Rich And Proud Of It: Why You Shouldn’t Apologize For Being Successful


You can be rich and proud of it, and you STILL don’t have to feel guilty if you’ve done that by producing things that other people voluntarily want.

So people usually think rich people are greedy, that capitalism is evil, that there’s a fixed amount. Ryan challenges those notions and says that the data proves otherwise as well.

People ask Ryan “how do you not feel guilty about being so rich and proud of it?”

It seems legitimate if Ryan is overcoming challenging circumstances. People are curious about his situation when he became successful.

Ryan’s guest claims that his rise to wealth was easy; he didn’t have any dependents; he was on his own; he grew up in a fairly wealthy family; he always did well in school. As a result, Ryan’s guest feels that he didn’t really have a hard path [to wealth].

How to Stay Motivated

What’s Ryan’s origin story?

Ryan’s dad was a schoolteacher and Ryan’s mom was a stay-at-home mom. Ryan’s parents split when he was 11/12 and from that point on he was on government reduced lunch programs. Ryan figured out that he had to be self-reliant at a very early age. Ryan felt that no one would take care of him or help him and that everything was on him.

Turns out, a heavy self-reliant streak was a very unhealthy belief for the long-term for Ryan. But, as a teenager, the self-reliance made him acutely personally responsible which was a necessity. Self-reliance may be a good strategy as a teenager but it’s certainly not effective as an adult as it really holds you back. Nothing is truly all on your shoulders. And believing that an cripple you and cause paralysis and inaction.

Ryan says that that period of his life really forced him to figure out how he wanted his life to be and what he wanted out of it.

We all spend so much energy today trying to insulate ourselves from hard times. But hard times are the things that actually build us. Responsibility doesn’t go away just because you hand it off to somebody else. The responsibility of you to control and for you to be autonomous over your own life–that is there…that’s infinite…that’s there until you die until you’re gone. And we try to stack the deck to insulate ourselves from hardship and doing hard work or responsibility…but it’s still there.

And you can either trade that and be less free or you can embrace it and create your own life.

So Ryan, at 12, basically became an adult. He started working at 12. He umpired. He was a janitor at Church. At 15 he started working at Dunkin’ Donuts & Baskin’ Robbins.

In fact, Ryan remembered that a friend of his in school, a kid in the computer lab on AOL instant messenger who was reading a message out loud that said “Hey do you want to get together after school today?” from a girl he was dating. And Ryan clearly remmebers thinking: “who the hell has time to hang out after school?!” Ryan worked, and then he studied, and then he slept when he could… and he did that through high school. And then Ryan started his first business at 18.

The good side: it made him a very hard worker. The bad side: it made him very dark and lonely for a very long time. Suicide. Depression. Feeling like everything was on his shoulders. Incredible darkness: another challenge that he had to overcome. And overcoming those challenges is how you become the person you’re meant to be. That’s how you uncover who and what you are.

You see, we spend so much time trying to hide from that. But in reality, that is the path through. We all have it. You’ve got junk. I’ve got junk. She’s got junk. We’ve all got it!

So the idea that we can use that junk as an excuse, pffft! Like yes, It’s a variable. But it’s also part of your uniqueness. And value is inherently unique. That’s the thing that makes you great.

No Guilt

You can be lazy as hell and be rich and you STILL don’t have to feel guilty if you’ve done that by producing things that other people voluntarily want. There is no guilt associated with that. Ryan feels more guilt about working too hard rather than the money in the bank. Why? Because there’s an opportunity cost to how much you work. Ryan is now, in his 30s, unlearning that very strict hard work ethic that he created as a teenager and in his 20s.

Ryan is a huge proponent of capitalism as a system of economics, so much so that he founded the capitalism conference and Why did Ryan start Capitalism Conference? As a way of connecting people and helping entrepreneurs and aspiring entrepreneurs help each other out. Because it’s not like there’s a lot of money in events (there’s essentially zero money in throwing events).

Why Capitalism Conference?

The impetus was that if Ryan really wants to go where he wants to go (which is to buy the Cleveland Indians), he needed to grow beyond the internet business thing (making $10,000 a month in your underwear). That’s what he did to get to a certain point of wealth. But then what? What matters to him? What is Ryan building that has a legacy to it? And Ryan, at the time of running those internet companies, didn’t even know how to ask those questions of himself. Why? Because there was no one around him asking those questions. You are, after all, who you surround yourselves with. He was surrounded with other ineternet entrepreneurs that talk all about hustle and grind and passive income. These are all great things but Ryan wanted to play a bigger game.  And to play a bigger game, Ryan needed to get access to different people. He didn’t have access, so he just paid them. Ryan used all of his retained earnings at the time. All of it.

