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

Friends & Colleagues,

Saturday Cup of Joe #51. It was another busy week in the industry:State regulators are gearing up to assert (re-assert?) themselves in the regulatory conversation. A state regulator trade group, CSBS, sued the Office of the Comptroller of the Currency (OCC) over plans that OCC announced some time ago to issue charters to fintech companies. See, you thought that was gonna be a boring sentence until I got to fintech, and now you’re interested. We’ve seen states pushing harder and harder in regulatory exams and blurring the lines between supervision and enforcement. With the House of Representatives moving forward with the Financial Choice Act (revision of Dodd-Frank) and CFPB under fire in the courts, it should make for a really interesting 2017.

I also spent some time this week looking at a new financial news source: Cheddar. Cheddar is an entirely streaming financial news channel explicitly focused on a younger audience. My free trial is only a few days old but already I’ve found the format to be familiar (2 people sitting behind a desk in NYC) but the tone to be irreverent, casual, and funny. I’m not sure if I’m going to pony the $2.99/month (I know, I know) but I’ll let you know if the content is worth it as I keep watching. When I fired it up Friday morning before work, they were discussing USAFacts, Steve Ballmer’s database that I wrote about last week.

This week we look at:

  • One man’s experience of home ownership (Of Interest)
  • Venmo: a case study (Got Me Thinking)
  • Lessons from brand management (A Look Ahead)
  • Shipping containers in the Motor City (This week in Detroit)
  • Building a network on authenticity (Walk the Walk)
  • Do you still dress for the job you want? (Efficiency)
  • Leadership lessons (Hard Work)
  • Thoughts, bonus and quote (all the way at the end)
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Of Interest: I read an article this week that was so good I wish I had written it. Not because I necessarily agreed with all the conclusions but, rather, because it takes time and discipline to outline all the complex factors and decision-points involved in home ownership. This week, Ryan Holiday, author of Ego Is The Enemy, published a long, explanatory article about his decision to buy a house. It includes significant insight into how many first-time homebuyers think or should think according to Holiday. I included it at the top this week because it’s the type of article that provides valuable insight for mortgage bankers, entrepreneurs, real estate agents and anyone wondering how the purchase market will fair in the future. Holiday takes a more sophisticated approach but the underlying values and desire to own a home is there. He can tell us a lot about how he approached the decision and how many more of his cohort are likely to think about the decision moving forward.

His success and income make him somewhat more flexible and privileged than most home buyers. For instance, many homebuyers might not be able to afford staying overnight in Airbnb homes in multiple parts of a new city to determine the best location. Many more are not able to afford multiple homes in the same area. Nevertheless, Holiday talks about how he approaches the investment, how he thinks about “the commitment” of homeownership and how he deals with real estate agents (spoiler alert — he’s much more favorable of the value of an agent in the transaction but he views agents as a mercenary of sorts which I favor. And apparently other millennials feel similar to Holiday…until they realize a standard commission, that is).

Perhaps Holiday’s most articulate point is his description of rent as freedom tax. An investment in mobility rather than community. It’s about commitment on many levels. A commitment to a place, to a story and to a priority. As if to further support the story aspect of commitment, Holiday encourages buyers to write a letter to the seller as a way of distinguishing themselves from other offers particularly in a seller’s market. To me, this is further indication that the new connection to homeownership, at least first time homeownership, is narrative.

As I’ve written before, I think we’re in a transition between a time when home ownership was not only the American Dream but the cornerstone of wise financial investing (earlier the better) to a time when it’s a statement of values, lifestyle and community. Lifestyle and lifestory.

Holiday’s article is long but valuable. The day after I read it, I noticed The New York Times publishedHow Do I Get a Mortgage?Not exactly an in-depth analysis. It did include a mortgage calculator. Mortgage calculators, in general, have often been the focus of much attention and criticism in the mortgage industry. Maybe I need to start working on my homeownership story generator to help millennials determine if we are really committed to the narrative that involves life in a new home.


Got Me Thinking: Last week I wrote somewhat passionately about the finely-tuned balance between regulation and reasonableness. In all honesty, I regretted it as soon as it was sent because I felt it was quick, immature, and unhelpful. Upon re-reading it, I realized that I overreacted, somewhat, being dramatic and all. On the other hand, simply denouncing an article as bad form isn’t enough.

