Gary Leland the Bitcoin Boomer

0:01Boom! Shake the room, Fire Nation. JLD here and welcome to Entrepreneurs on Fire. The only daily show interviewing the world's top entrepreneurs seven days a week. Today, we'll be breaking down the Bitcoin boomer. To drop these eyeballs, I brought Gary Leland into EO Fire Studios. Gary built his first e-commerce site in 1996, first podcast in 2004, and bought his first Bitcoin in 2017. He runs BitBlockBoom, which is the world's longest running Bitcoin conference. And today, we'll talk about the orange pill moments, Bitcoin's future, buying Bitcoin. We'll talk about micro strategy and Michael Saylor and so much more.

0:40And a big thank you for sponsoring today's episode goes to Gary and our sponsors. Is this your year to grow a successful business? Attend the world's highest rated business growth workshop taught personally by Clay Clark and now featuring football star Tim Tebow and President Trump's son, Eric Trump at thrivetimeshow.com slash EO fire. Again, request life-changing tickets today at thrivetimeshow.com slash EOfire. If you've ever considered launching a show on YouTube, I may have the solution for you after launching a very successful show on YouTube in 2024, MicroStrategy Today. I've learned a lot on what it takes to create a successful show and have launched a one-on-one mentorship program called YouTube 100.

1:22If you want to jump on a call and learn more about this program, shoot me an email, john at EOfire.com. This is the year of YouTube. Let's go. Gary, say what's up to Fire Nation and share something that you believe about becoming successful that most people disagree with. Well, hello, Fire Nation. It's good to be back on this show. It's only been like six years or something. I can't remember how long it's been, but it's been a long time. And I think that people need to do something that's their passion. I think if it's your passion, it's easier. But the other part of that is, if it's your passion, and this applies to whether it's not your passion, too many people give up too soon.

2:07And they're right around the corner from knocking that home run, but they don't want to watch that last pitch. They've kind of given up on themselves. They think, oh, it's not going to happen. It's not going to work. I've just been putting money into this, time into this. But sometimes I believe people give up too soon, and it's almost happened to me. and I almost gave up once on a business that I no longer own, but I'm still receiving money from. And I told my wife we needed to give it up. And she said, no, no, we can't. You put too much time into this. I feel you're right around the corner. And within a month, my main competitor went out of business.

2:41And within two months later, my other competitor went out of business. They both were having troubles. And I bought out their inventories. This was for a retail store for pennies on the dollar. And that business is still running today. So I think sometimes people just give up too soon. Fire Nation, go check out a YouTube video called Three Feet from Gold. It's pretty epic. I highly recommend it. And the reality is when Gary is talking at the beginning about the passion side of things, it's so much easier to stick with something when you're excited about it, when you have enthusiasm, passion for that thing.

3:15The people that are always giving up Three Feet from Gold is because they never really had passion for that thing in the first place. So start with passion. And of course, make sure that thing that you're doing is adding value to the world. It's going to allow you to stick with it till it works. Now, today we're talking about the Bitcoin boomer, just the whole movement around this. And we all, at least all of us who have gone into the world of Bitcoin, we have our orange pill moment, meaning that that moment that we swallowed the Bitcoin pill, we understood it, the light bulb went on. And for some people, it might have been when they read the Bitcoin standard.

3:53For others, it might have been when they were watching a keynote from Michael Saylor. Who knows what your orange pill moment was, Fire Nation. But Gary, tell us yours. It's a three shots thing. First time I was told about Bitcoin, it was$100. I'm not going to be able to say the year off the top of my head. And a good friend of mine, a podcasting friend of mine, I saw him. I was visiting someone else, someone who was named Callie Lewis at the time. And he had an office. He subleased there. And people were coming in and giving him money and walking out with thumb drives. And I was waiting for Callie to finish her on-air appearance in her studio.

4:28And I finally said, what is going on here? And he said, have you ever heard of Bitcoin? I said, no, I've never heard of it. And he goes, well, it's kind of like online stocks. And I said, well, I'm not interested in that at all. And I kind of dropped the subject. And to this day, every time I see him, I say, do you know how many millions of dollars you cost me with your online stock crap? and he goes um well you were an older guy so i thought you would understand that easier and i said yeah i understood online stocks i just didn't want to screw around with that and the next time i was having dinner with adam curry down in austin and he told me he we uh i heard him say on a show one of his shows uh episodes that he had some bitcoin and so i asked him about it i said have you sold that bitcoin yet and he said no i'm keeping it till well, it's a million dollars.

