Brew Markets Daily — Episode Summary

Episode Title: Why Rent The Runway is Out of Time & Gemini: Doubling Up on NASDAQ
Date: September 12, 2025
Host: Ann Berry
Podcast: Brew Markets

Overview

In this episode, Ann Berry and producer John Croteau break down major market stories: Oracle’s meteoric stock rise and CEO Safra Katz's pivotal role; why Rent the Runway’s “growth recapitalization” may be less lifeline and more life support; and the NASDAQ’s bold strategic investment in the newly listed Gemini Crypto Exchange. The show weaves together sharp industry analysis, financial context, and behind-the-scenes perspectives on the people shaping today’s markets.

CEO of the Week: Safra Katz and Oracle’s AI Surge

[00:02 - 04:33]

Key Discussion Points

• Safra Katz’s Journey at Oracle:

  • Joined Oracle in 1999 focused on corporate development.
  • Drove a $40B, 80-company acquisition spree transforming Oracle from database provider to enterprise software titan.
  • Became board member (2001), co-president (2004), and co-CEO (2014).
  • Sole CEO since 2019 after Mark Hurd’s passing — one of very few women ever to lead a Fortune 100 company.

• Oracle’s AI Drive & Financial Performance:

  • Oracle’s share price up from ~$60 five years ago to over $220 recently, spiking above $300 on AI-driven contract growth.
  • Under Katz, pivoted hard to cloud and infrastructure, directly taking on Amazon and Microsoft in the cloud arms race.
  • Renowned for rigorous cost management, consistent profitability.

• Her Wider Influence:

  • Background: Born in Israel, law degree from UPenn, ex-Wall Street Managing Director.
  • Board positions: HSBC (during/post-Financial Crisis); The Walt Disney Company.
  • Political connections: Served on Trump’s 2016 transition team; involved in current AI infrastructure initiatives linked to Oracle.

• Concerns and Outlook:

  • Analysts worry Oracle’s optimism rests heavily on OpenAI partnerships, which account for a significant chunk ($300B) of projected revenue.

Notable Quotes

• “Katz rarely gives interviews, but her influence is widespread.” — Ann Berry [03:35]
• “[Katz] is one of the toughest cost managers in tech, driving sustained profitability.” — Ann Berry [03:29]
• “As AI continues to dominate the market narrative, we’re going to be seeing a lot more of Safra Katz.” — Ann Berry [04:25]

Rent the Runway: Losing Steam and Losing Time

[04:57 - 13:45]

Key Discussion Points

• Origin and IPO Rise (and Fall):

  • Founded 2009, became a pioneer in the sharing economy alongside Uber and Airbnb.
  • “Literally a closet in the cloud, which is how founder and CEO Jennifer Hyman has described it.” — Ann Berry [05:17]
  • IPO’d in October 2021 at $21/share ($1.3B valuation); plummeted below $10 within weeks, under $2 by end of 2023.

• Persistent Losses & Financial Engineering:

  • Net losses: $171M (2021), $200M (2022), $138M (2023), $26M lost last quarter.
  • Extended debt maturity to avoid default. In April 2024, executed a reverse stock split to prevent NASDAQ delisting.
  • August 2025: “Growth recapitalization” — $260M debt converted to equity; public shareholders now diluted to <20% ownership; $20M cash infusion.

• Strategy for Growth?

  • CEO aims to double inventory, get brands to consign clothing for a cut of revenue (rather than pay cash up front).
  • Risk: Assumes more rental revenue — but growth remains stubbornly limited.
  • Prices recently hiked for the first time in 3 years, sparking concerns about subscriber retention and future hikes.
  • High customer acquisition costs ("$7.5 million in the last quarter alone" — John [11:00]) continue to thwart operating profitability.

• Competitive Landscape:

  • Urban Outfitters’ Nuuly outpaces RTR: 350,000 subscribers (>2x RTR), 50% revenue growth, record profits.
  • Nuuly benefits from existing in-store inventory and lower price points, easier access to everyday apparel.

• The Outlook:

  • “I think they're running out of time because… [with] about $75 million in cash today, and with $78 million spent on inventory last fiscal year... they've got about 18 months of cash runway left.” — Ann Berry [12:21]
  • Mounting competition, dilution, and stubborn losses spell trouble.

Notable Quotes

• “I don’t hear a growth recapitalization plan... I see this as a desperately trying to avoid bankruptcy, trying to buy some time plan.” — Ann Berry [11:45]
• “There is a hunger for it, people like it. But maybe that's just in my small population here in the city.” — John [11:16]
• “Do you use Rent the Runway or Nuuly? We'd love to hear from you.” — Ann Berry [13:45]

NASDAQ’s Investment in Gemini: A Strategic Crypto Alliance

[14:00 - 16:25]

Key Discussion Points

• Gemini IPO and NASDAQ’s Stake:

  • Gemini (crypto exchange; Winklevoss twins) IPO: $28/share, $3.3B valuation, surges up to 45% on debut day.
  • “NASDAQ plans to invest $50 million in the company,” offering Gemini’s custody services to institutional clients.
  • Gemini to resell NASDAQ’s Calypso solution (collateral management for institutions).

• Motivation:

  • This is not just about crypto trading — NASDAQ wants to be at the “center of non-traditional assets.”
  • Filed with SEC to allow tokenized stock trading (digital tokens representing real-world shares).
  • Positioning: NASDAQ, long known as a tech-forward exchange, seeks to harness blockchain for its future.

• Strategic Significance:

  • Moves NASDAQ closer to bridging traditional finance and digital assets — as “the first major traditional stock exchange to allow tokenized securities trading.”
  • Investment size ($50M) is small relative to NASDAQ’s cash (~$730M), but opens crucial, innovative lines of business.

Notable Quotes

• “NASDAQ’s been around since 1971... and it looks as though [it] is trying to figure out how blockchain will play a role in its next 50 years.” — Ann Berry [15:47]
• “A partnership with Gemini… is one tool Nasdaq’s using to get smart on the space.” — Ann Berry [16:20]

Rapid Market Wrap and Teasers

[16:25 - 18:00]

• Market close: Dow down 0.5%, S&P 500 flat, NASDAQ up (new record)
• Gemini IPO finished strong, closing at $32/share
• FAA fast-tracks air taxi rollout; Joby and Archer Aviation up >2%
• Teaser: StubHub’s oversubscribed IPO coming next week — will test public market appetite for tech and event companies, and founder control at public debuts.

Episode Highlights & Memorable Moments

• Sharp, candid analysis of Rent the Runway’s existential financial and strategic crisis.
• Deep-dive on Safra Katz’s understated but transformative tech leadership.
• Forward-looking discussion on how NASDAQ is “staking its flag” in the future of digital assets.
• Lively, accessible tone—encourages audience participation and market curiosity.

Timestamps Guide

| Segment | Start | End | |------------------------------------|----------|----------| | CEO of the Week: Safra Katz | 00:02 | 04:33 | | Rent the Runway Analysis | 04:57 | 13:45 | | NASDAQ x Gemini Strategic Review | 14:00 | 16:25 | | Market Wrap & Headlines | 16:25 | 17:25 | | Episode Teaser and Wrap | 17:25 | 18:28 |

For listeners intrigued by the intersection of leadership stories, financial strategy, and market innovation, this episode offers sharp insight into both individual and institutional decision-making in today’s markets.