Why Selling Bitcoin Might Be the Smartest Move Strategy Ever Makes with Brian Brookshire

Summary

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The Bitcoin Treasuries Podcast with Tim Kotzman

Episode: Why Selling Bitcoin Might Be the Smartest Move Strategy Ever Makes
Guest: Brian Brookshire
Date: May 7, 2026

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Episode Overview

In this episode, host Tim Kotzman sits down with Brian Brookshire to dissect the latest developments following the Q1 Strategy earnings call. The conversation focuses on the implications and rationale behind a potential Bitcoin sale by Strategy, exploring financial engineering, treasury management tactics, and the evolving narrative surrounding active Bitcoin treasury strategies. Brookshire offers insight into why selling Bitcoin could, counterintuitively, be a smart and strategic move for companies, drawing on historical precedent and current market dynamics.

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Key Discussion Points and Insights

1. The Optionality of Selling Bitcoin

[00:10 – 04:23]

• The episode opens with discussion of Strategy's earnings call and rumors about potentially selling Bitcoin.
• Historical Precedent: Strategy previously sold Bitcoin in December 2022 for tax loss harvesting without negative long-term consequences. Instead, the company performed exceedingly well afterward.

  • "We've seen a precedent for this before. In December 2022, Strategy sold Bitcoin...they did it for tax loss harvesting purposes...it did not end the company. In fact...to the height of the 2021 bull market, Strategy had a 36x bull run."
    — Brian Brookshire [00:31]

• Emphasis on financial agility: The ability to manage and optimize various treasury instruments (e.g., issuing new debt, performing share buybacks) can benefit shareholders and the business.
• Market pricing inefficiencies create arbitrage opportunities between instruments, supporting strategic flexibility rather than “Ponzi-ish” behavior.

  • "On paper maybe it looks Ponzi-ish, but...there are dislocations in markets. These instruments are not all accurately priced at any given time. That’s what gives you the opportunity for an arbitrage."
    — Brian Brookshire [01:41]

• Ultimately, all moves are meant to bolster the company’s long-term Bitcoin thesis.

2. Commentary on Strategy's Financial Engineering

[00:31 – 04:23]

• Strategy’s ability to toggle between selling assets, repurchasing shares, and managing convertible debt leads to enhanced operational flexibility.
• Brookshire compares these tactics to accepted practices in finance and references examples from banking and tech.
• Michael Saylor’s view on scaling plays a role:

  • “He would rather sell $500 billion at 11% than $50 billion at 9%...like the early days of Amazon free shipping...they basically took a loss for 10 years, but then they were the only player in the market.”
    — Brian Brookshire [03:20]

3. Interest Rates & Market Perceptions

[02:50 – 04:23]

• Discussion on dividend rates and the role of credit ratings in compressing spreads over time.
• Brookshire suggests that Strategy currently operates like an “asset backed security with a 70% equity buffer,” which he describes as nearly unparalleled.

  • “If you think about it right now, it's kind of like an asset backed security with a 70% equity buffer, which is almost unheard of. So there's a lot of safety built into it..."
    — Brian Brookshire [03:00]

4. Broader Ecosystem Impact and Changing Narratives

[04:24 – 07:19]

• Tim raises the question of whether this move will shift norms for other Bitcoin treasury companies, considering the traditionally negative view of selling Bitcoin.
• Brookshire responds:
  • The strategy will likely remain controversial; “buy and hold forever” purists may not agree.
  • Yet, flexibility (such as selling Bitcoin for buybacks or exploiting tax situations) is a practical advantage for companies.

  • “I think that ultimately it's a good thing for the company to have the operational flexibility. I mean, I wouldn't expect them to go out and just be selling a billion dollars of bitcoin every week...I think it'll be just much more opportunistic."
    — Brian Brookshire [05:48]

• Discusses how such tactics can help manage closed-end fund dynamics and fend off short sellers.

5. Tax Benefits and Timing

[07:20 – 08:24]

• Tim highlights the strategy’s mention of a $2 billion tax benefit opportunity.
• Brookshire notes the timing mirrors market cycle bottoms—echoing the last strategic Bitcoin sale for tax reasons.

  • “The first time we saw them sell bitcoin, it was for the tax benefit and it happened shortly after the bottom of the bitcoin bear market in 2022...here we are now...after the bottom of the bitcoin bear market in 2026, the same conversation is coming up."
    — Brian Brookshire [07:37]

• He suggests it wasn’t surprising, but it is significant that the playbook is reappearing.

