Every time I see somebody on the street asking for money, I give them $20. If someone is struggling badly enough to be holding up a sign that says "hungry," and I've got several hundred dollars in my wallet, the thing that feels right to do is help them. I love seeing the joy on someone's face when I hand them $20. Giving $20 is no big deal to me. When I go to a restaurant and the bill is around $40, I'll tip $20. The other day the bill was about $55 and I gave the waitress $80. She asked, "Why are you guys so nice?" And I said, it's nice to be nice to people.
There's a story I read one time about someone, I think it was Bill Gates, before he became a billionaire. He didn't have enough money for a newspaper, and the guy at the stand just gave him one for free. Later, after Gates was wealthy, he came back and wanted to give the man money, and the guy said, "I don't need your money. I barely have enough to live on, but I'm happy to give you something for free if you need it." Being rich and then being able to be generous is no virtue. To me, real generosity is this: if you can help somebody else out, will you do it? Most of us are in a position to help somebody else.
Why It's Harder Online
It is tricky online, because there are tons of people who will message me for money. For example, I gave one guy from the Philippines $20 randomly on PayPal. He just asked me on PayPal, so I sent it. Then everybody he knows, maybe not everybody, but he tells all his friends and family, and suddenly they're all hitting me up for $20 too. The issue with online is scale. There are around 7 billion people on earth, and I can't even give everybody on earth one cent, because that would totally drain me. So yes, it's challenging online, because there are so many people and you can reach so many of them.
But in person, how many people on the street am I going to run into in a day? Usually zero. I do have a friend who's homeless. I'll pull over if I see him walking and give him $20.
The Day All I Had Was Hundreds
I didn't have any twenties the other day, and that comes down to opportunity cost. If you keep a wallet full of $1 and $5 bills, your whole wallet ends up holding maybe $100 total in all that space. I like to not carry any small bills, no ones, fives, or tens, because of the opportunity cost. That same space could hold twenties, fifties, and hundreds. (And I'm saying this out in the open here, I don't have my wallet on me, y'all.)
So the other day, all I had was hundreds, because I'd already spent or given away all my twenties. I saw my homeless friend, and I had my two kids and my niece in the car. I said, "Oh, there's my friend, but all I have is hundreds." And they pushed my generosity limit a little. They said, "Give him 100." I said, "Give him 100? Really, y'all?" And they said, "Yeah, give him 100." So I gave my daughter a $100 bill to hand to my friend. When he got it, his response was, "I've never seen one of these before." I was just like, wow. There's almost never a day where I don't see one of those. All I see is $100 bills, and that's because other people give them to me. The only reason any of us have money is because somebody else gave it to us, unless you're the federal government printing it yourself. Somebody else gave you the money you have.
You Have Enough When You Can Give
So yes, we don't want to just give all our money away. I don't want to give one cent to a billion people and end up with nothing. That's true. At the same time, life doesn't usually put too many people in our path. There's a lot of joy I get when I give someone $20 and they're really happy. I don't get that joy from letting it sit in my wallet. And it seems the more I give, the more I get back. I'll give $20 to a person I see on the street, and then someone comes in and gives $20 on a super chat, and someone else comes in and gives $100 while I'm live, and then someone pays $350 for a call.
I'm big on the idea that there's enough to go around. Some people say, "You can never have enough money." In my experience, you have enough money when you can give to people who ask you for help. When you see someone who needs help, whether they've got a sign that says "hungry" or they've asked you directly, you've got enough money the moment you can give something.
I think it's crazy, because I live in St. Pete, Florida, and there's a lot of money here. There are million-dollar houses getting built next door to me. One day there was a guy sitting outside by the store, and I walked by but didn't have any money, because I'd walked to an AA meeting and either forgotten my cash or already given someone else my $20. So I walked all the way back home, got $20, got in my car, drove over, and he was still there. I gave him the $20 and he was so happy. I asked, "What do most people give you?" He said, "Most people don't give anything, and if they do, they give some change or a dollar." These are people driving around in new Teslas, going to work out in $100 workout clothes, paying to put their kids in private schools in my neighborhood. I don't live in the fanciest neighborhood around, but the houses here are probably several hundred thousand dollars on average, and the newer ones are getting built for over a million. I live in an area where there are a lot of people with a lot of money.
So I think, what are y'all doing? Somebody is desperate, and all you have is some pocket change. All you have is a dollar, all you have is five dollars. But you'll go spend all kinds of dumb money on a new car or a new house. You'll go to the liquor store and dump your money there. You'll spend money on absolutely insane stuff, buy all kinds of crap, but you don't have a dollar. You don't have $20 for somebody so desperate that they're sitting there with a sign that says "hungry."
"They Should Just Get a Job"
Now, yes, I hear the argument. Everybody says, "They're just going to go buy crack or alcohol, you can't support that, they should get a job." Well, have you ever been that desperate before? Is it just that easy? Is it just that easy for you to get a job if you got kicked out? I've been an alcoholic before, and the only reason I wasn't on the streets is because I had parents who took care of me, and I wasn't quite sick enough to be unable to stay mostly sober while I lived at home with them. Most of us are just one family member, one friend, or a few people away from being on the street. So saying someone should just get a job, that's something you say when you haven't had that experience yourself and don't see how easy it is to wind up on the street. Some of us are differently abled in this life, and it's not as easy for everyone to keep a job.
I can tell you, I haven't had a job in a decade, and I'd rather live on the street than work some job I hate. It's really nice now. I used to be the kind of person who would fight with somebody rather than give them a dollar. And what I can tell you today is that that's an unhappy way to live your life. It's an unhappy way to live when you don't have a dollar or $20 to help somebody else who's desperate, but you've got $100 to buy yourself a new pair of shoes, $1,000 to take a vacation, $10,000 or $50,000 to buy yourself a new car.
I hated myself and I hated the way I lived, the feeling and the scarcity mindset I had back then. I love how I feel now, when I've always got something to give somebody else. If you want to hear more about how I got from that old way of living to this one, I've shared a lot of it on my Life playlist.