Valuetainment - June 06, 2026


“Michael Saylor’s LAST Laugh” - Strategy Faces $11B Bitcoin CRISIS


Episode Stats


Length

11 minutes

Words per minute

197.65689

Word count

2,317

Sentence count

172

Harmful content

Misogyny

2

sentences flagged

Toxicity

8

sentences flagged

Hate speech

3

sentences flagged


Summary

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

Strategy Inc is facing renewed scrutiny as the company faces an unprecedented $10B of unrealized loss on its Bitcoin holding. Bitcoin is down 50% from its peak hit in the fall of 2017. What does Strategy do now?

Transcript

Transcript generated with Whisper (turbo).
Misogyny classifications generated with MilaNLProc/bert-base-uncased-ear-misogyny .
Toxicity classifications generated with s-nlp/roberta_toxicity_classifier .
Hate speech classifications generated with facebook/roberta-hate-speech-dynabench-r4-target .
00:00:00.760 Rosen lasagna, medium power, 15 minutes.
00:00:04.620 Sounds like Ojo time.
00:00:06.560 Let's play.
00:00:07.500 Feel the fun with Play Ojo, the online casino with all the latest slot and live casino games.
00:00:12.680 What you win is yours to keep with no wagering requirements, instant payouts, and no minimum withdrawals.
00:00:18.400 Hey, I just won.
00:00:19.700 Woo-hoo!
00:00:20.320 Feel the fun, Play Ojo. 0.73
00:00:22.640 Honey, forget about the lasagna.
00:00:24.100 Let's celebrate.
00:00:25.040 19 plus Ontario only.
00:00:25.760 Please play responsibly.
00:00:26.280 Concerned about your gambling or that of someone close to you?
00:00:27.300 Call 1-866-531-2600 or visit connexontario.ca.
00:00:30.000 He's got different kind of problems he's dealing with,
00:00:31.940 but he's staying cool, calm, and collected,
00:00:33.580 and that's Michael Saylor, who is $10 billion Bitcoin hole.
00:00:37.120 What does strategy do now?
00:00:38.520 I don't know if you guys have seen this.
00:00:39.500 Bitcoin is down now 50% of its high that it hit.
00:00:43.120 I don't know what the number is right now.
00:00:44.160 It could be between $59,000 to $61,000.
00:00:46.380 It's at $60,000 as of right now.
00:00:48.820 If you go max, go to five years, Rob, look at the peak right there.
00:00:52.320 Go all the way to the peak, $20,000, $125,000, $120,000-something.
00:00:55.980 So it's down 50% from its peak.
00:00:59.200 Just last fall.
00:01:00.000 That's right. Just last fall. And so Strategy Inc. is facing renewed scrutiny as the company faces an unprecedented $10 billion of unrealized loss on its Bitcoin holding.
00:01:10.520 Marking commentator Kyle argued on Exxon June 4th that the company's preferred share dividend obligations could turn Michael's sailor from Bitcoin's biggest buyer into potential for seller.
00:01:19.860 The company's Bitcoin accumulation model worked while the company funded purchases through equity issuance, convertible notes, and other financing tools that did not require near-term cash payments.
00:01:30.200 The concern now is that strategy's newer preferred shared products, including NASDAQ's STRC, carry yield obligations.
00:01:39.500 Strategy owns roughly 4% of Bitcoin's total supply, making a balance sheet one of the biggest swing factors in crypto markets.
00:01:45.160 Kyle argued that earlier strategy financing was easier for bulls to defend because common equity has no guaranteed return.
00:01:53.360 The company could sell the stock, but Bitcoin and rely on BTC's long-term appreciation to support share price.
00:01:59.720 Preferred shares changes the math, he said.
00:02:02.000 Tom, your thoughts on this?
00:02:03.420 So I take us back into history.
00:02:07.140 You know, let's go back to Elon Musk's difficult and painful 2018.
00:02:12.120 Remember when we talked about Elon Musk?
00:02:13.880 Oh, my gosh, the debt's coming due.
00:02:15.780 He has so much debt on the gigafactories, and he's doing this to build batteries.
00:02:19.640 He's doing all this, and he's spending all this thing,
