AIAI Holdings Enters $200M Stock Purchase Agreement with B. Riley

What Happened

• On September 18, 2026, AIAI Holdings Corporation entered into a Common Stock Purchase Agreement and a related Registration Rights Agreement with B. Riley Principal Capital II, LLC. The agreements give AIAI the right, at its sole option and subject to conditions, to sell up to $200,000,000 of newly issued Class A common stock to B. Riley over a period of up to 36 months after the registration statement is declared effective by the SEC (the “Commencement Date”).
• As part of the deal, AIAI issued 182,927 “Commitment Shares” to B. Riley (valued using a $3.28 per-share reference price), equivalent to 0.3% of B. Riley’s $200M commitment.

Key Details

• Maximum commitment: $200,000,000 of newly issued Class A common stock over up to 36 months after SEC effectiveness.
• Purchase mechanics: Company may direct Market Open Purchases (pre-open notice) and Intraday Purchases (notice between 10:00 a.m. and 3:30 p.m. NYC time); purchase price = VWAP for the applicable valuation period less a fixed 3.0% discount. Threshold Price to initiate purchases: prior-day close > $1.00.
• Caps and limits: Nasdaq cap limits issuances under the facility to 14,125,485 shares (19.99% of outstanding pre-agreement) unless shareholder approval is obtained or the average price paid equals or exceeds $3.33/share; B. Riley and its affiliates may not beneficially own more than 4.99% of outstanding shares.
• Other terms: B. Riley agreed not to enter into short sales or hedges that create a net short position during the term. The Purchase Agreement may be terminated upon certain events (e.g., 36 months after Commencement, $200M purchased, delisting, bankruptcy) or by the company with 10 trading days’ notice after Commencement.

Why It Matters

• This agreement gives AIAI optional, on-demand equity financing capacity up to $200M that the company controls (timing and amount), which can be used for working capital and general corporate purposes.
• Because sales are newly issued shares, any draws under the facility would dilute existing shareholders; however, Nasdaq issuance and 4.99% ownership caps and the $3.33 price condition provide limits on dilution and concentration.
• The facility is contingent on an effective SEC registration statement and has no obligation to sell—so it is a flexible funding tool but not a guaranteed cash inflow.