Greg Isenberg is a serial entrepreneur from Montreal with a Computer Science degree from McGill. His career arc reads like a masterclass in community-powered businesses.

Two Acquisitions Before 30

In 2012, he founded 5by, a social video discovery app that was acquired by StumbleUpon in 2013. He then built Islands, a community messaging app, which was acquired by WeWork in 2017. After the acquisition, Greg became Head of Product Strategy at WeWork, and later served as an advisor to both TikTok and Reddit on community and product strategy.

The Holding Company Model

In June 2020, Greg launched Late Checkout with a model he'd been refining through years of watching community-powered products succeed. Late Checkout operates three arms: an agency (running 30-day design sprints), a studio (building and acquiring its own products), and a fund (investing in community-based startups).

The playbook: find influential audiences, build products they need, find operators to run each business, then use the cash flow to acquire the next one.

8 Figures, $0 Outside Capital

Within three years, Late Checkout reached 8 figures in revenue with zero outside capital. Greg's 350K+ Twitter following became the primary distribution channel — every post about community-building, startup ideas, and internet businesses drove deal flow and client interest.

In 2024, Late Checkout acquired 50% of Boring Marketing, projected to generate $2-3M in free cash flow. The portfolio kept expanding through Greg's ability to identify undervalued internet businesses with strong community foundations.

• Previous exits: 5by (StumbleUpon, 2013), Islands (WeWork, 2017)
• Founded: June 2020
• Revenue: 8 figures ($10M+)
• Funding: $0 outside capital
• Twitter following: 350K+
• Model: Agency + Studio + Fund