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

Friends & Colleagues,

SCOJ#97. March Madness is upon us. In case you haven’t seen last night’s highlights yet: History was made Friday night. University of Maryland-Baltimore County will go down in history. The (golden) retrievers beat the UVA Cavaliers in the first ever 16 over 1 upset. Anything can happen.

For those not into basketball (and of a certain generation), you might have been sent the Kanye Madness bracket over the last week or so. Yes, it’s the top 64 Kanye West songs battling for a single winner. I choose my bracket based on “greatness”, but many people choose simply based on their favorite song(s).

It reminded me of the love-hate relationship I have with subjectivity. Not to tip my hand, but let’s be honest, there’s really no objectivity. We try to be “as objective as possible” by removing emotion, adjusting for irrational impulse, including data, establishing standard baselines, whatever we can do, but it’s all in the context of our own set of experiences and filters.

We’re all just varying levels of subjectivity.

And that’s fine. That’s what’s interesting about new ideas, new people and new stories.

It’s also what makes getting anything done efficiently (truly efficiently) nearly impossible. There are so many swirling judgments and assumptions going on all the time that almost everything we do is reduced, changed, or altered by the time the other person processes it, let alone acts on it.

That’s why this week I’ve been working hard on thinking a lot about how to add value in any organization. People do not pay for good ideas. People pay for value. Move the needle. Eliminate obstacles. Activate. Entertain.

How do you think about subjectivity in your own business? In your decision-making? Does it even factor in? If not, how are you accounting for judgments and assumptions on your team or in your company?

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Detroit riverfront


You may notice the format is a little different this week. I’m trying something new. More pictures, for one. I Hope you like the change of pace and find value in the chance to go more abstract and self-reflective in this week’s articles (and questions).

I’m aware that it can be harder to find value in these types of topics, so I’ll do my best to offer practical and actionable value…and we’ll see how it goes.


Included this week: It’s all over the place. So, good luck!

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From below
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From above


Valuable Lessons:

Be deliberate.

Be intentional.

I had two experiences this week that I found profoundly important. First, I read an important reminder thanks to Claire Lew. Good leaders are not busy. The reality is of course leaders are busy. Not acting busy and not allowing busyness to interfere with decision-making: that’s the leader’s challenge. It is specifically my challenge. I am always overcommitting and raising my hand. For a curious person like me, it’s second nature. This is why it’s critically important that I try to limit “busy” as much as possible from my conversations, first, and my schedule, second.

Second, I had a realization that important conversations, deep conversations, and meaningful moments do not just “happen.” We like to think they do because it is more romantic that way. But true connections and true conversations are intentional; or at least the setting should be intentional. This does not mean that we artificially drive conversations a certain way but that we do intentionally create time and space for them to happen.

In the midst of some of these thoughts and articles this week, I found a long essay on “slow thought.” Having never heard of slow thought, I was attracted to this idea as a distinct and necessary response to the speed of today’s technology-driven world. Slow thought is a deliberate and intentional approach to allow the time and space for contemplation, conversation, and comedy. Your thoughts?


Crazy, weird, beautiful, abandoned island.


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A poem titled “Think Well”


Gatekeepers — these are the functions in the company that serve the employees, not the customers.

Legal. HR. Finance. IT.

As companies grow, startups once focused on speed and action become slower and more bureaucratic. Everyone makes assumptions about the gatekeepers. People begin assuming what the in-house counsel will or won’t be okay with.

Assumptions are killers within organizations and within relationships.

What can you do about it?


Be an agile thinker

Prioritize service over response

Create one-pager for the business that avoids legalese and dense responses


Avoid the last minute request for approval

Hold gatekeepers accountable on metrics

Create one-pager for gatekeepers similar to what you’ll provide customers


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Lunch on Friday, Parks & Rec, Detroit, MI, USA


The box sells the cereal: You can be successful and productive but not well regarded. You can also be right in fact and wrong in presentation / style and end up losing your audience on whatever point you were actually right about in the first instance. What holds a person back is how the work is accomplished. Perception is not reality, but it’s just as important. Less friction means a smoother experience. Over time, smooth experiences create success.

