The Art of Ass Kicking

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

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 learned … 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

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

Leadership Performance December 11, 2019

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

… Read the rest

Culture Leadership August 26, 2019

Techstars Alexa

Midgame joins Amazon’s voice-focused startup accelerator

Midgame was accepted into The Alexa Accelerator, a program co-run by the Techstars startup accelerator and the Alexa Fund, a $200M fund for Amazon to invest in voice tech companies. We’re two weeks in and over the next few months, we’ll build and launch a voice assistant for gamers, alongside nine other companies who are also part of the program.

The announcement went live on VentureBeat last week as well as the Amazon Day One corporate blog.

The other companies in the program include include an AI-powered service that helps students learn, a health product that checks up on … Read the rest

Performance July 28, 2019