Valuetainment - May 09, 2026


＂Are The Cracks Starting To Show？＂ - Michael Saylor SHOCKING Rumor Of Selling Bitcoin


Episode Stats


Length

12 minutes

Words per minute

203.84

Word count

2,462

Sentence count

192

Harmful content

Hate speech

1

sentences flagged


Summary

Summaries generated with gmurro/bart-large-finetuned-filtered-spotify-podcast-summ .

A rumor surfaced this morning that Bitcoin evangelist Michael Saylor is considering selling the cryptocurrency he has long championed. Does this mean he will actually sell Bitcoin? Or will he continue to invest in Bitcoin and see it continue to rise in price?

Transcript

Transcript generated with Whisper (turbo).
Hate speech classifications generated with facebook/roberta-hate-speech-dynabench-r4-target .
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00:00:30.000 So a rumor came out that Michael Saylor is entertaining possibly selling Bitcoin.
00:00:33.740 What do you mean he's entertaining selling Bitcoin?
00:00:35.740 Isn't he the one that MicroStrategy keeps buying, buying, buying?
00:00:38.840 Yes.
00:00:39.860 He said he would never sell Bitcoin.
00:00:42.840 Now he's saying he might.
00:00:45.200 This is a story that came up from this morning.
00:00:47.880 Strategy's first quarter loss is bigger than expected.
00:00:51.720 Michael Saylor is the Bitcoin evangelist who has reportedly emphasized that he would never sell.
00:00:56.460 However, his company, MicroStrategy, announced a net loss of $12.5 billion for the first quarter of this year.
00:01:04.440 Saylor did what had been previously unthinkable.
00:01:06.920 He told investors on an earnings webinar that he would consider selling the cryptocurrency he's long promoted passionately.
00:01:14.140 Will probably sell some Bitcoin to fund a dividend just to inoculate the market, just to send a message that we did.
00:01:19.740 Look, the company's fine. The market's fine. The world didn't come to an end.
00:01:22.860 So what do you think is going on here with Michael Saylor, Jeff?
00:01:27.460 Look, the knock-on strategy was always that numbers don't add up.
00:01:32.700 If he has trouble raising funds through all of his creative ways of raising funds, liquid cash,
00:01:41.740 to be able to pay back all those investors and pay the dividends that needed to be paid,
00:01:46.060 eventually he was either going to have to bring in new investors or he's going to have to start selling Bitcoin.
00:01:49.660 That was always a knock on him, and he always said, no, we'll never have to do that.
00:01:53.060 Everything's fine.
00:01:54.600 I love how he's kind of spinning it here and saying, oh, we're doing this for the benefit of the market.
00:01:58.340 We're just going to test it out so that you can see that everything's good.
00:02:02.500 But you've got to give it to the critics here because I think the numbers are not adding up the way that they're supposed to,
00:02:09.720 and this is potentially something more substantial, and, of course, he's going to want to downplay it.
00:02:14.020 But, like I said, the knock on this has always been they don't have the cash flow to pay off the investors.
00:02:19.660 And the rates of return that they were giving new investors were just astronomical.
00:02:23.280 How is that sustainable?
00:02:24.240 It's not.
00:02:25.000 How is that sustainable?
00:02:25.860 That was the argument.
00:02:26.600 It was not sustainable.
00:02:27.560 Now, you have to wonder, is the crack starting to show?
00:02:30.760 The average price of the Bitcoin he bought is $75,500 to $76,000.
00:02:36.820 Total Bitcoin holding is $818,334.
00:02:41.520 roughly 64 to 67 billion dollars depending on bitcoin's price on that day is what the numbers
00:02:49.520 are at so strategy owns nearly four percent of all bitcoin that will ever exist as of today tom
00:02:56.060 your thoughts on this yeah i i agree at some point in time the music has to stop because you
