The Art of Ass Kicking

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?”

2020 may end the 20th century, the century of mass society.

Concerts, events,

… Read the rest

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

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

Leadership Performance February 21, 2020

Recharging is for batteries, not people

Why working less isn’t the answer to burnout at work

Last year, journalist Anne Helen Petersen wrote a widely shared piece in Buzzfeed naming millennials the “Burnout Generation”. According to Petersen, we’re overworked, underpaid, and often paralyzed by the systemic dysfunction of our increasingly volatile world. As a result, many of us struggle with even the most basic tasks of “adulting,” like paying bills or registering to vote.

One year later, things seem worse than ever. Wages have continued to stall, the U.S. is on the brink of war with Iran, and raging wildfires have killed more than a billion animals in Australia. Fifty-seven percent of tech workers … Read the rest

Culture Performance February 5, 2020

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

Leadership Product & Design Technology January 1, 2020

What We Should Learn from the Away Scandal

A debate about tech workplace culture in the era of Slack, #metoo, and self-care

The spectacular fallout from a recent investigation into Away, which portrayed the beloved luggage company as a toxic workplace, has revealed two schools of thought on how to treat startup employees.

The first says that staff should be cherished, because harnessing the passion and brilliance of “A players” is key to success. Think catered lunches, beautiful offices, and “Best Places to Work” lists. The second says that making a dent in the universe is hard, and employees should expect to work tirelessly under the directives of visionary and sometimes mercurial founders. Think “hustle culture,” Class B voting shares, and Steve … Read the rest

Performance December 14, 2019