20 Comments
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Emmanuel PaulMaah's avatar

needed this. a sneak-peek at the hell i'm running into ...

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Edward Corona's avatar

The journey from pre-seed to IPO is often glamorized, but the reality is packed with challenges and unexpected twists. Thanks for shedding light on the often unseen struggles and successes in building a startup.

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Rachel Maron's avatar

This piece is a mirror and a map: brutally honest, oddly reassuring, and refreshingly helpful. Founders often glamorize the early chaos or the IPO finish line, but this thread delivers the messy middle in full color. It’s not just a timeline; it’s a survival guide. The candid tone and hard-earned wisdom resonate deeply with anyone who’s ever questioned their sanity while chasing product-market fit at 2 am.

The takeaway? It’s not genius that separates success from failure; it’s endurance. Grit. The refusal to quit. Read this if you’re building, doubting, or just deep in the grind. Then keep going.

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Leader’s Lens's avatar

This hit the sweet spot—realistic, a bit confronting, and oddly comforting.

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Michael Spencer's avatar

That sounds truly exhausting. I love to read a piece that correlates the usual challenges faced at various periods of a startup's evolution.

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Sky Walker's avatar

Great insights, and wow…this is going to a ride 🫣

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Damien Kopp's avatar

Good post! I think it does question what success really means … is it your first raise? PMF? 1 M users? Profitability? Exit? IPO?

It’s probably all matter of perspective; each of these milestones don’t last.

I came to realize success is a process. A mindset. And it’s never finite.

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Zina Sarif's avatar

Oh my gosh! Year 3 here and I can confirm the first two sections 😅. The pre-seed, pre-sleep, pre-revenue joke is soooooo real.

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Harrison Chapin's avatar

Love this! I’m Harrison, an ex fine dining industry line cook. My stack "The Secret Ingredient" adapts hit restaurant recipes (mostly NYC and L.A.) for easy home cooking.

check us out:

https://thesecretingredient.substack.com

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AI Film Agency, LLC's avatar

Smashingly good.

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Meg Porter's avatar

Excited 🤣💕🤌🏻

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Gilles Cornelis's avatar

This is an exact timeline of all the feelings and hurdles of the past 10 years as a founder. Sprinting a marathon.

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Martin's avatar

One of the most accurate founder timelines I’ve read raw, honest, and painfully familiar. Especially love the framing that product-market fit isn’t a finish line, it’s a flirtation. Every early-stage founder should pin this to their wall.

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Gourav Khanijoe's avatar

Really valuable article!

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Todd Smith's avatar

This is the single most insightful and useful piece on entrepreneurship I have ever read. Year 9 here, and it totally tracks. If only I would have known there was a map for this journey.

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Alan Schweber's avatar

This one sums it up beautifully: Founders Are Marathoners Disguised as Sprinters.

I did it for 4 years and it felt like one.

Thank you for writing this.

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