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

Friends & Colleagues,

Saturday Cup of Joe #47. Detroit to Scottsdale. Is there a more dramatic transition? Leaving a city a few years removed from bankruptcy. Landing in a place with luxury that only a handful of cities can rival. There is a similar transition one can experience driving out of Detroit on Jefferson Ave toward the Grosse Pointes. I live off East Jefferson about a quarter of the way between downtown and the city line. Detroit ends at Altar Road. If we were driving together, I wouldn’t have to tell you that. You’d be able to tell. We’d cross the intersection and to a man, you’d say, “what just happened?” The orange and white construction barrels, the boarded up windows, the vacant lots all give way to old timey street signs, tree lined sidewalks and vibrant banks & schools. If you want to actually see 6 year old video of “the drive,” my friend Brad posted it to Vimeo. Not the same as experiencing it for yourself but you’ll get the idea (and you’ll have Brad narrating.)

I’m headed to Scottsdale on Thursday to celebrate the wedding of a close friend. It’s the perfect reason to get together and see loved ones & close friends. We’re excited to have a long weekend together with people we love. It’s just another reminder how lucky and blessed we are.

This week we look at:

· Every second counts (see graphic)

· Turns out managing brand is similar to managing culture (Got Me Thinking)

· The case for the #NextBelt (A Look Ahead)

· Diversity serves as a valuable lesson for how to live every day (Walk the Walk)

· Hunter S. Thompson on a meaningful life (Viewpoint)

· Self-reflection is hard but worth it (Careful thought)

· Don’t take the easy route (Hard work)

· Would you trust creativity in public policy (Sidenote)

· Thoughts, bonus and quote (all the way at the end)


One minute on the Internet in a graphic:

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As seen on LinkedIn this week


Got Me Thinking: How Credit Karma’s CEO talks about brand is how all managers should think about corporate vision and cultural. This is, admittedly, a fluff piece profiling the “courage” of Credit Karma and how the company transformed its brand through creative market research and advertising. From my perspective, it’s not as much courage as clarity. The conclusion is that CEO’s and brand managers should be honest, authentic and attentive. Shocking, right? Nevertheless, there are several great reminders in this piece.

Here are the highlights that remain useful as you consider your team, organization or business:

· Find out how to learn from your customers when they do not know you are listening. (i.e. monitor Reddit)

· Force yourself to clearly identify your key customer.

· Force yourself to clearly define your brand.

Takeaway: “Find your unique voice that cuts through the noise for your customers by channeling the personalities on your founding team, and being honest among the people who are poised to care about your company most.”

Bottom line — articulate internally and externally to save money and drive the brand.


A Look Ahead: #NextBelt. JD Vance, author of Hillbilly Elegy, wrote an opinion piece in the (succeeding?) New York Times last week that committed Vance and his family to moving back to Columbus, OH his hometown. I’ve been writing Saturday morning emails for 47 weeks but even before that, I was thinking about how the American Dream is changing, specifically what are the appropriate expectations of my generation. First, we heard that we should lower our expectations around Social Security. A few years later it was about lifetime income metrics for generations that entered the job market during a recession. A few years after which was just a few years ago, our generation gained the label millennials and almost immediately our work ethic and tenacity was questioned. Now, there are questions about whether we’ll be homeowners, whether we’ll choose urban, suburban or rural communities and how we want to work for companies with “values.”

I do believe that generations of people raised in together tend to behave in definable patterns creating shifts in everything from fashion to the economy. This declaration from Mr. Vance gave me hope that we’re seeing mainstreaming of a trend. A trend I believe in and one, frankly, I’m hoping to lead. Move off the coasts to a city that provides greater opportunity to participate in a community in a meaningful way. Live an urban or comfortable (privileged? even) existence in a town where your just being there matters.

