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Habits and Hustle

Episode 555: Jamie Siminoff: Why "Acting Like a CEO" Killed More Startups Than Failure Ever Did

Habits and Hustle

Jen Cohen

Entrepreneurship, Business, Self-improvement, Health & Fitness, Education

4.5818 Ratings

🗓️ 19 May 2026

⏱️ 88 minutes

🧾️ Download transcript

Summary

The biggest threat to a founder's success isn't failure. It's spending years trying to become someone they were never built to be. Jamie Siminoff never followed the CEO playbook. He followed the problem. He built Ring in his garage with a soldering iron, got publicly rejected on Shark Tank, never ran a single team meeting, and still built one of the most recognizable home security brands in the world. In this episode, Jamie shares why the traditional founder playbook is a trap, what actually drives a company to scale, and what AI is about to do to the entrepreneurs who never questioned how they build. If you have ever felt more pulled toward solving a problem than managing a team, this conversation will completely reframe how you think about building. What's Discussed: (02:01) Why "serial entrepreneur" is just a polite word for something else entirely. (05:13) The garage moment that started everything and why he almost missed it. (09:47) What pre-selling millions still couldn't save him from. (13:22) The Shark Tank rejection that became his biggest break. (21:15) How a lunch conversation changed the entire trajectory of Ring. (35:40) The Amazon courting story and why it took three years. (44:35) Why he never had a single team meeting and what he did instead. (51:20) The reason he walked away from a billion dollar company at its peak. (57:18) The wildfire that made him come back. (1:02:10) What AI just unlocked for Ring that wasn't possible before. (1:08:45) Why grit is about to become your most valuable asset. (1:19:46) The one thing he'd tell every founder who's still searching. Thank You to Our Sponsors!AirDoctor: Head to AirDoctorPro.com and use promo code HUSTLE to get up to $300 OFF today! AirDoctor comes with a 30-day money back guarantee, plus a 3-year warranty (an $84 value) FREE! Kion: Visit getkion.com/habits or 20% OFF Momentous: Ready to try supplements that actually do what they claim? Head to livemomentous.com and use code JEN for 35% OFF your first subscription.  Therasage: Visit Therasage.com and use code JEN to get 15% OFF your order. Your skin deserves this level of care. Magic Mind: Head over to magicmind.com/jen and use code JEN at checkout. Prolon: Prolon is offering listeners 30% OFF sitewide plus a $40 bonus gift when you subscribe to their 5-Day Program! Just visit prolonlife.com/JENNIFERCOHEN and use the code JENNIFERCOHEN to claim your discount and your bonus gift. Rho Nutrition: Go to RhoNutrition.com and try Rho's Liposomal Glutathione. Use code JEN20 for 20% OFF sitewide. Manna Vitality: Try it now by using the code Jennifer20 at mannavitality.com.  Find more from Jen Cohen:  Website: jennifercohen.com Instagram: @therealjencohen Books: jennifercohen.com/books Speaking: jennifercohen.com/speaking-engagements Find more from Jamie Siminoff:  Instagram: @jsiminoff Find more from Jamie’s Book: Facebook: Ding Dong Book Instagram: @dingdongbook TikTok: @DingDongBookYouTube: @DingDongBook

Transcript

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0:00.0

Hi, guys. It's Tony Robbins. You're listening to Habits and Hustle. Crush it. Do you know the story of Rolex? No. It's a non-for-profit. It is? This is a non-for-profit company. Hold that thought. We should, okay, I'm going to keep this in the podcast. That is crazy. I want to hear the story. Guys, I want to tell people who you want, because I'm already going. This is going to be on the podcast.

0:21.3

Okay, so we have Jamie Semenoff want to hear the story. Guys, I want to tell people who you are, because I'm already going. This is going to be on the podcast. Okay, great. Okay, so we have Jamie Simeonoff, just F by the way. Then we're going to tell you the Rolex story in two seconds. Jamie is the founder of Ring. He sold it for $1.1 billion.

0:33.1

$1.15. I mean, just like, you know, like semantics here. A little. Okay. And it was, it was bought by Amazon. He then went to, it was acquired, but now you're, you went to work with for Amazon and then you stopped. Stayed for five years. Okay. I was just, I mean, I was kind of burnt and whatever, left, left for a little bit. And then I came back last, I've been back like a year or now. Okay, then I came back last I've been back like a year

0:55.1

now. Okay then you came back to run. Now he's back at Amazon to run ring. Okay now before we even

1:02.8

talk about you tell us the Rolex story. Well so these guys do this podcast called Acquired.

1:07.6

Yeah. And what I think is interesting is some of the ones they do are companies

1:11.2

I just never would have known about. And Rolex, which we all know as I guess a company or we thought,

1:16.3

is actually like, I think it's like the largest non-for-profit in the world or something or one of

1:21.2

them. I've never heard that. Secretive non-for-profit thing that was started by this guy during

1:25.5

the World War I. Oh, wow. And he basically invented the watch because when you're in, when you're fighting in a war, it turns out that everything was a pocket watch. And so to be able to see time if you're like sitting with a gun or something, like you can't so like he basically put the pocket watch on your wrist. So it's like a crazy story. Go on. How did it become

1:44.8

a non-for-profit though? Like how did that? Uh, somehow, I think, I mean, because it was so old,

1:50.0

I think when he died or something, like gave it to this thing, it became like a charitable foundation.

1:56.4

Oh. And so it's like this gigantic company that's not a company that's like this brand.

2:02.7

It's just wild.

2:03.7

So it's a great, I mean, to anyone, it's a great podcast to listen to of a story that I think most people just had no idea.

2:11.6

No, never.

2:12.6

I just had zero, like, no idea about it.

2:14.6

I was basically like schooling, Jamie, before you, you know, before this whole thing

2:18.8

of what podcast he listens to. Has he heard of this? Does he like it? He's not wasting his time.

2:23.6

People do listen to it. And then that's how this whole story happened in the first place.

2:27.1

So this is like an unique way of start and intro. Yes. But I like the uniqueness of it.

2:33.5

Okay. Now let's talk about you. Okay, so Jamie has a lot of, I'm

...

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