# Matt Gray

> Matt Gray is a Canadian-born serial entrepreneur and founder of Founder OS, a company teaching founders to build personal brands and scalable businesses through organic content and repeatable systems. He previously co-founded Bitmaker (Canada's first major coding bootcamp, acquired in an 8-figure deal) and Herb (world's largest cannabis community, 14M users, $14M revenue). Today he runs a $13M+/year portfolio working ~4 hours a day, has 2.5M+ followers across platforms, and is known as 'The Systems Guy' in the creator economy.

- **Role:** Founder & CEO at Founder OS
- **Organizations:** Founder OS, Herb, Bitmaker Labs
- **From:** Sharon, Ontario, Canada
- **Nationality:** Canadian
- **Education:** Honors Business Administration (HBA), Marketing, Ivey Business School, Western University
- **Known for:** Co-founded Bitmaker Labs, Canada's first major coding bootcamp, trained 2,000+ software engineers, 8-figure exit from Bitmaker when General Assembly was sold to Adecco for $410 million, Built Herb into the world's largest cannabis community with 14 million users and $14M annual revenue

## Career timeline

- **2007** — Enrolled at Ivey Business School, Western University
- **2011** — Graduated from Ivey with HBA in Marketing
- **2012** — Co-founded Bitmaker Labs, Canada's first major coding bootcamp, in Toronto
- **2013** — Bitmaker raided by Ontario Ministry of Training; Matt navigated legal crisis and reopened within a week
- **2014** — Founded Herb, a cannabis media and community platform
- **2015** — Bitmaker acquired by General Assembly (GA later sold to Adecco for $410M); 8-figure exit for Matt
- **2017** — Herb raised $4.1M seed round from Lerer Hippeau, Slow Ventures, Liquid 2 Ventures (Joe Montana), Shopify CEO Tobi Lutke
- **2019** — Herb grew to 14 million users and became the world's largest cannabis community
- **2020** — Herb reached $14M in revenue with a team of 50; raised $6M+ total
- **2021** — Launched Founder OS while traveling internationally; stepped back from Herb
- **2022** — Founder OS newsletter crossed 100,000 subscribers within 18 months of launch
- **2023** — Reported $8.7M annual revenue from Founder OS portfolio; ranked top 1% LinkedIn creator
- **2024** — Revealed $13M/year revenue working ~4 hours/day on Ali Abdaal's podcast; newsletter surpassed 253,700 subscribers
- **2025** — Ranked top 1% on LinkedIn in business strategy; Founder OS community reached 5,000+ founders
- **2026** — Actively using AI tools; Founder OS Velocity Tier receiving strong community reviews

## Achievements

- Co-founded Bitmaker Labs, Canada's first major coding bootcamp, trained 2,000+ software engineers
- 8-figure exit from Bitmaker when General Assembly was sold to Adecco for $410 million
- Built Herb into the world's largest cannabis community with 14 million users and $14M annual revenue
- Raised $6M+ for Herb from top VCs including Lerer Hippeau, Slow Ventures, and investors like Shopify CEO Tobi Lutke
- Grew Founder OS newsletter to 100,000 subscribers in 18 months; now 253,700+ subscribers
- Built 2.5M+ combined social following with 2B+ annual content impressions
- Ranked top 1% of LinkedIn business strategy creators in the United States (Favikon score: 8,944/10,000)
- Generates 12,000+ inbound leads monthly through organic content alone
- $13M+ annual revenue portfolio while working approximately 4 hours per day
- Built a $13.8M business using only remote contractors - no full-time employees
- Replaced 15 employees with AI systems while increasing revenue 200%
- Consulting rate of $1,000/hour with a perfect 5.0 rating on MentorPass
- Speaking fees of $100,000-$200,000 per live event
- Visited 42 countries

## Latest updates

- **2026-04** — Actively promoting 'authenticity wins' as the 2026 content meta; Founder OS Velocity Tier receiving strong community reviews
- **2025-12** — Ranked top 1% on LinkedIn in business strategy for 2025; Founder OS community reached 5,000+ founders
- **2025-05** — Interviewed by Neville Medhora (SwipeFile) on building personal brands, communities, and media-first startups
- **2024-11** — Featured on Ali Abdaal's podcast for a business analysis session
- **2024-07** — Revealed on Ali Abdaal's podcast that he makes $13M/year working 4 hours/day; newsletter crossed 253,700 subscribers
- **2024-01** — Shared the Bitmaker government raid story on X/TikTok, which went viral in startup circles

## Links

- Website: https://www.founderos.com
- LinkedIn: https://www.linkedin.com/in/mattgray1
- Twitter/X: https://twitter.com/matt_gray_
- YouTube: https://www.youtube.com/@realmattgray
- Instagram: https://www.instagram.com/matthgray/
- TikTok: https://www.tiktok.com/@realmattgray

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Profile page: https://yespress.io/matt-gray
Published by YesPress — https://yespress.io
Last updated: 2026-04-28