What I call the #NextBelt are the Rust Belt cities that have been known for decay, blight and racism but are now transforming the future into opportunities in technology, entrepreneurship and energy-conscious living. Pittsburgh is home to Google offices and is building a new reputation for building a partnership between academia and industry. Louisville and Cincinnati always banking or finance centers for the Midwest have experienced an influx in revenue thanks to craft beer, bourbon and craft cocktail culture. Milwaukee has redeveloped the waterfront and is starting to attract a creative class looking for inexpensive restaurant, bar and artistic spaces. Detroit has defined itself post-bankruptcy as a national experiment in public-private partnerships and whether simply believing in success will be enough to create a new national hub for tech and entrepreneurship. All the cities I’ve mentioned have great bars & restaurants, die-hard residents, and some of the best / most romantic architecture in the whole country. There’s something about the former manufacturing/brick buildings, loft condos, water views, cheap beer and large Victorian houses that fuel the authenticity of these AutheniCities. There is a connection to people and place in the #NextBelt that is a perfect fit for many of us that want a big life without a big price tag or anonymous urban existence.

Sometimes you wanna go where everyone knows your name. Why not live there?


Walk the Walk: Open and candid. eBay’s Chief Diversity Officer, Damien Hooper-Campbell, is not only open and candid but makes an unassailable argument for the value of connection and inclusion in your business (and in your life!) Why is that so hard? Vulnerability plays a part. Let’s say you do take Mr. Hooper-Campbell’s advice and dive in. Get below the surface. Get real. It is really hard to trust that someone won’t take advantage of information, of weakness or of vulnerability. Everyone is about openness and honesty until they see an opportunity. How can we ensure people are treated fairly? It’s impossible. Someone will always take advantage when a friend, colleague or leader is too honest. If it happens among friends, how much more likely is it to happen among colleagues or co-workers?

We’ve seen myriad examples in life when the person taking advantage of the situation prevails. In sports, the player that retaliates is often the player penalized. The politician that plays dirty often wins the election.

“What we need to do is push beyond the boundaries of surface-level conversations. We need to do what we very rarely do as human beings when we first meet each other. We need to be okay being politically incorrect for the moment as long as we’ve established an assumption of good intent. That allows us to get our real views out there and gives us permission to call BS when we see it.”

What’s the solution? Inclusion. It’s not about diversity. It’s about opening up to human emotion and creating an environment for everyone to feel connected (regardless of gender, race and ethnicity).

“If diversity is getting invited to the dance party, inclusion is being asked to dance when you’re at the party.”

Bottom line — if you include voices from all around a well-built organization, you’ll have happier, healthier and more successful companies, not to mention people, to work with.


Viewpoint: When I started Saturday Cup of Joe, I wanted to do two things. Stay in touch with the most important relationships I had made by connecting each week. And strive to be a better leader, colleague and person by learning valuable lessons no matter the source. In fact over 47 weeks, I’ve enjoyed identifying valuable lessons in unlikely places. This week I stumbled across a new blog, Farnam Street Blog, and a letter Hunter S. Thompson wrote to Hume Logan on what it means to pursue a meaningful life. There were two themes that stuck out to me that I thought would be valuable to those of us pursuing leadership roles and looking for meaning in our work. The first lesson is we must strive to be ourselves in all we do. Thompson writes,But don’t misunderstand me. I don’t mean that we can’t BE firemen, bankers, or doctors — but that we must make the goal conform to the individual, rather than make the individual conform to the goal.

The second lesson is that we must enjoy the process. It is the “functioning toward the goal” and not the goal itself that matters. Thompson describes it like this: “a man must choose a path which will let his ABILITIES function at maximum efficiency toward the gratification of his DESIRES.”

Almost a decade ago now, one of my best friends, Ryan, once said to me, “what do you want to do everyday?” Because it isn’t the pinnacle or the ultimate achievement that brings fulfillment but the joy of the daily pursuit. It is a hard lesson that I’m still learning.


Careful thought: Apropos of Thompson’s letter was a piece in the Harvard Business Review on the power of self-reflection. In short, the meaning of life includes self-reflection. I was drawn to the article not because of the virtues of self-reflection, though there are many but of the author’s identification of all the reasons that leaders typically avoid it. I thought it was spot on. She writes that leaders avoid self-reflection because:

1. Leaders don’t understand or want to ask for help.

2. Leaders don’t like slowing down to process emotions of vulnerability and discomfort.

3. Leaders don’t like the results (i.e. weakness)

4. Leaders like to act not reflect.

5. Leaders don’t automatically see the ROI.

And yet, self-reflection is the most meaningful and efficient route to improvement. So…there’s that.


