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Questions to Ask When Interviewing at a Startup
A biweekly newsletter on navigating the chaos of building & investing in startups. Topics include venture studios, entrepreneurship, product management, analytics and more, leveraging a combination of best practices & instincts. Click to read Focused Chaos, by Ben Yoskovitz, a Substack publication with tens of…
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Someone Stole My Startup Idea – Part 1: Are Those My Initials?
In my 21 years of startups I’ve had my ideas “stolen” twice. Once it almost mattered. This is about the time it didn’t. Worries from the garage One of the worries I hear from entrepreneurs (not ju…
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Heroku: Commercial Launch (YC W08)
When Adam, Orion, and I started Heroku two years ago, we had no idea how much new technology we would have to build to realize our vision of an instant...
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Closure. "I had the only farm capable of nuclear weapons design."
For those that know me, I’m kind of a “life is too short” kind of guy. I liked to fail fast, move on, and not look back. However, in catching up with the VP of Sales of Ardent last night, I was rem…
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Reflecting on my failure to build a billion-dollar company (2019)
In 2011, I left my job as the second employee at Pinterest — before I vested any of my stock — to work on what I thought would be my life's work...
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Jason Calacanis: What to do if your startup is about fail
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It Doesn't Have To Be All Or Nothing With A Startup
Startup mythology demands that to create something great, you need superhuman sacrifices. You need to work for no pay, you need to put in 120 hours/week, you need to preferably sleep under the desk and live off pizza as a sole form of nutrient. As a result, you need to abandon your family and risk …
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A Newbie’s Guide to Startup Compensation (or “Stock Options will Make Me Rich”)
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Startup Blogs To Make You a Better Entrepreneur
As an aspiring startup founder, I’m always on the lookout for blogs that will help me become a more adept entrepreneur. Fortunately for me and for the startup community there’s a lot o…
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It Must Be A Marketing Problem
The Customer Development process is the way startups quickly iterate and test each element of their business model, reducing customer and market risk. The first step of Customer Development is call…
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How to Meet Your Next Cofounder
Over the last few months I’ve seen a number of people looking for cofounders on Hacker News or via their own personal blogs. I think this is, at best, a highly inefficient way to find a cofounder and, at worst, a way to fool yourself into finding the wrong cofounder. In any case, it’s a naive approach to finding the…
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Old, but gold - "Strategy Letter I: Ben and Jerry's vs. Amazon"
Building a company? You’ve got one very important decision to make, because it affects everything else you do. No matter what else you do, you absolutely must figure out which camp you’…
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Why Every Entrepreneur Should Write and Tips To Get Started
Why all entrepreneurs should invest time in writing and tips on how to get started.
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Starting a business isn't as crazy and risky as they say
If you're thinking about starting a new venture right now, you need to understand the risks, but you need the real risks. The truth (as always) lies between baseless off-hand remarks about how "95% of businesses fail" (false!) and those startup blogs that show only the rosy side of things.
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