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The Breakdown

How Strategy Insiders Insulated Themselves From the Crash

The Breakdown

Blockworks

Investing, Business

4.8806 Ratings

🗓️ 26 June 2026

⏱️ 22 minutes

🧾️ Download transcript

Summary

FOLLOW THE SHOW › David — https://x.com/dcanellis › The Breakdown — https://x.com/TheBreakdownBW › The Breakdown Newsletter — https://blockworks.com/newsletter/the-breakdown DISCLAIMER As always, remember this podcast is for informational purposes only, and any views expressed by anyone on the show are solely their opinions, not financial advice.

Transcript

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0:00.0

Welcome back to The Breakdown. I'm your host, David Tenless, as always. So, I mean, I think everyone is watching the price of Bitcoin right now and with good reason, because we ran an episode earlier this week that compared the similarities and differences between strategy and Stretch and Terra Luna in relation to the Bitcoin market.

0:22.2

Since then, Stretch has crashed another 15%.

0:25.6

It's now trading at 7380 in pre-market trade Friday morning.

0:30.4

So since that episode, Stretch has tanked another 15%.

0:33.5

Bitcoin is also on its way down.

0:35.5

It's now trading routinely underneath $60,000. Strategy is also on its way down as well, micro strategy stock, which means that indirectly you have gathered up a bunch of exposure just by holding crypto to the reality of what Sailor has cooked up and what strategy has done to Bitcoin and crypto over

0:55.8

the past two or three years. And a lot of us has been super positive. Please don't get me wrong

0:59.6

because it has, I mean, it's obvious. It has pumped Bitcoin way past 100K on multiple occasions

1:08.4

reaching everything 124K.

1:11.0

And you have to admit that strategy was a big part of that.

1:16.3

And, I mean, it kicked off the dat boom.

1:18.9

You have companies all around the world stacking sets,

1:22.1

trying to mimic what Sailor has done and trying to ride his coattails all the way to the moon and so on.

1:29.1

And that has done untold good. I can't deny that. But so while holders and users and

1:35.6

so on might be feeling the hurt right now, strategy insiders were able to really insulate themselves from the worst of the market.

1:46.8

It seems going by the amount of shares that they've sold throughout the past ball market

1:52.7

with Bitcoin on its way up and strategy mimicking those moves alongside it.

1:58.8

So I'm just going to spend this episode.

2:01.4

What we're going to do is we're going to look at the past few years of strategy inside of stock sales just to get a sense

2:07.5

that those at the top of this of this plan, I don't think they have much to worry about,

2:14.6

it seems, at least, at least going by the data that we can see from

2:19.0

the SEC disclosures over the past couple of years. So enough out of me. This is going to be

...

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