Who is Greg Isenberg the Canadian Podcaster, Entrepreneur and Mogul

Overview of Greg Isenberg

Greg Isenberg is a Canadian entrepreneur best known for his work in building internet communities and founding several successful startups. He is currently the CEO and Co-Founder of Late Checkout, a holding company that builds, acquires, and incubates internet businesses powered by online audiences and communities1234.

Career Highlights

Late Checkout

  • CEO and Co-Founder since June 2020.

  • Late Checkout is a product studio and design firm focused on internet communities, helping brands build genuine online communities and transforming isolated audiences into interconnected groups134.

  • The company operates as a holding company with a portfolio of internet businesses, many of which start as internet audiences or communities1234.

Previous Ventures

  • Islands: Founder and CEO of this messaging/community app for college students, which was acquired by WeWork. Post-acquisition, Isenberg served as Head of Product Strategy at WeWork12346.

  • 5by: Founder and CEO of this video discovery app, which was acquired by StumbleUpon just 11 months after launch. 5by curated short videos for users and was backed by Real Ventures. The acquisition led Isenberg to relocate from Montreal to San Francisco1235.

  • WallStreetSurvivor: Helped build and scale this financial education community, which became the largest stock market game on the internet and was later sold to a private equity group123.

Advisory Roles

  • Advisor to major tech companies including TikTok (growth strategy, 2019–2021) and Reddit (product strategy, 2021–2023)123.

Other Projects

  • Has built over 100+ products, with some achieving significant success and others not gaining traction. He emphasizes the importance of learning through shipping products124.

Media and Recognition

  • Featured in major publications such as Vanity Fair, Forbes, Mashable, Fortune Magazine, and the LA Times3.

  • Winner of Webby Awards for his work in digital product innovation3.

  • Known for his engaging online presence, sharing startup ideas and business insights through his newsletter (with over 145,000 subscribers) and podcast12.

Approach and Philosophy

  • Strong advocate for community-driven business models, believing that robust online communities are the foundation for successful internet businesses124.

  • Emphasizes rapid experimentation, learning from failures, and iterating based on real-world feedback4.

  • Passionate about “unbundling” major networks to create niche, standalone community platforms4.

Additional Ventures

Greg Isenberg is also associated with several agencies under the Late Checkout umbrella:

Personal Background

  • Originally from Montreal, Canada.

  • Moved to San Francisco following the acquisition of 5by by StumbleUpon125.

  • Known for a personable and supportive approach within the startup community, with a reputation for problem-solving and digital innovation from a young age5.

Verifiability

All information above is sourced from Greg Isenberg’s official website, his LinkedIn profile, reputable business publications, and interviews. Details about his career, acquisitions, and advisory roles are consistent across multiple independent sources, ensuring their verifiability123456.

Summary Table

Company/Role

Description/Outcome

Years

Late Checkout

CEO & Co-Founder; internet community businesses

2020–present

Islands

Founder/CEO; acquired by WeWork

2016–2019

WeWork

Head of Product Strategy (post-Islands acquisition)

2019–2020

5by

Founder/CEO; acquired by StumbleUpon

2012–2013

WallStreetSurvivor

Co-founder; acquired by PE group

N/A

TikTok

Advisor (Growth Strategy)

2019–2021

Reddit

Advisor (Product Strategy)

2021–2023

For more, see his [official about page]1, LinkedIn profile3, and coverage in business media45.