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Saturday Cup of Joe: a lending and tech(ish) newsletter from Detroit

Friends & Colleagues,


Week 152. This week’s edition of Saturday Cup of Joe was almost called the Decaf Cup of Joe because I spent much of my week on the road and much of my Friday night talking to my father and mother in law that I almost didn’t send it out.

I spent much of the week on the road including meetings in New England and DC. This week was spring break for Michigan schools or at least Detroit schools. My daughter, Tessa, had off. Luckily my in-laws came to stay with us this week and spend time with her. It was extra hard traveling knowing everyone was at home having so much fun.

When I got home late Thursday night, I didn’t really get a chance to do much beyond head to bed. That’s why on Friday night, I didn’t want to duck behind my laptop. Instead we got into a long political and cultural debate. Man, was it fun. I found myself deep into the American story, fairness, The Constitution, personal responsibility and the power of the press. We covered it all. In some ways I’m bummed we didn’t record it because I think I’d like to see more ideas out in the world (thus this newsletter) than battle over fewer.

It’s not easy to talk about politics anymore even with your own family. Everyone is on edge. We decided to push right through and get into it. I highly recommend it. Let’s get more debate, political or otherwise, out there. More voices. More views. I think at one point I may have called it “the arena of ideas.” Yup, pretty sure that happened. Oh man. My idealism on full display. It was fun.

This weekend is also my time to revisit some disciplines and commitments I made in my business around the new year. It’s the end of the first quarter and how are you looking on those 2019 goals? Might be a perfect time to consider a simple question — what are the 1 or 2 things I can do to address my Q2 or annual goals? Am I doing them? Why not? If you want to hit a mark in Q3, you have to take the steps today. More on this in a minute.


Passionate. Thoughtful. Provocative.

Excited to see my friend Mike Pieciak, Commissioner of Financial Regulation in Vermont, recognized as one of the leading Millennials working in public service and public policy today. Check out Mike’s accomplishments in this article. Congrats!


This week felt like a week of reminders and lessons. Reminders of how quickly priorities can overwhelm each other or “important work” can pile up. Despite my year end reflection and new year planning revolved around ensuring I had a limited number of really important focus areas, invitations and other ideas came to bear over the last few months. I found myself pulled into more “priorities” and spend part of Friday afternoon and evening thinking about what are the small amount of key initiatives I should be driving. Again, this is a practice I did not even 90 days ago and that’s just how quickly things can re-prioritize. For better or worse. In this case, doubling down on discipline and focus is key. I’m also using it to add something to my calendar to review my time management more regularly. Monthly?

As I think about this over the weekend and prepare to restructure my time next week and going forward, I came upon a smart look at how to make change happen. Trick yourself. Create a milestone, add it to your calendar and then treat it like a fresh start. I’m trying this tomorrow, 4/6, which is not a birthday, new year’s resolution or other. It’s just a reboot on my time management, priorities and travel schedule.

A (new) point of view: In a thought-provoking interview in CityLab, author Samuel Stein traces the evolution of urban planning in the midst of a real estate investment boom. The outcome, he proposes in his book, is a direct correlation or co-opting of urban planning by investors leading (directly) to gentrification. For example, Stein notes “It’s definitely getting harder for planners to be responsive. In the growing concentration of money in real estate, planners are becoming less responsive to everyday people, and they don’t have a separate group of capitalists, industrial capitalists, barking at them for an entirely different set of demands.”

This progressive perspective made me think of a conversation I had in DC this week that ended with the question asked of the group — “what type of world do you want to live in?”
It made me wonder if we shouldn’t be asking this question more often.

Back to the interview, later on Stein speaks to other urban planners saying, “I would encourage them to always think critically and not get discouraged. I think there’s a strong pragmatic strain in planning, which can be valuable, if it’s about translating radical ideas into an actionable program. But it can also be a dampener on radicalism and visionary thinking, and even utopianism, which is useful too in knowing where we’d want to be if we could…I encourage people to hold onto those impulses, and to find others who think the way they do, or who challenge their own thinking. In isolation, the system swallows us, but collectively we can imagine a better way to do urban planning and connect to the social movements that are challenging them.”

