Conflict Isn’t Always Bad

My natural tendency is to avoid conflict. The few times I fought in school, I was caught and punished for it and it didn’t seem never was worth the trouble.

It’s also the case that needless conflict can be harmful to both parties, because even if you “beat” the other party, now they’re holding a grudge.

But I’ve come to realize the value of productive conflict.

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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

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

17 Essential Best Practices for Making Things Happen

I previously wrote about my PIF coworker Sarah Allen’s little rules of working life, which I thought was pretty awesome. I decided to think through some of my own rules, or as I’m calling them, “Best Practices for Making Things Happen”.

The idea is that these are all maxims that I live and work by, that I’ve learned over time and that I believe have made me more effective in accomplishing meaningful things.

The list is neither complete nor fully elucidated, but that’s totally in line with BP #2 and #7. =)

Would love to hear what you think: … Read the rest

Sarah Allen’s Little Rules For Working Life

I’ve learned a lot of stuff working with the fellows in my program, particularly Sarah Allen, who’s paired with me on the Smithsonian Transcription Center. I noticed that she’d often mention a policy she had on doing (or not doing) certain things. I remarked that there seemed to be a lot of them and has she ever put them in one place?

Well luckily for us she has. Here are some my favorite policies of Sarah Allen, an incredibly accomplished software developer, manager, and entrepreneur, and my comment on it.

I never take a job where I

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Listen to everyone, then make up your own mind

Lessons learned from Ridejoy’s seed round

“Don’t take too much advice. Most people generalize whatever they did and say that was the strategy that made it work.”

Ben Silbermann, cofounder of Pinterest

When we raised our seed round for Ridejoy, we got lots of great advice from many smart, experienced people. This was wonderful except that much of the advice was contradictory:

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Great by Choice

The surprising lessons of how tech startups succeed over the long term

Summary: Great by Choice describes the results of a deep investigation into how young companies can survive and thrive in chaotic, turbulent environments to achieve spectacular results. The book is of great value startups and entrepreneurs seeking to build enduringly great companies. In this blog post, I look at how his concepts of fanatical discipline, productive paranoia, and empirical creativity apply to building a startup that succeeds over the long-term [1].

Introduction

I just finished reading Jim Collins’ new book Great by Choice: Uncertainty Chaos and Luck—Why Some Thrive Despite Them All (GBC from here on out). GBC is the … Read the rest