JWCA advises Upstart on its upsized $690 million zero-coupon convertible and capped call transaction to refinance its outstanding convertible notes

August 2025 | read press release

Transaction Background

Upstart Holdings, Inc. (“Upstart” or the “Company”) successfully raised an upsized $690 million (inclusive of greenshoe) in the convertible market at highly attractive terms (0.00% coupon and 30.0% conversion premium), while repurchasing ~$233mm (~78%) of its outstanding 2026 convertible notes

Upstart took advantage of strong underlying convertible market conditions to successfully execute its third convertible bond issuance in the past year

Upstart’s objectives included:

  • Opportunistically raise cash to the Balance Sheet

  • Efficiently repurchase a majority of the outstanding 2026 convertible notes to manage liabilities and capital structure

  • Protect against future equity dilution through a derivative overlay

JWCA provided extensive analysis on deal structuring and related items, including:

  • Convertible and derivative overlay structuring and tax implications

  • Refinancing tactics and analysis

  • Convertible and capped call documentation to ensure maximum value and future efficiency/flexibility for the company

  • Execution timing

  • Shareholder messaging

JWCA designed and ran a capped call auction process to achieve competitive terms

JWCA provided advice, support and analysis throughout the execution process

Results

Upstart’s convertible transaction was very well received by investors:

  • The transaction was multiple times oversubscribed, reflecting strong investor interest and demand in the Company’s convertible bond offering, leading to the issue being upsized by $100mm (20% of original $500mm base deal)

  • The 0.00% coupon represented the low end of the marketed coupon range

  • The 30.0% conversion premium represented the midpoint of the marketed conversion premium range

Capped call documentation and auction process produced meaningful savings for Upstart, driving economics in the Company's favor

The Company obtained favorable terms on a busy day for issuance: ~$1.5bn in convertible supply was available in the primary market