Ramaswamy Bets Big: $1.25M Preferred Share Purchase in Strive (ASST) Signals Confidence

Billionaire investor Vivek Ramaswamy just dropped a seven-figure vote of confidence in Strive Asset Management.

The biotech-turned-finance mogul snapped up $1.25 million worth of ASST preferred shares—a move that'll either look prescient or painfully ironic when the next market correction hits.

Preferred position: Ramaswamy's purchase gives him priority over common stockholders, securing his spot at the front of the line if Strive's 'anti-woke' investment thesis pays off.

Market reaction: ASST common shares typically move when the preferred side gets action, but today's trading suggests Wall Street still thinks ESG is eating Strive's lunch.

Closing thought: Nothing screams 'conviction' like locking in better terms than the retail investors you're supposedly fighting for.

TLDR

• Vivek Ramaswamy purchased 15,625 shares of Strive Inc Variable Rate Series A Perpetual Preferred Stock for $1.25 million at $80 per share on November 5, 2025
• The purchase was part of Strive’s upsized initial public offering that raised approximately $160 million in gross proceeds from 2 million preferred shares
• Following the transaction, Ramaswamy holds 113,877,916 shares of Class B Common Stock directly and 28,378,826 shares indirectly through a trust
• ASST stock closed at $1.51 on November 7, 2025, with a market cap of $141 million and a year-to-date return of 208%
• Strive recently appointed Ben Werkman as Chief Investment Officer and continues pursuing its Bitcoin-centric investment strategy

Vivek Ramaswamy purchased 15,625 shares of Strive Inc Variable Rate Series A Perpetual Preferred Stock on November 5, 2025. The ten percent owner paid $80 per share for a total transaction value of $1.25 million.

The purchase occurred in connection with Strive’s underwritten public offering. A FORM 4 filing with the Securities and Exchange Commission disclosed the transaction details.

Strive, Inc., ASST

ASST shares traded at $1.51 as of November 7, 2025. The company’s market cap stands at $141 million with a year-to-date return of 208%.

Following this transaction, Ramaswamy’s ownership structure shifted. He now directly owns 113,877,916 shares of Class B Common Stock and 15,625 shares of Variable Rate Series A Perpetual Preferred Stock.

The Ramaswamy 2021 Irrevocable Trust holds an additional 28,378,826 shares of Class B Common Stock. This brings his total stake across direct and indirect holdings to over 142 million shares.

Upsized IPO Raises $160 Million

Strive announced the pricing of its upsized initial public offering on the same day as Ramaswamy’s purchase. The company sold 2 million shares of Variable Rate Series A Perpetual Preferred Stock at $80 per share.

The offering generated approximately $160 million in gross proceeds. Settlement was scheduled for November 10, 2025.

The IPO represents an increase from the company’s earlier plans. Strive initially intended to offer 1.25 million shares before upsizing the deal.

The company plans to use proceeds for various corporate purposes. These include potential Bitcoin acquisitions and debt repayment.

Strive filed a prospectus for the potential resale of up to 1.28 billion shares of Class A common stock by certain selling securityholders. The company will not receive proceeds from these sales.

Trading Activity and Performance

ASST closed at $1.51 on November 7, 2025, up from $1.45 the previous day. The stock has shown strong short-term momentum after a sell-off earlier in the quarter.

The stock returned 37.3% over the past two weeks. However, it underperformed over the last three months.

Trading volume and options activity spiked recently. Over 278,000 contracts traded on November 7 with open interest totaling 3.48 million.

The stock’s 52-week range spans from $0.335 to $13.42. ASST currently has a beta of -0.71, showing reduced sensitivity to broader market movements.

The company’s P/E ratio stands at -1.62, reflecting ongoing net losses. High volatility continues with recent price support at $1.24 and resistance at $1.66.

Strive’s board and stockholders approved amendments to remove the maximum number of directors allowed on its board. This change takes effect December 31, 2025 and eliminates the previous limit of 11 directors.

The company appointed Ben Werkman as Chief Investment Officer. Werkman joins from Swan bitcoin and previously founded a Bitcoin treasury advisory firm and worked at KPMG.

Strive continues pursuing its Bitcoin-centric strategy. Recent filings emphasize its focus on accumulating Bitcoin and increasing Bitcoin-per-share to outperform Bitcoin as a long-term investment benchmark.