00:03:01.040 you need liquidity to go in and do this and and the theory that a lot of people had on micro
00:03:06.940 strategy was that they were going to be so far ahead on Bitcoin value that they could get low
00:03:14.140 cost commercial debt and then pay the dividends. And there's nothing wrong with that strategy
00:03:19.360 except for the back end of this little chart here, which is sort of taking you all the way back to
00:03:27.140 the beginning of 05. Just take the dot where we are now and go out and just draw a horizontal
00:03:33.680 a line across you see that pat you take away the the whole surge there the lump in the back of the
00:03:39.860 camel and you end up back in january of 2025 a year ago and then january 2024 two years ago
00:03:47.000 and now you're like wow okay also january 2021 though like yeah yeah january 2022 the first run
00:03:53.320 above i think that was 68 if you show that rob i think that was in january 21 a little bit high
00:03:58.680 You're right. You're at the right place. Just OK. You can do it. Got it.
00:04:01.580 Yeah, got it. Anyway, the point is he's been long on this.
00:04:05.180 And if it's if it grows enough, we'll look at it this way.
00:04:08.000 Real estate holdings grow, grow, grow, grow, grow.
00:04:10.400 And let's say you and me, Pat, owned a bunch of commercial buildings in Miami.
00:04:13.940 And now all these things are having, you know, the Citadel.
00:04:17.500 Ken Griffin's coming down, going to build a place with residences.
00:04:20.700 I'm sorry. He's doubling the size of the office because of New York forgot.
00:04:24.160 And all of the value of our portfolio goes up.
00:04:26.800 We go out and get commercial debt to do bigger improvements or buy more.
00:04:30.800 And I think that was the play here.
00:04:32.580 But he's kind of stuck.
00:04:34.000 So I think he's going to sell a little bit to show the system's working.
00:04:38.420 But I also think there's a test going on because Saylor is very astute about the crypto market.
00:04:44.000 I think he's testing the supply price drop.
00:04:49.260 I think there's a test.
00:04:51.020 If you're the biggest guy in the jungle and you jump in the pool, you make the biggest splash.
00:04:56.180 I think he wants to see, okay, how much water comes out of the pool if I jump in?
00:05:00.480 Hasn't moved anything yet.
00:05:01.600 I think that's great.
00:05:03.260 What I think that means, people under there are saying, hey, if he's profit-taking, maybe I'm going to be supply-taking.
00:05:10.200 Yeah, go to five days, Rob.
00:05:11.880 Go to five days.
00:05:13.440 Well, the other side of that too, Tom, is that he also has to take into account the investment market.
00:05:18.440 Is he saying that the investment market for not just strategy, but maybe overall has shifted so that it's not as friendly that he can continue to raise U.S. dollar funds from the investment market?
00:05:28.140 And therefore, he has to at least explore other options to maintain his investment position.
00:05:32.560 Yeah, you're going to be a Bitcoin balance sheet company.
00:05:34.660 And then the market says, well, maybe I don't like those at 3% debt.
00:05:39.360 Maybe I like them at 7% debt.
00:05:40.860 Or even 8% or 9%.
00:05:41.820 Yeah, exactly.
00:05:43.140 Well, no, no.
00:05:43.980 Pat and I experienced that.
00:05:45.360 You know, we we've studied roll ups and we can identify a couple of roll ups that had like, what was it, Pat?
00:05:51.940 Two billion, three billion dollars. And but there was a floating price on the debt, number one.
00:05:57.740 And number two, they were coming up on five to seven year windows on private equity investment.
00:06:02.620 And every five to seven years, private equity wants wants to take a big chunk out.
00:06:07.380 You've got to go find liquidity to do it. Yeah, that's a tough place to be.
00:06:10.940 But that's where he's at. I mean, look, the good thing about him is his temperament is so cool.
