Pinterest shipped its AI ad pivot while the founder's trust sold $24 million at falling prices
Pinterest trades at 9.3x forward earnings against a $30.30 analyst target, about 60% higher. This week the pivot meant to close that gap shipped its first deals, and the founder's trust kept selling into them at falling prices.
Vincent Jiang · 3 min read
Bill Ready's commerce pivot produced its first live deals this week, while the family trust of co-founder Ben Silbermann reported its 24th sale since 30 June, taking gross proceeds to about $24.1 million 12. Shopee affiliate Pins reached Brazil and Indonesia on 28 September and Wayfair's curated UK collections followed on 30 September 56. The trust's last print was $18.72 a share, against a peak of $23.88 on 11 August 12.
The pivot landed in one week
At Pinterest's 17 September advertiser summit, Ready said "Pinterest is now a performance platform, and AI is powering all of it" 3. The launches followed the sentence. Visual Search Ads, announced that day and opening across all Pinterest ad markets in the coming weeks, put the top slot in search results and Pin closeups up for bid 34. Shopee affiliate links let creators tag products in Pins and videos and collect commissions 5. A Wayfair UK program built curated collections from Pinterest trend data and booked a 4.5% incremental sales lift plus a 3.5 point lift in action intent 6.
One unnamed advertiser is the evidence
The flagship format's only published result is an up to 85% improvement in cost per install for a single unnamed US enterprise advertiser in an alpha test, a result Pinterest says may not generalize 4. The test window ran August 2025 to August 2026, with no control group disclosed 3. The value case also leans on a price gap: Pinterest CPMs of $2 to $5 against Meta's $8 to $14, a discount a widening beta should erode 3. The affiliate deals are lighter still. Shopee takes the order, creators take the commission, and Pinterest's piece is the ad it sells 5. The structure aims at the gap in the business: 377 million of 640 million users are in the rest of the world, where Pinterest booked $87 million of $1.18 billion in second-quarter revenue 7.
The founder's trust sold into it
The trust's Form 144 lists 23 sales of 46,875 shares between 30 June and 29 September, about $23.2 million, plus a 24th on 30 September worth $878,000: roughly $24.1 million in 13 weeks, all under a trading plan adopted 27 February 12. Realized prices, each sale's gross proceeds divided by its 46,875 shares, peaked at $23.88 on 11 August and slid to $18.33 on 29 September, a 23% decline through the pivot's launch week 12.
The trust sold twice a week as its realized price slid from the $23s to $18
Data
| Realized price per share | |
|---|---|
| Jun 30 | $21.45 |
| Jul 1 | $21.64 |
| Jul 7 | $22.63 |
| Jul 8 | $22.22 |
| Jul 14 | $22.25 |
| Jul 15 | $23.03 |
| Jul 21 | $22.54 |
| Jul 22 | $22.57 |
| Aug 11 | $23.88 |
| Aug 12 | $23.23 |
| Aug 18 | $23.4 |
| Aug 19 | $23.11 |
| Aug 25 | $23.53 |
| Aug 26 | $23.57 |
| Sep 1 | $21.63 |
| Sep 2 | $21.23 |
| Sep 8 | $20.07 |
| Sep 9 | $20.04 |
| Sep 15 | $19.22 |
| Sep 16 | $18.64 |
| Sep 22 | $19.5 |
| Sep 23 | $18.21 |
| Sep 29 | $18.33 |
| Sep 30 | $18.72 |
The other side of the trade was Pinterest
A February plan predates every launch in question and reads as plumbing, not prophecy; the trust still holds 34.2 million Class B shares 2. Pinterest itself spent over $2 billion on buybacks this year at an average $18.17, below the trust's cheapest print of $18.21 7. The business under both trades grew Q2 revenue 18% to $1.18 billion on a record 640 million users and still posted a $47 million GAAP loss 7. At $19.23, in the lower half of a 52-week range of $15.42 to $35.24, the stock trades at 9.3x forward earnings against a published $30.30 target, about 60% higher 8.
Growth reaccelerated to 18% in Q2, but guidance calls for 13 to 15%
- Revenue growth, year over year
- Estimate
Data
| Revenue growth, year over year | |
|---|---|
| Q3 '23 | 11.5% |
| Q4 '23 | 11.9% |
| Q1 '24 | 22.8% |
| Q2 '24 | 20.6% |
| Q3 '24 | 17.7% |
| Q4 '24 | 17.6% |
| Q1 '25 | 15.5% |
| Q2 '25 | 16.9% |
| Q3 '25 | 16.8% |
| Q4 '25 | 14.3% |
| Q1 '26 | 17.8% |
| Q2 '26 | 18.2% |
| Q3 '26 (estimate) | 14% (13–15%) |
What decides it
On 1 October OpenAI added global virtual try-on to ChatGPT, after retiring an instant-checkout experiment, stepping into the fashion discovery that Pinterest and Google have owned; Google shipped try-on last year 9. The bull case needs biddable comparison to out-earn the display model it replaces before assistants absorb the query, on Q3 guidance of just 13% to 15% growth 7. Pinterest spent the week putting a price on the comparison moment. OpenAI spent the same week giving it away.
Deepdive
AI-generated from this story and its cited sources. Not investment advice.
