What I Learned from My First (Blunder-Filled) Marathon

Respect the race or suffer the consequences

This piece was originally published in 2014 on the health and wellness site Greatist but has been lost after the site was acquired in 2019. Republishing it here because it’s a great lesson in humility and resilience.

Entrepreneur and former collegiate gymnastics champion Jason Shen had a less-than-awesome experience running his first marathon. Find out what went wrong and how we can all learn from his rocky road to the finish line. 

After many months of training, I ran my first marathon in the summer of 2012. It was agonizingly hard, and I made a lot of mistakes both in … Read the rest

Personal October 11, 2020

Fidelity vs Functionality

What Makes for an Effective Demo

A lot has been made about Apple’s hardware product prowess – the click wheel of the iPod, the slimness of the Macbook Air, but just as notable are Apple’s standout software like Safari, Keynote, iOS and many more. In Creative Selection, long-time Apple software engineer Ken Kocienda takes us into the world of software development, and the all important demo, which he gave directly to Steve Jobs on several occasions.

He describes his first experience with a great software demo shortly after joining Apple in 2002 and being tasked with building the Mac OSX’s web browser (which did not … Read the rest

Product & Design August 24, 2020

How Tech Workers are Finding Their Footing in a Pandemic

After a spike in burnout indicators, the industry is experiencing an uneven recovery

This piece first appeared in Fast Company

The start of 2020 should have been an energizing time for me, personally and professionally. I had just returned from a long-awaited holiday honeymoon and closed a new round of funding for my startup. But I found myself lethargic, dreading my inbox, and procrastinating on important tasks—telltale signs of burnout.

In fits and starts, the tech industry has finally begun to talk openly about burnout, mental health, and workplace culture, including toxic leadership and unhealthy work hours.

Recently digital strategist Ella Dawson spoke openly in a personal essay of feeling “a boiling … Read the rest

Leadership Technology June 29, 2020

On Protests and Movements

Thoughts on the fight for racial justice in 2020

This is an attempt to integrate a series of shorter, related writings that I’ve published in my newsletter over the last few weeks. Much of it touches on the Black Lives Matter movement, which I wrote about back in 2016, but much of it also applies for any kind of movement or social change.

💫 The Arc of Social Progress

There have been 14 days and nights of protests calling for racial justice and police/criminal justice reform in over 400 cities across the United States, and in dozens more across the world. Curfews have been set and defied, thousands have … Read the rest

Culture June 13, 2020
Jackbox-Head-Cover-Image

The Product Genius Behind Jackbox Games

How you can learn from the resurgence of an offbeat trivia game series

This article first appeared on TechCrunch

During this period of shelter-in-place, people have had to seek out new forms of entertainment and social interaction. Many have turned to a niche party series made by a company best known for an irreverent trivia game in the ’90s called “You Don’t Know Jack.”

Since 2014, the annual release of the Jackbox Party Pack has delivered 4-5 casual party games that run on desktop, mobile and consoles that can be played in groups as small as two and as large as 10. In a clever twist, players use smartphones as controllers, which … Read the rest

Product & Design May 11, 2020

How to Become More Adaptable

When a global pandemic turns the world upside down

It’s no secret that adaptability has become a critical trait for knowledge workers. To stay on top of a rapidly evolving world, we must assess new situations, make intelligent decisions and implement them effectively.

A 2014 research report by Barclays indicated that 60% of employers say adaptability has become more important during the last decade, and BBC called adaptability the “X factor” for career success in an era of technological change.

But even the most intrepid executive, entrepreneur or freelancer would be forgiven for struggling to adapt to a global pandemic. The impact of coronavirus has been unrelenting: … Read the rest

Performance April 12, 2020

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?”

… Read the rest
Leadership Technology April 4, 2020

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

Leadership Personal March 14, 2020

Finding Your Edge

No one wants a watered down Tesla

I want to talk about product design and positioning as it relates to Elizabeth Warren dropping out of the race. This is not about her politics (though I was a fan) but her brand as a candidate.

Promoting a political campaign is not unlike marketing a new piece of workout equipment or messaging app or podcast. How do you stand out and grow your audience?

Seth Godin (who we spoke about last time) talks about the idea of edge as “a free prize that has been shown to make a product or service remarkable”

His recommendation for marketers and … Read the rest

Product & Design March 9, 2020

Quit or Stick it Out

Book Notes on Seth Godin’s The Dip

I love Seth Godin’s books and his blog. I think he’s just incredibly good at articulating distinctly memorable ideas backed by both data and stories in a way that we could all learn from.

Godin, more than just about anyone, understands both the power of technology (he’s founded several technology companies, including an early direct marketing co that he sold to Yahoo) and how technology has shaped markets and human opportunity.

I took these notes back in 2008 and rediscovered them recently. A lot has been paraphrased but there are some direct quotes as well. Bolding is mine.

The … Read the rest

Performance February 27, 2020
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