Pinterest Founder Ben Silbermann Has Sold $541M Since the 2019 IPO

924 Form 4 Filings in Six Years

Ben Silbermann, the co-founder and former CEO of Pinterest (PINS), has sold $541 million in company stock since the April 2019 IPO. With 924 Form 4 transactions — roughly one every 2.4 trading days — Silbermann has maintained one of the most consistent insider selling programs among social media founders.

His selling mechanism is distinctive: convert Class B supervoting shares to Class A shares, then sell the Class A on the open market. This convert-and-sell pattern has been his primary liquidity tool for six years running.

Recent Selling: Q3 2025

Date	Shares Sold	Avg Price	Est. Value
Sep 10	~102,000	$36	$3.7M
Sep 17	~102,000	$37	$3.7M
Sep 24	~102,000	$35	$3.6M
Oct 1	8	$32	$0
Q3 Total	~306,000		~$11M

The October 1 sale of just 8 shares is notable — likely the tail end of a 10b5-1 plan execution rather than a deliberate micro-trade. It could signal a plan amendment or pause, which would be Silbermann’s first significant break in selling since going public.

The Convert-and-Sell Pattern

Pinterest went public with a dual-class share structure: Class B shares carry 20 votes per share, while Class A shares carry one vote. Silbermann’s selling mechanism converts Class B to Class A, then sells the Class A. Each conversion simultaneously reduces his voting power and generates liquidity.

The weekly cadence typically involves two batches: ~18,750 shares from one account and ~83,333 shares from another, for a combined ~102,000 shares per week at recent prices around $32–$37.

Career Numbers

• Total sell proceeds: $541 million since April 2019
• Total purchases: $0
• Transaction count: 924 Form 4 filings
• Remaining indirect shares: ~35.7 million
• Remaining value: ~$1.1 billion at $32/share
• Sold vs remaining: ~33% sold, 67% retained

From CEO to Executive Chairman

Silbermann co-founded Pinterest in 2010 and served as CEO for 12 years. He stepped down in June 2022, handing the role to Bill Ready (formerly of Google). Silbermann transitioned to Executive Chairman — a role that preserves his board influence while removing day-to-day operating responsibility.

His selling cadence did not change with the CEO transition. The program continued at roughly the same pace before, during, and after the handoff, consistent with a pre-arranged plan unaffected by title changes.

Pinterest IPO’d at $19 per share in April 2019. The stock peaked above $89 in February 2021 during the pandemic social media boom, then crashed to $16 in June 2022. It now trades near $32 — a 68% gain from IPO but 64% below its all-time high. Silbermann sold through every phase.

What to Watch

• The October pause — The sudden drop from 102K shares/week to 8 shares suggests Silbermann’s 10b5-1 plan may have ended or been amended. Watch for a new plan filing.
• Voting power dilution — Each Class B conversion erodes Silbermann’s supervoting control. At his current pace, he may eventually lose majority voting power.
• PINS stock trajectory — Pinterest is in the midst of a revenue acceleration under CEO Ready, with AI-powered shopping and ad monetization. Any re-rating could change the math on Silbermann’s remaining $1.1B position.
• Remaining 35.7M shares — At recent selling rates of ~$11M per quarter, Silbermann has decades of runway. His is a patient, multi-generational liquidity program.

Track Ben Silbermann’s insider transactions on his 13F Insight profile, or view institutional holders of Pinterest on the PINS stock detail page.