6. Closing – Where to Connect with Brian

[08:25 – 08:44]

• Brian Brookshire can be found on X (Twitter) as @btcoverflow, where he posts regularly on Strategy and Bitcoin treasury news.

  • “The best place to find me is on X and I am btcoverflow posting about strategy and related Bitcoin treasury commentary all the time.”
    — Brian Brookshire [08:32]

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Notable Quotes

• "We've seen a precedent for this before. In December 2022, Strategy sold Bitcoin...it did not end the company."
  — Brian Brookshire [00:31]

• “On paper maybe it looks Ponzi-ish, but...there are dislocations in markets.”
  — Brian Brookshire [01:41]

• "He would rather sell $500 billion at 11% than $50 billion at 9%...like the early days of Amazon free shipping..."
  — Brian Brookshire [03:20]

• "If you think about it right now, it's kind of like an asset backed security with a 70% equity buffer, which is almost unheard of."
  — Brian Brookshire [03:00]

• “I wouldn't expect them to go out and just be selling a billion dollars of bitcoin every week...I think it'll be just much more opportunistic."
  — Brian Brookshire [05:48]

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Key Timestamps

• 00:10 — Introduction to Strategy’s optionality and market reactions
• 01:41 — Market arbitrage and financial engineering explained
• 03:20 — Saylor’s Amazon analogy and company growth strategy
• 05:28 — Changing narratives on Bitcoin sales in treasury companies
• 05:48 — Brookshire on responsible, opportunistic Bitcoin sales
• 07:34 — Tax benefits and timing considerations
• 08:32 — Where to connect with Brian

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Recap

This episode offers a comprehensive look at the evolving playbook for Bitcoin treasuries, particularly the nuanced role that asset sales, buybacks, and financial engineering can play—not just as survival tactics but as strategic levers for long-term value creation. Brookshire makes the case that flexibility and opportunism, rather than dogma, should guide treasury management decisions, encouraging the industry to rethink what it means to be “Bitcoin maximalist” at the corporate level.

Transcript

[A]

Welcome back to the Bitcoin Treasuries podcast. I'm Tim Kotsman. I'm here with Brian Brookshire. Brian, thanks for joining us today.

[B]

Thanks for having me, Tim. Good to be here.

[A]

So we all witnessed history yesterday evening with the Q1 strategy earnings call. What were your takeaways? I think there was a focus on bitcoin per share, potentially selling bitcoin and optionality. So I'll, I'll give you the floor for your reaction.

[B]

Yeah, for sure. I think there are two main themes that I picked up on that were interesting to me. One is an optionality piece that you mentioned and you know, potentially the potentially selling bitcoin piece you see all over social media today, people freaking out, oh, strategy is going to sell bitcoin, it's going to end the company. No, it's not going to end the company. And actually we've seen a precedent for this before. In 2022, December 2022, Strategy sold Bitcoin. It's been done before. They did it for tax loss harvesting purposes, then did not end the company. And in fact from that point onward to the height of the 2021 bull market, strategy had a 36x bull run. So was not a problem for the company in the past. Don't think it would be a problem for the company in the future if they are more actively managing the capital stack. And just beyond selling bitcoin, we also saw them say that they might potentially have much more flexibility across all their instruments, potentially issuing strategies to pay down some of their convertible debt, which we've also seen precedent for in the markets we saw strive do that. Also potentially going back and forth between say stretch sales and common share buybacks and et cetera, et cetera, pretty much any combination of instruments to have potentially going back and forth between those. And I think some of the comments that I see, you know, the critiques I see of that are not well founded. You know, on paper maybe it looks Ponzi ish, but if you dig down to it, the fact is there are dislocations in markets. These instruments are not all accurately priced at any given time. And that's what gives you the opportunity for an arbitrage between them. And people also forget at the end of the day what all this financial engineering is going into is buying bitcoin. So it's not just strategy instruments trading around on the back end, it's going to buying bitcoin. The whole thesis is that you buy bitcoin for the long term, it appreciates in value and that's what makes all this financial engineering a valuable thing to do. Yeah. And then kind of the other theme I picked up on towards the end of the call is Saylor's outlook for what rates will look like. One of the things that we've talked about is kind of two different perspectives on this is what the long term rate trajectory looks like. A lot of the projects being built on stretch right now are really taking advantage of that high dividend rate though. But of course alongside that, you've had investors in the stock talk about how probably the long term trajectory is. You know, those rates come down. If strategy is able to actually able to get investment grade credit ratings or even just better credit ratings it has right now, then you would expect that dividend rate to come down over time, that credit spread to compress, which makes sense. I think a lot of people think that even today it probably deserves a lower credit spread than it has. Because if you think about it right now, it's kind of like an asset backed security with a 70% equity buffer, which is almost unheard of. So there's a lot of safety built into it, but it just takes time for the market to get used to the product. And one thing Saylor said that I thought was very important was that right now they are really focused on getting volume, getting network effects. And he would rather sell 500 billion at 11% than $50 billion at 9%. And he used the comparison of the early days of Amazon free shipping where they basically took a loss that for 10 years, but then they were the only player in the market and they increased prices and made a whole ton of money. And you see this common in banking too, that when you see a new banking product roll out, it will have a higher rate and early people do that, take advantage of it. And then later on down the line those rates tend to come down. So I think that's likely what will happen. I think it's a strategically sound play and it's good to hear them also say what their thinking is on the long term prognosis for rates.

