Short-Term Weakness, Long-Term Cycle Questions for BTC

August 20, 2025

Digital Asset Resilience Meets a Critical Macro Week

August 20, 2025

Seasonality & Futures Positioning Signal Crypto Headwinds

Key Takeaways

  • BTC & ETH seasonality points to flat-to-down Q3, rebound in Q4
  • ETH futures positioning bearish, historically the more reliable side of the trade
  • MSTR trades at 1.42x mNAV; ATM for BTC buys or arbitrage risk if premium persists

Digital Asset Commentary

Momentum in both BTC and ETH has stalled near record highs, with ETH still below its last all-time high from Q4 2021. Despite billions in inflows via ETFs and corporate treasuries, ETH’s 250% rally since the April low may require a prolonged consolidation before another leg higher. Seasonality for both BTC and ETH suggests a flat-to-down Q3, followed by a stronger Q4 rebound.

ETH CME Futures Commitment of Traders (CoT) data adds to the bearish case. Commercial hedgers now hold a record net short position, which has risen sharply in recent weeks. Historically, commercials tend to position correctly, while large speculators and retail investors often represent the crowded side of the trade.

On the BTC side, MicroStrategy (MSTR), the largest corporate holder, has slowed purchases in recent weeks while still trading at a premium to its BTC holdings (mNAV). Proponents argue this premium reflects liquidity advantages versus native BTC markets, the use of leverage through debt, scarcity of pure-play BTC equities, and optionality for future BTC acquisitions.

That premium currently sits around 1.42x, down from a 3.41x peak in November 2024. As long as it remains above 1.0x, further BTC buys via the at-the-market (ATM) program are likely. If the premium widens, short-MSTR/long-spot BTC pair trades become increasingly attractive as an arbitrage play. On the last earnings call, Saylor suggested MSTR would avoid ATM issuance below a 2.5x premium, but has since softened that stance, noting the company may issue below that level if advantageous. If MSTR doesn’t act to narrow the premium, as Jim Chanos has argued, the market eventually will.

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Steven McClurg

Founder, CEO

Prior to founding Canary, Steven co-founded and served as CIO of Valkyrie Investments, whose public funds business was acquired by CoinShares in 2024. He was previously a Managing Director at Guggenheim Partners, overseeing portfolio strategy for fixed income and private equity. He also founded Theseus Capital (acquired by Galaxy Digital) and served as an MD at Galaxy. Steven holds a Master of Science and MBA from Pepperdine University, where he has served as an adjunct professor.

Drew Hill

President, CLO

Drew is a seasoned digital asset attorney with deep expertise in securities law and fund compliance. Before Canary, he was GC and CCO at Valkyrie Investments and a key figure in Frost Brown Todd LLC’s Blockchain and M&A practice. He holds a BA in Finance & Spanish from the University of Oregon and a JD from Northwestern’s Pritzker School of Law.

Jamal Pesaran

Co-Chief Investment Officer

Jamal Pesaran, CFA, is Co-Chief Investment Officer for Canary Capital LLC. With 30 years of investment experience, he has extensive portfolio management, trade execution as well as client-facing experience.

As Senior Portfolio Manager with Guggenheim Partners, Jamal helped build the Guggenheim Equities business and developed the income focused and risk-managed strategies with AUM of over $4 Billion. With Morgan Stanley, as Senior PM and CIO for an Ultra High Net worth team, he managed both Active equity, fixed income strategies as well as overall portfolio allocations across alternative assets. Prior to joining Canary Capital, as Head of Capital Markets for Clifton AI, he helped develop and market a Gen-AI platform for Investment Research. His experience includes extensive portfolio management experience as Senior Equity Options Portfolio Manager, across European, US and Asian markets with Goldman Sachs and UBS Securities. He worked in Equity Derivatives Hedge Fund Sales with Lehman Brothers in New York and HSBC in Hong Kong.

He holds an MBA from UCLA Anderson where he was awarded the Edward Carter Fellowship for academic performance in the top 2% of the class.

Josh Olszewicz

VP, Head of Trading

With over a decade in digital asset markets, Josh leads Canary’s trading strategy and research. He previously headed crypto research at BraveNewCoin, was a portfolio manager at Techemy Capital, and served as Head of Research at Valkyrie Investments. Josh holds a BS in Human Biology and an MS in Biotechnology, and formerly taught lab sciences at the university level.

Linnea Steffy

VP, Finance

Linnea leads finance at Canary Capital, overseeing FP&A, fund accounting, and mid-office operations across the firm’s hedge funds, private funds, and ETFs. A strategic finance expert with a decade of experience, she previously managed over $850M+ in operating budgets at Discovery Inc., where she partnered directly with executive and creative leadership on major US networks including HGTV, DIY, and GAC. Linnea began her career at KPMG and holds a BS in Business Administration from the University of Tennessee, Knoxville.

Amber Reedy

Invetor Relations

Amber has over 15 years of experience driving growth through investor engagement, partnership strategy, and cross-sector business development. She’s known for building long-term relationships with institutional allocators and key stakeholders. Her strength lies in unlocking new revenue streams and delivering measurable outcomes across verticals.

Redding Shelby

ETF Operations Lead

Redding leads ETF operations at Canary Capital, managing daily fund activities across trading, accounting, and finance responsibilities. He is a fund operations professional with over five years of experience in ETF administration and business management. His expertise spans transaction oversight, reconciliations, and compliance for ETFs with exposure to digital assets. At U.S. Bancorp, Redding was instrumental in launching '40 Act ETF products and supporting the administrative needs of a leading national service platform. He excels at identifying and implementing process improvements, and collaborating across business units to drive performance. He holds a Bachelor of Arts in Finance from Ouachita Baptist University.

Alexis Busse

Executive Assistant

A graduate of the University of Wisconsin–Madison with a degree in Kinesiology and a certificate in Athletic Healthcare, Alexis serves as Executive Assistant and Office Manager. She brings management experience in hospitality and fitness to her role, supporting executive initiatives and overseeing daily operations to ensure organizational efficiency and seamless coordination across the company.

Dylan Farnick

Associate Trader

With over a decade of experience in digital asset markets, Dylan brings a strategic approach to trading and research. He quickly honed his skills in navigating digital exchanges and futures trading, with research focused on post-mortem analysis. His expertise extends beyond trading to include UI/UX consulting, working on trading interfaces and documentation for various platforms including Kraken and Tradingview, as well as community management, where he provided direct product feedback as a liaison with the crypto trading community.

Bronson Kaufusi

Business Development

A former NFL athlete turned business strategist, Bronson blends on-the-field experience with data-driven leadership. He brings expertise in consulting, real estate, blockchain, and data analytics, and has led initiatives supporting startups and athletic organizations alike. He serves as a board member at UVU, Head of Player Development at OG1 Athletes, and is active in nonprofit and entrepreneurial networks.