BenWerkman on Nostr: $MSTR - The De-Risking Bullish Roadmap for 2025 Trigger Warning - Crazy Long Post ...
$MSTR - The De-Risking Bullish Roadmap for 2025
Trigger Warning - Crazy Long Post
Alright, now that I've done an overview of what the unhinged bull case for #MSTR #Bitcoin accumulation looks like I thought it would probably be worth it to spend a little time on what a more measured approach
through 2025 might look like keeping risk in mind.
We already discussed how $MSTR has ~$65.2M available in cash flow annually to service convertible debt offerings with. At present, they are supporting $4.264B in open convertible offerings which require ~$34.6M in interest payments annually.
This puts MSTR at a very reasonable position of utilizing 53.05% of their cash flow for debt servicing. Even if they had taken a traditional $4.264B loan directly from a bank they would be in compliance the typical 1.75x Debt Service Covenants they typically impose. But that's not really relevant, so we'll move on.
So what does a reasonable world look like for MSTR?
First, they're going to deploy their $890M in remaining ATM. I'd almost count this as a given in Q4. They will want to collect these Bitcoin at lower prices so I will assume they get that completed at ~$65k per Bitcoin giving them ~13,600 #BTC.
Now if you are managing risk, you would want to ensure that you allow for fluctuations in your business cash flows as to not alarm the markets by being underwater on what is required to support your debt. I would argue that they could extend up to 75% if advantageous to them to do so, but it isn't required. That would allow for an additional $2.29B at their current rates of 0.625%.
But we're staying mildly more responsible in this scenario, so let's just stick with 60% as a max cap with a goal to lower throughout the year. So with 60% as a cap, I would expect $MSTR to do 1 more offering of $725M in Q4 which if executed at ~$70k Bitcoin prices would get them another 10,350 Bitcoin yet this year.
So what next?
Now we need to start looking forward. If Saylor and his team are as savvy as they seem to be, they are focused on capitalizing this cycle to really cement their advantage, but there is nuance to it.
Once they have reached the 60% utilization of their cash flow cap, they will now be looking for conversions. They have 1 convertible note which is well within striking distance for Q4 2024.
This would be the 2027 maturity notes at $1.05B. The 130% rule will kick in at $186.22 which is a mere 7.2% gain away from the current price as I write this. That seems very reasonable to qualify for conversion during Q4 2024 and ultimately converting in Q1 of 2025.
In our scenario, this conversion is less impactful than most. The reason is that these notes carry 0% interest rates, so it doesn't return any free cash flow from shedding interest expense so this doesn't allow for another convertible offering in Q1 of 2025 as they will still be at the 60% threshold we have established. He may elect for an ATM to not lose momentum, but I'm sticking conservative and will say Q1 is quiet with free cash flow from the quarter for purchases only of $6.5M netting them 69 Bitcoin (I know, not what we're used to).
What this conversion does do, is greatly lower the break even price and brings it down from $18,064 in our last scenario to $14,258 due to shedding the liability, so not a total waste since we are looking to control risk.
Now Q1 isn't totally meaningless. In my BTC purchase from cash flow above I assume BTC is ~$95,000 at this point in time, and that means that MSTR is likely trading conservatively around $285 per share. So what this means is that during this quarter, it is highly likely that 2 additional notes have become eligible for conversion in Q2 (now we're talking!).
The 2028 notes have a 130% trigger of $238.14 and the 2030 notes have a 130% trigger of $194.70. In our scenario is would seem highly likely those would have been achieved. It's also possible the 2032 notes with a trigger at $265.63 would have also been hit, but for the sake of conservatism I'll assume they didn't quite get the full 20 days they needed in a 30 day period.
So with the 2028 and 2030 converting in Q2 2025, we now drop $1.81B from our liabilities. I would expect this capital to get redeployed in Q2 2025 as the "last setup" before the bull run "concludes" (we'll see about that).