I did my best, in response, to highlight articles that add context to the fine line between reasonable regulation and suffocating regulation. In talking to a few other mortgage bankers this week, the regulatory burden is feeling more acute than ever (probably because there is a crack in the Dodd-Frank “dike”). States have been ramping up action to either assert authority or fill the perceived gap left by a “weakened” CFPB.

Nevertheless, it’s good to keep reasonable regulation in mind. CFPB overreach does not justify no regulation whatsoever. Fast Company published a profile of Venmo that outlined growth, compliance, and trajectory. As a financial services company, Venmo lived or is living much of what the mortgage industry experience, only to a lesser degree. And Venmo had the assistance of a mega-parent in PayPal. In looking at Venmo’s compliance, the article mentioned a few key ways Venmo approached data and compliance: “For instance, if a user is transacting with someone for the first time, Venmo can look at whether they have overlapping sets of friends to help determine if the relationship is legitimate.”

On the other hand, it took a little longer than expected for this author to call Venmo “back.” According to the article, it only took eight years. “Further proof that Venmo’s house is finally in order: Eight years after launching, it’s finally getting back to more creative endeavors and looking for ways to generate revenue.

We are just now beginning the process of trying to calibrate new companies, business models and platforms in the context of consumer protection and regulation. Venmo won’t be first or last but it’s a useful company to keep an eye on.


A Look Ahead: “Brand” has become a somewhat difficult word to pin down. Much like love and spirituality, “brand” has a different meaning to everyone. Nevertheless, we all recognize that our companies and our organizations have a brand and it is important for quickly communicating a lot of information about the company or product to the customer or client.

I believe people often struggle by looking too high in the clouds for leadership lessons — Kennedy, Reagan, Jobs, Zuckerberg, Buffett, Bezos, etc. These are once-in-a-generation visionaries or leaders. The ability to draw out valuable lessons and synthesize them to our work is critical to success. These lessons can be found everywhere. I was reminded of this again this week reading about how a Burberry brand manager turned CEO, Angela Ahrendts, views company goals. These key principles are true for Apple but applicable to your team or business as well.

1. Community: Feeling connected to other people.

2. Story: Compelling narrative builds lifelong relationships.

3. Future: Willingness to rebuild as audience changes.

4. Emotion: Underneath everything (even rationality), we make decisions first and foremost with our heart.

How we connect and represent these core elements in our companies and in our careers will determine how deep our value is (or is perceived to be). When in doubt, be authentic and tell meaningful stories.


This week in Detroit: We are rethinking retail, restaurants, and residency in shipping containers. 10 years ago it would have been a bad joke. Today, it’s innovative.


Walk the Walk: Some people will tell you it’s not what you know, it’s who you know. The truth is it’s what you know about who you know that matters. But seriously, it’s all about your network. FirstRound published a profile of Chris Fralic, a successful VC and founder of TEDTalks, focusing on his lessons learned to become intentionally well-connected. Here are Mr. Fralic’s “rules”:

1. Be genuine

2. Listen with intent

3. Employ humility

4. Be honest

5. Brainstorm their issues (don’t keep score!)

6. End on a positive note

7. Don’t try to do too much

Don’t forget that it’s obvious when you only reach out when you need something.


Efficiency: Remember the old adage,“dress for the job you want”? It’s not as easy as it used to be. For starters, companies have moved to relaxed dress codes. In the tech world, bosses are as likely to be in a hoodie as business casual. In finance or banking, many still wear suits 24/7. I remember the first conference I attended that began at 9 AM on a Sunday morning and I arrived in a suit, just in case. Almost everyone in the meeting was suited up too. On the other hand, I don’t necessarily think there’s a guaranteed rule of thumb. Wearing a suit can often send the wrong message in a meeting or to your team. When all else fails, being yourself is always the way to go.

That didn’t stop the Wall Street Journal from publishing an article recently about the 7 office dilemmas that men face.

