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

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East Riverfront, Detroit, MI, USA

Friends & Colleagues,

Week 114. A week of meetings and writing and travel. Tess is learning to ride her bike, with training wheels, and loving it. It’s amazing to watch “summer” through the eyes of a kid. It’s ice cream and pools and demands to stay up late.

One thing I attempted over the last week or two was selling some of our items otherwise stored in the basement. A tv stand. An old saxophone. I also sold my childhood baseball card collection. It was an oddly difficult moment. I had already taken the entire box to a local card collectibles store to ask for an estimate only to be told it was not worth anything to serious collectors. Apparently everyone my age collected baseball cards. The market is flooded with 80s and 90s players. Luckily, I found someone on Facebook marketplace that buys up baseball cards for his son. Even though I had no idea how or why I would have kept them, I still had some residual urge to hold them. Ultimately I sold them, happy to have “given” them to another kid.

Do you still have a collectible from your childhood? What’s your plan?


Are you going to be watching the World Cup Final this weekend? Hopefully the final game lives up to the amazing tournament we’ve seen so far.



Have a great, productive weekend.


What’s next? Cannabis? Cannabis capital? Benzinga, the tech investment site, is hosting a cannabis capital conference in Toronto and rolling out more and more content on the business of cannabis on the site. Check it out. Here’s the link to Benzinga’s Cannabis Conference. Here’s a link to the content.


List of the best hotel in each state? Impossible to resist. How many (if any) have you stayed in? I’m at 2. Long way to go, Meredith.


On writing: Strong verbs, short sentences.


On gentrification (in Chicago but really everywhere): This week the Chicago Tribune published an editorial outlining Chicago’s gentrification problem and highlighting the mayor’s efforts to address it. As Detroit struggles with the same issue on a smaller scale, I have been thinking a lot about this. The question is the same across the #NextBelt: will policy be able to address “the exclusivity that’s creeping into more and more neighborhoods”?

Can subsidized development funding with requirements on affordable housing units (20%) locked in for a period of time (15 years) get traction?

How does transportation play a part in gentrification?

The NBA has a luxury tax on teams that exceed the salary cap. Could a city like Chicago create a luxury tax on developers set on high-end housing that could be put to use for city residents elsewhere?

In Detroit, we want to keep the neighborhoods’ existing residents while building dynamic, diverse communities at the same time. Chicago is taking the challenge head-on, and we’ll be watching.


Artificial intelligence: Interesting in this essay on “machine learning” is the human intuition that initially programs these machines “to learn.” For instance, Google programmers respond with Western ideals. Russian programmers with “hard truths” and “tough love.” Where does it get complicated?

According to the article, “relationships are things into which we must ‘invest’; partnerships involve a ‘trade-off’ of emotional ‘needs’; and the primacy of individual happiness, a kind of affective profit, is key.”

The fear is the value judgments implicit in the programmed responses. These interactive artificial intelligence agents can “reiterate stereotypes and clichés about how emotions should be treated, mood-management apps go a step further — making sure we internalize those clichés and steer ourselves” upon them.

One of the most interesting aspects is whether the programmers are ever able to adjust or account for all inputs. Even if “we” could program without implicit emotions, what would they be able to learn? And how?


“You’re more likely to act yourself into feeling, than feeling yourself into action.” — Jerome Bruner, Harvard psychologist


Answer well: Peter Theil has a theory called the “steel man.” Instead of imagining his opponents’ weaknesses, or even the most likely outcome, Theil imagines his counterparty in the strongest possible light and then determines if he can still “win.” Similarly, one way to approach problems is inversion thinking. The process of thinking about what you want to achieve in reverse or thinking about what you do not want to happen. Focusing on “opposite solutions” creates preventative methods for solving or at least dealing with your problem. What techniques or ideas do you use to look at problems in a new way?


