God Bless the Insanely Rich

God Bless the insanely rich.

I listened to an interview with Mark Cuban tonight where the topic was his company Cost Plus Drugs, and it was a case study in why some people think he should run for president (and also why I’m sure he won’t).  It also reminded me of another venture, launched by one certified rich guy a few years ago and somewhat co-opted by another certified rich guy in 2025 – the Invest America Initiative, launched by Brad Gerstner then re-branded as “Trump Accounts” (what a terrible name – regardless of how you feel about DJT).

The topic of the Cuban interview was how to fix healthcare and specifically Cost Plus Drugs, his mail-order drug startup (one could reasonably argue that I’m oversimplifying the concept, but that’s basically what it is).

The line that got me – the discussion turned to why Cuban got involved in the prescription drug business.

Q: “Why did it have to be you guys coming in to do this? Why not somebody else?”

A: “Because I’m rich as fuck and I didn’t care about the money. My next dollar is not going to change my life.”

The message Cuban was sending is that he has so much money that he can take on the “the system” in a way that very few people can, and so he’s using his substantial bank account for good.

Now, I’ve heard Cuban make similar comments before, and I’ve also heard the criticism that he’s much more focused on the bottom line than he wants you to believe, and that he’s just playing up his populist persona.  That criticism may well be accurate – and so what if it is?  Two things can be true at the same time.

Everyone knows the healthcare system in the US is broken.  But Cuban is actually taking concrete actions to hack away at the issue, however large or small an impact it ultimately has.  His focus on cost transparency one of the best ways to make forward progress – no industry in the US thrives as much on price opacity and misdirection as the insurance/PBM industry (the two verticals are rapidly converging – I don’t consider them distinct industries).

So if an insanely wealthy individual wants to aim his money bazooka at a problem that helps all of society, why exactly would we criticize that and why would we care if he makes money?  One of the best features of capitalism is that if you solve a big problem you get a big paycheck.

Similarly, Brad Gerstner, a VC investor (among other things) has been working on an idea to create and fund investment accounts to all kids, regardless of their economic backgrounds.  Gerstner didn’t invent the concept but was the first to actually get traction on a national level.  And boy did he get traction - he also got Donald Trump onboard early in his 2nd term and, in a move that should surprise no one, Trump branded the concept the “Trump Accounts” which unfortunately made half the country immediately dismiss a great concept when it was passed into law as part of the “One Big Beautiful Bill” Act.  The nature of the “Trump Accounts” is still evolving, but at least one billionaire (Michael Dell) announced this past fall that he will be contributing $5 billion into these accounts.  Dell’s announcement highlighted a unique feature of these accounts – anyone can contribute to them.  This presents a great opportunity for the ultra-wealthy (and regular-wealthy) to contribute dollars directly into the accounts of some or all kids across the US.  Undoubtedly there will be unintended consequences, but this could also lead to the largest case of voluntary wealth transfer in history as billionaires who tire of swimming in their money “Scrooge McDuck” style instead elect to contribute to these accounts. 

Both of these guys – Cuban and Gerstner – are capitalists, no doubt.  But both are also examples of how the ultra-wealthy use capitalism as a tool to improve society.  These guys didn’t even feel the need to slap their names on their creations.  I love it.

Trust: The Alligator Closest to the Boat

Anyone who has spent any amount of time with me knows I like to use idioms to distill complex ideas.  One of my favorites is "the alligator closest to the boat" – a phrase referring to the highest priority item or most pressing challenge.

Today I spend a lot of time advising companies on their finance organizations and sometimes working in them. Often, I am there because things are not running smoothly.  And if things are not running smoothly, usually a lack of trust is lurking just beneath the surface (if not sitting right on top).    

If I had to choose the alligator closest to the boat in today’s professional world (and there are many), I would say it is easily distrust.  I've seen a lot of online “noise” recently around the increasingly transactional (even adversarial) relationship between employees and leaders, and something about it nagged at me.  The interactions generally skew to one or both of the following viewpoints:

-          Employee: “don’t trust your employer, extra work is wasted effort, clock out at 5 and go home. Loyalty is a sucker’s game"

-          Manager: “Why are employees today so entitled and lazy? It’s not even worth investing in them.”

Then one morning a few weeks ago, I looked out my office window and saw the scene below - the Wells Fargo name and logo being removed from the building at 150 Fayetteville Street in downtown Raleigh.  The sight caught me off guard, and also put this employee vs. manager conflict in a new light.  Here’s why.

