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Organic Startup Ideas
April 2010 The best way to come up with startup ideas is to ask yourself the question: what do you wish someone would make for you? There are two types of startup ideas: those that grow organically out of your own life, and those that you decide, from afar, are going to be necessary to some class of users other than…
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How to Kill a Unicorn
I took a deep dive on freemium pricing and decided to document it in this post. Why freemium? I think it’s how the little guys can win against market leaders. Basically, it’s how you kill a unicorn. Notion, Figma, Canva, Mailchimp, and Segment. What do all of these
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Your Job as a Founder Is to Create Believers
Before we launched HelloSign, I remember showing HelloFax to a family member. This person was normally supportive, but he took a glance and walked away. He wasn't the only one. A lot of people...
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'We're in a Bubble'
A lot of people have been saying we’re in a tech bubble for quite some time. Someday they’ll be right, but in the meantime, I thought it'd be fun to look back at some articles from the last 10...
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Candy Japan crosses $10K MRR
Japanese candy subscription box Candy Japan exceeded $10,000 per month in sales.
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Four years of running a SaaS in a competitive market
Looking back on the last four years, what worked, what didn't.
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How I Made $600K in the iOS Education Market (2012 update)
It’s been more than one year that I wrote “ How I've Made $200k in the iOS Education Market ” post which has been well received by the indie...
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The life and death of a startup
At DjangoCon Europe 2017 , and again at DjangoCon US 2017 , I gave a talk entitled “Autopsy of a slow train wreck: The life and death of a Django startup”. After I gave those presentations, a number of people requested that I publish the content in blog form so they could share it with colleagues.
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Projects and Companies
In the early days of my startup, I used to get slightly offended when people would refer to it as a “project”. “How’s your project going?” seemed like the asker didn't take us seriously, even...
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Using ChatGPT as a Co-Founder
In the quest to explore the capabilities of ChatGPT, I decided to utilized it as a startup brainstorming partner. From product description to building the product on AWS and GCP, crafting an elevat...
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If your product is Great, it doesn't need to be Good.
By now, everyone is tired of hearing about the iPad, but the negative responses are so perfectly misguided that it would be wrong to waste t...
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Want a killer product? Become more opinionated
I laugh at this tweet every time I remember it:
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Ramen Profitable
July 2009 Now that the term "ramen profitable" has become widespread, I ought to explain precisely what the idea entails. Ramen profitable means a startup makes just enough to pay the founders' living expenses. This is a different form of profitability than startups have traditionally aimed for. Traditional…
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Company as Code
Reimagining organisational structure for the digital age.
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Bubble talk
I’m tired of reading about investors and journalists claiming there’s a bubble in tech. I understand that it’s fun to do and easy press, but it’s boring reading. I also understand that it might...
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How I've built a profitable Slack bot as a side project in Rails
I've built a Slack anonymous messaging bot in Ruby on Rails and it is profitable. In this blog post I will describe what I did and tools I used to create, promote and monetize a simple SAAS product.
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The 100 hour gap between a vibecoded prototype and a working product
I spent 100 hours vibecoding an app and it's not as simple as people say.
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Want to Start a Startup, as a Software Engineer? Sell Something Online
When I decided to write and sell my first ebook, The Tech Resume Inside Out [https://thetechresume.com/], I expected to learn about the writing process. How to create a high-quality publication. How to work with editors. Designing a cover and illustrations for the book. And I have, indeed,
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1k True Fans (2008)
This is an edited, updated version of an essay I wrote in 2008 when this now popular idea was embryonic and ragged. I recently rewrote it to convey the core ideas, minus out-of-date details. This revisited essay appears in Tim … Continue reading →
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Myths About Working as an Engineer at a Startup
When I first graduated from college and went looking for a job with a startup I had no idea what to expect. I knew what I didn’t want - I had done ...
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How I got to $9.99 MRR after 7 years
Here's the tell-all behind the scenes story of how Cloakist got to $9.99 MRR after just 7 years