Ryan rolled all the dice on his first event and still, to this day, say that it was not nuts. Here’s why. Ryan knows that it’s a good investment to rolling all your dice on a good mentor. Ryan just knew that he couldn’t pay the mentorship fee of the people he wanted to be around. But…he could pay them for a day. For one day, he could fly them all to fly into Texas. And, if he spent 3 days with those people and invited other people to join, maybe he could mitigate the costs. And the booking fees for these people were $25-50k a person. So he was spending hundreds of thousands of dollars in just booking fees. And that doesn’t factor in all of the food, the liability insurance, the tables, and other small things. It seems crazy, but it wasn’t. Ryan considered this an investment in himself. What happened?

In the next couple of years, Ryan built a company to $10 M and sold it. Ryan started inspiring entrepreneurs all around the world. The reason is that he started to think differently. He started to put together the thought patterns of the sharks on shark tank, the Gary Vanderchucks, the people who ran big enterprises. The result of doing that is your brain just starts firing differently.

The Secret to Becoming a Millionaire

We can all think of a time where we met somebody and everything changed. One of Ryan’s friends, Jeff Woods, says “if you hit a plateau, it’s because you’re missing a person.” It’s not information. Think about it: how many times have you gone and watched a youtube video and you thought, ”well that was good information. But what do I do now?”

But when you meet a person, you change. Biologically. We literally change when we meet new people. Here’s some trippy stuff: if an alpha male dies, the second in line usually becomes the alpha male, and there’s a testosterone increase [in that second male] that prepares that person to become the alpha. In humans. How does that work? If Tony Robbins died and he had a second-in-command, and that second-in-command took over, there would be a physical change in that second-in-command when they take over. So you change, and you change your environment. All this to say who you surround yourself physiologically changes you. It changes what your habits are, it changes what you think about, it changes what you normalize. Everything is who. It’s not what. It’s not how. Sometimes, it’s when. But it’s always who. The hack? The hack to making a million dollars? Hanging out with other millionaires.

Yeah, certain algorithms and systems help. But you are not likely to force yourself to actually will yourself into doing those things but if you’re surrounded by people to where that’s normal and natural, you just become that person. You have to. The tribe says you have to.

So Ryan, every year, books the people he’s scared of. The people that challenge him. The people that make him play a different game. He brings them into Texas and puts it all on the line in the capitalism conference. Ryan makes money on other businesses. Ryan throws the capitalism conference for him and his people in order to play a different game. And that’s why Ryan’s life has changed in the few years that he’s been doing this. And everyone who goes to it says the same thing.

rich and proud

Ryan chose this path rather than an easier path (join an investment group, surround himself with grizzled, old deca-millionaires, self-help people, etc). But Ryan wanted a very specific group of people. Ryan wanted all of a bunch of different kinds of people in the same room at the same time. But why was he so specific about it? Because he would have probably received the same amount of worth if he joined some marketer’s group. But Ryan didn’t want to be around other marketers. He wanted to be around other marketers. Ryan wanted to be around business people and empire-builders. Ryan wanted to be around specific people. Why those people?

There were three years he booked year one: Gary Vaynerchuk, Robert Herjavec from Shark Tank and Grant Cardone. Why those three?

Gary Vaynerchuk has a similar goal of owning a franchise, and he was 10 years ahead of Ryan in terms of net worth and following (at that time). Ryan wanted to know how Gary thought different than Ryan. He wanted to know how he plans to own the New York Jets and what’s the strategy that he plans to use to do that. He had never talked about it publically before.

Robert Herjavec because Robert is following a model that Ryan’s really envious of that he wants to follow on his route to buying the Cleveland Indians. That is having a stake in a business and having a platform that makes that company grow. The whole reason that Ryan teaches this stuff is that he wants to have a stake in the business and have an impact in that business by the platform that he builds at Ryan wants to be the shark tank of physical product space.

Grant Cardone because he claimed to own millions of dollars in real estate. And if that were true, then Ryan building a similar real estate portfolio would make for a nice down payment on the Cleveland Indians. And Grant was 30 years older than me. So if Ryan could start to reverse engineer that now, then that would have been very interesting and lucrative.  

Everyone’s Got Junk

So what’s the big thing that Ryan learned from this, overall? What is the big personal thing that Ryan’s taken away from this?

Ryan’s discovered this and hasn’t told anyone: we all have got insecurities, imposter syndrome, junk, the thing that hold us back, stories, problems, reasons why we couldn’t. We all got it.

Grant Cardone was an addict for years and overcame it, and channeled it into business and is wildly successful now.

Gary was an immigrant from another country and started with nothing. He built everything he has from absolutely nothing.

Everyone has all got junk and reasons why you can make excuses: you’re this gender, this ethnicity, this setback. Some people overcome it. And that’s usually the result of things that are in your control: what you listen to, who you hang out with, the books you read, the habits that you practice. And the way to fast-track all that: change who you hang out with!

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