Essays

The power of avoiding stupidity for startups

One of the most critical challenges for startups is putting together an execution plan for success. Rather than focusing on what a shiny outcome would be, an incredibly powerful tool is to consider what a crap outcome would look like and avoiding that.

Charlie Munger, Warren Buffett’s late business partner, was often quoted saying “It is remarkable how much long-term advantage people like us have gotten by trying to be consistently not stupid, instead of trying to be very intelligent.”

How to Not Spoil a Child

Are we raising a spoiled child? I recently read Ron Lieber’s The Opposite of Spoiled: Raising Kids Who Are Grounded, Generous and Smart about Money and it was instantly one of the books that kept me up at night thinking and talking with my partner.

How to Write Your ‘Year in Review’

Every December, I sit down to write my year in review—capturing the highs, the lessons learned, and my aspirations for the coming year. This reflective practice has proven invaluable, providing me with profound insights and a roadmap for personal growth.

It’s a great practice which I would highly recommend. I have year in reviews going back to 2011 and paging through them helps me appreciate how far I’ve come. Depending on the year I’ll spend anywhere from an hour to half a day’s worth of time putting together my review. While the format has changed over the years, I want to share my current approach.

Frank Slootman on creating a high-performing culture

It’s much easier to find our leadership style if we have examples to engage with in a detailed way. I recently picked up Frank Slootman’s book Amp It Up: Leading for Hypergrowth by Raising Expectations, Increasing Urgency, and Elevating Intensity because I wanted to learn more about how he operates. Tldr; loved the book and found it an in-depth and fascinating look at a guy who operates in a way I never could.

How to Delegate Without Being a Micro-Manager

“If you want a thing done well, do it yourself”

If you, like Napoleon Bonaparte, have ever reached this conclusion, you are not alone. Delegating effectively is a struggle and it often feels faster and better to do it yourself.

The challenge is the devil is in the details on how to effectively delegate.

My Fellows Retreat with Leaders in Tech

In fall of 2018 I had one of the most formative self-development experiences I’ve ever had to date — attending a Fellows retreat with Leaders in Tech (LIT). My mind was blown because it is SO different from many of the offerings out there, and I wanted to write a post to share what this organization is about and how it’s made a difference. In fact, it made such an impact that I jumped on the opportunity to get more involved and joined their Board of Directors last year.

Podcast: How to make better decisions and build a joyful career

Listen: Apple Podcasts | Spotify | YouTubeTranscript: Lenny’s Podcast I was recently invited onto Lenny’s Podcast and had so much fun there talking about how to make better decisions, career strategy, and living a life aligned with our values. Topics covered: Have a listen and hope you enjoy it!

Make Better Decisions with Curiosity Loops

I think most would agree that one of the best resources for making better decisions is the advice of knowledgeable people who know us well. Unfortunately, it’s often an underutilized resource. The main challenge is, how do you actually do it?

I use something I call a curiosity loop to systematically extract wisdom from my network.

Build Your Inner Scorecard: A 10-Minute Exercise for Better Decisions

What defines you? What does success look like? How can I make good decisions for myself in the long term?

My belief is that it’s important to operate our lives by an Inner Scorecard. While an Outer Scorecard is based on how the external world sees you, judges you, and stacks you up in comparison to others, an Inner Scorecard is something based on what you truly want without thinking too much about what other people think of you*.

A Practical Guide: How To Find an Executive Coach (Part 3)

When I give advice to executives looking for a coach, I typically break it down for them into these straightforward steps on how to structure their search. This is Part 3 of my series on executive coaching based on insights from 80+ interviews with executives and coaches, focused on how to find a coach. Check out Part 1 for a rundown of the results and data, and Part 2 for what I’ve learned as a coach so far.