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7951

Why Free Plans Don’t Work

The following is a guest article by Ruben Gamez of Bidsketch . Not too long ago it seemed like every product I knew was offering some sort of free plan. The strategy was brilliant: get loads of people using your product and eventually turn them into paying customers. Everywhere I looked the

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What Happened to Yahoo

August 2010 When I went to work for Yahoo after they bought our startup in 1998, it felt like the center of the world. It was supposed to be the next big thing. It was supposed to be what Google turned out to be. What went wrong? The problems that hosed Yahoo go back a long time, practically to the beginning of the…

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IronRuby Manager Leaves Microsoft

Though Frank Sinatra says it best , “I’m leaving today” isn’t exactly accurate; my last day as a Microsoft employee was July 23rd, 2010. This post is almost two weeks delayed as Felicia and I have been on the road since the 26th, driving cross-country to the east coast; we also decided to leave Seattle in favor of New…

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The Future of Startup Funding

August 2010 Two years ago I wrote about what I called " a huge, unexploited opportunity in startup funding:" the growing disconnect between VCs, whose current business model requires them to invest large amounts, and a large class of startups that need less than they used to. Increasingly, startups want a couple…

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How To Pitch A Product

I’ve said a bunch of times on this blog that the perfect pitch is a very short intro to provide context followed immediately by a demo. Last night at the NY Tech Meetup, John Britton of our portfolio company Twilio showed how it is done. If you do a lot of pitches, spend the six […]

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Rethinking 'Fuck You' money

Now that I’ve stepped down from RescueTime, I’m pondering my next thing (whether it’s a product role at a very early stage startup or spinning up my own for the 3rd time). I figure it’s a good time to be introspective and consider my motivations. Why do startups? For me, it’s more about having the choice to work on…