Saturday Cup of Joe from Detroit


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Week 220 in Detroit. It was a productive week and as a result, a fast week. I did not have much time to keep up with the news or my usual free time activities. This summer, other than spending time with my wife and daughter, those have mostly been swimming in the pool, walking the dogs and listening to podcasts. The podcasts are mostly while trying to keep up with the yardwork. I don’t remember this much work last Summer. I either put it out of my mind, didn’t notice last Summer or the combination of rain and heat is just creating more yardwork than ever before.

Since the peaceful march across the MacArthur Bridge in Detroit, our family has not been able to participate in any more demonstrations or protests. We watch closely our city and others, like Portland, to understand what’s happening and to try to make sense of the response. This week we heard federal agents were being deployed to Detroit. My immediate reaction was one of overreaction. I could not understand the headline or the specifics of why that might be happening. In fact, I thought it was likely to do much more harm than good in terms of sparking or creating a more volatile situation.

In another sense, it felt that urban violence in many cities, like Detroit, was suddenly being intentionally manipulated by politicians who stand to benefit by making cities like Detroit appear more dangerous and unsettled than we are.

A provocation that would retroactively justify the narrative.

I still believe that is a threat here in Detroit.

There’s a scene in The West Wing where the First Lady, Abigail Bartlet, goes on the morning news to talk about child labor with a boy who started his own awareness campaign. The White House Deputy Communication Manager, Sam Seaborn, tells her, “Ma’am, there was no problem with the interview. Except it looked like you discovered there was a child labor problem because a fourteen-year-old boy named Jeffrey just told you about it this morning.”

It feels a little bit like an existing problem with violent crime in urban America is just now being used, for political reasons, as if it’s suddenly a problem.

If I’m not allowed to overreact when I hear the news of outside federal agents coming to Detroit, you don’t get to suddenly (over)react to urban gun violence cause it fits your narrative of good guys and bad guys and overwhelming force. Though, as I’ve been told many times since beginning the Saturday Cup of Joe, my desire for intellectual honesty is destined for frustration.

Feels a little like advice my Dad used to give, in the form of a question, “Do you want it done or do you want it done right?”

And so it goes…

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I was listening to a podcast earlier this week with Jocko Willik where Jocko talked about leadership from the perspective of the US Army field manual.

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Once concept Jocko highlighted is the “decisive point.” The decisive point is the moment in the plan where most inflection is possible. Also, read as the brink of success. If the objective goes one way or the other at this point will decide the outcome. The leader visuals the entire mission from the decisive point.

How are you thinking about the decisive point in the context of your year? Your team at work? Your career?

Have you considered the point at which your plan will be on the brink of success but not yet success achieved?

Jocko uses the jujitsu example where a player knows they’ve achieved the winning lock leg or arm bar but the match is not over. There is still the inevitable end, but the player knows the decisive point has been achieved.

As a leader, how are you looking at the decisive point and working backward from there to achieve a successful plan?

Planning from the decisive point in business is hard because it requires so much assumption of the variables involved, but just like the uncertainty of the military, if you cannot see a clear path to victory it’s a recipe for a war with no end.

Clarity will strengthen your work even if it ends up needing to be revised again and again as your business is an on-going practice and not a winnable war. My point is only that each engagement or way of thinking about planning and leadership should be working towards a decisive point and then another and then another. To build long term success is a series, however long, of increasingly ambitious decisive points.

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I recently heard a new take on that (now old) philosophy — you get what you measure — which is — you measure what you value.

You measure what you value.

That’s why it makes sense to hear the Dean of Wharton Business School at the University of Pennsylvania, Dean Erika James, say that the reason there is not more diversity in corporate leadership is the lack of priorities.

Q: Why has the business world been so slow to embrace diversity?

A: “I think if we can create social media platforms, if we can put people on the moon and if we can have self-driving cars, there’s very little that we can’t do,” James said during an interview on All Things Considered. “So the fact that we have not yet created a more diverse work environment means that we simply haven’t prioritized it.”

What I heard in Dean Erika James’ interview was the sentiment that we can do whatever want inside our teams and our organizations. We just have to value it and we have to prioritize our values.

Too often, value is diminished. Value is minimized.

Value shrinks down to a dollar-for-dollar evaluation of quarterly return.

Broadening our definition of value to include long term return as well as the quality of the process includes more perspective. Whether it’s internal diversity & inclusion goals or external environmental, social or governance goals, the entire outcome hinges on definition of value. For instance, the Department of Labor (DoL) issued a rule prohibiting ERISA investors from making ESG or other purpose-driven investing if it “sacrifices returns.” Here’s the exact quote describing the rule from Secretary of Labor Eugene Scalia, “remind[ing] plan providers that it is unlawful to sacrifice returns, or accept additional risk, through investments intended to promote a social or political end.”

This is quote is lazy and riddled with assumptions.

