What’s Going to Change

It’s April 4, 2020. I stopped going to the office on March 13, and according my Captain’s Log, we’re on Day 24 of this self-isolation. I don’t have any symptoms, but I’m assuming I have it and wear a mask whenever I go to grocery shopping (about 1x a week). This either is your reality now and or will be soon.

Coronavirus is the biggest global crisis we’ve had since at least WWII. Possibly ever. 

The natural question is “when are things going to get back to normal?”

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Captain’s Log

A dictated journal for an unprecedented moment

I’ve journaled on and off in various formats throughout my life.

I kept a paper diary, shifted to a “4 lines a day” style daily journal, moved to Day One’s electronic journal, and also do a personal review and quarterly updates to friends. Plus I write a monthly update for my investors for my business.

I’m trying something new that I wanted to share — a digital journal powered by voice.

Think of it like a captain’s log. The original term (sometimes ship log or logbook) was used to document a ship’s position, wind speed & direction, and … Read the rest

Adaptability is No Joke

Both startups and improv are about making shit up on the fly

I recently participated in an “Improv for Entrepreneurs” workshop run by Mary Lemmer, a founder-turned-VC who now teaches improv to companies and professionals. I’ve done a couple of these types of workshops over my career and seen a few improv shows — they’re really fun. Improv is like freestyle rap or live jazz: it might not be as polished as a studio album track, but it’s impressive and enjoyable to watch someone make stuff up on the fly.

If you like comedy but haven’t seen any improv before, I’d highly recommend it. Try taking a class or a workshop … Read the rest

How ClearBrain’s CEO Used These 7 Lessons to Create a New Product Category

Bilal Mahmood is cofounder and CEO of ClearBrain, a Y Combinator backed predictive analytics company that’s used by firms like Chime Bank. He’s also a good friend of mine and someone I greatly admire for his resourcefulness and resilience (important traits for any founder!)

Bilal’s company recently launched a product called Casual Analytics that uses a new algorithm that can automatically distinguish causation vs correlation, without running an experiment. I thought it would be a good opportunity to ask him about how they identified the need for this product, what problems they faced building it, and what they’ve … Read the rest

Why Generalists Beat Hyper Specialists

Book notes on “Range” by David Epstein

I’ve always seen myself as someone with a ton of interests, with a lot of useful skills and knowledge but not a world class expert in anything. And while that’s served me really well, I sometimes wonder if it puts me at a disadvantage.

Fortunately for me, I recently finished Range: Why Generalists Triumph in a Specialized World, a thoughtful and comprehensive read by David Epstein. It made the rounds on VC Twitter this summer, which makes sense because venture capitalists, especially early stage ones, are very much generalists who look across a broad set of industries.

I recommend … Read the rest

Community is just friendship

WeWork, well-being, and who we are

Working in tech, you hear the word “community” a lot. When I was starting my career more than a decade ago, the concept of a community manager was starting to go mainstream.

Today it forms the foundation of our industry’s latest IPO – WeWork. For years they have been crowing about the power of community.

From their mission page:

When we started WeWork in 2010, we wanted to build more than beautiful, shared office spaces. We wanted to build a community. A place you join as an individual, ‘me’, but where you become part of a greater ‘we’. A place

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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

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

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