On work: When in doubt, pay ’em. Vermont is putting its money where its “mouth” is and paying people to move there. Remote employees. Keep your job, move to Vermont, collect $10,000 in first 2 years. Any takers? I recommend Waterbury, Burlington or South Hero.


Gotta see this: a data visualization of the orientation of America’s city streets. Here’s a link to the story about the author.

By Geoff Boeing


I heard someone quote Dan Gilbert recently as saying, “time is the great equalizer.” He obviously didn’t invent the concept or anything, but it’s a valuable insight. We all have the same time in a day — 24 hours. How do you think about your day? Your time?

“What you do today is important because you are exchanging a day of your life for it.” — Unknown

It’s a profound statement. What are you exchanging right now?

Annie Dillard writes, “How we spend our days is, of course, how we spend our lives.”

Thomas Oppong writes, “busyness is a decision.” But I’d take it a step further. Everything is a decision. You are required, actually physically required, to do almost nothing anymore. The consequences of refusing to do something can be steep in some cases, but you can ALWAYS decide to do or not do everything in your life. Why don’t we think of more things as a decision? Why are we so passive?

Is it our nature that we have to overcome? If so, how do you think about it? Do you attempt to overcome it?

The amount of time may equalize; but the ability to decide how to use it differentiates. How will you differentiate yourself this week?


Future of work: I tend to watch the “future of technology” columns and interviews closely as a personal curiosity. There are three general narratives — 1). Robots are taking our jobs 2). Computers will someday turn on us 3). Artificial intelligence is the next logical step in human progress. What is often left out of these is the moderate view — the future of work will be integrated human and computer experiences that play to the strengths of each participant. It’s almost at the level of being a “4th general narrative” in my book but not quite there.

One valuable lesson for me out of the whole practice of reviewing this stuff is that my ability to synthesize information, ask the right questions and make quick, accurate decisions will determine my success regardless of technological advances. In short, how well do I still learn and apply what I’ve learned? I don’t know why, as leaders, we don’t refer to our value as learning. Fundamentally, we take new information, apply it to an existing reality, and alter our behavior or actions according to the result.

This New York Times blog post captured it well (but still didn’t apply it to business). “Understanding how the brain processes, stores and retrieves information can also improve your study habits.” To me that means improve my recall, improve my ability to synthesize.

Bottom line — signal to the brain something is important information, space out the learning to allow it to soak in and be sensitive to optimal intervals or optimal contexts (sounds, locations) for learning.

Oh, and as with everything else, get a healthy amount of sleep.


As seen on Instagram.


On Death: Montaigne posed the same question somewhat differently in his magnificent meditation on death and the art of living: “To lament that we shall not be alive a hundred years hence, is the same folly as to be sorry we were not alive a hundred years ago.”


On Grief: I do not know, fully, why I am compelled to share this essay by a writer who lost his father at age 4. Well written. Insightful. Creative turns of phrase — “death and breakfast.” Not sure where you are at in your experience here, but perhaps this will touch you too.


Today’s thought: Clouds and dirt. Gary Vee made a Youtube video titled “Clouds and Dirt” about how to keep your ambition high (clouds) and your actions grounded (dirt). The theory caught on and Gary Vee even designed shoes on the theme. Mine arrive this weekend.

I took this “clouds and dirt” idea and made it my own. For me, it is less about maintaining my ambition while staying grounded. Instead, it’s about strategic thinking (clouds) and practical results (dirt). I need to be able to see the whole field and operate at a sophisticated level but can never lose sight of the goal — driving actual business. Real customers. Clouds and dirt. How do you maintain your hustle? How do you fuel your fire? What imagery works for you?

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My new shoes.


Quote: “You can’t connect the dots looking forward. You can only connect them looking backwards. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down and it has made all the difference in my life.” — Steve Jobs

Bonus Content: A story about the threats to narwhals and an interesting concept known as “geographic bottleneck.”

Continued success and continue to answer well,

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

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