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Who Is Tobi Oluwole? The 7th-Attempt Founder, Explained by Data (2026)

Creazione di contenuti

Naïlé Titah

Ultimo aggiornamento: 28 ago 2026

Tobi Oluwole landed his first big tech role "at Shopify on my 7th attempt," and that one number is the spine of almost everything he posts. At MagicPost, we analyzed 689 of his LinkedIn posts across the last two years: what he writes, when, for whom, what earns him the most, and what makes his style worth studying.

This is who Tobi Oluwole is, according to the best possible source: his own posts, measured. He is the founder of Magnate Ventures in Toronto, an angel investor and speaker behind roughly 386,000 followers.

Tobi Oluwole: identity card with key LinkedIn numbers

His story, in his own posts

You do not need a biographer for Oluwole. He retells his own life on LinkedIn constantly, and the data shows which chapters he treats as load-bearing.

The arrival. "I came to Canada against my will in 2010," he writes in one of his most-shared posts. Then the hard middle: "There was a year when I crashed on friends' couches because I didn't have a place to stay. Most of my side hustles were started because I absolutely needed the money to live!"

The 7th attempt. The pivot of his whole narrative is one job application that finally worked: "in 2020, I landed a role at Shopify on my 7th attempt and that was the start of my new life." He comes back to that recruiter again and again. In another post: "When I met the recruiter that helped me land my job at Shopify on the 7th attempt, I gave her a massive hug. And said 'You changed my life!'" The 7th attempt is not a detail, it is his founding myth.

The IKEA mattress. His marriage is the other recurring chapter. "My wife and I got married at 24," he writes in a 2025 post, "We had an IKEA mattress (no bed frame), a second-hand sofa & a TV that a friend donated to us... we somehow had less than $1,000 in savings." The payoff line is fixed: "Who you choose to marry is the most important decision you will make."

The exit. Then the leap out of corporate, told in a launch-event post: "I left my corporate job before my 29th birthday and never looked back." And the businesses behind it: "In 2024, my business generated over $1 million in 12 months," after a string of failures ("In 2010, I was selling noodles in high school... Most of these businesses failed in less than 6 months").

One pattern our data surfaces that a normal bio never would: his life story is not a post, it is a template he re-ships. The "came to Canada against my will" timeline appears almost word for word twice in our sample (a May 2024 version and a February 2026 version), and the IKEA mattress marriage post runs in at least three near-identical cuts across 2024 and 2025. Very Oluwole: when an origin story works, you re-run it with the dates updated.

Tutto ciò che ti serve per crescere su LinkedIn.

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Naïlé Titah

CEO @ MagicPost

LinkedIn ha nuovamente cambiato il suo algoritmo. E questa volta, è evidente.

Sono in una buona posizione per saperlo:

Tutto ciò che ti serve per crescere su LinkedIn.

Scrivi con la tua voce, trova idee, pianifica, analizza, coinvolgi…
MagicPost è realizzato esclusivamente per LinkedIn.

Prova MagicPost

Naïlé Titah

CEO @ MagicPost

LinkedIn ha nuovamente cambiato il suo algoritmo. E questa volta, è evidente.

Sono in una buona posizione per saperlo:

Crea il tuo primo post su LinkedIn in meno di 5 minuti

Con MagicPost, risparmi fino a 4 ore a settimana, a partire dal tuo primo post. Dedica meno tempo alla scrittura e più tempo a far crescere la tua attività.

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What he actually talks about

What Tobi Oluwole talks about on LinkedIn, measured by topic

By volume, Entrepreneurship is his single biggest topic (283 posts), with Leadership, Coaching and Sales filling most of the rest. But the volume ranking hides the most interesting thing in his data, which is what his audience actually rewards:

His business topics under-perform; his workplace topics over-perform, by a lot. Entrepreneurship, the thing he sells, earns about 958 median likes, and Sales just 308. Meanwhile Employee Engagement pulls about 4,182 median likes, HR about 3,302, and Leadership about 2,851. When Oluwole writes about good bosses, bad bosses, raises and remote work, his audience responds three to four times harder than when he writes about founding a company.
By register, his most common post type is punchy standalone advice (236 posts), well ahead of selling through value (66) and personal challenge stories (49). He is, first, an advice writer who occasionally sells.

The takeaway is almost ironic: the founder of a venture firm gets his biggest reactions writing about the employee experience he left behind.

Who he writes for

His reader is explicit in his own words: the corporate employee who suspects there is a better life on the other side, and the early founder who keeps failing. He writes for the person "who want to retire from corporate in the next 5-10 years to live life on their own terms" (his words), and addresses the reader directly: "Stop telling yourself you are not qualified enough," "Choose yourself," "Never give up on your dreams." The offers match: a founder's program, LinkedIn lead-generation training, and a community waitlist.

His best posts of 2026

His biggest posts of 2026 so far, reproduced from our data (click through to the originals):

Tobi Oluwole's top 2026 post: coming to Canada against his will

6,705 likes. The full immigrant-founder arc in one post: couch-surfing, the 7th-attempt Shopify role, citizenship, two homes, then "Never give up on your dreams." A signature story, re-shipped, that still lands two years on.

