How I Lost Everything Twice and Kept Going (Rachel Hollis Interview) | Ep 852
episodePreviously titled “How I Lost Everything Twice and Kept Going (Rachel Hollis Interview) | Ep 880” — renamed by the publisher on Aug 2, 2026
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What is the reality of hard work and sacrifice?
Welcome back to the game. This is a guest spot on Rachel Hollis' podcast. Main things I talked about in this podcast are the reality of hard work and sacrifice. You can't get around it. Learning from some of our failures and investing in companies in the early days of acquisition.com. And I also mentioned a little bit, as is the Hormozy way, talk about death to gain freedom of mind. There is a little bit of my story in this one. And so if you are somebody who's heard my story, then I would, you know, skip forward a little bit. And then you can get to the mini stuff that is not my story that you've probably already heard. All right. Rock and roll. Love you. Enjoy.
Okay, so I know this is annoying but I do feel like we have to give a tiny bit of your backstory to the audience who has not met you before because a big part I'll just like lead you down the garden path in advance a big part of what I'd love to talk to you about today's mindset because what I'm so in love with in your story is how many times it has all fallen apart and that you've rebuilt yourself. Because I feel like the world is in a place of really needing that conversation. So will you take the audience on a backstory of how you got to where you are today?
Yeah. And I will highlight my exceptional proclivity for finding a way to lose everything. You know, pulling defeat from the jaws of victory. Yeah. The quick story is that I was a management consultant out of college, got to what I would consider a rock top experience where I was 22. I owned my own condo on like a pretty nice high rise, had a balcony, I was looking over the city and I was like, is this it? Like, I just do this until I die and maybe marry somebody. And I was like, this feels terrible. And so I quit. That whole quitting process took me six months from when I decided that I didn't want to do this anymore until I actually quit. And I still think to this day that was the hardest decision I've ever made. Because I think in the beginning it's like you have to forego what you know for something that is unknown. And so you can quantify what you have to lose but not what you have to gain. And I think that's what makes the decision so hard. Now, obviously, on the other side, it's very easy in retrospect.
Like, I can't believe it took me so long. It's like, yeah, but you didn't know. Yeah. It's like saying, oh, I should have just, you know, invested into the stock market for every year for 20 years. It's like, yeah, but every single time you're about to do it, it's like, oh, but it's down now. It's about to go. Like, there's all this uncertainty. Maybe it's different now. But just for context for the audience so that I don't seem more heroic than I am, I ended up – quitting my, I'll say quitting my family, not hardcore like that, but more so like the harder discussion was getting my family to be on board with the idea that I was going to quit my job more so than me quitting. Like quitting the job actually felt like the easy part. The telling everybody else that I was changing my life was the hard part. And so I drove across the country.
And when I was in like halfway point, I called my dad to let him know. that I'd quit my job and that I was going to do this other thing. And he was like, well, just come over. We'll talk about it. Because he'd like talked me off the figurative ledge a bunch of times over the last however many months. And I was like, I'm gone. And then that's when obviously like he was upset about it.
I feel like that's an important moment to pause because there are a lot of people listening who have these dreams and ideas but are terrified of the people closest to them and what they will say. And I think because I know your story, I know that culturally it was really important for your dad that you went to college and had this amazing job. And he sounds like a pretty authoritative force in your life. So did you care that you were disappointing him? You finally got to the place where you're like, fuck it, I'm out? Yeah.
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