Earlier startups: PhoneTag and Unsubscribe

A Note from James:

Imagine going on Shark Tank in front of Mark Cuban, Mr. Wonderful, Lori Greiner, Robert Herjavec, and the rest of the Sharks. You’re offering 10% of your business for $700,000, which values the company at $7 million. They all say no. Then, a few years later, Amazon buys your company for a billion dollars.

That's gotta feel really good, and that's the experience of our next guest, Jamie Siminoff.

Jamie built the company behind the video doorbell that lets you see who’s at your door—Ring—and helped turn a simple household object into a home security platform. He went on Shark Tank in 2013, didn’t get a deal, kept building anyway, and eventually sold Ring to Amazon.

Jamie has a book coming out right now called Ding Dong: How Ring Went from Shark Tank Reject to Everyone's Front Door. What really impressed me about Jamie was the simplicity of all his business ideas, since this was his fourth business. A doorbell you can answer from your phone. A way to turn voicemail into text. A tool to unsubscribe from unwanted emails. The kind of ideas that make people say, “Someone must have already done that.” But we talk about this very thing and how critical it is for entrepreneurs to get over these feelings of like, "Oh, I can't do that."

That’s the lesson. Sometimes the obvious problem is still unsolved. And sometimes the person who wins is the one naive enough—or stubborn enough—to fix it anyway. 

Episode Description:

James sits down with Ring founder Jamie Siminoff to talk about one of the great modern startup stories: a rejected Shark Tank pitch, a product investors dismissed as “just a doorbell,” and an eventual billion-dollar acquisition by Amazon. But the episode is not just about the sale. It’s about how entrepreneurs see problems before markets know what to call them.

Jamie explains why investors misunderstood Ring at first. They looked at it as a doorbell business, not a home security company. That framing made the market look tiny. But customers were already showing something different: they wanted to know who was at the door, feel safer, and use video in a new way around the home.

The conversation also moves into Jamie’s earlier companies, including PhoneTag and Unsubscribe.com, and what those taught him about declining markets, customer behavior, and the difference between a clever product and a durable business. From there, James and Jamie talk about AI, why software is easier to build than ever, why that does not make startups easy, and why simple pain points still matter.

What makes this episode useful is Jamie’s clarity: don’t start with the technology. Start with the problem. If something is broken, fix it. And don’t automatically assume that because an idea sounds obvious, someone has already solved it well.

What You’ll Learn:

• Why Ring looked like a tiny doorbell business to investors—but became a massive home security company.
• What Jamie learned from being rejected on Shark Tank while already showing real sales traction.
• Why simple ideas are often dismissed precisely because they seem too obvious.
• The difference between being an “inventor entrepreneur” and a market-first operator.
• Why declining markets can make even beloved products hard to scale.
• How AI changes the cost of building software, but not the difficulty of building a valuable business.
• Why Jamie believes entrepreneurs should focus on problems and solutions, not technology for its own sake.

Timestamped Chapters:

• [02:00] Jamie on why a doorbell sounded like a “steam engine” idea
• [02:39] A Note from James: from Shark Tank rejection to Amazon acquisition
• [04:03] What Jamie does now inside Amazon
• [04:32] Looking back at the Shark Tank pitch
• [05:51] Why the Sharks misunderstood Ring’s market
• [06:44] Doorbell company or security company?
• [07:45] Why obvious ideas are hard to see in real time
• [08:22] The objections investors kept raising
• [10:10] Simple ideas, doubt, and the fear that “someone already did this”
• [10:50] The hardest period after Shark Tank
• [11:43] PhoneTag and the voicemail-to-text opportunity
• [12:31] Why declining markets are hard businesses
• [13:16] Building products you personally want to use
• [14:00] Jamie as an inventor entrepreneur
• [14:33] Unsubscribe.com and the “gray mail” problem
• [16:27] The path from earlier startups to Edison Junior
• [17:05] How Ring came from a garage problem
• [17:40] Jamie’s lifelong habit of fixing what’s broken
• [19:14] Why naivete can be an entrepreneurial advantage
• [20:19] James and Jamie on Claude Code and AI app-building
• [21:29] Why AI’s “brain” has outrun its scaffolding
• [22:44] Coding may be easier—but deployment is still clunky
• [23:37] The future of building apps without seeing the sausage made
• [26:25] Why Jamie might have sold Ring early for far less
• [27:52] Hardware is ugly until it gets big
• [28:47] Why investors are often too early or too late
• [29:58] OpenAI, Anthropic, and whether AI becomes a commodity
• [31:48] Why Jamie expects another major AI shift
• [32:39] What happens when you raise VC money
• [33:18] Swinging big or dying fast
• [34:25] Why Amazon bought Ring
• [35:34] Choosing Amazon instead of an IPO
• [36:23] How life changed after the sale
• [37:41] Ring’s AI work on lost dogs
• [39:14] Why people do not always use obvious solutions
• [40:38] How Ring’s lost-dog feature works
• [41:23] Privacy, consent, and community video
• [41:45] Fire Watch and using Ring cameras during wildfires
• [42:57] Why Ring focuses on safer neighborhoods, not cameras
• [43:48] Building a startup in the AI era
• [45:03] Why SaaS is not dead
• [46:10] Where Jamie would look for startup ideas now
• [47:47] Why people will still pay for useful small software tools
• [48:23] Ring’s app store and the long tail of camera use cases
• [49:55] Horse monitoring, elder care, and unexpected AI applications
• [51:41] Shark Tank relationships after the Ring sale
• [52:29] Jamie’s advice for standing out on Shark Tank

Additional Resources:

• Ding Dong: How Ring Went from Shark Tank Reject to Everyone’s Front Door
• Ring official “About” page.
• Jamie Siminoff’s LinkedIn profile.
• Amazon’s article on Ring Search Party for Dogs.
• Ring Search Party / Fire Watch information page.
• TechCrunch coverage of Unsubscribe.com.

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