UPDATED 00:06 EDT / OCTOBER 04 2018

EMERGING TECH

Back from the brink: Tech CEOs face down sharks, losses and near-failure

Multiple species of sharks navigate the Pacific Ocean off the coast of Southern California and, on a bleak day five years ago, one of the area’s tech entrepreneurs swam with the sharks, figuratively speaking. It did not go well.

Appearing on the hit ABC TV series “Shark Tank,” Jamie Siminoff (pictured) brought his idea for a video doorbell to the investor judging panel in November 2013 and left empty-handed.

“I went back to my garage broke and broken,” said Siminoff, speaking at GeekWire Summit 2018 in Seattle Tuesday. “The drive home sucked. When your office is in your garage, failure is a double hit.”

The technology industry has often been built on stories of perseverance and Siminoff’s experience stands out as a prime example. His “Shark Tank” failure was followed by renaming his company from DoorBot to Ring and picking up Virgin Group founder Richard Branson as an investor, after the billionaire entrepreneur had seen Siminoff’s dismal appearance on the TV program. It was the largest investment Branson ever made in a non-Virgin company, according to Siminoff.

Amazon buys firm for $1 billion

Ring Inc., with technology based on the concept of not just protecting a homeowner but the surrounding neighborhood as well, was acquired by Amazon earlier this year for $1 billion. And the set, complete with fake door and a prototype doorbell, that Siminoff built with $20,000 of his own money for the ill-fated “Shark Tank” appearance, resides in the lobby of Ring’s California corporate headquarters today.

“I had so much invested in this thing, all I could do was keep going,” said Siminoff. “To build a real company is always next to impossible. Thankfully, we didn’t make a mistake that killed us.”

The tech entrepreneur is often asked by other people for advice on how to get acquired by Amazon. Siminoff claimed it was not something he set as an original goal, but the relationship was built over time as both companies realized the two firms had similar intentions for the technology-oriented home. In September, Amazon released a new Alexa-enabled Ring Stick Up camera that notifies users of suspicious motion inside or outside the home.

“We realized that Amazon had a core culture very similar to Ring,” said Siminoff, which he characterized as starting with the customer and working backwards from there. “It really came together very naturally.”

Disrupting real estate

There was another chief executive at Tuesday’s GeekWire event who could relate to Siminoff’s near-career death experience. Glenn Kelman was the co-founder of Plumtree Software Inc., a portal technology firm that started in 1996 and was ultimately sold to BEA Systems Inc. in 2005.

Kelman was nearly fired from his product oversight role by the company’s chairman in 1999. In subsequent interviews, Kelman described how he cried, begged forgiveness and vowed to change his management style. “I was a hero and then I was a zero,” Kelman said.

Since taking the helm at Redfin Corp. in 2006, Kelman has been engaged in a different struggle, one that involved reshaping the real estate world using a model where buyers would do more of the work, thereby lowering cost through reduced fees paid to agents.

“The fundamental problem is about cost,” said Kelman. “It’s too dang expensive. We still need to make real estate more affordable.”

Reaching that point has been a struggle. Kelman set out to disrupt the entrenched real-estate model, one that he famously once called “the most screwed-up industry in America.”

PropTech takes off

Redfin is now publicly-traded, but it has 13 years of losing money and the process of buying and selling homes seems much the same as when the company began its quest. To complicate matters further for Redfin, the venture capital community has suddenly taken a significant interest in real estate startups, a movement more commonly known as “PropTech.” According to data from PitchBook, a record $1.3 billion has been raised by real estate startups in 2018 alone and there are three months left.

“We don’t think much of the money coming into the space is focused on improving the consumer proposition,” said Kelman.

Kelman’s experience as a CEO has reshaped him into an unusual technology executive, one more outspoken than most about the high stakes game he is in. He told the GeekWire Summit audience that he has not sold “one friggin’ share” in the company and claims he’s in for the long haul out of a mission to use technology for the benefit of consumers well outside of the executive suite.

“I hate the baloney-gorged, bullshit-filled corporate world, and my goal is to build a business that goes beyond that,” Kelman said.

The tale of two tech executives who faced adversity and lived to tell about it is a cautionary tale that the technology world is not for the faint of heart. And it sometimes has a way of coming full circle.

“Shark Tank” will kick off its 10th season this coming weekend and one of the guest judges appearing in a taped episode will be none other than Ring CEO Siminoff. Did he tell them they made the biggest mistake letting him out with no investment five years ago? “I’m not that kind of person,” Siminoff said, pausing. “Yes, I did.”

Photo: Dan DeLong/GeekWire

A message from John Furrier, co-founder of SiliconANGLE:

Your vote of support is important to us and it helps us keep the content FREE.

One click below supports our mission to provide free, deep, and relevant content.  

Join our community on YouTube

Join the community that includes more than 15,000 #CubeAlumni experts, including Amazon.com CEO Andy Jassy, Dell Technologies founder and CEO Michael Dell, Intel CEO Pat Gelsinger, and many more luminaries and experts.

“TheCUBE is an important partner to the industry. You guys really are a part of our events and we really appreciate you coming and I know people appreciate the content you create as well” – Andy Jassy

THANK YOU