33

Developing a new mantra

I turned 33 a few weeks ago.

I remember when my gymnastics coach turned 33 and told me about it. I was 12. He was not only my first serious gymnastics coach, he was one of the owners of the gym. He was in charge and he seemed to know everything.

I replied by saying that he had run through a third of his life. Probably not what he wanted to hear and but given he was a smoker, it was actually a pretty optimistic forecast.

Turns out of course that you don’t have it all figured out at 33, … Read the rest

Starting Over

Due to an unfortunate combination of bad actors and my own neglect, I’ve had to do a full reboot of my blog. I should be able to recover / republish many of the posts over time, but backlinks may be an issue, perhaps indefinitely.

While this is of course frustrating, there’s also a sense of relief. A fresh start. There’s something uplifting about a blank slate and having a chance to redefine myself and what I write about.

Early on, I tried to make everything I wrote a direct reflection of personal experience. My shield was always “this is what … Read the rest

Long hours are BS

Squaring tech’s penchant for long hours with elite athletic training

Lots of people in tech are obsessed with putting in long hours. Elon Musk once said that “nobody ever changed the world on 40 hours a week” and suggested that the correct number was between 80-100 hours. Freelance marketplace Fiverr, with venture funding to the tune of $111 million, came under fire for an ad campaign that described an aspirational lifestyle where lunch is coffee and sleep deprivation is “your drug of choice.”

Or there was the time when the cofounder of Coursera launched a machine learning company called DeepLearning.ai and in a job post suggested that the team … Read the rest

How to Facilitate

Lessons from master facilitator Piper Anderson

Piper Anderson is no stranger to difficult conversations. As an educator and cultural organizer, she’s spent over 17 years facilitating discussions about some of the most hot-button issues facing U.S. society. In 2016, for example, she gave a TED talk about Mass Story Lab, her storytelling series focused on how the U.S. criminal justice system impacts communities of color. “Yes, I’m the person who brings mass incarceration into polite dinner conversation,” she quipped.

In a time when two black men can be arrested at Starbucks just waiting for a friend, it’s clear that these conversations need to happen. Yet … Read the rest

32

Reflections on turning 32

I turned 32 a month ago and long-time readers know I try to use birthdays as opportunities to reflect and learn. The past couple years are here: 313029282726.

The past 13 months have seen a lot of change — I was part of a mass lay off, worked as a freelance product manager, got engaged, gave a TED talk, started a new company, raised capital, and helped people find exciting new job opportunities. As such, I have a new set of thoughts, sometimes a re-statement of … Read the rest

Introducing Headlight

A Performance Hiring Platform

Editor’s note: Headlight was acquired by Woven in March of 2019.

In late 2017, I started a company called Headlight with my friend and former coworker Wayne Gerard. We’re building a performance hiring platform that helps employers screen candidates for their ability, not their pedigree.

What is Performance Hiring?

We believe that the best way to understand someone’s fit for a role is to study how they respond to scenarios related to the job. This is not a new concept — athletes try out for teams and teachers do mock lessons when interviewing for a new school — and yet in … Read the rest

Book Notes on the Fuzzy and the Techie

A rebuttal to tech’s “STEM or die” mentality

I just finished Scott Hartley’s new book The Fuzzy and the Techie: Why the Liberal Arts Will Rule the Digital World. It is an inspiring read full of compelling stories and ideas about the rapidly evolving world around us.

The central thesis of the book is that instead pushing every last student to major in a STEM field, we need to recognize that the liberal arts provide a crucial human perspective in a world increasingly governed by machine algorithms.

As a venture capitalist who has served as a Presidential Innovation Fellow (we were part of the same round) and … Read the rest

Goodbye Etsy, Hello World

Leaving Etsy and Starting Something New

I joined Etsy in August of 2015, five months after the IPO. I had admired Etsy from afar for years and I was excited do product at an established, publicly-traded technology company after leaving a privately-held B2B software company.

Over the past two years, I’ve built products and features to support our global seller community of 1.7 million creative entrepreneurs. I helped launch a marketing / promotional tool called Shop Updates, oversaw a major rewrite of the system we use to assess listing and transaction fees, and introduced powerful new functionality for Sell on Etsy, our seller-facing iOS and Android … Read the rest

31

31 Lessons at 31

It’s sort of a tradition at this point for me to do a post around my birthday (see: 3029282726. This year, I decided to write down 31 lessons I’ve learned in the past few years. Anything older than that tends to become a “known fact of life” and stands out a lot less.

These were initially written with modifiers like “most”, “often”, or “tend to”, but since that makes the points less pithy, I’ve taken them out. However, know that I don’t mean these lessons literally to be true in all … Read the rest

Ridejoy: Lessons Learned

On April 24th, 2011, I sat down with my friends Kalvin and Randy for an intense 10 minute interview with Paul Graham, Sam Altman, Jessica Livingston and several other partners at Y Combinator (YC). We were hoping to convince the world’s most powerful startup accelerator to accept our Reloveit, our idea for “a Mint.com for photo books”, into their Summer 2011 batch of startups.

YC prides itself on making a day-of decision about whether to accept a startup, so that evening, I found myself pacing back and forth at an outside patio by Kalvin’s childhood home. I was 24 years … Read the rest