00:02:21.840 and he went down and he's trying to build a launch pad at the end of Texas.
00:02:25.920 What's he going to do?
00:02:26.960 And you remember all this, Adam?
00:02:28.000 You remember this.
00:02:28.560 We talked about this.
00:02:29.560 All of a sudden, guess who will show up?
00:02:31.780 Middle East financers show up, or he comes up with a bond and shows up.
00:02:36.240 Great entrepreneurs find a way out.
00:02:38.320 Right here, the real question isn't, oh, my gosh,
00:02:41.360 is he going to sell the Bitcoin and it's going to crash?
00:02:43.620 Maybe that happens.
00:02:45.440 What happens if the market crashes tomorrow and Bitcoin bounces back to 115 or 120 or beyond it?
00:02:51.120 What if Bitcoin gets to 140 because our own Senate can't get out of its own way and we can't get things passed and we have this debt and we have all the things going on and we have the inflation spike statistics get used and Kevin Warsh is forced to actual raise rates, which I don't think is a good idea.
00:03:09.960 What happens if all this happens?
00:03:11.440 You know what happens?
00:03:12.200 guess what the market's going to crash it's going to be going to be tough and what a bitcoin bounces
00:03:18.200 back as the alternative asset at that point where's michael saylor then i think people's
00:03:23.700 are talking here are just you know they love to point at him he was the first balance sheet
00:03:31.740 company right where you the bitcoin on the balance sheet is really the reason to own the stock yeah
00:03:36.700 You know, I bet that's how I feel, Pat. I think people are making a lot out of this.
00:03:41.780 The math they're doing is correct. He does have dividends to hit.
00:03:45.180 But I remember 2018, how hard it was for Elon Musk, you know, and how he had to go back.
00:03:52.740 And in 2018, but guess what? He found financing partners. He got it done.
00:03:58.060 He then achieved the launches on SpaceX. He launched more Starlinks.
00:04:03.580 He figured out great entrepreneurs find a way to get it done.
00:04:06.860 And I think Michael Saylor will find a way to figure out the financing and to figure out what he's going to do on this.
00:04:12.560 Because guess what?
00:04:13.960 If a stock goes down, if you owned 100 shares of NVIDIA, let's say a month ago, and you bought them at $2.30, I think three weeks ago, two weeks ago, it was like $2.30.
00:04:25.540 And now today it's like at $2.20, and you own 100 shares.
00:04:28.960 I lost a little bit.
00:04:29.480 On paper, you're down $20.
00:04:31.480 It's now $2.11 this morning.
00:04:33.300 it's down $746. I'm buying.
00:04:36.300 Right. But do you see my
00:04:37.880 pick? You're holding the shares
00:04:39.760 that you bought for $230.
00:04:41.940 You bought them for $230
00:04:43.680 and go back one month.
00:04:46.040 Just go one month. There should be a $230 in there.
00:04:48.020 There it is. So you bought it at
00:04:49.660 $235. And yet today
00:04:51.860 it's here. But you're holding the share.
00:04:53.860 Until you sell it, there's
00:04:55.740 no loss and there's no gain.
00:04:57.140 And so Michael Saylor
00:04:59.180 has got to find his way out of this.
00:05:01.000 True. He wants $840
00:05:03.140 440,000 Bitcoins in his company.
00:05:05.440 Wow.
00:05:05.740 And he owns 17,000 to 18,000 personally.
00:05:08.980 So personally versus the company.
00:05:12.120 You know, if Bitcoin goes to a million dollars, his net worth is around $100 billion, give or take.
00:05:15.840 So this guy's banking on it long term.
00:05:17.800 And by the way, to be in the business you're in, you have to be cool.
00:05:21.820 What do they say?
00:05:22.420 Cool as a cucumber?
00:05:24.220 You have to be so cool.
00:05:25.840 He's got the right.
00:05:26.880 Chill.
00:05:27.340 Imagine somebody that panics, anxiety, all that stuff.
00:05:30.160 If you're going through it right now, sell all of it.
00:05:32.100 Sell it all.
00:05:32.520 You have to be able to be like him.
00:05:34.400 By the way, this guy is either going to be one of the richest people in the world
