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kottke.org posts about Fred Wilson

The secret to success: take risks, work hard, and get lucky

posted by Jason Kottke   Jul 05, 2016

Tech investor Fred Wilson recently gave the commencement address for the very first graduating class at the Academy For Software Engineering. In it, he shared the secret to his success:

So with that, I am here to tell you that the secret to success in your career comes down to three things, take risks, work hard, and get lucky.

I essentially1 agree with Wilson here. Earlier today I was listening to the latest episode of the Recode Media podcast where Peter Kafka’s guest was Daring Fireball’s John Gruber. Gruber recounted how he got started blogging about Apple and eventually turned it into a very successful business. I’ve heard the story before and it conforms nicely to Wilson’s path to success.

1. Take risks. Gruber bet heavily on three things for Daring Fireball: Apple, blogs, and (later) podcasts. None looked that impressive from a business standpoint when his bets were made. In 2002 when he started writing DF, Apple was still an underdog computer company whose partisans had mostly stuck with the company through its lean years of offering products that weren’t competing well and which didn’t exemplify the ideals of the Apple of yore. The iPod had just come out a year earlier and the life- industry- company-changing iPhone was years in the future. But Gruber never viewed Apple as an underdog…to him it was a legendary company in the world poised for future greatness. Professional blogs were just starting to be a thing back then as well, and it was far from certain that you might be able to earn even a partial living from them, especially on your own. And when he started his Talk Show podcast in 2007, podcasting was still largely a hobbyist endeavor. Sure, you could make some money doing it, but 9 years on, there’s big money to be had for the most popular shows. Three risky bets that paid off.

2. Work hard. Tens of thousands of posts and hundreds of hours of podcasts over the past 13+ years, yeah, I think that covers it. Gruber has put in the necessary ass-in-chair time.

3. Get lucky. There’s a lot of luck sprinkled around the success of DF, but perhaps the biggest break Gruber got was Apple’s decision to open up the iOS App Store to outside developers. Suddenly, you had all of these developers, startups, established software companies, and venture capitalists pouring money into the development and promotion of iOS apps. So these companies had money and needed somewhere to advertise their apps, a place where they could be sure all of the most influential and rabid Apple aficionados would see their message. Daring Fireball was the obvious place and the site’s RSS sponsorships were the perfect format.

  1. Although I would assign a much larger role to luck than he might. Being born white and male in the US in the late 20th century is a massive advantage that is often brushed under the carpet in such discussions. “Take risks” can be literally dangerous in an institutionally racist/sexist/classist system.

We Work Remotely

Properties of successful web apps

posted by Jason Kottke   Apr 13, 2010

From VC Fred Wilson, The 10 Golden Principles of Successful Web Apps.

A transcript is here.