Saturday Cup of Joe from Detroit


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Source: Pure Detroit on IG

I spent some time this week thinking about this question — “what would have to happen for me to be ok with the police killing my daughter?” My daughter is 7 years old, so admittedly, it’s unlikely right now. At the same time, it’s a helpful question — what would have to happen where I’d understand that the police needed to shoot my daughter in the back?

Have you thought about it?

What’s your response?

When would you be ok with your child being shot by the police?

This week was not the first time I heard a question like this, but it might have been the first time I listened. What I thought was meaningful about reflecting on the question was that many people’s (many white people’s) first response is — well, my child would never be in a situation like that. Not myyyyy child. That’s where assumptions and misconceptions begin. Those assumptions are systemic racism. The subtle, unconscious bias that says “it must be ok because….<insert the random fact about the man or the case that supposedly justifies police killings>…” is the problem. That’s the moment the Black Lives Matter movement is pointing to in white America’s mind that is unconscious (or, in some cases, conscious) racism.

My response to the police shooting of Jacob Blake in Kenosha, WI was there but by the grace of God go I. I realized just how fine a line it is in life between a normal day and a violent interaction.

It’s hard enough to navigate the human experience as it is before you layer on assumptions, misconceptions, racism and potential violence.

Why police brutality needs to remain a front-and-center issue for our society is not only how destructive it is to the trust and stability for all Americans in all our communities but also how prevalent it is. According to, there have only been 12 days in 2020 where the police did not kill someone. In fact, there have been 751 police killings in 2020. Obviously not all of them are murder, like in the case of George Floyd. The police walk around with the legal ability to kill someone every day. Every interaction with the police involves at least one deadly weapon because the police are wearing a deadly weapon and bringing it to every interaction.

So, the question should not be “what did Jacob Blake do?” The question is what circumstances should be true for the police to be allowed to kill you or me or Jacob Blake?

My goal with the Saturday Cup of Joe is to ask better questions and hopefully bring something interesting, valuable or curious to your week. My goal with my writing, my leadership and my life is up my game and ask more provocative questions that drive meaningful change in the lives of those around me. Merging these two in the Cup of Joe has had starts and stops over the years but feels more natural than ever before.

I believe now is the time to be asking better questions and demanding better answers. One of my favorite mottos, in fact the one I’ve made my personal mantra, is answer well. Answer well to every questions, every challenge, every opportunity in my day.

There is nothing more precious than life and recognizing the value of everyone, all people in our communities. It felt like much of the debate around police brutality glossed over or took for granted the humanity of everything we’re talking about. When a 17-year old walks into any community and murders someone on the street, he’s completely lost fundamental values and the value of humanity. Glossing over the horror, finding justification for police brutality and killings (even if legally one exists today), refusing to address painful history of violence, all diminish the humanity we share.

There but by the grace of God go I.

This week I’m asking the question: What would have to be true if … ? As my way to answer well.

What’s your question going to be?

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Mexican sunflower with bee.

“We are seduced by the idea that not liking some element of reality is powerful enough to will it to be different.” — Ryan Holiday

In reality, facts dictate facts. A post titled “Hard Facts” that Ryan sent out to his subscribers this week dove into some perspective on how many people are reacting to COVID-19 and police brutality and other controversial topics in today’s world.

Yes, it gets a little political but I didn’t read it as politics as much about how we approach everything we filter throughout the day — news, articles, posts, conversations. This week was a lot of politics and so it makes sense to start there.

Secretary of State Dean Acheson once observed about the presidency, “there are no easy choices. All are between evils, the consequences of which are hard to judge.”


Because the Presidency is, in fact, where the buck stops. On my team we like to say escalate the hard problems, escalate the difficult choices, make the leaders do their job. It’s true for me leading a business area as it is for the EVP leading 700 people or a CEO leading 20,000. It’s not always a science — knowing when to decide versus when to escalate. Therein lies the rub.

But that does not mean we should let leaders off the hook. Jocko Willink writes about “leading up” when dealing with your boss or leader. Too often, we’re letting the leader set the ground rules or determine when we were right or wrong for escalating something. Not so.

Instead (and this is especially true for the President of the United States), we should demand clarity and decisiveness when we’ve escalated a problem. President Trump acts like if something “didn’t reach my desk” that somehow absolves responsibility. Not so. Every CEO in America knows that if it happens inside the organization, it’s the CEO responsibility regardless.

If we escalate tough choices and receive clarity, that clarity can still be ownership. The CEO can turn around and say, “No, I’m empowering you to make this decision.” Even the better as then we know we’ve been given the authority to act.

Over time the team that escalates everything will sabotage their authority and limit future opportunities. The team that escalates nothing will ultimately miss a critical decision point or piece of information that leadership needed to make a better decision.

The right balance is where all the action lives.

This fact should be inspiring. We should be looking for leaders, CEOs and, yes, Presidents who understand and own that dynamic, nuanced and hard fact of life.

Imagine working for a CEO who only ever told the company how scary and dangerous the customers are or how evil the competitors are. If you don’t do your job, we’re going out of business in 3 months! Yikes.

Don’t misunderstand me. This does not mean ignoring data or avoiding bad news. Quite the opposite.

