Episode 555: Jamie Siminoff: Why "Acting Like a CEO" Killed More Startups Than Failure Ever Did
5/19/20261 hr 29 min
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
Clips
Showing 10 of 11Transcript preview
First 90 secondsJamie Siminoff· Guest0:00
[upbeat music] Hi guys, it's Tony Robbins. You're listening to Habits and Hustle. Crush it. Do you know the story of Rolex?
Jennifer Cohen· Host0:08
No.
Jamie Siminoff· Guest0:08
Like, it's a non-for-profit.
Jennifer Cohen· Host0:09
It is?
Jamie Siminoff· Guest0:11
Ro- Rolex is a non-for-profit company.
Jennifer Cohen· Host0:12
Hold that thought. We should... Okay, I'm gonna keep this in the podcast.
Jamie Siminoff· Guest0:15
It's freaking, like, insane.
Jennifer Cohen· Host0:16
That is crazy. I wanna hear the story.
Jamie Siminoff· Guest0:17
So, like, I just, like, you learn about this stuff.
Jennifer Cohen· Host0:18
Guys, I wanna tell who, people who you are, 'cause I'm already going.
Jamie Siminoff· Guest0:20
Okay.
Jennifer Cohen· Host0:20
This is gonna be on the podcast.
Jamie Siminoff· Guest0:21
All right, we're going. Okay, great.
Jennifer Cohen· Host0:21
Okay, so we have, uh, Jamie Siminoff, just f- by, by the way. [laughs] Then we're gonna tell you the Rolex sto- story in two seconds. Jamie is the founder of Ring. He sold it for $1.1 billion. Um- 5, 1.15.
Jamie Siminoff· Guest0:34
But I mean, it doesn't matter.
Jennifer Cohen· Host0:34
Oh, sorry. [laughs] I mean, just like, you know- It's, it's, there's so many ... like semantics here.
Jamie Siminoff· Guest0:37
[laughs] It's, it's- A little, okay?
Jennifer Cohen· Host0:38
And, um, it was, it was bought by Amazon. He then went to... It w- It was acquired, but now you're, you went to work with, for Amazon- So- ... and then you stopped ...
Jamie Siminoff· Guest0:47
stayed for five years.
Jennifer Cohen· Host0:48
Okay.
Jamie Siminoff· Guest0:48
I was just, I mean, I was kinda burnt and whatever.
Jennifer Cohen· Host0:50
Right.
Jamie Siminoff· Guest0:51
Left, left for a little bit, and then I came back, uh, last... I've been back, like, a year now.
Jennifer Cohen· Host0:55
Okay, then you came back to run- Been back. So y- Now he's back at Amazon to run Ring.
Jamie Siminoff· Guest1:00
Ring, yeah.
Jennifer Cohen· Host1:01
Okay, now w- before we even talk about you, tell us the Rolex story.
Jamie Siminoff· Guest1:04
Well, so these guys do this podcast called Acquired.
Jennifer Cohen· Host1:07
Yep.
Jamie Siminoff· Guest1:07
And what I think is interesting is s- some of the ones they do are companies I just never would've known about. And Rolex, which we all know as a, I guess, a company, or we thought- Yeah ... is actually, like, it's, I think it's, like, the largest non-for-profit in the world or something, or one of them. It's this, like- I've never heard that ... secretive, non-for-profit thing that was started by this guy during the World War I.
Jennifer Cohen· Host1:26
Oh, wow.
Jamie Siminoff· Guest1:27
And he basically invented the watch because