From denim icons to billion-dollar athletes

This week’s stories range from a $1.4B denim takeover to distressed capital plays and billion-dollar athlete endorsements. Plus, a tactical deep dive with WRK Marketing’s Brad Ploch on how to scale plateaued brands.

👖 Guess Goes Private: $1.4B Takeover by ABG

Guess, once a 1980s denim icon, is being taken private by Authentic Brands Group for $1.4B. The four-act boardroom drama is worth a recap:

  • Act I: Guess + WHP partnered on rag & bone (Guess ops, WHP IP).

  • Act II: WHP bid $750M to take Guess private.

  • Act III: ABG countered with a more imaginative deal—taking 51% of IP while Guess founders retained 49% and 100% of operations.

  • Act IV: Founders sided with ABG, cashing out shareholders but staying in the driver’s seat.

A case study in creative deal structuring — founders retained operational control while monetizing IP at scale.

💸 Distressed Capital: Rent the Runway’s Recap

When does $240M of debt become 80% of a company? That’s the live experiment at Rent the Runway (RTR).

  • APS converted $240M of debt into equity, injected $20M fresh capital, and now owns ~80–85% of RTR.

  • Kept RTR public to avoid bankruptcy optics and preserve brand equity.

  • Shareholders got diluted, but at ~$20M pre-deal market cap, there wasn’t much equity left to lose.

A smart move for control without the chaos of Chapter 11.

🎾 Federer: The Billion-Dollar Athlete

Roger Federer earned ~$100M in prize money across 20 Grand Slams. Impressive — but the real wealth came off-court:

  • $300M, 10-year deal with Uniqlo

  • ~3% stake in On Running, now worth ~$450M

Federer’s net worth crossed $1B not through tennis alone, but by translating cultural capital into brand equity.

🚨 Deal Alert: $300m CPG company looking to divest a non-core DTC coffee brand.

The business will do $7M in revenue and $900k in EBITDA in 2025.

Brand has 8,000 recurring subscribers, built on Shopify, powerful organic marketing presence.

Just needs a new home.

📩 DM or Connect for intros or details.

🎙 Podcast Spotlight: Scaling Past the Plateau with WRK Marketing’s Brad Ploch

What happens when a brand hits mid–seven figures and stalls? On this week’s pod, Brad Ploch of WRK Marketing walks through his framework for diagnosing and breaking through the ceiling.

Key takeaways:

  • Instrument first: Split new vs. repeat revenue, MER vs. CAC, and cohort paybacks before guessing bottlenecks.

  • Creative with intent: Tag by persona/pillar so you know why ads work, then match with congruent landers.

  • Retention that scales: Meta campaigns targeting lapsed customers can double repeat revenue.

  • AI as floor-raiser: Automate variants and scoring so humans can focus on big swings.

  • Play the long game: From $150K to $700K/month or $1M to $15M — no silver bullet, just disciplined systems.

A must-listen for founders or operators who feel “stuck” on growth.

🎧 Watch on YouTube, listen on Spotify.

That’s it for this week.
If you liked this issue, forward to a friend who obsesses over brand strategy, capital flows, or exit timing.

In the Money – following the flow of capital in consumer

P.S. We love talking to brands interested in exiting in the next 3-18 months. If you know of any brands interested in exiting, or any firms trying to help port cos manage turnarounds, we'd love to share a POV.

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