5:14And I was like, okay, right, right, right. But the next time, which is the third shot, and like I said, I think it's pretty common if you talk to a lot of Bitcoiners, it takes them three shots to get it. I was speaking at a Dallas conference. I was speaking as a marketing conference called the Big D Conference. And I was speaking about podcasting, of course, because back then I was into podcasting, you know, as part of a podcast movement. And I was walking in a hallway and I saw about four or five of my friends hanging out in the hallway. So I went and joined with them and a good friend of mine, Tony Cicallo, was talking about Bitcoin, and I missed half the conversation.

5:49But he said something in the conversation, one phrase that made me stay and asked him, hey, could you tell me more about this? Because I missed the first half. He said that Bitcoin was the only missing protocol from the Internet. It was the protocol for money. It had never been invented. And, you know, I started my first e-commerce site in 96, and by this time I probably had 10 e-commerce sites. So when I heard a protocol for money, the missing protocol for the internet, I mean, that was most of my business. That's all I did all day was work on websites. So I said, Tony, could we sit down and talk about this and you tell me the first half of this again?

6:27Well, this was at one o 'clock and at six when the conference was over, we were still on the couch. So I drove home, listened to a podcast about Bitcoin on the way home. When I got home, I called him up and said, hey are you going to be at the conference tomorrow i want to talk about bitcoin some more he said sure i drove back listened to another bitcoin uh podcast we sat on the couch for a couple hours and went to his house he was gpu mining at the time uh he was mining zcash so he could convert that into bitcoin because you could not mine bitcoin at the time without a um basic miner, which is a much more expensive and higher quality mining machine.

7:08So we talked about it. He helped me buy some Bitcoin on Coinbase. That was one of the few places all they had was Bitcoin, Litecoin and Ethereum at the time. And I bought some Bitcoin, maybe$100 worth, put it on a wallet that I bought from him, went home that night and bought a substantial amount of Bitcoin. Not a substantial amount, but now it would be a substantial amount for damn sure. I think it was$20 ,000 worth I bought that night. And then I've been buying Bitcoin ever since. In 2020, I went in 100 % into Bitcoin. All my investments were in Bitcoin starting 2020. Not only buying Bitcoin, but all my stock investments moved over the Bitcoin also.

7:57with micro strategies, for instance, which we'll probably talk about later, mining companies, but I transferred all my stocks into Bitcoin stocks. So at that moment, I went in 100%. What would you say is the number one question that people have around Bitcoin now that it's 2025 and beyond, and you are looked at as a thought leader in the space? What just seems to be that number one question that people are asking that you want to just address right now? They say they don't understand it. And even after you explain it to them, they don't understand it. And I say, do you really or I don't know how it works.

8:33And I say, do you know how email actually works or how HTTP works? I say, no, but you use these things every day. So that doesn't matter how it works. The fact is, Bitcoin's been around now for, what, 15, 16 years, and no one has been able to hack into Bitcoin. No one has been able to destroy Bitcoin. All it does is get better. It's proved itself. I mean, I don't know if you think it's going to take 100 years to your dad for it to prove itself, but it's pretty much proved itself. I mean, you can buy it, you can sell it, you can move it around, you can pay for stuff. I hear that a lot, too. I can't pay for anything.

9:09And now I'm just at the point. It doesn't matter if you can pay for your coffee with Bitcoin. That's not the issue here. It's way more than that. So I would say, and the funny thing is, John, when you talk to someone older like me, I'm 70, or I turn 70 next month. When you talk to someone older like me, this is a great example. I think I talked to my landlord one day. He came up to me, this was four years ago, and said, Gary, I know you're into Bitcoin. I don't understand it. Could you kind of explain it to me? And I love this guy. He was the best landlord I ever had at one of my businesses. And so I spent a strong 20 minutes going over this with him, telling him everything I thought he knew, needed to know.

