Confessions of a FinTech Junkie

One of the most common questions that people get asked regularly from friends, family and co-workers is: “How was your day?” The question is about as basic as a question can be but because it requires context to answer our typical response is rarely “good” or “bad”. Instead, the question becomes code for “tell me about your day” and usually is the basis for a commentated recap of the day’s highlights reel.

But, at it’s core, the question is an important one to answer for a host of reasons with one reason being more important than all the rest.  The reason:

It’s well documented through countless psychological studies that bad outcomes feel many times worse than good outcomes feel good. And to make matters worse, the bad outcomes stick with us and are hard to shake over time.

We all know this at our core and can point to countless examples in our personal and professional lives that back this up. For instance, for many years I was a very active mid/high stakes poker player (mainly $25/$50 PLO) and I can very clearly recall every detail about the biggest poker hands that I lost but I can only vaguely recall the biggest hands I won. Losing a 1000+ big blind pot with double suited aces still stings to this day and conjures emotions that aren’t pretty.  Similarly, I can also recall just about every painful event in my professional career (there are a lot of them) but can’t recall a single detail related to any of my promotions.  The situations associated with being yelled at and almost getting fired (or actually getting fired) are never forgotten.  Never.  Pain sticks with us while pleasure is ephemeral.  This is sad but one of life’s truths.

So, to be happy we need to experience 10X, 20X or sometimes even 100X the number of “good days” relative to “bad days” but what’s amazing is that most of us can’t answer the simple question “How was your day?” unless it was a painful one! This issue is magnified in the business world because the majority of our waking hours are spent at work, and for many people work is responsible for much of their stress and defines a big piece of their identity.  The result is that the work environment will produce bad days with some regularity.  It’s nearly impossible to avoid and I bet each and every one of us have many scars to prove it.

Fortunately, I recognized this issue very early in my career and it significantly shaped my thinking about how I managed people and projects. Fundamentally, I wanted everyone who worked for me to be able to answer the question “How was your day?” so I could create an environment that manufactured good days and attempted to avoid bad ones.  And to do this, I had to help each and every person on my team define what a good day looked like. Did I always succeed?  Most definitely not.  Defining what a good day looks like sounds so simple yet it’s incredibly difficult to do well. But when I was able to do it right it made a palpable difference in the happiness of the people I was responsible for.

For instance, I remember spending a few weeks listening to calls being taken by Collections Agents in Capital One’s call center and coming away thinking that the Agents had really tough and stressful jobs. They were constantly hung-up on, cursed at, lied to, and told very sad stories by customers who weren’t able to pay their bills on time or at all. Many of the Collections Agents I spent time with were very good at their jobs but if you asked them the question “How was your day”, there were almost always only negative answers.

I wasn’t naive enough to think that I could change the core nature of the job to make it more fun and less stressful, but I did put a lot of effort into defining what a good day looked like as a step in breaking the negativity of the Agents. And with a bit of effort, I was able to put daily metrics and weekly feedback sessions in place that helped immensely. Being able to point to things that mattered to the organization as well as things that mattered to our customers was at the foundation of the good/bad feedback loop. Proving to an Agent that their efforts were bringing customers current (which would start the cycle of repairing their credit) and that they were scoring well on a comprehensive set of quality metrics was at the foundation of defining a good day. And it was important to make sure that it was possible for each of our Agents to have a good day just about every day. They were still dealing with very emotional and frequently verbally abusive customers, but they could now focus on the good vs. the bad and leave the day knowing if it was a good one.

What’s interesting is that as much as I’ve believed in this theory for most of my working career, I recently realized that I lost sight of it in my own job as a Venture Capitalist. If I’m honest, defineably good things don’t happen that frequently in my line of work but fire drills unfortunately do. I love my job and can’t picture doing anything else in the world, but given a portfolio of highly volatile early stage companies and the intense desire to be an active participant in their journeys, the fractional good/bad ratio has a heavy weight to it.

So, I’ve taken it upon myself to think hard about what a “good day in VC land” looks like so that I can start redefining daily success. After giving it some thought, I’ve been able to define a good number of things that are worth savoring in this line of work.

A few obvious ones are:

1) Liquidity. Writing checks is easy but getting money back isn’t simple.

2) Investing in a company. When the money is wired it’s official.

3) Getting a term sheet accepted. There’s still work to do post-term-sheet but getting a company to say yes to your term sheet is an important step in the process.

Less obvious ones:

4) Meeting a company or a Founder that you want to spend more time with. Believe it or not, this doesn’t happen that often so when it does it’s exciting. Great Founders know how to create energy and excitement for their ideas and it can be contagious if you become a believer.

5) Learning something new. Insights can come from conversations with Founders or fellow Venture Capitalists or practitioners in and around the ecosystem and insights are the foundation for being a good Venture Capitalist. New insights should be cherished and sought out.

6) Putting out a fire. Fires are going to pop up frequently and some of them can turn into extinction events. So when they’re put out, the relief is palpable and should be celebrated.

7) Helping a company land talent. The best companies have foundations rooted in amazing talent, so placing talent is an important component of success in the future.

8) Participating in a Board meeting where there was uniform alignment. Companies are difficult to build when the Investors and Management is aligned but significantly more difficult to build when there are too many diverse points of view around the table. Diversity of advice might seem like a good thing but it actually isn’t until a company is on rock solid footing. Unity of direction and diversity of Rolodex/skills is a mantra I live by.

9) Listening to a Founder’s excitement when something is going right.  There’s very little that’s more fun than talking to a Founder when their company lands an important client or they blow out their monthly forecast for growth or an important test comes back with favorable results.  Being part of “up and to the right” conversations is energizing.

10) Hearing words of appreciation. So much of what I do in my job is give advice and share insights and it’s nice to know when someone feels it’s actually helping.

I’m giving myself advice that I hope to follow in the future and I can only encourage that you do the same. Every job is different but it’s too easy to focus on the bad and under-appreciate the good. Flipping the script and recognizing good days when they occur might just make us all happier and better at what we do!