00:05:37.660 or he's going to lose it all, okay?
00:05:39.100 And we'll see what side it's going to go.
00:05:40.720 Adam, thoughts?
00:05:41.420 Look, I think Michael Saylor is going to have the last laugh here.
00:05:44.460 To all the people, all the haters out there who are basically saying,
00:05:47.480 you know, he's the poorest guy in the world.
00:05:50.160 All right, give it a couple months.
00:05:52.500 Let's see who wins here.
00:05:54.160 Because, you know, it's always the people that don't have Bitcoin
00:05:57.120 or that don't have money that want to hate on the people that have money.
00:06:00.380 That's kind of how it works.
00:06:01.940 And there's also people on the flip side of things, what I call the get-rich-quick crowd.
00:06:06.640 What people are learning here is that Bitcoin is no longer the get-rich-quick, right?
00:06:11.400 There's a term in Bitcoin in the crypto world.
00:06:13.340 It's called hodl, hodl, H-O-D-L, hold on for dear life.
00:06:17.440 I guess some guy thought it was hold and hodled, and that's what I ended up doing with Bitcoin.
00:06:22.600 And everything that you end up buying at any single point, if I see it's buy low, sell high, or just hodl.
00:06:29.140 So I bought Bitcoin, I think, at $10,000, then at $20,000.
00:06:32.240 By the way, you know who also did that?
00:06:33.900 Michael Saylor.
00:06:34.600 Michael Saylor bought it, I think, in early 2000s.
00:06:39.360 I'm sorry, early 2020.
00:06:41.220 Bought it at $11,000.
00:06:42.380 Then he bought it for $10,000.
00:06:43.480 Then he bought it for $19,000.
00:06:45.100 Then he bought it for $20,000.
00:06:46.140 Then he bought it for $30,000.
00:06:47.540 And then a lot of what he bought in the last few years, last year or so, has been in the $70,000 range.
00:06:52.560 Now, when you're buying at $70,000, which essentially it's a little bit lower now,
00:06:55.580 you think it's going to go to $140,000.
00:06:57.680 Do you think it's going to go to $200?
00:06:59.180 Do you think it's going to go to $1 million one day?
00:07:01.420 And I'm thankful that every single time that Michael Saylor came on the show,
00:07:04.900 because it's been at least three or four times, I bought another Bitcoin.
00:07:08.600 By the way, way lower it is now.
00:07:09.920 So I said, thank you, Michael Saylor.
00:07:11.300 Here's my message to the people out there.
00:07:13.440 I'm not the smartest guy when it comes to investing, but I know this.
00:07:16.640 There's short, medium, and long-term investments.
00:07:20.300 There's low risk, medium risk, high risk.
00:07:22.860 Just understand your asset allocation.
00:07:24.800 I always keep what they call dry powder.
00:07:26.400 just cash. Straight up, I always keep a significant amount of cash. Then I have my
00:07:30.560 short-term investments for basically five years. And then I have my long-term investments for
00:07:35.260 retirement. And then here's the point. I have my risky investments, my GoGo account. And that
00:07:40.640 enabled me to buy Bitcoin, buy risky investments, buy Ethereum. And you know what? That's the money
00:07:47.700 that a lot of entrepreneurs use to start other businesses. That's the money that Elon Musk used
00:07:52.940 from Tesla to start SpaceX.
00:07:55.000 And that's the money that a lot of entrepreneurs
00:07:56.700 use to start other companies.
00:07:58.760 So to me, all the haters out there that are wishing
00:08:00.960 for this guy's demise, I think he's going to get
00:08:02.980 the last laugh. I think so as well.
00:08:05.280 But again, Tom
00:08:06.920 said something. If all of a sudden
00:08:09.140 shit hits the fan 1.00
00:08:10.560 and inflation, 1.00
00:08:12.960 market goes in a certain way because
00:08:14.980 this war continues and there's cost
00:08:16.820 and all that other stuff, in
00:08:18.800 three months, six months, Bitcoin could go to $130,000 0.98
00:08:21.340 and everyone's going to say, holy shit,