Consider this within your team, your company or your community: Avoiding friction does not have a unit measurement, but it does have a value. Even if you cannot measure it, begin with the confidence that others will feel it and even without knowing it, over time, they will favor the smoother colleague/boss/partner.


Quirky Content: Seth Godin writes a daily blog. I couldn’t help but notice earlier this week when one of his topics touched on this week’s theme. Well-intentioned, well-meaning, and even those who answer well can get there a different way or believe in a different process altogether.

In order to move beyond the tense, emotionally-charged conversations we’re currently having with those who disagree with us on political or social issues, we’re going to have to agree on two things. First, everyone is just a subjective bundle of their experiences filtered through their own chemistry (or is it biology?). There aren’t two schools of thought. There are 9 billion. Finding out why the specific person you are talking to (or voting for) believes what they believe is the whole ballgame. Approaching every conversation, political or not, this way will really make life more interesting for everyone. Second, it’s worth it. It’s worth your extra energy and your extra time to try to understand how they might be looking at the world.

Isn’t it interesting that when a child misbehaves or overreacts, we often assume the child is tired or hungry or cold?

When an adult overreacts or lashes out, we often assume the person is rude or scheming against us.

Next time you are faced with someone at work or at the store (or on Facebook) that is acting out in some way or posting something you find preposterous, consider their subjective bundle of chemical impulses and decide whether they are really out to get you or whether the world is still a pretty interesting place.

Here’s what Seth wrote on the topic. Click the link for his full write-up. I just cherry-picked my favorites.

When well-meaning people can’t see it the same way

By Seth Godin

People don’t believe what you believe, and they don’t know what you know.

Some of the gaps [in the way people think]:

What will they say? — keep an eye on those that are watching me
What will my mom say? — doing the right thing, even if someone is looking, and especially if no one is

Change — because things can get better if we let them
The status quo — because change is risky

Civility — because we’re working to keep it all from falling apart
Conflict — because if you can’t handle it, get out of the way

The long haul — because none of it is worth it if we poison ourselves
The short run — because the long haul manages to take care of itself

The strongest — because the pack moves fastest if the strongest are supported and rewarded
The slowest — because we’re only as good as the way we treat the weakest among us

Family first — because you take care of your own
Community first — because everyone is in your family

Show your work — because finding an error in my work helps us both, transparency pays


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View down Griswold Street, Capitol Park, Detroit, MI, USA


Leadership: “[Top] leaders are somewhat self-effacing individuals who deflect adulation, yet who have an almost Stoic resolve to do absolutely whatever it takes to make the company great, channeling their ego needs away from themselves and into the larger goal of building a great company. It’s not that Level 5 leaders have no ego or self-interest. Indeed, they are incredibly ambitious — but their ambition is first and foremost for the institution and its greatness, not for themselves.” -Jim Collins


Today’s Thought: This week, I gave some thought to fear and risk. What is there to fear in our careers? Or in our organizations? I think the biggest risk is the thing you think is true, but it’s not. Somewhat dangerous in relationships, it is deadly in business. To protect against this err in judgment, there are a few things leaders can do. Articulate it as a risk for you and your team. Ask a lot of questions. Create mental “alarm bells” that go off anytime you make any assumption. Speak with clarity and consistency. When wrong, and we’re all wrong sometime, take ownership and move quickly to remediate or resolve.


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Detroit, MI, USA



What do you stand for?
Are you an activist? What are your city plans for?
Are you an accident? Are you just in the way?
Your native tongue contradicting what your body language say?
Are you a king or are you jokin’?
Are you a king or you posin’?

- Kendrick Lamar


Bonus Content: Please check out Debbie Hoffman, co-Founder and CEO of Symmetry Blockchain Advisors, on Lykken on Lending.

Continued success,

Written by

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

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