Nakamoto feels pressure on its debt structured near Bitcoin’s all-time high

Nakamoto Holdings, formerly KindlyMD, is feeling the pressure of falling BTC prices. The company has posted collateral to its BTC-backed debt twice in the past days. 

Nakamoto Holdings (NAKA), which was created after a reverse merger with KindlyMD, is feeling pressure from the recent drop in BTC prices. The company had to post collateral twice to its structured debt backed by BTC. 

The company’s stock was already weakened from postponing the Q3 report, as the final result may include a $59M loss on the acquisition of Nakamoto Holdings. 

Nakamoto Holdings is within the top 20 of BTC treasury companies and is officially a ‘playbook’ company. This has affected the holding’s debt structure, as it used various instruments to build up its treasury. 

Nakamoto explains outflow from BTC treasury

In the past week, Nakamoto was the only BTC DAT company to remove BTC from its treasury. In total, the reserves peaked at 5,764 BTC, with most of the funds acquired in one tranche in August. 

The treasury moved 367 BTC, but the CEO, David Bailey, explained the coins were not sold. Instead, Nakamoto used the BTC to invest in other treasury companies. 

Just to clarify, we didn't "sell" bitcoin. We invested the Bitcoin across several international treasury companies @Treasury_BTC @Metaplanet @future_hodlings, as a core part of our strategy is monetizing our bitcoin balance sheet. Our direct Bitcoin balance does not capture the… https://t.co/9StHuB7C6g

— David Bailey🇵🇷 $1.0mm/btc is the floor (@DavidFBailey) November 20, 2025

However, the community still suspected that some of the BTC had been sold. Bailey claimed exposure to BTC was what counted, but the company no longer controls the coins, instead holding the shares of DAT companies. Not all shares give exact exposure to BTC. As of November, the community is also calling for Nakamoto to post a more transparent version of its holdings. 

Nakamoto’s debt required additional BTC collateral

During the more bullish months of 2025, Nakamoto Holdings had ambitions of buying up to $1B in BTC. Some of the funding came from an agreement with Antalpha to offer custom solutions for financing BTC purchases. 

Nakamoto set out the conditions for a $250M loan from Antalpha based on BTC prices at over $124,000. On-chain data shows the company posted collateral twice to avoid liquidation, with the latest addition on November 21. 

Nakamoto has a $250M convertible note with Antalpha backed by Bitcoin, structured at BTC's $124K ATH

They've now posted additional collateral twice this week, latest was 20 mins ago.

Clear margin pressure highlighting the risks of levering up at cycle peaks. Watching closely. pic.twitter.com/fDlA2FpBFV

— Emmett Gallic (@emmettgallic) November 21, 2025

The company posted 1K BTC to Cobo Custody, still potentially regaining the coins. However, the worsening price conditions have put pressure on the company’s margins, making its loan a high-risk addition to the balance sheet. 

Nakamoto posted the collateral from a smaller wallet with around 770 BTC. The selling and collateral posting have raised additional concerns with the potential for playbook companies to fail due to low BTC prices. 

The collateral was posted as BTC briefly dipped to $82,000. Currently, NAKA shares are trading near an all-time low of $0.55, down from $25 in May. The company has a mNAV metric of 0.439, falling below the 1.0 ratio threshold, which means the company cannot use its stocks to buy more BTC. 

The current market cap of the company is now lower than the Antalpha debt facility, showing deep imbalances in Nakamoto’s attempt to run a BTC playbook similar to Strategy. Nakamoto also made a singular purchase and has not added more BTC since August.

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