Begin at the End

I spent my last 4 years as a banker in this building with the Wells Fargo sign on top.

Then I left Wells in late 2012.

Not quite 4 years later the top 2 execs at Wells had been fired, forced to give up more than $150 million personally (fines and clawed back compensation), and banned from the financial services industry as a result of what is commonly referred to as “the fake accounts scandal”.  The situation was so crazy that one of those executives who had retired just as things were coming to light was retroactively fired by the Board of Directors.  Talk about closing the barn door after the horses are gone …. I guess the Board was testing the limits of the saying “it’s never the wrong time to do the right thing”.

To vastly oversimplify the cause of the scandal, Wells executives abused the trust placed in them by their employees and customers.  These executives pressured front-line retail employees to act unethically in the name of customer service and when the issues were discovered they threw those employees directly under the stagecoach.

When the fake account scandal at Wells first came to light, the bank fired a number of the front-line employees and their direct supervisors for wrongdoing and portrayed them as bad actors (making them basically unemployable at another bank).  However, the employees were doing exactly what their managers pressured them to do (and incentivized them to do).  Their managers, in turn, were also following orders (but got much bigger paychecks for their trouble).  Wells leadership had cloaked this scam in its characteristic “gee whiz” mid-western way, so the rank-and-file didn’t pick up on it right away.

The Wells Fargo case is certainly audacious and salacious (and makes for very interesting reading), but Wells did not invent this idea of exploiting (and sometimes scapegoating) junior employees for the benefit and protection of those further up the food chain. I also don’t think they intentionally did so – but they intentionally let it fester.

Against that backdrop, why would a young employee NOT be cynical?  Here’s why.

The Good Old Days?

The building at 150 Fayetteville was the throughline for many of the most impactful relationships and experiences of my professional life.  As I mentioned, I spent my last 4 years at Wells Fargo in this building.  But I actually worked in this building twice - before it was the Wells Fargo tower, it was the Wachovia tower. I spent 15 years with the bank formerly known as Wachovia and then Wells Fargo (many of those years in this same building) after Wells scooped up Wachovia in the 2008 financial crisis (another situation about which I have strong feelings that are best saved for another day). 

Early in my career (when the building signage had just switched from the green First Union to the blue and green of Wachovia), I observed, worked with, and learned from some of the best and most-respected bankers in the business, in this building.  Many of them now hold senior positions in some of the most well-regarded banks in the US (or did before they retired).  Fortunately for me, some saw that I was generally a hard worker and that I tried to keep our customers’ (and shareholders’) best interests in mind, and they began to offer me opportunities and challenges.  There was generally no promotion or bonus tied to whatever I worked on, and I was too naive to think there should be.  I just knew that somebody I respected was giving me a shot to try something new.  And each time I learned something new, I became better at my job and more valuable to the bank and to our customers. 

Looking back at that time in my career, so many people were unreasonably generous towards me with their patience and guidance.  But relationships like this require trust in both directions - I trusted the people I worked for to support me, and they trusted me to not embarrass them by doing something stupid.  It certainly wasn't always rainbows and sunshine and I made my share of mistakes, but that time for me was rich with opportunity and I made the most of it.  In fact, I was fortunate enough to have 4 different careers (and was moved 4 times) during my time with the bank.

Ten years after I first moved into this building, the Wachovia logo had been replaced by the red and yellow Wells Fargo stagecoach. The culture of the organization had also changed; the trust, loyalty, and empowerment leaders had earned and modeled (which made the job fun and interesting) were gradually replaced at the top by micromanagement and a drive for “solutions”.  That is what ultimately drove me to leave.

This story illustrates two points relevant to this current inter-generational “cold war”. 

First – if you are an established professional in a leadership position, you didn’t get there by yourself. You had mentors and bosses along the way who helped you. You have an obligation to those coming after you to be trustworthy and loyal - be as transparent as possible, use good judgment in ambiguous situations, and be unreasonably generous with support and guidance for those who report to you.  Honor your commitments - and if circumstances change and you can’t for some reason, then own it.  Help your people grow and develop, even if that means losing them.  You won't always get it right – I haven’t - but it is your obligation to try.  If you protect, grow and inspire your people then good things will happen.  If you don’t do these things, then you’re just overhead.

