Table of Contents As filed with the Securities and Exchange Commission on January 29, 2026 Registration No. 333-291492 UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 Amendment No. 1 to FORM S-1 REGISTRATION STATEMENT UNDER THE SECURITIES ACT OF 1933 Grayscale Investments, Inc. (Exact Name of Registrant as Specified in Its Charter) (State or Other Jurisdiction of Incorporation or Organization) Delaware 6221 39-2149041 (Primary Standard Industrial Classification Code Number) 290 Harbo ...

Core Viewpoint - Graycliff Exploration Limited successfully closed a private placement, raising gross proceeds of $440,000 through the issuance of 4,400,000 common shares, aimed at improving its financial position and supporting ongoing exploration activities [1][5]. Financing Details - The private placement included $113,000 in new equity financing and $327,000 in debt settlements for common shares [2]. - All securities issued are subject to a four-month hold period and applicable resale rules, with no finder's fees paid [2]. Related Party Transaction - The offering is classified as a related party transaction, with insiders subscribing for 2,220,000 common shares [3]. - The company is relying on exemptions from certain requirements of Multilateral Instrument 61-101 due to financial challenges [3]. Shareholder Changes - Following the offering, Arndt Roehlig will hold 1,500,000 common shares, representing approximately 17.04% of the issued shares on an undiluted basis [4]. Company Overview - Graycliff Exploration is focused on mineral exploration, particularly on its 1,468 hectares of land near Sudbury, associated with the historic Shakespeare Gold Mine [6]. - The company has drilled over 12,500 meters at the Shakespeare project, identifying visible gold in multiple holes [6].

Core Viewpoint - Graycliff Exploration Limited has appointed Arndt Roehlig as the new President and CEO, effective immediately, highlighting his extensive experience in the resource and technology sectors [1] Group 1: Leadership Changes - Arndt Roehlig has been appointed as President, CEO, and director of Graycliff Exploration Limited, bringing decades of corporate experience and a successful track record in raising funds for public companies [1] - James Macintosh will continue to serve on the board and has been appointed as Chairman of the Company [2] Group 2: Financial Activities - The Company has arranged a non-brokered private placement to issue up to 4,400,000 common shares at a price of $0.10 per share, aiming for gross proceeds of up to $440,000 [3] - Proceeds from the Offering will be utilized for general corporate and working capital purposes, with the closing subject to regulatory approvals [3] Group 3: Company Overview - Graycliff Exploration is focused on mineral exploration, particularly on its 1,468 hectares of land located approximately 80 kilometers west of Sudbury, associated with the historic Shakespeare Gold Mine [4] - The Shakespeare Project includes one crown patented lease, two crown leases, and 40 claims, with over 12,500 meters drilled and visible gold identified in multiple holes [4]

Core Viewpoint - Grayscale's 2026 digital asset outlook report anticipates significant structural shifts in digital asset investing, driven by macro demand for alternative stores of value and improved regulatory clarity, marking the beginning of an institutional era in cryptocurrency [4][5][9]. Market Overview - Bitcoin is currently trading at approximately $87,000, while Ether is just below $3,000, and XRP has seen a slight decline to $186 [1][2]. - The cryptocurrency market is experiencing slight downturns, coinciding with declines in tech stocks, particularly affecting companies like Nvidia and Meta Platforms [2]. Regulatory Landscape - Grayscale emphasizes the importance of regulatory clarity for the growth of the cryptocurrency market, noting that comprehensive regulations are necessary to protect consumers and integrate blockchain technology into the mainstream financial system [8][10]. - The anticipated bipartisan market structure legislation in the U.S. is expected to provide clearer guidelines for various digital assets, potentially categorizing many as digital asset securities [15][21]. Investment Trends - The report suggests that the demand for alternative stores of value, driven by economic factors such as debt and fiat currency risks, will continue to attract new capital into the cryptocurrency market [6][18]. - Grayscale forecasts that Bitcoin may reach a new all-time high in the first half of 2026, supported by macroeconomic conditions and regulatory advancements [17][20]. Product Development - Grayscale expects an increase in the availability of crypto assets through exchange-traded products (ETPs) in 2026, facilitated by regulatory clarity from the SEC [23][25]. - The company has recently launched several ETPs, including those for Solana, XRP, and Dogecoin, and anticipates further product expansion with features like staking rewards [26][27]. Digital Asset Treasuries - Grayscale believes that digital asset treasuries will not significantly influence crypto markets in 2026, viewing them as relatively stable and less dynamic compared to previous years [28][30].