[A]

It sounds like you're saying that even though you may have some people saying this is a narrative violation, that if the math, maths, then it is what it is. Like this makes a lot of sense. What impact, if any, do you think this is going to have on the ecosystem, the other treasury companies to be able to follow the leader and have that optionality instead of maybe a slap on the wrist because they sold some Bitcoin or they're trying different, different strategies, trying to use different tools that they have. As far as, I mean, it seems like even six or 12 months ago when you had new companies launching and executives saying we will buy and sell bitcoin, that was not well received. Other strategies other than just buying and holding I don't think were initially well received or there was a lot of, a lot of commentary around it for sure.

[B]

I think it's a topic that will continue to be controversial. Strategy is a clear leader in the space, actively managing their Treasury a little bit more and potentially doing some opportunistic sales of bitcoin, I think will definitely ease the burden for other players in the market doing it. But I think even within die hard bitcoin treasury fans, you've seen mixed reactions. You've seen, well, no, no, the strategy is to just buy, hold bitcoin forever and then other folks saying, well, okay, yeah, but then that kind of leads to closed end fund dynamics where, you know, potentially you trade at a discount that you can't close. And if you retain some flexibility to sell bitcoin to do share buybacks or something like that, then you're able to not only close the gap, but also potentially scare off shorts who might think that they can just keep leaning on your stock. So, yeah, I mean, there are a few different ways to look at it. I think that ultimately it's a good thing for the company to have the operational flexibility. I mean, I wouldn't expect them to go out and just be selling a billion dollars of bitcoin every week. And that's not what's going to happen. I think it'll be just much more opportunistic. If the stock trades at a discount to Nav, then maybe that's the time when you'll see the bitcoin sold to pay dividends or to do share buybacks instead of selling shares. If it's a raging bitcoin bull market, they're probably not going to sell the bitcoin. If they wind up in a situation where they have a paper loss, then there are some manipulations they can do to get tax advantages. And I think all these plays can and should be on the table without the market freaking out and thinking, oh, they're fundamentally changing the strategy here. They're selling bitcoin now. That's not what's going on. They're being more proactive about managing their balance sheets and I think it makes sense to do in a sensible way.

[A]

Did it surprise you when you heard them mention over $2 billion kind of tax benefit that's just kind of sitting there that they could use to their benefit. And what was your reaction to that?

[B]

Well, I think the timing is very interesting because like I mentioned, the first time we saw them sell bitcoin, it was for the tax benefit and it happened shortly after the bottom of the bitcoin bear market in 2022. And here we are now, what many people think is perhaps after the bottom of the bitcoin bear Market in 2026, the same conversation is coming up about potentially taking advantage of the tax situation. So it was something that I questioned if they would ever do again or if it was kind of a one time thing because they have leaned pretty hard on the don't sell bitcoin rhetoric, to be fair. But I think it was something that made sense to do then, it's something that makes sense to do now. So was it a surprise? Not really, but it was interesting to get confirmation of whether or not this is a play that would come back on the table.

[A]

Where can people reach out to you to have a conversation? Where's the best place to find you these days?

[B]

The best place to find me is on X and I am btcoverflow posting about strategy and related Bitcoin treasury commentary all the time. Happy to talk to anyone who comes by.

[A]

Awesome. Brian, thanks for joining us today. Appreciate your time.

[B]

Thanks for having me, Tim.

[A]

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