The WSJ chose topics ranging from hair dye and cowboy boots to etiquette in the office gym and whether a boss can make you shave a beard. This made me think of a story that my best friend Brad told me about the one time he grew a beard in his 20s. The CEO of United Way passed him in the hallway and said, “it’s good to see you no longer care about your career.” This was well before the current beard trend. Brad was ahead of his time (or his leader was behind the times). Either way, there’s no question these choices can matter. I’m sure all the women reading this are thinking — “oh please, if you guys only knew” — and I agree wholeheartedly. It’s not that big a deal for us. That’s why my rule has always been “be thoughtful,” because choices send a message. Whether it’s conscious or not, many people internalize your presentation and make assumptions. That doesn’t mean you have to overdress. All it means is don’t underestimate appearance and make sure whatever you are going for is what you are trying to go for. I thought I’d include one of the WSJ’s questions and responses because it’s probably something we can all relate to. Agree or disagree with the advice? Here it is:

I think a co-worker’s appearance is damaging his chances for advancement. Should I tell him? If delivered correctly, advice about appearance doesn’t have to be unsettling or hurtful. Don’t: Make the suggestion part of a PowerPoint presentation. Do: Take the offending man aside. While web designer Mr. Picón (the man with the gray hair question) was an art director at a magazine, human resources asked him to talk to a freelancer whose body odor had garnered complaints. “He used to ingest echinacea, osha root and garlic pills,” said Mr. Picón. “It was a lethal combination.” The conversation, tough for both sides, yielded positive results. “He took it well because I came to him personally,” said Mr. Picón. “He felt like I had his back.”

It doesn’t always work. Thomas Isen, 24, director of communications and development for luggage company Raden, recalls telling a friend that his jeans were too tight for the office. “If you can see the outline of your quads, that’s embarrassing.” The friend didn’t listen, which Mr. Isen believes may have hurt him. “If you’re in any industry aside from fashion and media and you dress a certain way, you’ll be taken less seriously.” he said.

If that advice isn’t helpful, you can always listen to Jack Donaghy.

Hard work: Leadership: Kinda like baseball, it’s 90% mental and the rest is half rhetoric. Seriously, though, I found an interesting article this week that analyzed some of the “great” leaders of our time. More than that, the article had some helpful insight into inspiring action. Leadership is more than speeches that spark men and women to believe.

The author offered several helpful reminders about leadership and inspiration alike.

1. Leaders should be, or can be, a mirror. “Churchill asked his people to see their hardship as a chance to be great. If a message is a mirror that shows the audience who they are, he showed them courage and selflessness.”

2. Leaders are led by fortitude and honesty, not popular opinion. “What would Jesus Christ have preached if he had taken a poll in Israel?” ­– Harry Truman’s notecard

3. “Our communication tools don’t just deliver our ideas — they also change the ideas.”

As leaders in our businesses, organizations, and teams, I cannot overstate how important the way we communicate is to what we’re ultimately communicating. I’ve seen people fired not because of what they said, but because of how they said it. You can be right and wrong, if you know what I mean.

The internal fortitude and consistency of values mentioned in the article — Churchill, King, Mother Theresa — is special, but the way these individuals were able to communicate it to the world made them unique among all the peers of history. Don’t undersell the delivery.

Today’s Thought: Value is what we make of it. I was struck by 2 things this week. First, on Monday I heard entrepreneur Gary Vee say that the current market rate for Kendall Jenner to promote a product on a single Instagram post is $1.3 million. $1.3M per post! It is incredible how valuable an attentive audience is today. All I can think is how great that is. It’s making value out of thin air. Another great example of this is Sophia Amoruso the author of #GIRLBOSS and the CEO of Nasty Gal. Her life is the profile of a new series on Netflix called, appropriately, Girlboss. I highly recommend it. Not just because the music is phenomenal and the main character (and her best friend) are fantastic but the show does a great job isolating and highlighting those moments in her life where she knew she had something special but nothing to show for it or failure mounted and she doubted herself or more dramatically where she must decide between her business and her friends. It’s also filmed in SF which doesn’t hurt. She “flips” old and vintage clothes into new, unique style pieces. I like how stark the example of market value is in the show. Sophia buys a piece for $9 and sells it for $650. Pure market.

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Quote: The minute you start compromising for the sake of massaging somebody’s ego, that’s it, game over. — Gordon Ramsey

Bonus Content: National Geographic posted an interesting article on genius. One of the things I appreciated was how the article profiled famous geniuses throughout history while tying out the interpersonal, societal, and biological implications. Long but fascinating.

Continued success,

Written by

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

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