The whole theory behind the rule assumes that investors are a). sacrificing return for purpose and b). the only way to deal with it is a federal rule. It’s lazy because the rules should be about investors making it clear to shareholders what they are investing in and why NOT making it unlawful for investors to make decisions that are clear and disclosed to shareholders. This rule is short-sighted and cynical.

For starters, there is proof that ESG investing does not limit shareholder value. In fact, ESG designation is often a sign to investors about the long-term value and long-term viability & sustainability of a company or an asset. In other words, companies creating ESG opportunities have a competitive edge over those that are not thinking about the future. Second, ESG investing tends to be based on cutting edge data in emerging industries and as a result, old (boring!) credit models do not update fast enough to account for it. In other words, companies create value by moving consumers and markets to where the economy is headed not where its been.

The bottom line is that the fiduciaries should be responsible to those invested to execute on the best interest and stated strategy of the fund or investment. Why do we need the Department of Labor involved there? This is not some shareholder protection rule. This is an attempt to control fiduciaries and limit values-based investing instead of letting the market — fiduciaries, investors and shareholders — determine for themselves the definition of value.

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The definition of value often boils down to the age-old problem of perception versus reality. The perceived value of the future often exceeds the actual value of the present. Tesla is worth more than Bank of American and American Express combined — perception versus reality. In the auto industry alone, Tesla is worth more than Volkswagen, GM, Honda, Fiat Chrysler and Ford combined.

The market values above are real but are they based on perception?

I’m thinking about the perceived value of a lot of things these days — being in the office, business travel, and even serendipity. One of the top reasons that keeps popping up as to why being in the office or being in a specific city is important is serendipity. The idea that by being in Silicon Valley or, by extension, San Francisco, success is more likely.

In fact, Meredith, my wife, and Rob, my friend & colleague, sent me the same article about the perceived value of Silicon Valley. It’s an incredibly well written defense of serendipity. But, unfortunately, it over values serendipity. The perception is that by being available for coffee or the random introduction on the street outside Stanford, a founder who otherwise might not have been successful will get funded or meet the co-founder.

Don’t get me wrong, I believe in the idea that one needs to increase the surface area of which luck can stick.

At the same time, I do not believe that means I have to live in SF to launch my own company. In fact, I would agree that my path to my own company is more authentic by not pitching it as a Silicon Valley start-up.

No one knows exactly what such a new system might look like. And there is a risk if we don’t get it right. History’s creative hubs have been ephemeral.”

This may be toward the end of SF’s “required” status as the epicenter of tech and entrepreneurship.

Just like working from home created distance between my team and the office drama that can often hijack a day, being outside the Valley or working from home can actually improve the business plan AND the pitch.

So, beyond being unsustainable, the Valley is also overvaluing serendipity as a component of innovation or success.

And that’s not easy for me to say.

I have long subscribed to the big break theory.

The big break theory is the idea that simply by being in the right place or meeting the right person, the opportunity will present itself.


The big break theory is characterized by attending too many events, volunteering for too many high profile projects and working hard to place oneself next to the right people (or perceived right people) in the right rooms at the right time.

It’s exhausting.

At the same time, I read articles like this one about Carlton McCoy and recognize that sometimes the introduction-turned-4-hour-conversation turns into a life-changing job offer. In this case, Carlton McCoy meets the billionaire Gaylon Lawrence Jr. at the Little Nell Hotel where McCoy is the director of the hotel’s wine program. McCoy got a big break because everything aligned.

After the curated experience McCoy set up, McCoy is hired to run the Napa Valley vineyard Lawrence just bought. As the first African-American CEO of a Napa winery, McCoy experienced the type of serendipity historically reserved for straight white men.

But McCoy is the diamond in the rough exception considering the rarity of the story and the historic discrimination that kept black men out of that type of room for so many years. Most big break stories are the exception but those are the ones we read in books or newspaper profiles.

So until we find equality of serendipity, the only thing left to do is focus on the objective value of an idea, product or business at an “emotional distance” from the work.

One thing my team found during our work-from-home strategy is that we are clearer on what we’re working on and why. Clarity and step-by-step work removes the need for serendipity.

Trust the process.

One founder and CEO that trusts the process is Matt Mullenweg. Matt runs a billion-dollar company called Automattic (owner of, Tumblr). Automattic has been fully remote from day 1.

15 years. Matt stands by the philosophy recognizing the benefits that literal (and emotional) distance from colleagues and coworkers can work. We don’t need to be in the office. We can return and there are some benefits but we can stay home and succeed, as well.

I think it requires leaders to be more specific about projects, outcomes and goals. With attention and intention, we can trust measurable value and methodical process. Process over serendipity.

I think what I’m trying to say is this -

Let’s not mourn the loss of serendipity in one area of life, let’s go find it in others. The loss in Silicon Valley just means we have to explore, adapt and experience it in other areas and in other ways.

So let’s goooo…

Quote: “Skills direct behavior in a known situation. Attributes direct in the unknown.” — Rich Diviney

Bonus Content: How Remote Work Divides America

Continued success and continue to answer well,

Written by

Thinker, curious leader, once an attorney…always trying to answer well.

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