This is a big chunk, so I'd continue to keep it as 2 separate notes and because we now have no maturities in 2028 and no maturities in 2030 I'm going to recycle these into the same structure, but now the conversion price will move up to $370.50 based on the assumption that MSTR is trading around $285 at this time.
To de-risk, I'm only redeploying $1.5B this time around in 2 offerings of $750M each. This will lower the cash flow requirements by ~$2M annually and will lower my average maturity per year to ~$725M which seems reasonable. We don't want maturity concentration risk that could result in unnecessary selling of BTC in any one single year.
I'm going to assume Bitcoin is now at $100,000 so this nets us 15,000 new Bitcoin to the treasury at the time of purchase. It also lowers our break even price down to $12,460 due to the additional Bitcoin and reduced debt load. Additionally, our cash flow utilization is now down to ~57%.
So what else happens in Q2?
With Bitcoin at $100,000 MSTR is likely trading in a range around $330. So this allows us the potential for 2 additional notes to convert, the 2031 and the 3032. These notes have 130% trigger prices of $302.54 and $265.63 respectively.
With those notes hitting that trigger, they would now convert in Q3 dropping $1,403,750,000 off the liabilities.
But now we are nearing the potential tail end of the cycle, and these won't be eligible for the 130% rule until Q1 of 2026 so we are going to get a bit more conservative now.
I like round numbers, and MSTR in my scenarios is now at a stones throw distance to 300,000 Bitcoin. So that is going to be our target. I'm going to assume we are trading around $120,000 Bitcoin in Q3 so that means we will need to redeploy ~$1.05B to hit our target.
Since these note maturities are still farther out and we now have nothing on the books in 2031 and 2032 we will split this between the two years with $525M each. The 2031 has an interest rate of 0.875% which we will keep, but the maturity has now shortened to the 2032 Notes enough from their initial pricing at 2.25% so I will assume we can now get 1.5% for these (all cash flow improvements matter).
With these changes our cash flow utilization plummets to 40.45% and our BTC break even price reduces to $10,917. The risk management is certainly working! The treasury would now hold an even 300,000 BTC.
Excellent. But the show goes on so let's bring it home.
With Bitcoin prices in Q3 around $120,000, we are probably looking at a MSTR price of ~$370 (likely far higher, but I've been keeping mNAV expansion and mania out of this). So this means that our last note that was put in place in Q4 of 2024 is now eligible for conversion in Q4 of 2025 due to the $327.60 130% trigger price.
This is our last hurrah in out quest to de-risk our cash flows exiting the cycle. So now we freed up $725M from the 2029 convertible offering. To de-risk, we are going to replace this note with another 2029 offering of only $525M (to match the last 2 we just did).
Let's assume Bitcoin runs up to $140,000 in Q4 so we are able to collect 3,750 Bitcoin with this one.
What a year 2025 has been! Let's recap where we close out.
Throughout this process MSTR has acquired 51,530 new Bitcoin from start of Q4 2024 to end of year 2025 ending at 303,750 BTC in the treasury. That is a whopping 20.4% increase in holdings. That's an accomplishment in its own right. It also lowers the BTC Break Even Price to $10,123.
Exiting the year, MSTR would now have $3.075B in convertible debt offerings on the books. That is a decrease of -$1,188,750,000 or 27.9% from the start of Q4 2024 which is a serious lowering of the risk here.
MSTR would now require $25,125,000 annually to service these new notes. That is down -$9,470,313 or 27.4% from start of Q4 2024. This leaves us with cash flow utilization of 38.53% and a debt service coverage ratio of 2.60x. These are significant improvements to the metrics and greatly reduce the risk profile. The beauty is we did all this without taking our foot off the gas (with some cooperation from Bitcoin of course).
MSTR would now be in an amazing position to exit 2025, as strong as ever with a huge amount of Bitcoin on the balance sheet. There is still upside in a mania where more debt falls off in Q1 2026, but I have to stop this story somewhere. It's fun to think through regardless.