9:52And when I got through, when I finished, he asked me, do you have one on you? And I'm going, oh, my gosh, how bad of a job did I do? I spent 20 minutes on it. And he still doesn't understand that it's not a physical product. Because, you know, every time you see MSNBC, Fox Business, anyone talking about Bitcoin, they bring that coin up in the background with the B on it. And some people believe, and I know this is hard to believe if you're into Bitcoin, and I bet there's a listener here that actually thought that was a Bitcoin. So now if I talk to someone that's over 50, I start out with, well, you realize that's not a physical item.

10:32It's not a coin like you see on TV. and get that out of my way because if they still have that in their thought pattern they can't absorb a lot of what you're saying you know because they're thinking okay how does that work with this coin i don't understand how this coin could do that you know so that's the first thing i do with the older person is get that out of the way it's not a physical product and i think that's i know it sounds stupid but i found it to be true and maybe that's because i deal with so many boomers just in my peer group you know people i hang out with parties i go to yeah i've started kind of moving towards Michael Saylor's very common commentary around this, where Bitcoin is the perfect preservation of capital.

11:14Like he's really moving away of using Bitcoin in conjunction with currency and with spending, because the reality is this, like you mentioned, you're not going to be able to walk into Walmart today and say, oh, let me just pay you in Bitcoin. Like that will happen in the future with lightning and all these different things. But the reality is, can you use real estate right now to go into Walmart and say, well, I own a piece of property down the street. Like it's worth this much money. I want to use some of it. No, you can't do that. So you can't use real estate as money. Or gold. I mean, chip off a piece of this gold and give it to you and you can weigh it out.

11:45And whenever I talk to gold bugs too, and they're just like, well, I mean, what if, what if like the apocalypse happens? I go, okay, you have 50 gold coins and the apocalypse happens, tell me how that works because nobody else has gold coins within a 10 mile radius of you. So how are you actually going to, who's going to care at that point? They're going to be concerned about water and food. And those are the important things. And of course there will, well, anyway, we're not going to go down that path. But the main point that I want to make around Bitcoin right now is that's how I'm looking at it is a preservation of capital.

12:20It's 21 million. It's scarce. it is there's a great um video they just came out with what's called this called what's the problem it's a 40 minute clip you might have seen it is just recently kind of been circling around x gary and it's about the uh fiatellos versus the satoshis have you seen that video no i haven't seen that one yet and i watch a lot of content okay but i can tell you this will be the best piece of content you've seen in 2025 i'm not gonna say ever but this this year it is unbelievable And what is it? Because I'll probably watch. You definitely should. You have to. It's called What's the Problem?

12:57If you just search that on Twitter or on X, you'll find it. And it's so amazing. And I think you'll start using that to send to your boomer friends because I'm not going to go into super detail because I want to get on some other things, but it's about a fictitious group of people who are shipwrecked on an island and they both decide that they're going to use Bitcoin, which is perfect money, perfect preservation of capital going forward, nothing else, except one half of the people say we're using Bitcoin, but there's going to be a big red button that we can quote unquote print more or we can make more Bitcoin.

13:29But we're not going to use that button unless we have to. And they build a wall down the middle and then one side. You know what happens there. You know what happens there. And it's so well done, though. It's so well done. So highly recommend it. Hey, I want to say if you want to see also what I think is one of the best videos I've ever seen explaining Bitcoin. I like it so much I made a short link on my website to it. It goes straight to it. It's by Michael Saylor. The short link is GaryLeland.com slash salt. And one time we were over at Michael's. Kathy and I were over at Michael's for brunch.

14:01And I told him, I said, that's the best video I've ever seen explaining Bitcoin. He said, that was my goal, just to make it an explanation video that you can watch. So if anyone wants to, if they're not familiar with Michael and they want to see his thought train or find out about Bitcoin, I think that's one of the best videos I've seen. This may be even better. But I'm just saying that's a great explainer video. Well, you get back to me after you watch that and let me know what you think. I think it's fascinating. And I'm going to watch what you just shared as well. We have a lot to talk about around this topic, Fire Nation.

14:33When we get back from thanking our sponsors. Is this your year to grow a successful business? Are you looking to learn the proven processes and success systems that have been used to create thousands of millionaire success stories? See thousands of success stories and testimonials from real people just like you who Clay Clark has mentored and coached into prosperity at Thrivetimeshow.com slash EOfire. Clay's proven business coaching program is month to month and it costs less money than hiring a minimum wage employee. Yes, it's month to month and it costs less money than hiring a minimum wage employee.

