Can you walk through the unique three-way deal structure when you sold thinkorswim to TD Ameritrade in the middle of the 2009 financial crisis?

Tom Sosnoff
Replied byTom Sosnoff

Co-founder & CEO at Lossdog

Niche: Finance
Revenue: Pre-Revenue/month
Location: Chicago, Illinois, USA
Started: 2025

In early 2009, during the depths of the financial crash, we received three acquisition bids within days because investment bankers cannot keep secrets. TD Ameritrade wanted to acquire thinkorswim, but because their stock price was depressed, we preferred equity rather than cash. Simultaneously, the Ricketts family wanted to purchase the Chicago Cubs but needed immediate liquidity. We structured a three-way transaction where we received TD Ameritrade equity, the Ricketts family received the cash payout from the transaction to purchase the Cubs, and TD Ameritrade took ownership of thinkorswim. The entire deal was executed in roughly two days.

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