00:06:15.360 If there's a guy that you will look at him and he just lost $12 billion.
00:06:20.620 He's like, yeah, how are things?
00:06:21.540 Great.
00:06:21.820 I just had great salad.
00:06:22.920 Things are good.
00:06:23.520 We're excited about where Bitcoin's going.
00:06:25.040 Bitcoin's the greatest.
00:06:25.920 He knows how to keep it very smooth there.
00:06:28.460 Brandon, where are you at?
00:06:29.120 Loss is just a word at a point in time.
00:06:31.160 That's all it is. 0.61
00:06:34.360 That was good.
00:06:36.720 No, I think, like Tom said, the plan could work in theory if he wasn't buying so much
00:06:42.140 at the top like that chart that Rob showed
00:06:43.980 showed way more buying at like high
00:06:46.060 prices than low prices but
00:06:47.580 do you see how much
00:06:49.980 the stock got hurt, the MicroStrategy stock
00:06:52.140 got hit with just like a sheer
00:06:53.720 120 to 80 drop in Bitcoin. It went
00:06:56.080 from 400 down to
00:06:57.800 130.
00:07:01.120 So it lost
00:07:02.040 $6 billion. In how long?
00:07:04.420 From October 2025.
00:07:06.000 Go to six months, Rob? Six months, yeah.
00:07:07.680 Go to year to date? Yeah, one year.
00:07:10.440 No, go one year, one year.
00:07:12.140 There you go.
00:07:12.740 So it was at $4.50 in July last year.
00:07:17.260 Down to $185 today.
00:07:19.120 Yeah.
00:07:19.980 So the market cap's a steep drop-off.
00:07:22.400 Yeah, so the market cap's $64 billion.
00:07:24.420 So what, it's lost, what's that, 75% of it's $4.50 down to like $180?
00:07:29.700 Yeah, it's a lot of money.
00:07:30.920 So that means it used to be probably $150 billion market cap.
00:07:34.220 And hit all time quick, Rob.
00:07:35.580 So look what happened to it in the dot-com bubble.
00:07:37.440 So I mean, I think a similar thing's going to happen there.
00:07:40.400 It's going to look just like that.
00:07:42.140 You think he's going to have that big of a drop off?
00:07:43.980 Yeah, because I mean, I think I just think that it's not sustainable.
00:07:46.280 Like the, you know, the average price of 77, like there's going to be bigger drops in Bitcoin than this.
00:07:50.700 So I think he put himself in a delicate position with being so reckless with it.
00:07:54.180 Like it could have been a sound strategy if he just bought the dips more, but he just like aggressively bought at the top.
00:07:59.560 It was almost like he took on just a ton of Bitcoin leverage right at the top or at least a recent top,
00:08:04.100 believing that the market was going to turn around really quickly.
00:08:06.780 And then the numbers would all look at being in his favor.
00:08:09.180 And then, you know, the market would still continue to give him a huge premium and he could leverage that to continue the cash flow.
00:08:14.080 It was a tight strategy in a narrow window.
00:08:16.820 Do you hold Bitcoin?
00:08:18.020 I don't know.
00:08:18.900 Do you hold Bitcoin?
00:08:19.700 Yeah, a little bit of crypto.
00:08:20.300 Tom, do you hold Bitcoin?
00:08:21.280 Yes.
00:08:21.600 Are you going to sell or are you going to just stay on it?
00:08:23.360 I'm on it.
00:08:23.980 Yeah.
00:08:24.260 Are you staying?
00:08:24.860 Is it changing anything you're doing?
00:08:26.980 No, because it's not.
00:08:27.760 And like sell everything I have and go in as much as possible to buy it the way.
00:08:31.500 Like I'd be stressed out if I did that.
00:08:32.920 I mean, he took a very different position, but I think the people that are owning crypto and they're long on it, they're like, yeah, okay.
00:08:39.180 Great. You chose to build your business model this way, not me.
00:08:42.840 That's a lot of stress. Respect you. If you make trillions, awesome.
00:08:45.400 If you don't, this guy's either going to be a trillion or he's going to go bust.
00:08:48.520 That's going to be one of those two things.
00:08:49.700 That's kind of what he's shooting for, right, on what's going to happen.
