This Week in M&A Issue #236

Amazon Is Turning Its Logistics Engine Into a Business

Advertising in ChatGPT just got a whole lot more accessible.

The biggest change is that the $50,000 minimum spend is gone. In its place, OpenAI has launched a self-serve ads manager (currently in beta), where U.S. advertisers of all sizes can apply for access. If approved, you can run campaigns directly, upload creatives, set budgets, control pacing, and track performance without going through a partner.

They’ve also made the pricing more flexible. Originally, ads were sold on a CPM basis at $60 per 1,000 impressions. Now, you can choose between CPM (focused on reach) or CPC (focused on clicks). For CPC campaigns, OpenAI suggests starting bids between $3 and $5. The system runs on a relevance-based, second-price auction, so better-matched ads can win without always paying the highest bid.

Tracking has improved too. There’s now a Conversions API and pixel support, so you can measure actions like sign-ups, leads, and purchases. Reporting includes impressions, clicks, spend, CTR, CPC, CPM, and conversions, along with export options and UTM tracking.

Ad targeting works differently from traditional search. Instead of keywords, ads are matched to conversations based on context, your ad creative, and your landing page. They appear below responses and are clearly labeled.

OpenAI says ads do not influence ChatGPT’s answers. Ads currently run for Free and Go users in the U.S., Canada, Australia, and New Zealand, excluding Plus, Pro, Business plans, and users under 18.

It’s still early, but this is the first real chance to test ads inside ChatGPT without a huge upfront commitment. If you like getting in before a channel gets crowded, this is worth keeping on your radar.

One of the web’s longest-running search brands has gone dark.

Ask.com, originally launched as Ask Jeeves in the late 1990s, officially closed on May 1, 2026 after nearly three decades online. The company confirmed the shutdown in a message on its homepage, saying parent company IAC decided to discontinue its search business as part of a broader shift in focus.

Ask.com’s homepage now carries a farewell message thanking users, engineers, and employees who supported the platform over the years, adding that “Jeeves’ spirit endures.”

Ask Jeeves launched before Google became dominant, but it struggled to compete once Google turned search into a faster, cleaner, algorithm-driven experience. IAC acquired the company in 2005 and rebranded it as Ask.com in 2006. By 2010, the company had already scaled back its own search technology and shifted toward a question-and-answer format.

For a lot of early internet users, Ask Jeeves stood out because it let people type full questions instead of just keywords. Long before AI chatbots existed, users could ask things like “How do I fix a leaky faucet?” or “What are the best restaurants in Rome?” in natural language.

Modern search is moving back toward conversational interfaces through AI products like ChatGPT, Gemini, and AI-powered search summaries. In many ways, Ask.com was trying to build that experience almost 30 years ago. The technology was just not ready yet.

Ask.com may not have survived the search wars, but many of the ideas behind it ended up shaping the next generation of search anyway. Farewell Jeeves.