Integrity systems: the theme behind sustainable success

Plus Right Action, "Should I raise money?" (the definitive infographic) and more...

Whatever you’re doing this Friday, wherever you’re going or whatever box you’re checking, I invite you to take a moment, just now, and stop doing it at all.

I’m excited to share with you my favorite news, analysis, insights and advice about leadershipentrepreneurship and Work (capitalization intentional) from this week.


1. “It’s on my list, and when it’s on my list, that shit gets done.”

An accomplished entrepreneur and leader doing me a favor this week did me a second one by illustrating the foundational difference between struggle and sustainable success.

Every consistently successful person I know (success being defined as attainment of one’s goals, whatever they may be) has a formal system to manage their integrity with themselves. This founder, he wouldn’t put anything on his list until it reached a certain threshold of importance, but once it passed the test and got on the list, you could actually see him lock in. The task, no matter how insurmountable, was toast.

Integrity, or doing what one said one would do, is not limited to the things you tell other people. In fact from my perspective your commitments to yourself are arguably even more important. Getting good at keeping my word to myself changed my life.

My integrity system is verbal. When I give my word, verbally commit to something, it’s as good as done. I think things all the time and don’t take those too seriously (since I’ve long since learned I don’t control my thoughts). I even put things on my to-do list which never get done. But once I say, out loud, that I’m going to do something, it’s on my list. That’s my system.

Everyone’s system is different, but every consistently successful person I know has an integrity system. The integrity system is the foundational tool you need to start a business, build a culture, a relationship. Anything.

Armed with an iron-clad relationship with your word, you need only speak your dreams and watch your life change.


2. Right action can lead you to be the CEO of a publicly traded company, and get investigated by the FBI

I finished The Surrender Experiment, by Michael Singer, recently, and have recommended it at least five times since then. Particularly to business people who are struggling, as I did for a long time (and sometimes still do), to let go of results and simply be content with taking the right action.

“Connecting actions to results can be useful, but it’ll break your heart.” — Parker Palmer

For the first decade of my startup career I lived and died by results. Beat monthly numbers: I’m a good CEO, worthy of this job and quite probably should have gotten a larger raise last year. Missed monthly numbers: I’m worthless and should be fired, and had better lock myself in my office and pound away so that maybe the board can be convinced to not fire me even if only because I am willing to outwork other candidates. Closed a fundraising round: on top of the fucking moon…and then a pit of dreadful obligation settles into my stomach.

I didn’t start to really get a handle on this whiplash until the last couple years. Part experience—surviving through a few WFIO moments has a way of turning the volume down on some of the smaller things—and part the result of a concerted focus on detaching from results (meditation helps). I found that I began to level up as a CEO and leader, becoming that steady boulder in the middle of the storm, to the degree I was able to take the right action without my self-worth being attached to whether or not it produced the result I wanted. “Good work, done well, for the right reasons” (to use Jerry Colonna’s paraphrasing of David Whyte), a phrase that always makes me think of the Buddhist term Right Action, which I blogged about extensively here.

Part of what took me so long was a concern, exacerbated by much of startup culture, that if I truly let go of results my results would suffer. Singer’s book blows a hole in that theory, as he went from a yogi living in the woods to a CEO of a public company being investigated by the FBI (he was exonerated), all by simply doing this:

My practice of surrender was actually done in two, very distinct steps: first, you let go of the personal reactions of like and dislike that form inside your mind and heart; and second, with the resultant sense of clarity, you simply look to see what is being asked of you by the situation unfolding in front of you. What would you be doing if you weren’t being influenced by the reactions of like or dislike? Following that deeper guidance will take your life in a very different direction from where your preferences would have led you.


3. Should I raise equity capital?

As I’ve started to come back into the startup world from my much needed sabbatical, I’ve begun meeting with entrepreneurs more and more often. The question I’m most often asked, winning by a landslide against all other questions, is “should I raise (equity) capital?”

Rather than answering the same question in conversation after conversation, I figured I’d write the answer down. Only, when I wrote it it came out as an infographic. So, if you’re asking yourself whether or not you should raise capital, please refer to this infographic for my perspective, after 10 years and $21m experience, on your answer.

(Also, if you’ve raised capital in the past, I’d love your feedback on how this tracks to your experience as well. Email me back or post in the comments, and I’ll try to incorporate other perspectives into a revised version I’ll release publicly at a later date. Right now this is just for subscribers.)

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4. Usually when I look back at myself from years ago, I’m embarrassed. I usually take that as a good sign, in that I’m changing and growing and becoming more valuable with age. Like a fine wine, or deadstock sneakers.

But sometimes I’m impressed. 24 year old me knew something that I’m still trying to learn now:


5. The question we technologists should be asking

I read what I think is a pretty important piece in the Wall Street Journal about technology and income inequality in the time of COVID. Short version, it’s bad, policy is making it progressively worse, and COVID is making it much worse.

Couple highlights to provide context:

Technology + capitalism = concentrated wealth and influence in an increasingly fewer number of hands. *COVID. The evidence suggests this is just math.

The problem I see is the fatalistic attitude most people take to this math, and the way that attitude lets us off the hook.

We don’t have to simply accept this as inevitable. We are innovators. We are entrepreneurs. We need only the right question, and we can solve anything. Yes, we use technology and many of us want to make a lot of money through our businesses. But we can use “avoiding unacceptable toll on humans” as a design constraint, and I think the world, and we, would be better for it.

One question we could be asking is: Given the technological changes that will inevitably happen (Moore’s law, etc), how could we design work and wages so they don’t have these inequality consequences?


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