The Second Mountain Startup

Pursuing meaning through the largest paintbrush known to man: business

You may have noticed that the name of this newsletter has changed.

Friday Sabbatical served me well for six months, the perfect wrapper for my transition out of the company I founded and poured my heart and soul into over the past 10 years. It captured the intentional introspection, the radical self inquiry, which was so critical in evaluating and redefining my life during that period of uncertainty.

But it’s time. After 10 years of chasing the shiny brass ring, acquiring highly coveted gold star after gold star only to toss them over my shoulder immediately afterward, I’ve realized that, for me, no amount of gold stars will ever satisfy. I need my work to be about more than just winning a finite game. It may be all vanity in the end, but I want my work to do some good for others while I’m here.

My Work has become increasingly clear:

  1. To help entrepreneurs build and scale companies that do well by doing good for the world.

  2. To help entrepreneurs paint their masterpiece using the most powerful paintbrush known to man: business.

  3. To help entrepreneurs build their company in a way that adds to the richness of their lives, rather than taking and taking and taking from it.

My work is to help entrepreneurs build life-giving companies. And it’s time that this newsletter reflects that.

So welcome to the newly focused Second Mountain Startup, a weekly deep dive into the art of entrepreneurship and leadership for those who want more than just success. (Many of you will recognize the nod to David Brooks’ masterpiece, which if you haven’t read you should do yourself the favor.)

I’m so glad you’re here. Let’s dig in.


1. Flipping the script on the good life

People who are stuck in a particular area of their lives tend to talk about that area in a particular pattern: Have => Do => Be.

For example: First I need to have a lot of money, so that then I can spend more time painting, and finally become an artist.

I’ve used this pattern in my own life plenty of times, each time reliably staying stuck in neutral despite my grand visions. First I need to hit this quarterly revenue number, then I can focus on building a customer centric business and finally doing some good for the industry. First I need to close this financing, then I can focus on making our employees happy and being the kind of leader I know I can be.

This logical process is natural. It is also toxic, in that it places an impossibility (having something you don’t) as a condition for progress, thereby justifying indefinite procrastination.

Life, and business, at its most dynamic and most successful, works the exact opposite: Be => Do => Have.

First I will recognize that I am an artist. Right now, this moment. Then as an artist I will paint. Right now. And then, eventually, I’ll become successful and make a lot of money.

First I will be the best kind of leader I can be. From that place I will make the decisions that are in keeping with my best form of leadership, and the quarterly revenue numbers and closed financing rounds will follow.

Often people attempt to live their lives backwards: they try to have more things, or more money, in order to do more of what they want so that they will be happier. The way it actually works is the reverse. You must first be who you really are, then, do what you need to do, in order to have what you want. — MARGARET YOUNG

If you find yourself stuck in an area of your life, or your business stalled on an important project, look for the way you talk about progress. Simply focusing your efforts on what you can control—who you are and what you do—is the fastest way to get unstuck.

And if you find yourself running a startup to make a lot of money, so that someday, eventually, you can focus on using business to help people and be the human that the world needs you to be (not that that’s anyone we know), well, it works there, too.


2. Author and former director of the World Bank, Steve Denning, interviewed 2017’s world’s #1 management thinker, Roger Martin, about his new book: When More is Not Better.

It’s a fascinating article, with two longtime mainstream management thinkers going back and forth about how the discipline has evolved from “maximizing shareholder value” (what Martin calls “the dumbest idea in the world” in his 2012 book: Fixing the Game) to managing holons of complex adaptive systems inside of complex adaptive systems.

In its simplest form, the craft of management is now being recognized by its leaders as having moved from football to basketball. From complicated to complex.

From Brave New Work, by Aaron Dignan:

Contrary to popular opinion, among people who study systems theory, “complicated” and “complex” are distinct words with precise meanings. The engine inside a car is complicated. A complicated system is a causal system—meaning it is subject to cause and effect. Although it may have many parts, they will interact with one another in highly predictable ways. Problems with complicated systems have solutions. This means that, within reason, a complicated system can be fixed with a high degree of confidence. It can be controlled.

This is not to say that a complicated system can’t be confusing or inaccessible to the layperson. Quite the contrary. Understanding a complicated system, such as an engine or a 3-D printer, requires specialized expertise and experience. Here, experts can detect patterns and provide solutions based on established good practice. This is the domain of the mechanic, the watchmaker, the air traffic controller, the architect, and the engineer.

Traffic, on the other hand, is complex. A complex system is not causal, it’s dispositional. We can make informed guesses about what it is likely to do (its disposition), but we can’t be sure. We can make predictions about the weather, but we cannot control it. Unlike complicated problems, complex problems cannot be solved, only managed. They cannot be controlled, only nudged. This is the domain of the butterfly effect, where a small change can lead to something big, and a big change might barely make a dent. Here expertise can be a disadvantage if it becomes dogma or blinds us to the inherent uncertainty present in our situation.

About time.

Business has never been complicated, despite decades of management theory trying to make it so. This book is important because once HBR talks about it, Fortune 500 businesses listen. The mainstream is recognizing what the edge has used as their competitive advantage for years: that business is complex, and the best way to manage that is highly engaged, empowered, and aligned people.


3. The former Head of People at Lever, Jennifer Kim, said recently:

Speaking in absolutes is a useful strategy to help ideas spread on Twitter, so I’m willing to ignore her false dichotomy here and assume she was merely trying to illustrate each end of the spectrum. Fair enough.

But it’s how she illustrated this that I found so telling.

There are two types of company cultures…1: Results oriented leaders, 2: Nice leaders.

This equivalency, that the leader = the culture, is dead on. Intentional or Freudian slip, Jennifer illustrated one of the hardest truths for many leaders to grasp:

No matter what you write on the wall, what you yourself do will drive company culture.


4. People don’t change. They grow.

Stumbled upon this excellent video from Kaley Klemp, Executive Coach and author of The 15 Commitments of Conscious Leadership, from her TedX talk in Boulder, CO.

My favorite takeaway is that people don’t change, no matter how much you want them to. But they do grow.

People are who they are, and there is a positive side of each person, where she is open, conscious and loving, and a negative side, where she is shut down and protective (defensive). The best we can hope for, from ourselves and from each other, is to live as much of our lives from the open and loving version of ourselves as possible. To bring consciousness to each moment, so that we can catch ourselves when we react out of ego defenses and, again and again, open up to the moment.

The good news, according to how science tells us habits work, is that the more we do this the easier it becomes.


5. Finally, Laura sent me this article, in which Tim Ferriss, author of The 4-Hour Workweek, gives 11 reasons to not become famous. Some of them are very creepy.

I’m a long way from famous, but I’ve certainly wanted to be at points in my life, so his perspective was enlightening. Food for thought for any entrepreneur whose business success requires a large audience.

I agree with Jim Carrey:

“I think everybody should get rich and famous, and do everything they ever dreamed of, so they can see that it’s not the answer.”

Whatever you think you need, whatever business success or career growth or peak experience, it’s not the answer.

I needed 10 years to figure that out. Sometimes we all need to learn the hard way.


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