There have clearly been significant new federal enforcement actions against Big Tech since late 2021, matching the first part of Friedberg’s forecast:

• DOJ sued Google over its ad‑tech business in January 2023; in April 2025 a federal court found Google had illegally monopolized key ad‑tech markets and unlawfully tied products, with potential structural remedies on the table. (en.wikipedia.org)
• DOJ and multiple states sued Apple in March 2024 over alleged iPhone and ecosystem monopolization, explicitly challenging its walled‑garden model. (justice.gov)
• The FTC and 17 states sued Amazon in 2023, alleging it illegally maintains an online retail monopoly; this case is still ongoing. (ftc.gov)
• Separately, Amazon agreed in 2025 to a record $2.5 billion settlement with the FTC over Prime “subscription traps,” which forces major design and disclosure changes. (ft.com)

So the “something’s going to happen” via major federal enforcement clearly did occur in the “coming years” after the 2021 podcast.

However, no major new federal tech‑specific regulatory statute has actually been enacted. High‑profile bills such as the American Innovation and Choice Online Act, the Open App Markets Act, and the AMERICA Act have remained proposals without becoming law. (en.wikipedia.org) That undercuts the “new regulatory” half of the prediction.

The hardest part to evaluate is Friedberg’s claim that these actions would be “clumsy” or “overreaching” and cause substantial “collateral damage.”

• There is substantial criticism from business and policy groups that the FTC under Lina Khan and related antitrust efforts constitute overreach that harms competitiveness, chills investment, and creates broad uncertainty. For example, a Fortune op‑ed argues Khan’s antitrust “overreach is hurting American competitiveness” and contributed to a sharp drop in biotech VC funding, describing serious knock‑on effects outside the targeted firms. (fortune.com) Other commentators and organizations (U.S. Chamber of Commerce, CEI, taxpayer and free‑market groups) similarly accuse the FTC of ideological, poorly targeted enforcement that risks harming consumers, innovation, and broader economic performance. (uschamber.com)
• At the same time, many regulators, academics, and public‑interest groups argue these same actions are necessary course‑corrections after decades of under‑enforcement, stressing consumer harms from dominant platforms and portraying recent suits and settlements (including against Amazon and Google) as overdue, not clumsy. (theguardian.com) In some high‑profile Big Tech cases, courts have either sided with the government (e.g., finding Google’s search and ad‑tech monopolization illegal) or limited remedies rather than condemning the enforcement itself as abusive. (en.wikipedia.org) Meanwhile, consumer‑protection actions like the Amazon Prime settlement are widely characterized as wins for users, not as harmful collateral damage. (ft.com)

Because reasonable observers sharply disagree on whether these enforcement waves are a clumsy overreach causing substantial unintended harm, and because the concrete long‑run “collateral damage” (to innovation, smaller firms, or consumers) is still being debated and empirically unclear, that part of the prediction cannot be judged as simply true or false.

Overall: major new enforcement did happen, but whether it is in fact “rusty‑knife” overreach with large collateral damage is contested and not objectively settled. That makes the prediction’s outcome ambiguous rather than clearly right or wrong.