Hard work: Is this true? “The brain’s natural impulse is to take the easy route almost all the time until you think and act otherwise.” This blog post is classic. I thought it was both encouraging and cliché. There are a lot of these articles out there. A LOT. Instagram posts. Facebook videos. It can be really difficult to connect the dots. Read the post. Be inspired. Get to work. Get to work on what? How long does inspiration last? Write a post? I can feel productive to write a post or brainstorm an idea for a business or book. It’s the key moment where execution begins that makes all the difference.

I’ve written before that James Morin quotes Tony Robbins, “You either need inspiration or desperation to be success.” And that’s true of overcoming the “easy path.” I was reminded of that quote reading this post on that path of least resistance. Inside an otherwise mundane blog post was this gem that really got me thinking: “If everything is too good, you’re probably stuck not being awesome.” There are suggestions to overcome it, but for me, I always come back to the other quote — desperation or inspiration.

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As seen everyone on social media, all day.


Efficiency: One reason I highlighted this article, Is Empathy Overrated?, was to emphasize how easy it is for our emotions and limited capacity (meaning, our minds and hearts have only so much bandwidth) to distort our judgment and reaction. I don’t think empathy is a bad thing and I’m not advocating to remove it from our professional or personal lives. (Evidence of where empathy is necessary is understanding the importance of inclusion mentioned earlier in Walk the Walk). At the same time, it is good to filter all the information we receive through potential bias or prejudice. According to Paul Bloom, “In this regard, empathy distorts our moral judgments in pretty much the same way that prejudice does.” This article was more focused on the large moral judgments we make but is useful to read and consider in the context of leading our organizations and how we’re asked to respond each day.


Sidenote: Is creativity rewarded? If so, in what industry? There are so many ways creativity can’t get off the ground. Skeptics everywhere. An interesting article this week profiled a group called Home Town Detroit. As you may be aware, we have abandoned properties all over the city. Many are bank foreclosures. Many, however, are tax foreclosures. Back property taxes remain unpaid, the city claims the property and auctions it off for $500, $1400 and $3400. You get the idea. A few years ago the city partnered with Quicken Loans to tear down blighted homes making room for those the city could salvage. Admittedly, less than honorable buyers, speculators and schemes popped up, and community advocates are rightly wary of any new group claiming to have a solid plan. But when the group can also benefit financially or can see a big upside (here, the group would retain ownership rights when the tenant does not pay off the entire debt), the powers that be often won’t take a chance. Too risky. Too much “headline risk.” Unfortunately that mentality can also prune beneficial ideas before they can even prove the concept. As a leader, how do you decide when to take a chance on creativity and ingenuity?


Today’s Thought: Accept leadership lessons in bite sized pieces. I was having a conversation this week that reminded me that most leaders do not become leaders overnight. The CEO did not become the CEO overnight. If you are a new manager or young executive, you don’t need a promotion to CEO. You need to learn one of the lessons that a CEO will need one day every few months (or even years depending on your career goals). Take many experiences and lessons gained over years of interactions, trial & error, and mistakes strained through your personality, your specific set of skills, to create the mindset of a true leader. One of my temptations has always been move quickly to move up quickly. What I’ve thinking about this week is that expert and experience begin with the same root word. The only way to get that experience are the bite sized pieces that come along on our way up and not once we’re already given the position. I know this is obvious to anyone who has been through a career of lessons, but given all my brash declarations each week (including above this week), it felt important to note that these observations and realizations are happening too. Finding valuable lessons is the first step. Internalizing them and improving as a result is the key.

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You gotta pick

Quote: “Desire is a contract you make with yourself to be unhappy until you get what you want.” — Naval Ravikant

Continued success,

Written by

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

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