Leading Through Generosity

We’re all going to need to step up our generosity in a meaningful way because a large void was created in the world this past week with the passing of a legend.

Today’s content is shorter on bullet points, and longer on inspiration.

My first true experience with leading through generosity.

In the Southeastern part of Maine, sits a little beach town that has played an integral part in my life and my family’s life. I grew up going there each summer, learned to ride a bike there, and built a lifetime’s worth of beach forts. It has remained an important destination to this day.

Tongue-in-groove walls make up the 100 yr old beach cottages - the kind that have 5 rooms but sleep 15.

Deep porcelain sinks, screened-in porches to protect from Maine’s state bird (the mosquito), waves crashing, flip-flops, t-shirts, bikes, ice cream, low-tide, cold water, and friendly people.

The place is glorious in its simplicity.

And while this is all about the beauty and the importance of generosity, the irony is not lost on me that for this one, I’m keeping the name of the place all to myself.

Why that place matters relates to a story that embodies a leader who led with generosity and a giving heart.

A leader who would create the centerpiece for my understanding of what caring in leadership can (SHOULD) look like, and how approaching life through a lens of giving, gratitude, recognition, and thanks helps us all win together.

My former boss Jimmy Fay passed away this past week after a brutal battle with Early Onset Alzheimer’s. He was 59.

This is not an obituary. And while it is in some way a tribute, Together UP! Is about curating lessons through experiences and story, to help inspire us to lead better, build better teams, and do all of it Together.

This edition serves as a means to have lessons of leadership and giving taught by Jimmy Fay live on so hopefully, everyone can lead like he did…or at the very least add the willingness to give as a requirement for leadership.

Jimmy serves as the foundational element in my understanding of what culture can be. 

He gave with ease, and is a crystal clear example of someone who shows us why “this isn’t hard.”

Yet we still seem to make it hard.

Lead with generosity. Give your time, your resources, your knowledge, your understanding.

Leaders and coaches have knowledge to share. Transfer that knowledge. Give, in order to support those you lead, show them you care about them, and you will create trust, engagement, resilience, teamwork, performance, and culture. Period. Stop.

I’ll repeat it for those in the back row.
Lead with generosity. Give your time, your resources, your knowledge, your understanding. 

THE MERCEDES S-500 ROLLS THROUGH THE SLEEPY BEACH TOWN IN MAINE

I was a first-year junior trader on the equity trading desk at Merrill Lynch. “Mother Merrill” as the place is affectionately known.

I didn’t sit at the bottom of the totem pole, I was the bottom of the totem pole.

Naturally, I wasn’t jumping into vacation time or asking for much.

My family was headed to that same little beach town in Maine. It was very important for me to be there with them, and I was trying to navigate how I could join for at least the weekend. Naturally, as a junior trader I wasn’t even going to bring up the topic of taking a day off or bother anyone with it.

But it came up - in a conversation with Jimmy - who was very much my boss and a senior member of the desk.

The conversation went something like this:

Jimmy: “Jonny Hess what’s going on for the weekend!” (BTW he was genuinely interested… this wasn’t a space filler)

Jon: “I don’t know, my family is in Maine, I’m trying to get up there for the weekend”:

Jimmy: “How are you planning on getting there?”

Jon: “Trying to figure it out, but I’ll prob just have to rent a car if I can make it work.”

Jimmy: “Nonsense, take my car”

(Jimmy drove a S-500 Mercedes….like.. the big nice one, and I knew it. )

Jon: (now mortified and embarrassed at the suggestion). No way Jimmy. I’m not taking your Mercedes to Maine. If I go I’ll rent a car.

Jimmy: “Hess. If I find out that you either didn’t go to Maine, or that you went to Maine and rented a f’ing car, I’ll beat the shit out of you. What’s a car rental gonna cost you $500? I park my car across the (Hudson) river every day. You’ll take the ferry over first thing on the bell on Friday and just drive it back and leave it there Sunday night.

Sooooo…..

As I pull into the sleepy beach town in Maine, in the way too big for me, Full-Sized Silver S Class…and as my parents greet me, I pretty much got exactly what was coming to me: “This whole wall street thing seems to be working out pretty well for you, huh Jon??” 

The “my boss made me do it” didn’t quite fit this one…. I took the verbal jabs that were coming to me.

That wasn’t going to be their son’s experience and it wouldn’t be at any point in my time at Merrill Lynch, and it had nothing to do with the type of car I was rolling in with. I was going to be alright because, at the very least, the people I worked with and for, cared.

This is one of countless (truly countless) examples of pure generosity and caring from Jimmy - a high level leader to the kid at the bottom end of the totem pole. And I wasn’t alone in receiving this from him by any stretch.

