Stage 2: Watch out

Pro design, photo and layout apps that were famous for one-off pricing; now free under Canva, with AI tools behind Canva’s subscription.

Paid homework help losing students fast to AI chatbots; subscribers fell by almost a third in a year.

University courses online, now buying its biggest rival, Udemy.

The file-sync pioneer, now pushing AI as its core business plateaus; your files remain easy to take elsewhere.

The original everything-notebook, now owned by Bending Spoons, with its free plan capped at 50 notes.

A photographers’ community owned by SmugMug, funded by Pro subscriptions; free accounts have been capped at 1,000 photos since 2019.

The free app behind Garmin watches; a paid Connect+ tier arrived in 2025, but existing features stayed free.

Launched with free unlimited storage; now part of paid Google One, and the default photo app on most Android phones.

The meditation app turned mental-health company, which moved its staff therapists onto part-time and contract work in 2024.

The largest shared e-scooter and e-bike network, newly public and still loss-making.

Ad-free, member-funded publishing, but your followers and distribution live on Medium’s terms.

The question-driven dating site, now one of Match Group’s brands, with a regulator record on how it handled users’ data.

Commission-free trading paid for by order flow, with a regulator settlement over gamified design.

Ticketmaster’s main rival, with exclusive venue deals of its own and lawsuits over late-disclosed fees.

Paid, open-source, end-to-end encrypted messaging that needs no phone number, now under private-equity ownership.

Travel reviews losing their search traffic to AI answers, with an activist investor pushing for a sale.

Crowd-sourced traffic navigation, now folded into Google’s maps and ads organisation.

Bing-powered results with a new ad-supported AI answer engine, owned by private equity.

Differentiated dating brand with the same premium tiers, spotlight features, and engagement optimization as peers.

Self-serve events and ticketing—easy for organizers until fees, feature tiers, and payout rules become the product.

Open-core DevOps platform: self-host option preserves some exit, SaaS still pushes seat-based upsell.

The default map for most of the world: superb data and routing, increasingly packed with promoted pins, ads, and Gemini features built around Google's priorities.

Designed-to-be-deleted marketing meets roses, boosts, and subscription gates—dating app economics in a nicer skin.

Outdoor accommodation marketplace for camping, glamping, and farm stays; host-aligned fee structure and a niche that resists the race-to-the-bottom commoditisation of hotel OTAs.

Canonical film/TV metadata within Amazon—indispensable lookups with ads, Prime nudges, and data leverage across commerce and streaming.

Tips and memberships with lighter branding than Patreon; Gold tier and shop features add platform dependency over time.

Creator subscriptions with high take rate and policy whiplash; payment processors and brand risk shape who can stay on platform.

Answer-first search with citations; Pro tier and publisher deals raise questions about who gets traffic and margin.

Still user-respecting by default, but growing reliance on the nonprofit’s roadmap and network effects builds soft lock-in.

Dominant PC games client; strong library lock-in and social graph, still delivering real value to buyers.

Secondary ticket marketplace—liquidity and buyer protection on one side, fees and volatile pricing on the other.

Newsletter + payments with clearer creator cut than ad platforms; network features and video push toward fuller stack lock-in.

Swipe economy: tiered subscriptions, boosts, and pay-to-play visibility monetize anxiety and asymmetry.

Social P2P app folded into PayPal: instant transfer fees, crypto and card upsells, and default public feed history (since reined in).

Frontend cloud with stellar DX: usage-based billing and framework coupling can still surprise teams at scale.