Though Stein is speaking of urban planning’s battle with real estate development, I couldn’t help but take away a few key phrases that I want to remember in my business.

“translating radical ideas into an actionable program” (interesting take on innovation, no?)

“find people…who challenge their own thinking”

Hope this was thought-provoking and challenging to your thinking in some way.

Washington DC. This week.


Kara Swisher gives up her car. This may not be shocking to you. For starters, you might be thinking “who is Kara Swisher?” Or, perhaps, “why do I care?” Finally, “is she really selling her Ford Fiesta because I could kinda use a new commuter?” It also might not be shocking if you know Kara Swisher because you might be thinking, “She still had a car?”

Spoiler alert, not that shocking either way.

Kara Swisher is the tech writer and Silicon Valley insider who also “cut the cord” in 1998 a few years (decades?) before it was cool. Also, when it meant something else like actually getting rid of a landline. But her cool factor is not why you should care. You should simply consider what this means or could mean for your own experience? Your area? Your business? How can you capitalize or prepare to capitalize on this trend?

Many of my readers are in real estate, real estate investing or mortgage finance. Invest in more densely populated areas? Move to less densely populated ones? It might just be another column to fill inches in The New York Times, but it also might be the future. How are you thinking about these trends?


Gig economy, what gig economy? As much as things change, things stay the same. I wrote recently on the lack of yeast in numbers of tax fillers and other working adults reporting multiple forms of non W-2 income and/or other alternative forms of income. (“Lack of yeast” is a TV reference that I’m confident Meredith and Michelle will both recognize, anyone else?) A follow-up report went further to wonder if we’ll actually see the growth promised in the gig economy. This Planet Money article focuses on the lack of other gig opportunities and on “the strength of the firm” as possible reasons.

I actually see something else. I tend to think (hope?) that Uber and Lyft drivers or Airbnb hosts are a red herring for a deeper trend. These are the first public examples used, but not the most disruptive form. Freelance and consulting are the most disruptive to traditional employees and employers alike. Getting smaller, hyper-focused and measurable results from different people more often is far more threatening to traditional employment than utilizing your car for income around or between other employment.

The mindset or, better put, the evolution of the mindset on the part of employers is what will ultimately be disruptive.


Downtown Detroit. In iron.


This article asks who is to blame for the cost of American higher education. I ask — chicken or the egg? Did cultural trends that demanded both more access to a degree and more comfort while doing so create bloated college spending? Or did the financing of the education feed the beast? I can’t begin to trace all the different factors involved here but the history of many aspects is interesting and informative. So I’ll just leave this here.


Should we regulate technology like we regulate cars and driving? It is the information superhighway after all.



Today’s Thought: The presenter asked “what is the definition of a hero?”

“Ordinary person doing an extraordinary thing.” An audience member called back.

“How dare you call yourself ordinary?” Kevin Brown responded.

I was grateful to be in the audience to hear Kevin Brown remind me and roomful of people that being conscious, sensitive, thoughtful and responsive to others is not ordinary. In fact, it’s pretty damn rare. Remember to not be ordinary. Give of yourself to those you love and serve with no expectation.

Be a hero.


Quote: “Consider.”

Bonus content: Do you believe in the Illuminati? How about the moon landing? FiveThirtyEight published a post on conspiracy theories and the scientific research surrounding them. I love a good story so I’m not looking for conspiracy theories to go away, but I was struck by the proposed solution. Empowerment. A person’s sense of control over their own outcomes was a key factor in their beliefs.

Continued success and continue to answer well,




where the future is written

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Thinker, curious leader, once an attorney…always trying to answer well. Working on what’s next and next and next.

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