What’s it like to pitch your dream on Shark Tank, get rejected on national TV in front of 8 million people — and then turn that failure into a company Amazon later buys for more than $1 billion? Ring founder Jamie Siminoff did just that.

A serial inventor and entrepreneur, Siminoff joins us on this episode of the GeekWire Podcast to talk about his new book, Ding Dong: How Ring Went from Shark Tank Reject to Everyone’s Front Door (out Nov. 10), sharing the messy, high-stakes, and ultimately inspiring story behind the company.

Now back at Amazon as a vice president leading Ring and the company’s home-security businesses, Siminoff reflects on failure, reinvention, and what comes next in the age of AI.

Listen below, subscribe on Apple or Spotify, and keep reading for highlights.

What he learned writing the book: The book was almost therapeutic — just going back and looking at this stuff. … My best traits, my most powerful traits, the things that make me successful, are also the worst ones.

The importance of having a bigger mission: At Ring, if we had failed, I could still sit here today and say “We tried to make neighborhoods safer.” At least we were successful at trying something. And so that’s where I think mission is just so powerful.

Establishing a company culture with a strong point of view: A real culture is something that not everyone feels matches them … Two things can coexist at the same time: You can have a ton of empathy and care about people and also be a hard-charger.

The inventor’s mindset: Invention is not just product. Invention’s everything. It’s the process. And I think you can invent everywhere. … If you boil down what an inventor is, anything I see that’s broken, I’m fixing it. I can’t help myself.

Returning to Amazon: The thing that you get from leaving and coming back is the clarity of everything. I got to really see clearly everything we did, what we did wrong, what we did right. And so coming back, I feel like I have a newfound clarity for the business.

The impact of AI: What’s crazy now is with AI, all those timelines are collapsing on themselves. In the next 12 months, I can’t even imagine what we’re going to be able to accomplish. … AI understands more like a human, [which] allows you to do things that are just completely different and more efficient.

Related links and stories

• Pre-order the book on Amazon.
• GeekWire: Ring founder Jamie Siminoff rejoins Amazon in new VP role
• Business Insider: Amazon VP says his division is hiring and promoting based on employees’ AI usage
• Inc.: The tech founder who wants to fix small-town America

Subscribe to GeekWire in Apple Podcasts, Spotify, or wherever you listen.

Keonne Rodriguez, one of the co-founders of the cryptocurrency mixer Samourai Wallet, was sentenced to five years in prison on Thursday for his role in operating a service that allegedly laundered “hundreds of millions of dollars” derived from illegal dark web activities and fraudulent schemes. 

US District Judge Denise Cote imposed the maximum sentence for the charge of conspiring to run an unlicensed money-transmitting business during a hearing on Thursday.

Rodriguez Pleads Guilty In Samourai Wallet Case

Rodriguez entered a guilty plea to this charge back in July as part of a plea agreement with prosecutors. In a memorandum submitted by prosecutors on October 31, they requested five-year sentences for both Rodriguez and his fellow co-founder, William Lonergan Hill.

The filing alleged that for nearly a decade, the duo operated a significant money laundering operation through Samourai Wallet, facilitating the laundering of more than $237 million in criminal proceeds between 2015 and 2024. The transactions linked to their service were tied to various criminal activities, including fraud and even murder-for-hire plots.

At the sentencing, Judge Cote criticized Rodriguez for facilitating the laundering of funds often stolen from unsuspecting victims. “You chose to use your considerable talents to make it harder to recoup those stolen funds,” she remarked.

The Samourai Wallet case stands out as one of the few crypto-related prosecutions to survive President Trump’s pro-crypto administration, which led to the withdrawal of various enforcement actions by US regulators against significant firms such as Coinbase (COIN), Uniswap, and others. 

Recent guidelines released by the Department of Justice (DOJ) in April have raised the bar for prosecuting crypto mixers and service providers for the actions of their users, making Rodriguez’s case particularly noteworthy.

Founders Reach $237 Million Forfeiture Deal

Rodriguez’s defense team had requested a lenient sentence of just over a year, arguing that he had no prior criminal record and was seen as a model citizen and family man. 

They contended that when he started Samourai Wallet, his intention was to create a legitimate business that enhanced the privacy of cryptocurrency transactions. 

However, they acknowledged that over time, he became aware that some users were employing the service to transfer Bitcoin (BTC) from illicit activities, yet he continued to operate the business without taking steps to prevent such transactions. His lawyers characterized this behavior as regrettable criminal conduct.

Expressing his remorse during the sentencing, Rodriguez told the judge, “I am truly sorry and I understand the seriousness of my crimes.”

As part of their plea deal, both Rodriguez and Hill agreed to forfeit $237 million and pay a $400,000 fine. Hill is set to be sentenced on November 19. 

The case against Samourai Wallet bears resemblance to the DOJ’s prosecution of Tornado Cash, where developers were accused of facilitating over $1 billion in illicit transfers. 

Featured image from DALL-E, chart from TradingView.com