I first setup my Airbnb account in 2011 as Hilary, Oliver, and I set out to travel around Europe for 5 weeks. Since then I’ve stayed at dozens of Airbnbs and loved all but one (unfortunately it’s not an interesting story). Over the years I’ve always wanted to see the other side of it as […]Mental frameworks for making decisions
Now that I lead a team of 25 there are a lot more decisions to be made. Fast decision making is a major advantage to being a small company and something I’d hate for us to lose as we grow. To help, I’ve started listing out several mental frameworks I use for decision making. These frameworks […]2016 in Review — The year I became a CEO
My last few year-in-review posts have been written as “x years after [life change].” 2 years after I quit my job. 1 year after I quit blogging. And 2016 seems to be one of the biggest years of change I’ve ever had. Not because I made a different decision or some event happened, but instead because […]2015 in review — 1 year after I quit blogging
Wow. What a year. At the end of last year I made the largest business decision I’ve ever made: stop working on my very profitable training business (to the tune of $20,000 to $50,000 per month!) and instead put all my time, effort, and money into my failing software company. I also almost entirely stopped […]Unsolicited Advice
The rock skipped five times across the water before sinking into a small wave. Not bad, considering the water was rough. As Barrett searched for another rock to beat his new record, we discussed a new idea: what if we gave people all our advice and opinions they never asked for? I was with four of […]Why do you want to become an Authority?
I felt confused and a little sad as I walked along the Seattle waterfront. It wasn’t the conference topics that had me confused, but instead my own emotions. I came to An Event Apart (a web design conference) in Seattle hoping to meet like minded designers. They were all around me, but I was too […]The only app you need to become a better writer
“What app do you use for writing?” That’s a common question I get from people just starting out building a blog or writing a book. And it’s one I wish people would stop asking. It’s not a bad question all together, but it’s the wrong question. At least for the majority of people asking. These […]