00:08:51.680 Yeah, they're sitting there at their board meeting, and it's like having Princess Leia there.
00:08:55.880 Help me, Obi-Wan Kenobi. You're my only hope.
00:08:58.040 Only it's help me, Kevin Walsh. You're my only hope.
00:09:00.440 Yeah. Those of you guys that did the survey, we originally thought, because it's a lot of questions.
00:09:06.240 It was 27 of them.
00:09:08.040 We said, we're going to give a $25 gift card.
00:09:10.180 So we sat with finance and we said, guys, it's not like it's going to be that many anyways.
00:09:14.280 We said, let's put a budget of $25,000 to $50,000 for these $25 gift cards.
00:09:19.540 Well, the report comes out this morning from our digital marketing team.
00:09:25.060 11,976 of you did the survey.
00:09:29.760 Wow.
00:09:30.220 Which is going to cost us $290-some-thousand for this gift card.
00:09:36.820 And a lot of you guys were tweeting saying, am I going to get the gift card?
00:09:39.820 If you completed the survey, you check your email.
00:09:43.400 Today at 9 o'clock, they started sending all the gift cards from Shopify to go to vtmerch.com.
00:09:49.380 And so check your email.
00:09:51.300 If it hasn't, just remember, it's 12,000 people.
00:09:54.560 so all of a sudden it was put in the system you're probably gonna if you haven't already
00:09:59.080 gotten it if you check your mail you uh you will check your email you will in the next
00:10:03.740 15 30 minutes one hour but go to vtmerch.com that 25 dollars it's a straight up gift card
00:10:10.460 buy whatever you want we have a lot of good things that people don't look at there's some
00:10:14.120 unique accessories that we have you can go look into uh yesterday we had an event at our cigar
00:10:18.520 lounge we have this value taming cigar set with cutters lighters there's so many great gifts
00:10:24.280 that you can give somebody, but you have your $25 gift card to use.
00:10:29.340 And by the way, for those of you guys that are watching saying,
00:10:32.120 it is so revealing, the report that came back.
00:10:35.620 FYI, just so everybody knows, nobody knows what the results were.
00:10:39.160 Tom doesn't even know the results.
00:10:40.460 It's driving him insane.
00:10:41.580 But I get teased a lot.
00:10:42.980 Yeah.
00:10:43.600 Brandon this morning is like, come on, tell me where am I?
00:10:46.460 And him and Humberto are getting to him.
00:10:47.900 Humberto's holding people hostage.
00:10:49.140 I don't like what he's doing, but he loves it.
00:10:51.140 He loves this kind of stuff.
00:10:51.980 If you want to see what the report results were, we may make a one-pager, two-pager to kind of share with the audience.
00:10:59.440 If you text the word PBD to 310-340-1132, again, text the word PBD to 310-340-1132, that report will be sent out to the audience.
00:11:12.180 Our YouTube guy called and says, wait, you guys did a survey on your audience to ask what they didn't like and did like?
00:11:18.540 Yes, we did.
00:11:19.620 Nobody does this.
00:11:20.880 and you gave away $25 gift card, how many people, you spent $300,000.
00:11:25.280 You said, well, we weren't expecting $300,000, but it's already too late.
00:11:28.420 So there you have it.
00:11:29.480 So everybody that completed it, I want to say thank you on behalf of the team.
00:11:33.200 This is great intel for us on finding ways to improve the product that we have here.
00:11:37.960 And without your feedback, we're going to read every single one of the pieces of feedback.
00:11:41.860 And some of you guys may even get a call from us.
00:11:44.240 So, again, text PBD to 310-340-1132.
00:11:47.560 too. We may send a report to you guys specifically in a text once we have that report. And some
00:11:55.300 people are not going to like it, but it is what it is. The report was very good for all of us.
00:11:59.100 If you enjoyed this video, you want to watch more videos like this, click here. And if you
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