Group 1 - The Grayscale Zcash Trust (ZCSH) experienced a significant price rally of 300% since the beginning of the year [1] - The article reflects the author's insights as a former media research analyst with a focus on crypto, BTC miners, metals, and media equities [1] - The author shares personal investment strategies and insights without being an investment advisor [1] Group 2 - The author holds a beneficial long position in BTC-USD, ETH-USD, ZEC-USD, and ZCSH through various financial instruments [2] - The article emphasizes that the author's opinions are independent and not influenced by any business relationships with mentioned companies [2] - There is a clear disclaimer that past performance does not guarantee future results, and no specific investment advice is provided [3]

Core Insights - The Grayscale Ethereum Trust ETF (ETHE) has experienced significant developments in the past eight months, prompting a reevaluation of its investment potential [1]. Company Analysis - The fund's performance and developments are critical for investors interested in cryptocurrency, particularly Ethereum [1]. Industry Context - The article highlights the importance of monitoring developments in cryptocurrency funds, as they can present both opportunities and risks for investors [1].

Core Insights - The crypto industry's IPO window may be closing, prompting Grayscale Investments to act strategically by pursuing a public listing now [1][3] - Grayscale's revenue has decreased by 20%, with net income for the first nine months of 2023 reported at $203.3 million on revenue of $318.7 million, down from $223.7 million and $397.9 million respectively in the same period last year [2][5] Group 1: Financial Performance - Grayscale reported a net income of $203.3 million and revenue of $318.7 million for the nine months ending September 30, 2023, reflecting a decline from the previous year's figures of $223.7 million in net income and $397.9 million in revenue [2] - The company's revenue has declined by 20% compared to the same period last year [1] Group 2: Strategic Considerations - The timing of Grayscale's IPO filing is seen as a strategic move to navigate potential political uncertainties ahead of the 2026 midterm elections [3] - Analysts expect a revival in the IPO market following the end of the longest government shutdown in U.S. history, creating a narrow window for companies like Grayscale to go public [3] Group 3: Market Position and Regulatory Environment - Grayscale manages approximately $35 billion in assets and has established itself as a significant player in the crypto industry [5] - The company achieved a landmark court victory against the SEC in 2023, which facilitated the approval of spot bitcoin ETFs, marking a regulatory milestone for the industry [5] - Grayscale is among several crypto companies, including Circle and Gemini, that have taken advantage of the regulatory environment shaped under the Trump administration to go public [4]

Core Viewpoint - Graycliff Exploration Limited has announced a share consolidation, reducing the number of outstanding shares to approximately 4,402,460 on a basis of one post-consolidated share for every four pre-consolidated shares [1][2][3]. Group 1: Share Consolidation Details - The consolidation ratio is set at one (1) post-consolidated common share for every four (4) pre-consolidated common shares [1][2]. - Following the consolidation, the total number of outstanding shares will be approximately 4,402,460 [1][3]. - The company's name and trading symbol will remain unchanged [1][3]. Group 2: Trading and Order Information - All open orders will be canceled at the close of business on November 28, 2025, and dealers must re-enter their orders considering the share consolidation [2][3]. - Trading on a consolidated basis is scheduled to begin on December 1, 2025 [4]. - The record date and anticipated payment date for the shares are also set for December 1, 2025 [4].

Group 1 - The company, Graycliff Exploration Limited, announced a share consolidation on a one post-consolidation Common Share for every four pre-consolidation Common Shares basis [1] - The consolidation will reduce the number of outstanding Common Shares from 17,609,841 to approximately 4,402,460 [3] - The company has obtained a new CUSIP and ISIN for the shares, and the consolidation is subject to approval by the Canadian Securities Exchange [2] Group 2 - Registered shareholders will receive letters of transmittal and must send their pre-consolidation share certificates to the company's registrar and transfer agent [4] - Graycliff Exploration is focused on mineral exploration, particularly on its 1,468 hectares of land near the historic Shakespeare Gold Mine [5] - The company has drilled over 12,500 meters at the Shakespeare Project, with visible gold identified in multiple holes [5]

Core Insights - Grayscale Bitcoin Trust (GBTC) has been a significant vehicle for institutional investors seeking indirect exposure to Bitcoin prior to the approval of Bitcoin ETFs in the U.S. [1] - Grayscale Investments has been a pioneer in linking traditional finance (TradFi) with cryptocurrency, allowing institutions to invest in crypto without managing private keys directly [3] - Grayscale is planning to go public with an IPO, having filed with the SEC to list on the NYSE under the ticker GRAY [5][6] Group 1: Grayscale's Investment Products - Grayscale offers a variety of investment products, including the Grayscale Bitcoin Cash Trust (BCHG) and the Grayscale Ethereum Classic Trust (ETCG), which manage over $191 million and $157 million in assets respectively [2] - The Grayscale Digital Large Cap Fund and the Grayscale DeFi Fund are examples of diversified and thematic funds offered by Grayscale [4] Group 2: IPO Structure and Control - The IPO is structured as an "Up-C" transaction, allowing Grayscale to convert from a private to a public company while DCG retains 70% of voting power through Class B shares [6] - Class B shares will not have economic power, meaning they will not earn dividends, which designates Grayscale as a "controlled company" under NYSE rules [6] Group 3: Underwriters - The lead underwriters for Grayscale's IPO include Morgan Stanley, BofA Securities, Jefferies, and Cantor [7]