So in summary...
Bullish.
Trigger Warning - Crazy Long Post
Alright, now that I've done an overview of what the unhinged bull case for #MSTR #Bitcoin accumulation looks like I thought it would probably be worth it to spend a little time on what a more measured approach
through 2025 might look like keeping risk in mind.
We already discussed how $MSTR has ~$65.2M available in cash flow annually to service convertible debt offerings with. At present, they are supporting $4.264B in open convertible offerings which require ~$34.6M in interest payments annually.
This puts MSTR at a very reasonable position of utilizing 53.05% of their cash flow for debt servicing. Even if they had taken a traditional $4.264B loan directly from a bank they would be in compliance the typical 1.75x Debt Service Covenants they typically impose. But that's not really relevant, so we'll move on.
So what does a reasonable world look like for MSTR?
First, they're going to deploy their $890M in remaining ATM. I'd almost count this as a given in Q4. They will want to collect these Bitcoin at lower prices so I will assume they get that completed at ~$65k per Bitcoin giving them ~13,600 #BTC.
Now if you are managing risk, you would want to ensure that you allow for fluctuations in your business cash flows as to not alarm the markets by being underwater on what is required to support your debt. I would argue that they could extend up to 75% if advantageous to them to do so, but it isn't required. That would allow for an additional $2.29B at their current rates of 0.625%.
But we're staying mildly more responsible in this scenario, so let's just stick with 60% as a max cap with a goal to lower throughout the year. So with 60% as a cap, I would expect $MSTR to do 1 more offering of $725M in Q4 which if executed at ~$70k Bitcoin prices would get them another 10,350 Bitcoin yet this year.
So what next?
Now we need to start looking forward. If Saylor and his team are as savvy as they seem to be, they are focused on capitalizing this cycle to really cement their advantage, but there is nuance to it.
Once they have reached the 60% utilization of their cash flow cap, they will now be looking for conversions. They have 1 convertible note which is well within striking distance for Q4 2024.
This would be the 2027 maturity notes at $1.05B. The 130% rule will kick in at $186.22 which is a mere 7.2% gain away from the current price as I write this. That seems very reasonable to qualify for conversion during Q4 2024 and ultimately converting in Q1 of 2025.
In our scenario, this conversion is less impactful than most. The reason is that these notes carry 0% interest rates, so it doesn't return any free cash flow from shedding interest expense so this doesn't allow for another convertible offering in Q1 of 2025 as they will still be at the 60% threshold we have established. He may elect for an ATM to not lose momentum, but I'm sticking conservative and will say Q1 is quiet with free cash flow from the quarter for purchases only of $6.5M netting them 69 Bitcoin (I know, not what we're used to).
What this conversion does do, is greatly lower the break even price and brings it down from $18,064 in our last scenario to $14,258 due to shedding the liability, so not a total waste since we are looking to control risk.
Now Q1 isn't totally meaningless. In my BTC purchase from cash flow above I assume BTC is ~$95,000 at this point in time, and that means that MSTR is likely trading conservatively around $285 per share. So what this means is that during this quarter, it is highly likely that 2 additional notes have become eligible for conversion in Q2 (now we're talking!).
The 2028 notes have a 130% trigger of $238.14 and the 2030 notes have a 130% trigger of $194.70. In our scenario is would seem highly likely those would have been achieved. It's also possible the 2032 notes with a trigger at $265.63 would have also been hit, but for the sake of conservatism I'll assume they didn't quite get the full 20 days they needed in a 30 day period.
So with the 2028 and 2030 converting in Q2 2025, we now drop $1.81B from our liabilities. I would expect this capital to get redeployed in Q2 2025 as the "last setup" before the bull run "concludes" (we'll see about that).