00:08:22.820 what happened to that guy that could happen i think that's more of a likelihood than it's going
00:08:26.620 down to 20 or 30 we we don't know if you look at the cyclical cycle of bitcoin go go to the five
00:08:32.400 year cycle of bitcoin if you just kind of see what's going on and then remember i don't want
00:08:36.400 to speak out of pocket because this is not my world so i'm not a bitcoin guy but the bitcoin
00:08:40.820 guys if you study it watch what happened right there in 2022 can you go to the 21 22 all the
00:08:45.260 way to the back right there right there peak peak of 21 rob right 64 000 then go to exactly where
00:08:50.780 123 is go exactly what's that 16 000 so it went from 63 64 000 to 16 that's it dropped 75 then it
00:08:59.580 went from 16 to what go to the peak all the way at the top which is 120 to 125 so it goes 16 to
00:09:05.280 122 that's what 8x 9x and then it dropped to what to 60 and to be honest with you it can go all the
00:09:11.940 way down to 30 000 just so you know if it does what it did before it goes to 30 000 but then 30
00:09:18.520 can turn into what 250 yeah so this this is the part that if you're in it long term you're in it
00:09:23.360 long term if you're not just step out if you can't handle the stress that comes with it do not do not
00:09:28.480 invest in these types of things massive news from our friend here vinnie massive news that you guys
00:09:33.780 have been waiting for go ahead vinnie well thank you pat uh the black the hat that i'm wearing right
00:09:37.700 now i'm gonna take it off my hair is gonna be messed up is the new faith over fear black and
00:09:41.540 gold we have our shield here and i'm talking about gold stitching like actually like not real gold 0.88
00:09:46.940 But look at how ridiculous that is.
00:09:48.460 Cross. 1.00
00:09:48.880 Gold in the back, snap back with the Hebrews, 1.00
00:09:51.540 our crosses on the inside. 0.50
00:09:53.100 And I'm telling you guys right now, Pat,
00:09:54.240 I wore this hat to breakfast with Humberto
00:09:58.340 and an older, late, 80 years old,
00:10:00.720 her name was Amy, she grabs me, 0.65
00:10:02.120 she's like, I want that hat.
00:10:03.640 And I felt so bad because I couldn't give it,
00:10:05.260 I couldn't, I'm like, I got a pitch for the podcast.
00:10:08.080 And Pat, she went on this story for 20 minutes,
00:10:10.840 ask him, he's my witness,
00:10:12.080 about cancer and beating it and having faith in her.
00:10:15.120 She was so calm, Tom, saying that.
00:10:17.420 She's like, even if I didn't, I still have faith that God would take care of me.
00:10:20.620 It was an emotional bite.
00:10:21.600 I forgot that we're even eating breakfast.
00:10:23.900 But this, I'm telling you, besides just a hat, it's a conversation starter.
00:10:27.900 It's letting people know.
00:10:28.680 I can't tell you how many times in that same diner, Pat, I'm sitting there at the counter,
00:10:32.600 and there's a congregation.
00:10:33.620 People are telling their stories.
00:10:35.000 So this hat is out right now.
00:10:37.060 People have been asking for it.
00:10:37.960 And the white and black just got restocked.
00:10:40.720 We sold out on this hat in nine hours, Pat.
00:10:43.360 So, everybody out there, please, I want to say thank you, number one.
00:10:46.900 Number two, go to vtmerch.com.
00:10:48.700 I guarantee you this is going to be sold out in two days.
00:10:52.860 Get on vtmerch.com and get them because people message me on Instagram
00:10:56.480 and they're like, hey, why didn't you? 0.74
00:10:58.520 They're sick. 0.98
00:10:58.860 The hat's sick. 0.94
00:10:59.680 The sweater's sick.
00:11:00.760 The hoodie's sick.
00:11:01.400 The shirt's sick.
00:11:01.880 Everything.
00:11:02.540 Look at that.
00:11:03.340 And go to church on Sunday with it.
00:11:04.820 If you enjoy this video, you want to watch more videos like this, click here.
00:11:07.840 And if you want to watch the entire podcast, click here.
00:11:13.360 We'll be right back.