For a while, when we were working in offices, Jay Farner (CEO, Quicken Loans) had a sign hanging outside his office that said “Bring in your problems, but don’t enter without a solution too.”

I find inspiration in reality, in the hard facts. It can be frustrating and include significant time & toil. But engaging the the problems and solutions as objectively and realistically as possible brings us closer to optimal solutions. Though I know we’ll never get there, the closer the better, am I right?

Embracing the messiness of data. Embracing the difficult, gray areas of the challenge or of life frankly is where the action is. That’s where the fun is.

If the problem already had a solution, it wouldn’t need to get to the CEO or the President of the United States. But just because it’s hard, complex does not mean we abdicate our role in the solution. And it certainly does not mean allowing the big boss off the hook. It means engaging. It means challenging. It means bringing solutions.

Bring the solutions this week.

Systemic racism is unconscious bias: Bloomberg highlighted the disparity in black venture capitalists in a strong article this week. For me, this felt very much like how unconscious bias materializes in our businesses. The best example is “fit” as a category or descriptor when hiring. Often, someone will say that a candidate is “not a good fit” for the team. Pushed harder hiring managers will reveal that those candidates who are a good fit are candidates that remind the manager of themselves. You recognize something familiar in the candidate and that translates to chemistry or “a good fit.” Diverse backgrounds whether in race, gender or life experience do not signal the familiar and are called a less optimal fit.

That unconscious bias in hiring rings true in the way VCs in the Valley say they “just couldn’t get excited” about a product or idea.

The U.S. population is 13% Black, and just 4% of the VC industry is African-American, according to 2018 data from the National Venture Capital Association — compared with 3% two years earlier.

Representation is not there and so VCs do not see the “fit” of the founder or market or both.

Also from the article, a black female VC named Sydney Sykes said “Black-led startups don’t gain backing because, in general, they haven’t achieved category-defining successes and are viewed as too much of a risk.”

So what are we going to do?

Use a framework. Evaluating founders, start-ups, and presentations using the same framework each time will help avoid subjectively reacting to ideas. Consistent process is one way to ensure everyone is given a real look.

Invite more perspectives to the table. Be intentional about bringing in differing views and life experiences when making decisions.

Ask better questions. As I said above, I want to constantly ask better questions. So, be direct with your team and ask — what are we overlooking? What are our misconceptions or assumptions that can be challenged?

These steps can work for any evaluation on your team even if you are not a VC or investor.

Source: Detroit.history on IG

All Suburbs are not created equal: The Wall Street Journal published a defense of the American suburb. The authors — the president of the United States and Secretary of HUD — describe a romantic view of the suburbs as if the suburbs are a monolithic thing. The problem is they got it wrong. In reality, the American suburb is not one thing. Fear and threats have always been used to attack cities and/or gain political support. This is nothing new. What’s new or gaining momentum is the way we study housing and cities, in particular. Data collection and data analysis improves. Sharing information across the country informs trends.

For instance, the Brookings Institute responded to the op-ed with a more nuanced picture of how we live in today’s America. “When Trump and Carson vow to protect a ‘shining example of the American Dream,’ they’re talking about single-family residential neighborhoods, a form of suburbs that have already proven adept at protecting themselves. Although single-family neighborhoods have been on the rise across metropolitan America over the last few decades, they still represent fewer than one in five suburban neighborhoods. While we may not be building as many of them these days, duplexes, triplexes, fourplexes, and other kinds of apartments — yes, even the occasional high-rise — already exist in most suburbs.”

In my theme of this week’s Saturday Cup of Joe, ask better questions, I thought this was a helpful framing of an issue likely to be at the heart of Trump’s reelection campaign. As Dan Rather tweeted this week, the Donald Trump reelection strategy appears to be that only Donald Trump can save us from Donald Trump’s America. This tells me that a central theme of both campaigns will be “your way of life.” One campaign pointing to all the things threatening our “way of life” and offering the cure. The other campaign vilifying the first campaign for using threats and fear. Since home is such a fundamental component of life, you’d think housing would be a more central political issue. It’s really not.

The Biden campaign issued a housing plan and Trump’s op-ed points to his positions on housing but it’s generally not something that gets the attention of healthcare or immigration or jobs.

When I think about celebrating suburbs or diminishing certain cities (or all cities!), it’s as dangerous as generalizing across people or people groups.

Instead of highlighting “big, beautiful suburbs,” we need to be talking about how stability results in opportunity, specifically economic opportunity. If everyone is well housed, our communities are more stable. Stable households learn better, spend better, live better. Yet we are so quick to credit the infrastructure — the suburbs — with stability but blame people — individuals — for instability.

Stability is stimulus. Public safety is stability. Housing is stability.

Stability is good for communities, for business, for everyone.

“No person has the power to have everything they want, but it is in their power not to want what they don’t have, and to cheerfully put to good use what they do have.” — Seneca, Moral Letters, 123.3

Bonus Content: My guest appearance on ClearCast podcast with Kenon Chen and Jeff Allen of Clear Capital

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As seen on Twitter this week.

Continued success and continue to answer well,

Written by

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

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