Lessons Learned in 2019

A year ago I wrote a post on my Lessons Learned in 2018, which I closed with the call to action: “do something scary in 2019”. Sure enough, this past June I followed my own advice and quit my job to start a new investment firm (more on that later). If my lessons in 2018 followed themes of objectivity, risk and decision making, 2019’s lessons are about the human elements of any narrative. Just like it can be easy to fall trap to hindsight bias and convince yourself that the ending of a story was inevitable, we can often forget how differently things would play out in life and business if the characters involved were swapped out.

When I first quit my job last year I spent a couple of months catching up casually with some of the entrepreneurs I had come to admire (and in some cases consider friends). Our conversations were refreshingly devoid of the tension typically present in founder/VC meetings and they were honest. When I’d ask the founders what keeps them up at night, their answers differed dramatically from what they might have told me in previous fundraising conversations and carried a consistent theme: people. How do they scale their culture? How do they motivate a struggling employee? How do they let someone go who might be close friends with the rest of the team? How do they navigate a difficult co-founder dynamic?

People problems are often the biggest, scariest and most ambiguous challenges an entrepreneur (or any of us) will face, and yet they’re rarely discussed in the early versions of their respective narratives. To better understand these individuals I admire so much, and frankly to be a better entrepreneur myself, I sought out the biographical reflections of the people below.

1. The law is human

Smart laws do not assure justice any more than a good recipe guarantees a delicious meal. The law is merely an instrument, and without the involvement of human hands it is as lifeless and uninspiring as a violin kept in its case. The law cannot compel us to love each other or respect each other. It cannot cancel hate or conquer evil; teach grace or extinguish apathy. Every day, the law’s best aims are carried out, for good or ill, by human beings. Justice is served, or thwarted, by human beings. Mercy is bestowed, or refused, by human beings.
— Preet Bharara, Doing Justice

I find nothing more motivating and empowering than tackling an important challenge with an outcome that I’m capable of changing. We unfortunately have a tendency to craft narratives and re-tell stories as if the result was inevitable. At best this can make people feel unimportant. At worst it can make them rationalize unethical behavior.

I loved so many things about Bharara’s book, but my favorite lesson was that the justice “system” is not a set of writings but a collection of people. Similarly, the companies that seek out to change the way we live our lives are defined by the people who build them, not just the products they make. As someone who spends a ton of time with these people every day, that was a really inspiring reminder to me.

2. If you want someone’s trust, show them you’re in the boat

I know how he appreciated that I had as much skin in this one as he did, though, and we could share the burden of what it meant to be responsible for the first Star Wars film not made by George Lucas. In all of our interactions, from initial conversations about how the myth should unfold to visits to the set and the editing room, I tried to communicate to J.J. [Abrams] that I was a partner in the project and not just a CEO putting pressure on him to deliver a great film and a big box office success. There was more than enough pressure to go around for both of us, and I wanted him to feel that he could call me at any moment to discuss any problem he was wrestling with, and that I would call him with ideas that I had. I was a resource for him, and a collaborator, but not someone who needed to put my stamp on this film out of vanity or title or obligation.
— Bob Iger, The Ride of a Lifetime

I often say I love my job because I deeply admire entrepreneurs but have neither the skill set nor mindset to do what they do. Being an investor in emerging consumer brands is the closest I can come to being on their team in an impactful way; and yet, there is an ever-present dynamic in our relationship that I have a portfolio of X while the founder has a portfolio of 1. While I want their business to succeed more than anything, I can afford things to go wrong and they cannot.

This is why I love Bob Iger’s approach so much. Rather than keep a lifeboat inflated and ready for escape, Iger makes it clear to his directors that he is in the boat with them. Many people underestimate the positive impact of establishing with a founder that you’re in the boat. The trust borne from that fact is so productive — all of a sudden you are a thought partner, a teammate that can be confided in and meaningfully contribute to a successful outcome. There’s no bigger honor in my career than a founder texting or calling late at night to discuss something they’re struggling with. It shows they trust you, and that is everything.

