The Tobi Oluwole LinkedIn Playbook
400k followers · Toronto Canada · 2026 Snapshot
Known for
Tobi Oluwole is known for the corporate escape. He spent 11 years failing in corporate, quit Shopify at 28, and built a $1M one-person business he runs 3 days a week. That story is the spine of everything he posts. Founders follow him to see the exit; they stay because he keeps it human.
What they write about
| Pillar | Share |
|---|---|
| Founder Journey | 21% |
| Business Playbook | 19% |
| Client Win / Spotlight | 16% |
| Mindset / Motivation | 13% |
| Workplace Cautionary | 12% |
| Personal / Family | 10% |
Top 5 posts
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1. “I came to Canada against my will in 2010.”
6,729 likes · 460 comments
View on LinkedIn →2. “I'll never forget the first real mentor I had.”
6,398 likes · 548 shares
View on LinkedIn →3. “One of my friends burnt out after 3 years at a company.”
5,842 likes · 394 comments
View on LinkedIn →4. “Never forget the people that took a chance on you.”
5,675 likes · 625 shares
View on LinkedIn →5. “My wife and I got married at 24.”
4,780 likes · 438 comments
View on LinkedIn →
What they do well
- Opens with a person and a number. 48% of his top 50 posts hook with a specific figure in the first line: "a 60% raise," "$38 an hour," "married at 24."
- Makes you feel something before teaching you something. 32 of his top 50 posts (64%) are workplace stories, family moments, or mindset pieces. His emotional categories out-earn his how-to content roughly 3x per post.
- Earns the lesson with the story. Every post lands on one universal takeaway, but only after the anecdote has done the work. The advice never feels preachy.
- Never misses. 6.2 posts a week, every week. His top posts average 3,592 engagement vs 908 for the rest, a 4x gap he sustains by simply always being in the feed.