I Spent a Week with $100,000,000 Business Owners. Here's What I Learned.

Every entrepreneur experiences doubt and shame and fear. But if you just sit with that long enough, on the other side of that is where success comes from.

I was recently on vacation visiting some friends in Vail, Colorado, and I was showing up with this group a little bit differently than I usually am because I just feel, I'm like, I'm in this period of my career where I feel, feel ready to shift, and I feel that shift happening in me. My expectations of myself are starting to rise the way that I think is bigger. I'm starting to desire my hundred million dollar thing, and I don't know what it is yet, and it doesn't matter, but I just, I feel myself ready to shift. And that's really exciting. The interesting thing is that these three friends of mine all have much bigger businesses than me, right? And like, there's no judgment. Sometimes we pick on each other and joke with each other, but like, I have the smallest business in the group, but I'm in this period where I'm ready to make that jump. And so I was showing up, like, really ready to soak in whatever advice they had for me or whatever perspective they had. And one of the dinners we were having, they were talking about their businesses in a way that I couldn't relate to them because they're talking about what it's like to run, you know, having 30 employees or crossing $100 million in sales. These are things that I'm interested in. But I didn't have a whole lot to add to the conversation. And for the first time, this little thought came up in my brain and the thought was, I don't fit in here. Taken by itself, the thought I don't fit in here is a neutral thought, right? Because none of us always fit in. I pay to not fit in places. I pay to be in masterminds and go to events and seek out mentors. I don't want to always fit in. I want to be around people that stretch me and grow me and give me a different perspective. So there was nothing wrong with not fitting in, but I judged myself for it. I was like, wait, I don't fit in with my people? Maybe, maybe I'm not good enough to have $100 million business.

Maybe I'm not good enough to ever reach their level. And all of a sudden the self criticism started to come in of like, I'll never be good enough. I've never had a business. And you know, that thought train just goes on and on with the negative. The negative critic that's always telling you what you can't do. And remember that past failure. Remember that project that didn't work out? Remember when you said you'd be here by now and that voice started to come up and it was like this twinge of shame about what I hadn't accomplished rather than what I had accomplished. Now, thankfully, I'm self aware enough to catch it. Apparently I'm not self aware enough for it to not happen, but I was self aware enough for me to catch it and observe it. Because the part of me that doesn't want to deal with that or feel that wanted to leave the table, wanted to leave my friend group and isolate myself and not feel that and go home early and avoid the conversation. But if I just sat with it and observed it and let it process, you realize that it's just BS mental noise that isn't real. It reminded me of what it might feel like for an overweight person to go to a gym and see all the buff dudes lifted in front of the mirror and be like, I don't belong here. I don't want to be here. Everybody's looking at me. And that shame that comes up of being the fat kid at the gym, everything that kid wants to do is run back home and eat donuts and cupcakes, soothe himself rather than feel the negative emotion that comes up. But we all know the best thing for that kid to do is stay at the gym.

Feel the shame. Just feel it. Just. Just be ashamed. If you feel shame, just be ashamed. If you don't know how to lift the weight, lift it wrong. The irony is that the gym is probably full of people who would be happy to help because.

We all love to root for the fat kid. We all love to. We all love transformation stories. We love stories about people who lose £100 or went from rags to riches or lost everything and made it back or had no shot and then they came back and won. We love the underdog. We love come from behind victories. Like, we love that because we can all relate to feeling like the fat kid. We can all relate to that. So the best thing for the fat kid is to just stay at the gym and maybe get some pointers from the annoying buff dude who's lifting in front of the mirror. And in the same way, I felt like feeling like the fat kid was the best thing in the whole world for me. In fact, I was able to get to a place where it was like, wow, actually really glad this is coming up. Like, that means. Means we're ready to go. Like, we're ready to grow, ready to do some things. It means I'm shifting. It means that my old doubts are like making a last ditch effort before they get out of the way. But once again, that flinch, that like initial reaction was like, uh, I don't fit in. I should get away from the table. Like, maybe I should book a fly heartland. Which is ridiculous because the best thing for me to do is just sit in the room with your friends who care about you, that make a lot more money than you and just listen and listen to their feedback about where your business and your mindset is broken and you're not gonna like it and you're gonna have to deal with it and it's the best thing that you can possibly do. And most people are just terrified of feeling that half a second of negative emotion. And you know, I could have chosen to not feel that, not go on the trip, not hang out with my friends, not talk about business, not ask them to critique what I have going on. I would have felt better about myself in the short term, but I wanted to pull out that thorn. Entrepreneurship and money is a great journey to bring up all of those thorns. Because as you move forward, as you unlock the next level, there's just like, oh, there's more thorns there. Oh, more stuff here. There's doubt I didn't know was there about myself. There's patterns I didn't know that I had built. There's beliefs I didn't know were there. There's hard work that I'm afraid to do here. There's things that I don't wanna learn. There's resistance I have here, and we're all playing with that. When we have a goal and we're making progr.

If those negative thoughts are coming up, it's usually because we're bumping up against some sort of a ceiling that we've had in the past. And so lately feeling shame is my favorite thing. As you go through the journey of making more money, building businesses, achieving everything that you want to achieve, you are going to come up against levels that make you feel junk. Pursue those. Go into the room where people make you feel that most people won't enter the room. They're like, ah, I don't want to hang out with those people. They're stuffy millionaires.

Don't you realize that you projecting the stuffiness onto the millionaire is your own stuff that's preventing you from being a millionaire? Pursue that discomfort. Pursue letting that come up and moving through you and be honest about it. Don't posture against it. Don't try to mask it. Like, just feel it. Just let it move through you. This is why most people never make more than 100 grand a year.

Because being in a room where people make way more than that, too uncomfortable, too much of a stark difference brings up stuff. So they tend to hang out with people at their income level and below. But if you're willing to lean into that discomfort, the shame, the doubt, the not enoughness. I used to try and coach myself through it, but now I'm just like, oh, this means I'm bumping it up against the limit. It means that I'm at the edge, I'm growing. Those voices are putting up a fight to keep me safe, but I want to move through it. I promise you, if you do that, if you let yourself do that, if you let yourself feel like the idiot, like the fat kid in every area of life, you won't be the fat kid for much longer. If the fat kid just stays at the gym, just keeps lifting weights, just keeps hanging out with the big buff people or the super slim people that are way ahead of them, their brain won't let them stay the fat kid, their brain says, nope, not gonna go to shame. Nope, I am gonna go to desire. Desire. Normalizing all the things that I see around me. My brain wants to fit in. I now do the things that slim people do, and I do the things that rich people do. I now do the things that confident people do, and the brain moves right through it. And you become the person.

That is capable of being rich, happy, success, confident, whatever it is that you want. Lean into that. My friends. Get into the room that makes you uncomfortable. The next day when I was on vacation, I did a cheers and I said cheers to my friends who make me feel like the fat kid. I feel so grateful to have peers that bring up my stuff, show me where my limits are and allow me to be more than I was yesterday. I wish that for you too. I'm Ryan Daniel Moran. I'm an entrepreneur who builds businesses and invests the profits. I'm trying to buy the Cleveland Guardians and I'm documenting the process about the journey along the way. I'd love it if you subscribe to the channel where I also share along the journey with other entrepreneurs who are building businesses. Thanks for watching. See you soon.