This is a big chunk, so I'd continue to keep it as 2 separate notes and because we now have no maturities in 2028 and no maturities in 2030 I'm going to recycle these into the same structure, but now the conversion price will move up to $370.50 based on the assumption that MSTR is trading around $285 at this time.
To de-risk, I'm only redeploying $1.5B this time around in 2 offerings of $750M each. This will lower the cash flow requirements by ~$2M annually and will lower my average maturity per year to ~$725M which seems reasonable. We don't want maturity concentration risk that could result in unnecessary selling of BTC in any one single year.
I'm going to assume Bitcoin is now at $100,000 so this nets us 15,000 new Bitcoin to the treasury at the time of purchase. It also lowers our break even price down to $12,460 due to the additional Bitcoin and reduced debt load. Additionally, our cash flow utilization is now down to ~57%.
So what else happens in Q2?
With Bitcoin at $100,000 MSTR is likely trading in a range around $330. So this allows us the potential for 2 additional notes to convert, the 2031 and the 3032. These notes have 130% trigger prices of $302.54 and $265.63 respectively.
With those notes hitting that trigger, they would now convert in Q3 dropping $1,403,750,000 off the liabilities.
But now we are nearing the potential tail end of the cycle, and these won't be eligible for the 130% rule until Q1 of 2026 so we are going to get a bit more conservative now.
I like round numbers, and MSTR in my scenarios is now at a stones throw distance to 300,000 Bitcoin. So that is going to be our target. I'm going to assume we are trading around $120,000 Bitcoin in Q3 so that means we will need to redeploy ~$1.05B to hit our target.
Since these note maturities are still farther out and we now have nothing on the books in 2031 and 2032 we will split this between the two years with $525M each. The 2031 has an interest rate of 0.875% which we will keep, but the maturity has now shortened to the 2032 Notes enough from their initial pricing at 2.25% so I will assume we can now get 1.5% for these (all cash flow improvements matter).
With these changes our cash flow utilization plummets to 40.45% and our BTC break even price reduces to $10,917. The risk management is certainly working! The treasury would now hold an even 300,000 BTC.
Excellent. But the show goes on so let's bring it home.
With Bitcoin prices in Q3 around $120,000, we are probably looking at a MSTR price of ~$370 (likely far higher, but I've been keeping mNAV expansion and mania out of this). So this means that our last note that was put in place in Q4 of 2024 is now eligible for conversion in Q4 of 2025 due to the $327.60 130% trigger price.
This is our last hurrah in out quest to de-risk our cash flows exiting the cycle. So now we freed up $725M from the 2029 convertible offering. To de-risk, we are going to replace this note with another 2029 offering of only $525M (to match the last 2 we just did).
Let's assume Bitcoin runs up to $140,000 in Q4 so we are able to collect 3,750 Bitcoin with this one.
What a year 2025 has been! Let's recap where we close out.
Throughout this process MSTR has acquired 51,530 new Bitcoin from start of Q4 2024 to end of year 2025 ending at 303,750 BTC in the treasury. That is a whopping 20.4% increase in holdings. That's an accomplishment in its own right. It also lowers the BTC Break Even Price to $10,123.
Exiting the year, MSTR would now have $3.075B in convertible debt offerings on the books. That is a decrease of -$1,188,750,000 or 27.9% from the start of Q4 2024 which is a serious lowering of the risk here.
MSTR would now require $25,125,000 annually to service these new notes. That is down -$9,470,313 or 27.4% from start of Q4 2024. This leaves us with cash flow utilization of 38.53% and a debt service coverage ratio of 2.60x. These are significant improvements to the metrics and greatly reduce the risk profile. The beauty is we did all this without taking our foot off the gas (with some cooperation from Bitcoin of course).
MSTR would now be in an amazing position to exit 2025, as strong as ever with a huge amount of Bitcoin on the balance sheet. There is still upside in a mania where more debt falls off in Q1 2026, but I have to stop this story somewhere. It's fun to think through regardless.
So in summary...
Bullish.