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Oliver Buchannon
Simon Litt

I'm the Brand Operations Manager for Digital Entrepreneur—which, if you think about it, technically makes me the B.O.M. I've helped found and grow multiple financial media brands, including—most recently—The CFO Club. You might also see my byline on Wealthsimple, where I'm a contributing writer and editor.


🛠️ AI won't replace you

🛠️ AI won't replace you

Not if you play this right, anyway.

Mar 2, 2026

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12 min read

🧊 Optimism is expensive

🧊 Optimism is expensive

94% of founders expect growth. Only 31% can survive it.

Feb 24, 2026

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14 min read

🧹 Getting paid is boring

🧹 Getting paid is boring

Why founders still pick markets they can't brag about.

Feb 17, 2026

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12 min read

🔍 Demand leaves footprints

🔍 Demand leaves footprints

The market already validated your idea. You just have to look.

Feb 10, 2026

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12 min read

🍼 Think like a baby

🍼 Think like a baby

The 50-year debate that explains why you're stuck.

Feb 3, 2026

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11 min read

🌱 Stop pulling seedlings

🌱 Stop pulling seedlings

Most of us default to extraction. Here's how to stop.

Jan 27, 2026

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10 min read

🍞 A breader way to price things

🍞 A breader way to price things

Your customers know when you’re full of it.

Jan 20, 2026

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9 min read

🪫 Trying to use an empty battery?

🪫 Trying to use an empty battery?

January’s exciting... and exhausting. And that’s okay.

Jan 13, 2026

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10 min read

🧭 Are you still on track?

🧭 Are you still on track?

Ambition creates a planning gap. Here’s how to close it.

Jan 6, 2026

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7 min read

🙈 Ignore 90% of your data

🙈 Ignore 90% of your data

Find the single metric that simplifies your growth.

Dec 30, 2025

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9 min read

🪨 Apple told AI to kick rocks

🪨 Apple told AI to kick rocks

And their share price thanked them for it.

Dec 23, 2025

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8 min read

🥊 Don't try to fight the giant

🥊 Don't try to fight the giant

Monster and Liquid Death blew up using counter-positioning.

Dec 16, 2025

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10 min read

🧩 Turn side projects into sellable assets

🧩 Turn side projects into sellable assets

What to keep, what to sell, what to kill.

Dec 9, 2025

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11 min read

📆 I added a new month to my year

📆 I added a new month to my year

The math on automation is embarrassing once you see it.

Dec 2, 2025

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10 min read

🐢 Last place is the best place

🐢 Last place is the best place

Why Google, Facebook, and Shopify were all happily late to the party.

Nov 25, 2025

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10 min read

🎨 Creative block is a curation problem

🎨 Creative block is a curation problem

The biggest hurdle to better conversions is pattern recognition.

Nov 18, 2025

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8 min read

👋 The art of a non-pushy follow up

👋 The art of a non-pushy follow up

80% of sales need five follow-ups, but most people quit after one.

Nov 11, 2025

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10 min read

🎸 The song that failed its way to #1

🎸 The song that failed its way to #1

Are you being resilient or just stubborn?

Nov 4, 2025

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11 min read

⚠️ The hidden cost of being helpful

⚠️ The hidden cost of being helpful

Every “just this once” teaches clients your boundaries don't matter.

Oct 28, 2025

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9 min read

💵 Your business should pay you first

💵 Your business should pay you first

How to guarantee your paycheck before expenses eat it all.

Oct 21, 2025

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9 min read

😳 Why perfect buyers still say no

😳 Why perfect buyers still say no

​​Four anxieties kill deals. Here's how and when to address each.

Oct 13, 2025

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13 min read

➕ Startup’s favorite equation: 1 + 1 = 3

➕ Startup’s favorite equation: 1 + 1 = 3

Why splitting authority can actually lead to faster AND better decisions.

Oct 7, 2025

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11 min read

❤️‍🩹 The campaign that broke LinkedIn

❤️‍🩹 The campaign that broke LinkedIn

What do Snoop Dogg and marketers have in common?

Sep 30, 2025

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7 min read

🪜 A ladder every growing business builds

🪜 A ladder every growing business builds

The universal pattern that comes from the customer.

Sep 23, 2025

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10 min read

🤨 Work less... earn more?

🤨 Work less... earn more?

This founder's “Hell No” list unlocked $375k in monthly revenue.

Sep 16, 2025

•

8 min read

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