3. Higher highs come with lower lows

A five. The dealer flipped a goddamn five, for another twenty-one. On a positive-fourteen deck, Kevin had lost one hundred thousand dollars in two hands. He sat there, frozen, watching the dealer sweep away his money. Then he rose and stumbled through the crowd. By the time he reached the elevators that led upstairs to his suite, his face had gone numb. He used his key card to access the VIP floor. After exiting the elevator, he stumbled down the hallway to his room. He lay down on the plush shag carpet, arms outstretched. He stared at the ceiling. A hundred thousand dollars in two hands. Overall, the team was still way up on the month. But it was a painful lesson to learn all at once. No matter the count, the cards could go bad. Over time, winning was inevitable, a matter of pure math. But in the short run, the game could go either way. Even math left room for luck. It was a good twenty minutes before Kevin felt strong enough to rise from the floor and search for the room-service menu.
— Ben Mezrich, Bringing Down the House

A mentor of mine once told me, after leaving his job at a big investment firm to join a startup: “When I got here I realized my best days at my old firm were a 6, and my worst days were a 4. Now I’ll regularly feel both a 1 and a 10 on the same day”. There is something to the idea that while we opt into bigger experiential upside we accept the risk of bigger emotional bumps along the way. Still, it’s hard putting to words how violent that turbulence can feel the first time you fly through it.

The lesson for me is that no matter how sure you are that you’ll get through it and how worth it that will be, the feeling in the moment can be crippling. In Kevin’s case above, he knew mathematically that he had made the right decisions and would make that money back, and yet he still couldn’t move for twenty minutes and surely carried the loss with him for much longer. It’s important we find ways to manage the feelings of our own losses, and to empathize with what may be boiling beneath the surface for the people around us.

4. Be open to new characters changing your story

You’ve climbed the mountain. And part of your job, aside from parsing abstract intellectual property issues for big corporations, is to help cultivate the next set of young lawyers being courted by the firm. A senior partner asks if you’ll mentor an incoming summer associate, and the answer is easy: Of course you will. You have yet to understand the altering force of a simple yes. You don’t know that when a memo arrives to confirm the assignment, some deep and unseen fault line in your life has begun to tremble, that some hold is already starting to slip. Next to your name is another name, that of some hotshot law student who’s busy climbing his own ladder. Like you, he’s black and from Harvard. Other than that, you know nothing — just the name, and it’s an odd one.
— Michelle Obama, Becoming

No matter how tightly-woven your five-year plan may feel, nothing goes completely according to script. People are the biggest wild card, an immeasurable set of random inputs that are programmed to change the narrative dramatically. While Michelle meeting Barack and diverting from lawyer to First Lady is an unusual case, someone’s story changing on a dime due to someone they meet happens all the time. It’s also not only romantic: business partners, mentors and best friends are great examples.

The lesson I took here is not to abandon life planning or goal setting. My takeaway is only that we be open to these individuals and the way they might alter our course. As humans we are magnets for meaningful social interaction, and while new characters are not universally positive contributors there is so much to gain by pursuing these relationships with an open mind. For what it’s worth, five years ago my five-year plan looked very different from where I am today and I hadn’t met my now fiancée…I thank my lucky stars I didn’t live out the plan.

5. Life is long if you know how to use it

I am over fifty years old and have attended my fair share of sixtieth, seventieth and eightieth birthday parties. In case you are younger than me and have not yet celebrated so many birthdays of high, round figures, I can tell you that the most common remark heard at these parties is: “All of those days that came and went — I didn’t realize those were life.” It is cunningly formulated. The guests nod knowingly, smacking their lips. Yes, we fear death to varying degrees, but the fear of not having lived is even stronger (…) Instead of elaborating about the years that came and went with a champagne flute in hand, we should turn rather to the stoic Seneca on twenty-first birthdays: “Life is long if you know how to use it.”
Erling Kagge, Silence: In the Age of Noise

Maybe I’m crazy for closing with this quote for risk of seriously bumming out anyone who read this far, but bear with me. My interpretation is one of optimism, and this passage probably stuck with me more than anything I have read in years.

New years is a time of reflection, and upon my own recent reflection I can be quite honest that I am very much a millennial. I believe people should hunt for their passions and do something fulfilling as a career, even if that means jumping around faster than previous generations would approve of. I also am so addicted to my phone that I set a daily limiting clock on Twitter and Instagram. I admittedly waste a ton of time on things that don’t make me happier or better.

I’m also very much in control of how I spend my time. Through my reflection, I’ve come to realize what does make me happier and better: spending time with unique and special people who are passionate themselves. If at my 80th birthday party I’m reflecting that life moved too fast, it won’t be for lack of time spent with my fiancée, my family and friends, and an incredible collection of colleagues and counterparts who I am constantly learning from.

I find it motivating to learn this lesson in life before it’s too late to do something about it. The other characters in your story, and their fascinating humanity, is what makes your story worth reading.

Embrace that in 2020 and you won’t regret it. Happy New Year!