First, I Lost on ‘Shark Tank.’ Then, I Sold My Startup for Over $1 Billion

ABC's 'Shark Tank' - Season Five
ABC's 'Shark Tank' - Season Five. Getty Images.

In late 2013, all the Sharks on Shark Tank declined to invest in Jamie Siminoff’s Wi-Fi-enabled video doorbell company, which he started in his garage in Los Angeles. This February, Amazon announced that it would acquire Ring in a deal reported to be worth more than $1 billion. –As told to Emily Canal

In 2011, I was 35 and I had my midlife entrepreneurial crisis. The problem was, I would have an idea but I would turn it into a company too quickly. Ring, at the start, was a way for me to see a delivery person at the front door while I was in my garage. It wasn’t changing anything. But I had to let myself explore it.

Goals that are achievable are boring and unsatisfying, because you just get there. It should be tough to achieve great success. I think if you want to achieve something great, you should be challenged along the way. That’s what gets me through rejection. I was in the fortunate position–I mean this semi-jokingly–where stopping work on Ring would have meant financial death.

I was broke when I went on Shark Tank. I drove there from my garage, went on the show, drove back to the garage afterward, and went back to work. I was a real American dreamer going on the show to get money, and it was hugely disappointing.

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The years 2015 to 2017 might have been the toughest. If I’d stopped, I would have lost my house. I had a 3-year-old and the only thing I could do was keep trying. There were nights when I woke up at 3 a.m. in tears. Bawling. How were we going to make it to tomorrow? Luckily, no matter how mentally hard that was, I had one choice, which was “Pick yourself up, Jamie, and get back out there.” Because stopping would have resulted in the end.

People used to ask me, “What would you do differently?” I’d say, “Raising $100 million right off the bat would have been much better.” They would kind of look at me like, “Why didn’t you?” Well, I didn’t because nobody would give me a friggin’ $100 million. Someone else said to me, “I heard a fund pulled out of one of your rounds.” A fund? Try 250 funds! I wish it had been one fund. Everybody pulled out of my rounds.

I hope that the extreme lows are over. But it’s not like we’re going to Amazon thinking it will lavish us with stuff, and we’re going to have three meals a day for free. Amazon celebrates being frugal. I like that. We celebrate being frugal too. I hope I have bad days. That means you’re fighting and going forward. It’s like when you’re skiing: If you don’t fall, that means you’re not challenging yourself. You don’t want those falls to kill you, but you still want to fall.

The credibility and the awareness that Shark Tank brought was probably worth $10 million of ads. It really launched us. The Sharks liked the idea and said nice things. Mark Cuban said, “I think it’s a great business. I think you’ll be successful. It will be worth $20 million. I just can’t invest in something that’s not going to be $70 million someday.”

As a fan of the show who went on it from his garage, and with Ring now the largest company ever to have appeared on it–that achievement is incredible. And, obviously, I think they wish they had invested.