Tobi Oluwole on the first mentor who put him in rooms

6,379 likes. Six short lines about his first mentor, ending on "Try to get you into rooms you don't know exist." Note the ratio: 550 reposts, the kind of save-and-share number that comes from a clean, quotable lesson.

Tobi Oluwole on never forgetting who took a chance on you

5,613 likes. "I helped more than 20 people get hired at Shopify... Because someone gave me a chance that 7th time I applied." The 7th attempt again, this time framed as paying it forward, with 621 reposts.

Tutto ciò che ti serve per crescere su LinkedIn.

Scrivi con la tua voce, trova idee, pianifica, analizza, coinvolgi…
MagicPost è realizzato esclusivamente per LinkedIn.

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Naïlé Titah

CEO @ MagicPost

LinkedIn ha nuovamente cambiato il suo algoritmo. E questa volta, è evidente.

Sono in una buona posizione per saperlo:

Tutto ciò che ti serve per crescere su LinkedIn.

Scrivi con la tua voce, trova idee, pianifica, analizza, coinvolgi…
MagicPost è realizzato esclusivamente per LinkedIn.

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Naïlé Titah

CEO @ MagicPost

LinkedIn ha nuovamente cambiato il suo algoritmo. E questa volta, è evidente.

Sono in una buona posizione per saperlo:

Crea il tuo primo post su LinkedIn in meno di 5 minuti

Con MagicPost, risparmi fino a 4 ore a settimana, a partire dal tuo primo post. Dedica meno tempo alla scrittura e più tempo a far crescere la tua attività.

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Is he still growing?

Tobi Oluwole's median likes per post, year by year

Here the data is honest in a way a follower count is not. His median post earned about 1,571 likes in 2024, then about 1,111 in 2025, and about 806 so far in 2026, a steady decline in engagement per post even as his audience climbed toward 386,000. This is the most common shape on LinkedIn right now: reach gets compressed, feeds get more crowded, and a creator's median softens while their follower number keeps rising. It is not a verdict on the writing (his all-time peak, a leadership post he says reached "over 15 million people," predates this window). One honest note: we measure engagement per post, not followers over time, so this chart shows how hard each post hits, not audience size.

Where do these charts come from? Everything on this page runs on MagicPost's LinkedIn analytics, and it works on your profile too: your best posts, your audience, your benchmark, even a side-by-side with creators like Tobi Oluwole.

How he writes

Here is Oluwole measured against the average creator, and the headline is not "short":

How Tobi Oluwole writes versus the average creator, measured

Metric (per post)	Tobi Oluwole	Average creator*
Words	~148	185
Words in the hook	9	11
Words per paragraph	11	13
Words per sentence	11	10
Emojis	0	2
Hashtags	10	0
Exclamation marks	0	1
Hooks built on numbers	42%	22%

*Median across the 3,344 creators we analyzed with 20+ posts each.

Two numbers carry his whole style. First, 42% of his hooks open on a number, nearly double the 22% benchmark: "I helped more than 20 people," "I lost a $500k deal," "80% of your revenue will come from 20% of your efforts." The specific number is the hook. Second, and unusually for a creator at this level, he runs about 10 hashtags per post where the typical top creator now runs zero. His paragraphs and sentences sit at the average length, so the white-space-minimalist label does not fit: what makes an Oluwole post is the one-line-per-thought rhythm plus a concrete number in the first line and a one-line moral at the end. In one word, our system calls his voice: narrative.

The "AI tells" in his style (read this the right way)

Run Oluwole's writing through the patterns people now call "AI tells," and the result is reassuringly human:

The AI-pattern fingerprint of Tobi Oluwole's style

About one post in five uses the "It's not X, it's Y" contrast formula ("Leaving is not the same as quitting"), and about one in six leans on a generic advice frame. A handful open with "Here's how". Those are the only patterns that recur.

Do not read it backwards. Oluwole does not write like an AI; AI writes like Oluwole. These moves read as robotic today because the models trained on the best creators of this platform and then stacked all of them into every post. Oluwole uses one, occasionally, where the story earns it. The rest of his fingerprint is what AI cannot stop itself from adding: he never hedges ("it's worth noting that...") and never opens with a throat-clearing transition like "Moreover." The discipline is the signature. (Full story: how to spot AI writing on LinkedIn.)

When he posts

Oluwole publishes about 6.6 times a week, favorite slot Monday around 10 AM Toronto time, with nearly all of his posts in the morning and about 23% on weekends. That morning-heavy, near-daily cadence fits what our best-time research finds about early windows, and his volume sits inside the high-output band in our posting-frequency study. Monday is worth noting against our best-day analysis too. And if part of your own playbook is showing up in his comments, that is exactly what an engagement feed is for: his posts, every morning, without hunting the timeline.

