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It all started in 2019, when a relatively small software company called MicroStrategy (now known as Strategy) knocked on investment bank Jefferies' door after being turned away by Wall Street giants.
At the time, Michael Saylor's firm had a market cap of nearly $2 billion and was looking to raise capital to buy bitcoin—something bulge bracket banks were reluctant to support.
Jefferies took a chance on Saylor, marking a pivotal deal for the investment bank and the digital assets sector.
Now, Saylor's firm is worth about $111 billion in market cap, other companies are buying bitcoin for their balance sheets, and large Wall Street firms are piling into the digital assets sector.
And Jefferies? The firm is now a full-service investment bank for the crypto and blockchain space, and it's doing billions in deals without the crutch of a trillion-dollar balance sheet or FDIC-insured deposits.
“We don’t change our stripes too often, but when we see opportunity, we move fast,” Alexander Yavorsky, head of FIG investment banking at Jefferies, told CoinDesk in an interview.
The crypto commitment
The game-changing MicroStrategy engagement in 2019 kickstarted a much deeper foray into the asset class for Jefferies.
By 2020, Jefferies had become the first major full-service investment bank to dedicate a senior banker exclusively to crypto. Tim Shea, now co-head of digital assets coverage, spends 100% of his time on the asset class.
But don't call them a crypto shop as Jefferies has been consistently doing deals across the board, putting the firm sixth globally in the last twelve months, according to data from Dealogic.
Diving deeper into deals that Jefferies worked on, the firm revealed that it has advised on 120 transactions with over $150 billion of deal value across fintech, market structure, and exchanges since 2015.
This track record, particularly handling deals that involve applied technology and complex regulatory footprints, uniquely equipped Jefferies to handle the hybrid world where crypto meets traditional finance.
“We are a full-service investment banking firm, rather than a crypto shop,” Yavorsky said, "but we’ve built deep sector knowledge, and we know how to structure deals and move quickly."
Over the past three years, Jefferies has steadily increased its involvement in crypto and crypto-adjacent dealmaking, building a track record across capital markets, M&A, and restructuring.
One of the standout deals the firm advised was NinjaTrader on its $1.5 billion acquisition by Kraken, a notable example of consolidation between traditional trading platforms and digital asset exchanges.