Good Morning, Builders.

Today’s signal: execution beats access. A cold email lands Mark Cuban, legacy platforms get rebuilt with AI, and big tech keeps testing where trust actually breaks. Let’s get to work.

I. The Headlines

1. Mark Cuban Just Funded a Startup That Slid Into His Inbox


AI PR startup Clipbook raised a $3M seed round co-led by Mark Cuban after founder Adam Joseph cold-emailed the billionaire. Cuban responded with intense skepticism, pushing Joseph through dozens of questions and a real-world test, which included producing a media intelligence report for CostPlus Drugs. Clipbook passed, showcasing its AI-native approach to media monitoring across press, podcasts, and video capabilities. Do we now have definitive proof that cold email is alive and well? (The Tech Buzz)

2. Bending Spoons Buys Eventbrite, Betting on AI and a Second Act for Live Events

Eventbrite will be acquired by Bending Spoons in an all-cash deal worth about $500M, taking the events platform private at $4.50 per share, an 82% premium to its recent average stock price. Bending Spoons is known for snapping up mature tech platforms like Vimeo, Meetup, and Evernote and says it plans to rebuild Eventbrite’s product with better messaging, search, AI-assisted event creation, and new monetization levers, marking a reset for the company away from public-market pressure and toward a more tightly optimized, software-driven future. (Business Wire)

3. ChatGPT’s App Experiment Looked a Lot Like Ads (Even to Paying Users)

OpenAI faced user backlash after ChatGPT began suggesting apps inside conversations in ways that felt uncomfortably close to ads. This included a Peloton app recommendation dropped into an unrelated discussion for a $200/month Pro user. While OpenAI insists there’s “no financial component” and says this was simply early testing of its in-chat app ecosystem, the poor relevance and lack of user controls made the feature feel intrusive. The episode highlights OpenAI’s ongoing dilemma of how to turn ChatGPT into a platform without breaking user trust, especially when paid users expect utility, not upsells. (TechCrunch)

4. Saudi Arabia, Netflix, and Paramount Lead $60BN+ Bidding War for Purchase of Warner Bros. Discovery

Warner Bros. Discovery is weighing second-round acquisition bids from Netflix, Comcast, and Paramount, with each suitor proposing a fundamentally different future for the studio. Netflix has shifted to a mostly cash bid focused on content and streaming, Paramount has lined up an all-cash offer backed by Apollo and sovereign wealth funds to buy the entire company, and Comcast is pitching a stock-heavy deal that would merge NBCUniversal assets into WBD. The board now faces a high-stakes decision: sell the company whole, split off its linear TV business, or push for another bidding round. (The Hollywood Reporter)

5. Amazon’s Delivery Arms Race Just Hit the 30-Minute Mark

Amazon is piloting a 30-minute delivery service called Amazon Now in parts of Seattle and Philadelphia, offering ultra-fast delivery of groceries, household goods, electronics, and more directly through its main app. Prime members pay $3.99 per order, while non-Prime users face higher fees. Deliveries are fulfilled from small, local micro-warehouses designed to compete with DoorDash and Instacart. The move marks Amazon’s latest attempt to win the ultra-fast delivery space after multiple prior shutdowns. (The Verge)

6. Is Cruising the Next Remote Work Destination?

Virgin Voyages is debuting its 30-day Alaska season passes starting at $26,000 per cabin for two. Launching alongside the line’s first Alaska season in summer 2026 aboard the Brilliant Lady, the passes bundle a full month at sea with Wi-Fi built for remote work, laundry, drink credits, spa access, shore excursions, and even sightseeing gear. With multiple departure windows priced as high as $38,000, Virgin is clearly testing demand for extended “live-aboard” cruising. This one’s aimed at travelers who want to slow down, work remotely, and treat cruising less like a vacation and more like a seasonal lifestyle. (Travel Weekly)

To the Arena,
- Nathan

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