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15:47Let's talk YouTube. Have you ever considered launching a show on YouTube or do you currently have one that's struggling to gain traction? I may have the solution for you. After focusing on audio for 13 years, I launched my first YouTube show in late 2024 and have seen fantastic results. Over 12 ,000 subscribers, every show getting well over 10 ,000 views, all 100 % organic, zero dollar spent on promotion or advertising. That is the beauty of YouTube. If you create the right content with the right cadence, YouTube will make sure it gets in front of the right people. My show is called MicroStrategy today and I'm having a blast creating content on a daily basis because it's on a topic I love about a company that I truly admire.

16:31What excites you? What fires you up? If you wanna launch a show around that passion or improve your current one, I'm launching an exclusive coaching program called YouTube 100, where in 100 days, I will mentor you one-on-one and together we will create a show that you love and that's successful. I hired the best mentors when I first started and have learned so much along the way. I'm ready to help you ignite your show and let YouTube do the heavy lifting of building a meaningful audience that will allow you to grow and monetize your show in ways you might not currently think possible. If you want to jump on a call and learn more about this program, shoot me an email, john at eofire.com.

17:10Put YouTube 100 in the subject line and we'll schedule a time to chat, j-o-h-n at eofire.com. This is the year of YouTube. Let's go. So Gary, we're back and I want to talk briefly about the future of Bitcoin. I mean, we have our first ever pro-Bitcoin, pro-crypto government. I mean, by the time this episode goes live, I mean, there will be a couple months into the Trump presidency where his cabinet, the people that he's bringing on as a staff, they're passing regulations rapidly that are going to be, you know, giving actual clear regulation and guidance. And there's going to be a lot of really interesting things that are happening in the world for the next four years at a minimum.

17:53And I'd love to know what you think the future of Bitcoin looks like. January the 1st, last year, I predicted 100 by Christmas. I was pretty damn close. Hit 108. I mean, you know, so I feel like I'm pretty good at thinking the future on this. Let's hear it, buddy. What do you got? Well, I want to be right second year in a row. So I'm going with 175 because I can't help but be right. I mean, and when you talk, John, when you talk bigger numbers than that, people think you're crazy. They think you're crazy. They think you're crazy. Yeah. When I used to tell people it would hit a hundred soon, they, years ago, they got up.

18:25Then they gave up. They just cut it off. But what's crazy about 175 is that's not even a 2X. That's not even a 2X. That's why I said, there's no way I can't be right. I hope that you're wrong by orders of magnitude to the upside. But I still would be right that it hit 175. That's true. That's true. 108, still hit 100. That's a big point. So I want to move into micro strategy. I mean, you're friends with Michael Saylor. About six months ago, I've been orange-pilled for many years now, but about six months ago, I got red-pilled with micro strategy because I just started consuming everything that Michael Saylor was putting out.

19:03I wish that I had been red-pilled years ago, but better late than never. Well, all my stock investments are in micro strategy. Well, I love that because I got so passionate. Speaking of our first topic that we talked about today, I got so passionate and excited about MicroStrategy. I launched the first and still only daily show. We're talking seven days a week, Gary. It's about 15 minutes long. Thank you, buddy. I appreciate that. It's called MicroStrategy today. It's the thing that I look forward to. I'll never get burned out of doing it because it's so much fun. What are your thoughts on MicroStrategy?

19:36Michael is like one of the smartest people I've ever met. I always feel like I'm the dumbest person in the room around hardcore Bitcoiners because usually the long old Bitcoiners are really smart people. But when I'm around Michael, I really feel like an idiot. I mean, and not because he tries to make you two because he's just not that kind of person. He's pretty humble in all reality. I mean, he's been humbled. I mean, when he was running MicroStrategy since 1989, they went through decades of despair. I mean, he's grinded it out. He has. he had a choice of watching micro strategies go bankrupt or making a drastic move.

