Greg Isenberg

Activities

Early entrepreneur from Montreal — started building niche communities and online projects in his teens and early 20s.
Founded 5by (social/video discovery app). 5by focused on surfacing short-form video recommendations and was acquired by StumbleUpon in the early 2010s.
Built WallStreetSurvivor (stock market simulation / education community); later sold to private equity.
Founded Islands, a community/messaging product oriented around campus and niche social groups. Islands was later acquired by WeWork; following that acquisition Isenberg served as Head of Product Strategy at WeWork.
Repeated a pattern of rapid experimentation and shipping many small products — he estimates dozens (100+) of small projects that informed later successes.

Co-founder & CEO of Late Checkout — a product studio / holding company / fund that designs, builds, and acquires community-first internet businesses. Late Checkout’s model prioritizes building an audience or community first, then layering product and monetisation.
Advisor / operator roles: public reporting shows advisory relationships with platforms such as Reddit and TikTok (growth/product advising during scale phases).
Content creator and audience operator: publishes a high-volume newsletter (thousands of free startup ideas distributed since 2020), hosts/co-hosts podcasts (including “Where It Happens” and a frequent “Startup Ideas” format), and runs paid and free community products (e.g., “The Room Where It Happens”).
Active on Twitter/X (handle: @gregisenberg) and uses social threads, newsletters and podcasts as a funnel: build audience → deepen via long-form content → launch products.

Companies: Late Checkout, 5by, Islands, WeWork, StumbleUpon, WallStreetSurvivor. Works with and advises large platforms (Reddit, TikTok) and has consulted for or built products with brands like Microsoft, TechCrunch, FedEx and NASCAR.
People & network: strong ties to early-stage founders, creator-economy operators, and product-led growth practitioners. Co-hosts and collaborators include Sahil Bloom (podcast collaborator) and a broad network of entrepreneurs and investors involved in Late Checkout deals and community events.
Investment / studio partners: associated with small funds and angel networks (publicly noted as a venture/partner in some builds and portfolio activities).

Continued focus on the community-first company playbook: launching audience-driven products, then scaling monetisation and distribution once a core community is established.
Expand Late Checkout’s portfolio of small-to-medium consumer/community businesses — the studio/holding model lets him iterate quickly across multiple verticals.
Deepening involvement in creator-economy strategies and helping creators build productized businesses that compete with legacy CPG/brands.
More public content and idea distribution (newsletter, podcast) as both a distribution channel and deal-sourcing mechanism for new Late Checkout projects.
Likely to incorporate AI and tooling to accelerate idea discovery, audience growth, and product iteration across the Late Checkout portfolio.

Community building and audience-first product design.
Product strategy for consumer and social platforms.
Content funnels (Twitter → newsletter → podcast → product) and creator-driven businesses.
Startup idea generation, rapid experimentation, and shipping multiple small plays to find repeatable winners.

Greg Isenberg — personal site: https://gregisenberg.com
Late Checkout / product studio & community pages: https://latecheckout.co (company site / portfolio pages and descriptions)
The Room Where It Happens / community & podcast pages: https://theroomwhereithappens.co
Twitter profile (public activity & threads): https://twitter.com/gregisenberg
Podcast listings (Where It Happens / Startup Ideas) — Apple/Spotify search results and show pages
Press profiles and interviews (various): coverage in outlets such as Forbes, Vanity Fair, Fortune, Mashable, LA Times (searchable archives)