They walked away empty-handed, built $1B company

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Jamie Siminoff walked onto Shark Tank in 2013 with a smart doorbell called DoorBot. He pitched all five Sharks with confidence. Kevin O'Leary called it a horrible investment. Mark Cuban passed. Barbara Corcoran passed. All five Sharks said no.

Five years later, Amazon bought his company, renamed Ring, for over $1 billion.

Every Shark who passed publicly admitted it was one of their biggest mistakes. O'Leary called it "the deal that haunts me." Cuban said he "blew it completely."

The wildest part? This keeps happening. Some of Shark Tank's most successful companies got rejected by every single investor on the show. Because validation from experts and actual market value are often completely disconnected.

Siminoff's doorbell nobody wanted to fund

In 2013, Jamie Siminoff had spent years developing a Wi-Fi video doorbell. The technology worked. Early customers loved it. He needed capital to scale manufacturing.

He went on Shark Tank asking for $700,000 for 10% equity, valuing his company at $7 million. The Sharks tore the pitch apart.

Kevin O'Leary said the valuation was insane. The technology was too complicated for average consumers. The price point was too high. The market was too niche.

Mark Cuban worried about competition from big companies with more resources. Why wouldn't Honeywell or ADT just crush a startup in this space?

Barbara Corcoran didn't see the mass market appeal. Robert Herjavec and Daymond John both passed for similar reasons.

All five Sharks said no.

Siminoff walked away empty-handed but not defeated. He kept building. He found other investors who believed in the vision. He refined the product and expanded distribution.

The company, rebranded as Ring, became one of the fastest-growing smart home companies in America. In 2018, Amazon acquired Ring for over $1 billion. Some reports suggest the actual price was closer to $1.2 billion.

The Sharks who passed on a $7 million valuation watched it become a billion-dollar exit. Siminoff later returned to Shark Tank as a guest investor, a gracious reminder of their mistake.

The pancake mix that didn't make sense

Joel Clark appeared on Shark Tank in 2014 pitching Kodiak Cakes, a whole grain pancake and waffle mix his family had been making for decades.

He asked for $500,000 for 10% equity. The Sharks were skeptical immediately.

Robert Herjavec said the pancake mix market was too competitive. Kevin O'Leary didn't see how they'd compete against Aunt Jemima and Bisquick with massive marketing budgets. The margins seemed thin. The scalability looked questionable.

All five Sharks passed.

Clark left without a deal but with something more valuable than their money. National television exposure. That visibility helped Kodiak Cakes land retail partnerships with Target, Costco, and other major chains.

The company grew explosively. By 2022, Kodiak Cakes was generating over $500 million in annual revenue. Private equity firm L Catterton acquired a stake valuing the company at several hundred million dollars.

The Sharks passed on a company that became one of the most successful natural food brands of the decade.

GrooveBook's "dying category" that wasn't dying

Brian and Julie Whiteman pitched GrooveBook in 2014. Their app let people print smartphone photos into physical books mailed monthly for $2.99.

Mark Cuban didn't think people wanted physical photos anymore. Kevin O'Leary said the margins were terrible at that price point. The others questioned whether the business was sustainable or just a fad.

All five Sharks passed.

The Whitemans kept building. Within months, GrooveBook gained hundreds of thousands of subscribers. The viral growth caught attention from an unexpected buyer.

In 2015, just over a year after the Shark Tank rejection, Shutterfly acquired GrooveBook for $14.5 million. The Whitemans built a multi-million dollar exit in less than two years after every Shark said their idea wouldn't work.

Why smart money misses obvious opportunities

The Sharks are successful, experienced investors. They've built companies and made fortunes. But they saw DoorBot, Kodiak Cakes, and GrooveBook through the lens of conventional business wisdom.

Too niche. Too competitive. Too low margin. Too complicated.

Every reason they said no made perfect sense based on traditional analysis. And every reason was completely wrong about market reality.

Investors look for companies that resemble past successes. Ring didn't look like previous smart home hits. Kodiak Cakes didn't fit the CPG playbook. GrooveBook seemed like a dying category. Pattern matching rejected all three.

The more successful investors become, the more they have to lose. Established Sharks prefer safer bets over risky visions. Founders with nothing to lose take swings that wealthy investors won't.

Shark Tank gives entrepreneurs minutes to pitch. Investors make split-second decisions. Ring's potential took years to materialize. Quick judgments often miss slow-building opportunities.

What rejection actually means (and doesn't)

Five experienced investors said no to three companies that generated over $1.5 billion in exits. Rejection doesn't predict failure. It predicts you're doing something experts don't immediately understand.

Maybe Siminoff's pitch needed work. Maybe Clark didn't articulate the health food trend clearly. Rejection often means you haven't explained the vision effectively, not that the vision is wrong.

Sharks have wealth to protect. They can afford to pass on 100 Ring opportunities and still be fine. Founders need only one success. Your risk calculations should differ dramatically from theirs.

Siminoff didn't argue with the Sharks. He built Ring and let the billion-dollar exit make his point. Your best response to rejection is success that makes them regret their decision.

Even rejected Shark Tank contestants get millions of viewers and immediate credibility. The exposure matters more than the investment for many companies.

Ring had customers who loved it. Kodiak Cakes had loyal buyers. GrooveBook had engaged users. When customers vote with dollars, expert opinions matter less.

External validation is nearly worthless for predicting success.

Five successful investors with decades of experience said no to Ring, Kodiak Cakes, and GrooveBook. They were confident in their analysis. They had good reasons for every rejection. They were completely wrong.

Vision beats validation. Customer demand beats expert opinion. Your ability to see what others miss matters more than getting famous investors to agree with you.

Emil | Founder of Income Ivy