Jimmy Fay would go on to take me to play golf for the first time ever at a place that didn’t have artificial mats for tee-boxes. A beautiful spot in Westchester County, NY (I didn’t have clubs or shoes - not a problem for Jimmy! He brought both for me).

I practically became an honorary member of Arcola Country Club, in NJ, where Jimmy belonged, and each time I visited, I left with a new golf shirt - courtesy of Jimmy.

I fell in love with the game through Jimmy, because even on a golf course, he supported me and made me feel awesome and confident.

A couple of years later as I was walking out the door to head to my bachelor party (A Georgia at Tennessee SEC football game), Jimmy, still my boss, apologized profusely for not being able to be there, and handed me a little chunk of cash to use in whatever way I needed to or wanted to. I ended up giving half to my best man (another great leader named Jimmy) who was running the show that weekend and used the other half creatively to make sure everyone had an awesome time - always with the mindset of honoring that gesture.

His generosity was constant.

While I realize these examples all fit in a category of having somewhat ample resources to be able to share, it’s what he gave that was FREE that was worth the most.

Jimmy. Thanked. Me. CONSTANTLY.

He, the big boss, thanked ME, the bottom of the totem pole.

He, the guy who was guiding me, thanked ME.

He, who seemed to have it all, or have it all under control, thanked ME.

Gratitude is free.

Showing people you appreciate them is free.

You do not need cash or an S Class or Golf Clubs to show people they matter and they are valued.

Jimmy’s generosity simply spanned all fibers of life, from simple thank you’s to grand gestures.

So when it came time for Jimmy to pivot to leave Merrill Lynch for a different firm, the best way to show him that all that he had taught me and all of the support he had given me had sunk in, and the best way to REPAY HIM, was to simply thank him.

In my two-page-long thank you letter to Jimmy, I outlined my recollection of the scenarios where Jimmy thanked ME.

I laid out my appreciation for his support, and made it clear it mattered.

And I made it clear that with all of the beautiful gestures he had offered, that his “Thank You’s” were what stood out to me as the greatest lesson.

It was the grandest way I knew to make it resonate with him that he had changed the way I viewed leadership, lessons, and how to treat people.

2 years later, one of our friends/former colleagues/a fellow culture carrier and head of the desk at ML, Leo Ressa came up to me and said - “Hey Jon. Jimmy showed me the letter you wrote him. I don’t think you realize just how much that letter meant to him.”

When you give, you receive.

Jimmy Fay taught me how.

Jimmy Fay taught me that we’re better together.

Thank You, Jimmy Fay.

Together UP!

Where to from here?

Readers of Together UP! know that I will usually offer 3 things you can do right now to take action.

This week, instead, I’m going to ask 3 questions. And the suggestions on what we can do right now are going to come from Jimmy’s rules for life.

On Motivation: I ask you, As i returned to work that Monday after Maine, did I feel like everything would be handed to me and I wouldn’t have to work or need to work? Or did I feel connected, empowered, and motivated to work hard for the team at ML?

On Engagement: I ask you, Did Jimmy’s giving spirit make me feel more, or less engaged to the place and its people?

On Resilience: I ask you. If Jimmy had to have a tough conversation with me about my performance at work, would I leave feeling like I was useless? Or would it be received knowing this person had my best interests in mind? Would I be able to handle feedback with greater resilience?

These questions aren’t hard.

This isn’t hard.

Yet we make it hard.

Jimmy’s Rules For Life
As read out loud by his three Children

• Never say no to dessert.

• Write thank you notes.

• Coach your kids sports teams and give the underdog a chance.

• Nurture friendships.

• Be kind.

• Work hard but play harder.

• Naps are critical for success.

• Never let your friends 4-putt

• Dream holy shit big.

• Be generous with all you have.

• Sit your ass on a beach as frequently as you can.

• Frame accomplishments.

• Let your children believe in Santa until 7th grade.

• Don’t stop laughing.

• Stay organized and keep your space clean.

• Always get a large popcorn, Diet Coke AND peanut M&Ms at the movie theater.

• Hold the door and use your manners.*****Note

• You’re never too old for a blankie.

• Treat your mother like a queen.

• Call grandma.

• Love with your whole heart.

*****Note…When I visited Jimmy last year at his full-time care facility, we sat outside. There was still signs of Jimmy inside him, but anyone that knows Alzheimer’s knows just how scrambled everything can be and feel. Up pulled a car to the front, and an elderly woman was in the passenger seat. Jimmy sprung from his seat. Went up and opened the car door for her, escorted her to the front of the facility.

In Jimmy’s darkest days, where nothing made sense to him, his instincts to give and live by his rules shined through.

In his darkest days, where nothing made sense to him, he was still teaching me.

Jimmy. You were a gift. Thank You.