20:11And he had the balls of cojones to do it. I mean, basically, and I don't think that's much to say. He said it on air. So and also, you know, with the return on micro strategies, whatever Bitcoin goes up, you know, and I'm not real good at numbers, precise numbers or amounts, but I know whatever if Bitcoin goes up, micro strategies goes up more, you know, percentage wise. so um i guess so i'm i'm all in matter of fact i found two thousand dollars that was or two hundred thousand dollars the other day that was in a rock that my wife had i didn't know was sitting there and i don't even know what in the hell it was in uh that my uh our financial guy was handling that for her and it made 20 and i said we're moving this out of here and we threw all that in that other two hundred thousand in the micro strategies i don't even know how i had missed that before Wow.

21:00Like I said, better late than never. And I mean, I could not be more bullish. I think we're going to have another 10X coming up within the next year or two. A split, a 10 times split or something. Yeah, 10 to 1. And that's one of the reasons they just did that$10 billion share authorization. So they have space to do a stock split when the time is right. So they have space to continue to do ATM at the market selling so that they can do convertible bonds. And by the way, if this doesn't make any sense, Fire Nation, I'm sorry, but we just get really excited about this because this is like a conversation between two people who are passionate about Bitcoin and as a result are passionate about micro strategy.

21:38So there's a lot of exciting things in the future. And you have the BitBlockBoom Bitcoin Conference. Tell us more about that. BitBlock Boom is the longest running Bitcoin conference that there is. This is our eighth year coming up in Dallas, Texas. We are a Bitcoin conference. We're not a crypto conference. As you know, there's Bitcoin and there's 20 ,000 cryptocurrencies. We're not a cryptocurrency conference. We are a bit. We're kind of like micro strategies. We're in one thing. We're into Bitcoin. That's all I'm into is Bitcoin. And that's all this is. And I bring some of the best people from all over the world to the conference.

22:15I have people come from, I have a contingency of people come from Australia, Europe. I mean, they come from everywhere to come to BitBlock. Boom. So it's, I have more people from, before COVID hit, I had more people from the Netherlands than I had from Dallas. And it was in Dallas. I mean, you know, that's, I mean, we have, you know, Friday is workshops all day. What is Bitcoin? What is lightning? What is mining? and then Saturday is the main conference day. And all in all, it's a four-day event. But vipblockboom.com, we have a code. I'll give you a BBB1. We'll give you a discount. Ooh, BBB1, BBB1, Fire Nation.

22:58Gary, we've been rocking it today. We've been talking about a lot of cool stuff. Give us in just one or two sentences the single takeaway you really want our listeners to get from our conversation today. I have like 7 ,000 hours studying Bitcoin. Wow. So, you know, and that's not even counting the books I've read or the conferences that I've hosted or been to. So Bitcoin is kind of like I'm tunnel vision on that. And that's just the way I am. When I like something, I get tunnel vision on it. I want people to understand that Bitcoin is more than what we've talked about. It's more than money because we've talked about it from the money kind of aspect.

23:36Blah, blah, blah. Holding your money, preserving your money, spending your money. whatever you want to look at it. Bitcoin is not only that, but it's a world-changing technology. It's going to change the entire planet for the good. Someday, I'm not saying it's going to happen tomorrow, and I'm not going to say it's going to happen in 10 years, but someday, I believe the entire planet will be on the Bitcoin standard. It will be on a standard. Countries won't even bother to print fiat because nobody will want that fiat anywhere, the fiat money. And when we get on a Bitcoin standard, the world will be such a better place.

24:14Wars will start ending because you run out of money. You got to stop the war. You can't spend all your reserves on a war like the United States does. We've been in war for 30 years now. I mean, you know, back in the days of old, they used to pretty much settle those wars somewhat after a while because they were running out of money and money to get from their people. Right. They had to. Yeah. Now we don't have to. So a Bitcoin standard, that's just one thing that's going to happen in the future. But a Bitcoin standard is going to change the world. And I think that's one of the big differences are in the past.

24:46It was a big difference between a Bitcoiner and a Bitcoiner is that a Bitcoiner wanted to change the world. They want to get money. Don't get me wrong. They want to make money like everyone else, but they realize that what they're putting their money into, what they're working with, what they're promoting is going to change the world. Where most crypto people, that's not on their brainwave at all. All they're thinking about is, can I buy this this morning and sell it next week for an extra 50 cents or an extra dollar gain? Where Bitcoiners are making that gain and they want to make it, but they know they can change the world at the same time.