessment, not a formal or independently measured ranking of every investment the Sharks passed up.

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Ring’s later reported acquisition value made the episode a striking outcome, but it does not prove the company’s eventual success or sale terms were knowable in 2013. Siminoff later described the company at the time of the pitch as lacking meaningful customer wins and product-market fit. The Sharks were evaluating an early-stage product and business, not the company Ring would become after further investment, exposure, and expansion.

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