If "he who laughs last laughs best," Jamie Siminoff should be having the greatest laugh of all time. Five years ago, he appeared as a contestant on Shark Tank, pitching his startup Doorbot, maker of a doorbell with a camera that sent video to users' smartphones. He came away without a deal, broke, and dejected. But his TV appearance gave the company much-needed visibility and attracted the attention of Richard Branson, who invested. After years of Siminoff's hard work, a rebrand of the startup with the new name Ring, and working to integrate Ring with Alexa, Amazon's voice assistant, Amazon acquired Ring for a cool $1 billion. That made it the highest-valued company ever to have appeared on the show.

But Siminoff really got the last laugh more recently when he got a phone call from a producer at Shark Tank, inviting him to appear as a guest Shark in the 2018 season. "That was a quick yes for me," he says. Not, as you might think, because he wanted to gloat (although he did give the other Sharks a little good-natured ribbing about rejecting him) but because he wanted to pay it forward. "Ring would never have survived or been where we've been if it hadn't been for that exposure," he explains. Even though he didn't get a deal, appearing on the show allowed him to live his dream, so he was eager to help others do the same. 

Now that he's a Shark himself, Siminoff says he understands how the Sharks five years ago failed to recognize the potential in Doorbot, given the speed with which information flies around on the show. "We were at the point where we had sales, we had a good product, but we had such a complex business," he says. "We couldn't show how we were going to get to the next step. We were at that awkward adolescent phase." 

If he could go back in time and change anything about his pitch, he says, it might be the valuation he was looking for. He asked the Sharks for $700,000 for a 10 percent stake in Doorbot, suggesting a valuation of $7 million. At the time, he says, Doorbot had about $3 million in annual sales, and given the product's obvious potential, he thought it was enough to justify the $7 million valuation. But, he says now, "We came in high for what we could show at the time."

"I'm out"

A similar mistake--but worse--stopped Siminoff from backing a product on his first episode as a Shark, even though it seemed like a natural fit for him: a padlocked box for leaving packages by front doors that can be unlocked by scanning a package's tracking number. That product, called BoxLock, was at the manufacturing stage at the time the episode was shot, with some preorders in hand but no items delivered to consumers yet. Still, the founder asked for a $1 million investment for a 5 percent stake in the company, giving his company a total valuation of $20 million. "Asking for a $20 million valuation, it's so far away for me that I'm out," Siminoff said on the show, and none of the other Sharks were willing to invest at those terms either.

But Siminoff did decide to invest a much more reasonable $100,000 in Bear Minimum, a company with husband-and-wife founders. Bear Minimum makes cooking pots that collapse to a small, flat square for use on camping trips. "It's the kind of company I like," Siminoff says. "I'm much more into companies that are not in my own area of technology. I like entrepreneurs who are out there struggling and trying to build something. They were very up front with the struggle they've had." (Bear Minimum's founders lost their first company during the financial crisis when a business partner disappeared with their inventory and cash.) 

Siminoff has had several phone calls with Bear Minimum's founders since shooting the episode. "For a small company like that, the exposure on Shark Tank is going to be so big compared with anything else they're doing, and I have a fair bit of knowledge about how to prepare for a Shark Tank bump," he says.

What was the most surprising thing about going back on Shark Tank as a Shark? "How fun it was," he says. "I thought it would a great, satisfying goal to meet these people and try to give back, but I really enjoyed my day being there. [Multiple episodes are shot in one day.] All the Sharks are beyond nice, super welcoming and thoughtful."

Five years ago, just appearing on the show seemed like a pinnacle of achievement, he added: "It was one of the biggest entrepreneurial accomplishments I could have happen. I thought it was such a big deal, and it was a big deal for us. Going from one side to the other is surreal."