Second – if you are early in your career, seek out leaders and mentors who are empowered, loyal and trustworthy.  By empowered, I mean your boss should have the authority to make decisions that impact your work and success.  By loyal, your leader should advocate for you when you’re not in the room.  By trustworthy, I mean you should have confidence that your boss acts honestly and in good faith.  If these things are present, then look for the extra work, and take the extra assignment.  Those interactions will make you more valuable not just in your current role, but also in every future role.  If these things are not present - start planning for your departure (you’ll thank me later). 

I’ve worked for good leaders and bad leaders – hell, I’ve been a good leader and a bad leader.  But while a bad leader (or employee) can still be trustworthy, you cannot be a good leader or employee if you are not trustworthy.

Don't get me wrong – it’s called work for a reason; your leader is not your friend and is not responsible for your happiness.  However, even in bad times you should be able to trust your leaders to act in good faith. 

Organizations are ultimately stronger when trust exists – and weaker when it disappears.  Look around today.  Every professional relationship begins and ends with trust and loyalty.  Contracts and handbooks may be helpful for clarifying roles and obligations, but if you suddenly need to refer back to them, you're already in trouble.

Whenever I see the building at 150 Fayetteville, I feel gratitude.  I owe so much of my success to the folks who worked in that building.  And I have to say, I’ve always preferred the blue and green over the red and yellow.

Somebody's gonna do it, so it may as well be you...

Much of my business lies in providing advisory services to organizations and their leaders, and sometimes taking on special projects or providing interim leadership. Over the years, I have noticed a couple of interesting and nearly universal themes.

First - the nature of my work is such that when an organization engages me, it is typically not because things are running smoothly. It’s usually because things have gone sideways (technical term). The cause is often multi-factorial and occurs in stages.

Second - More often than not, one or more of the causes are “difficult” decisions that were avoided altogether.  The leadership team either lost objectivity and discipline around a question, got stuck in a state of denial, or just got used to the dysfunction.  But, as a wise woman once told me, “By not making a decision, you are making a decision – and not the right one.”

One of the interesting things to me is how management deals with an issue when given objective feedback. 

Some teams get on the same page immediately, as if they were just waiting for the right moment; these engagements are fun, because everyone is pulling in the same direction, it strengthens the group, and they can celebrate wins as a team. 

Some teams, however, are too entrenched and just can’t see past their own short-term interests.  Honestly, these engagements are often entertaining to a third-party (in the same uncomfortable way I used to find the TV show “COPS” entertaining), but are very difficult for the client team and have a much lower probability of success until leadership makes a couple of roster changes.

I was once hired to evaluate the finance organization of a distressed company by its Board of Directors and then, as a follow-up to my assessment, the Board asked me to mentor the first-time CFO, who was a battlefield promotion (had been Controller when the prior CFO was let go), and was struggling to be an island of effectiveness in a sea of ineffective managers. The Board had taken an increasingly active role in the company given the operational and leadership challenges, which is how I came to be involved.

In one of our sessions, the CFO and I discussed a minor but meaningful issue that the CFO had actually raised to the Board. The Board tasked the CFO with resolving the issue.

As we talked through the issue, the solution quickly became clear. The CFO knew it, and I knew it. But the solution would also be unpopular in some parts of the organization, including with the CEO, who was also a first-timer and struggling in some key areas.

The CFO couldn’t get past the immediate discomfort required to make the hard decision. “People around here don’t like to be told no, especially [CEO]; this could cost me my job.”

My feedback was direct - “Well, the Board asked you to fix the issue. So the way I see it, you have two options. Clean up this issue and [CEO] might fire you (an ill-advised decision he’d have to explain to the Board), or you can drag your feet, and I promise you the Board will fire you.”

“Either way, somebody’s going to fix the issue, so it may as well be you and not the person who replaces you.”

Remarkably, this CFO chose to avoid the short-term discomfort and gave in to the CEO rather than working together to help the CEO understand the situation and why the change was needed.  That situation was the beginning of the end.  The CFO had failed a pretty basic leadership test and cemented concerns about effectiveness, and didn’t make it through the quarter.  The CFO’s successor addressed the issue quickly, and within a few months the CEO was also “made available to the market” after refusing to make a few more simple (but difficult) decisions. Once both executives were replaced with leaders who understood the messy work of making difficult decisions, the organization gradually stabilized.

Like in so many other aspects of life, sometimes we think we get stuck on a “hard” decision, when the decision is actually the easy part. The difficulty lies in the execution and managing the outcome. As a leader your paycheck depends on outcomes, and outcomes are driven by decisions and actions.  You’ll have enough “hard” decisions.  Don’t waste time and energy agonizing over the simple ones.