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Starting Something in a Slow Year
Should you build when the world is on pause?
Jun 24
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Os Ishmael
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Starting Something in a Slow Year
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Pitching to a Room That Doesn’t Care
What to do when you're giving it everything and they’re giving you… nothing.
Jun 18
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Os Ishmael
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Pitching to a Room That Doesn’t Care
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The Best Startup Advice I Got From People Who Don’t Work in Startups
Some of the most useful things I’ve learned came from people who’ve never raised a round or written a pitch deck.
Jun 10
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Os Ishmael
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The Best Startup Advice I Got From People Who Don’t Work in Startups
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The Pitch That Finally Made Sense
When I stopped trying to sound smart and just told the truth.
Jun 3
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Os Ishmael
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The Pitch That Finally Made Sense
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When to Say No to an Investor
Not all interest is real. Here’s how to spot when an investor is wasting your time and how to walk away without regret.
May 27
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Os Ishmael
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When to Say No to an Investor
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The Investor Gap
Why founders misread what investors actually want — and how to fix it before the deal falls apart.
May 20
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Os Ishmael
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The Investor Gap
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We Really Wanted to Invest — But We Didn’t
A story about a promising startup, a tough call, and what founders often miss when raising capital.
May 13
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Os Ishmael
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We Really Wanted to Invest — But We Didn’t
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Is Your Startup Built to Last or Just Built to Launch?
The difference between a product moment and a real business.
May 6
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Os Ishmael
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Is Your Startup Built to Last or Just Built to Launch?
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Startups Don’t Usually Crash. They Erode.
What I learned the hard way about small cracks, compounding problems, and what actually kills a business.
Apr 29
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Os Ishmael
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Startups Don’t Usually Crash. They Erode.
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Pick the Right Hill to Climb
A story about almost becoming a musician, and why your startup field matters more than you think.
Apr 22
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Os Ishmael
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Pick the Right Hill to Climb
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What Is a Startup, Really?
It’s more than tech. It’s more than funding. It’s a beginning.
Apr 7
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Os Ishmael
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What Is a Startup, Really?
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The Hidden Cost Most Founders Miss
Why timelines slip, what it does to your business, and how to plan for it.
Apr 4
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Os Ishmael
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The Hidden Cost Most Founders Miss
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For founders and builders (or anyone else) who want to stay focused, think clearly, and move with intention—especially when things get messy. No fluff! No hype. No pressure. Just something steady to read with your coffee.
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