What to steal from Tobi Oluwole

Lead with a specific number. Not "I helped a lot of people," but "I helped more than 20 people get hired at Shopify." 42% of his hooks are a number; the concreteness is the hook.
Build a signature origin story and re-run it. His "came to Canada against my will" and IKEA-mattress posts run in near-identical cuts across years and still pull thousands of likes. Your origin story is an asset, not a one-off.
Write about the world your reader lives in, not the world you sell. His employee-experience posts out-earn his founder posts three to four times over, because that is who is reading.
One moral per post. Each ends on a single portable line ("Choose yourself," "Give people a chance"), which drives his high repost counts.
One AI-era move per post, never six. A contrast line where the story earns it, then nothing bolted on. That restraint is the line between a signature and an AI tell.

Study him, then study yourself. With MagicPost you can dig into Tobi Oluwole's numbers the way we just did, analyze your own LinkedIn analytics with the same depth, and write in the spirit of his style, in your own voice. The data on this page is the product.

Where this data comes from

Everything here is MagicPost's own research. MagicPost analyzed 689 Tobi Oluwole posts from the last two years: timing, engagement, topics, writing metrics, and the AI-pattern profile from a 30-post style sample. Every biographical claim is quoted from one of his own public LinkedIn posts and linked to it. Oluwole is not affiliated with MagicPost; his style is one we track most closely, which is why we built this page.

Tutto ciò che ti serve per crescere su LinkedIn.

Scrivi con la tua voce, trova idee, pianifica, analizza, coinvolgi…
MagicPost è realizzato esclusivamente per LinkedIn.

Prova MagicPost

Naïlé Titah

CEO @ MagicPost

LinkedIn ha nuovamente cambiato il suo algoritmo. E questa volta, è evidente.

Sono in una buona posizione per saperlo:

Tutto ciò che ti serve per crescere su LinkedIn.

Scrivi con la tua voce, trova idee, pianifica, analizza, coinvolgi…
MagicPost è realizzato esclusivamente per LinkedIn.

Prova MagicPost

Naïlé Titah

CEO @ MagicPost

LinkedIn ha nuovamente cambiato il suo algoritmo. E questa volta, è evidente.

Sono in una buona posizione per saperlo:

Crea il tuo primo post su LinkedIn in meno di 5 minuti

Con MagicPost, risparmi fino a 4 ore a settimana, a partire dal tuo primo post. Dedica meno tempo alla scrittura e più tempo a far crescere la tua attività.

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Prova gratuita al 100%.

Domande Frequenti

Who is Tobi Oluwole?

A Toronto-based founder, angel investor and speaker, founder and CEO of Magnate Ventures. He moved from Nigeria to Canada in 2010, landed a role at Shopify "on my 7th attempt," left corporate before his 29th birthday, and by his own account built a business that generated over $1 million in a year. He has about 386,000 LinkedIn followers.

How does Tobi Oluwole make money?

By his own public posts: he runs Magnate Ventures and a founder's program, sells LinkedIn lead-generation training, and invests as an angel, with a business he says "generated over $1 million in 12 months" in 2024.

How often does Tobi Oluwole post on LinkedIn?

About 6.6 posts a week in our data, most often on Monday around 10 AM Toronto time, with nearly all of his posts in the morning and about 23% on weekends.

Does Tobi Oluwole write with AI?

His style reads intensely human: zero emojis as a rule, a one-line-per-thought rhythm, and none of the filler AI adds (no hedging, no throat-clearing transitions). The twist is that AI tools learned from creators like him, which is why about one in five of his posts contains the "It's not X, it's Y" pattern people now mislabel as an AI tell.

Is Tobi Oluwole still growing on LinkedIn?

His follower count keeps climbing toward 386,000, but his median likes per post have softened from about 1,571 in 2024 to about 806 in 2026, which is the common reach-compression shape across LinkedIn right now, not a verdict on the writing.

Can I write like Tobi Oluwole?

You can learn the mechanics: MagicPost learns a creator's writing style (length, rhythm, number hooks, signature stories) and helps you write in that spirit, in your own voice.

Tutto ciò che ti serve per crescere su LinkedIn.

Scrivi con la tua voce, trova idee, pianifica, analizza, coinvolgi…
MagicPost è realizzato esclusivamente per LinkedIn.

Prova MagicPost

Naïlé Titah

CEO @ MagicPost

LinkedIn ha nuovamente cambiato il suo algoritmo. E questa volta, è evidente.

Sono in una buona posizione per saperlo:

Tutto ciò che ti serve per crescere su LinkedIn.

Scrivi con la tua voce, trova idee, pianifica, analizza, coinvolgi…
MagicPost è realizzato esclusivamente per LinkedIn.

Prova MagicPost

Naïlé Titah

CEO @ MagicPost

LinkedIn ha nuovamente cambiato il suo algoritmo. E questa volta, è evidente.

Sono in una buona posizione per saperlo:

Crea il tuo primo post su LinkedIn in meno di 5 minuti

Con MagicPost, risparmi fino a 4 ore a settimana, a partire dal tuo primo post. Dedica meno tempo alla scrittura e più tempo a far crescere la tua attività.

Prova MagicPost

Nessuna carta di credito. Nessun impegno. Solo risparmi in tempo reale.

Prova gratuita al 100%.

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His story, in his own posts

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What he actually talks about

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Who he writes for

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His best posts of 2026

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