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Startup Stories from the Trenches

Jack Zerby

Want stories and tips from the trenches after 20 years of building startups?

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Substack
PricingOnly free issuesPublishesWeekly
Issues6Founded6 years agoLast Issue6 years ago
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Artwork for Startup Stories from the Trenches

Latest Issues

Can't see the forest for the trees.

There have been many times in my career where I just couldn't see it...

One day at Vimeo, I looked over my monitor and saw Zach Hoeken (nickname Iowa), one of our engineers working on some sort of CAD robot drawing.

I remember being pisse...

6 years ago
4
3

How a deal with Etsy fell apart at the 11th hour

“Hey...um…honey…I need to get groceries for this week, is there any money in our checking account?” my wife Marisa said to me after nervously opening my office door.

I checked the balance, swallowed back tears, and said “no…just give me a...

6 years ago
4

An embarrassing story about a Myspace acquisition meeting...

On June 11, 2010, my partner Jonathan forwarded me this email.

Turns out Myspace CEO Mike Jones wanted to “connect”. They were working on their new version, trying to win users back from Facebook.

In smoke and mirrors Silicon Valley speak...

6 years ago
3

A story about saying no to Facebook

As I was wrapping up work at 5:52pm on October 10, 2010, I got an email FWD from my partner Jonathan.

When I read the words “Facebook” and “acquisition offer” my heart skipped a beat. I immediately called Jonathan because I thought for sur...

6 years ago
2
1

A story about pitching Gary V and saying no 🤦‍♂️

At the time I was working in the Vimeo office (around 2009) and we were jammed into the back corner of the College Humor office. We had to be quiet most of the time because CH was recording their new MTV show. In between takes of taser wars...

6 years ago
3
1

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  • Jack Zerby

    Head of Design at Gumroad

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