Love Your Work
Rolling boulders and building cap tables
I work a lot.
Like all the time.
It feels like I’m always working on something.
Whether it’s professional* -Early mornings shuffling my “actual job” emails around, late night calls with friends and colleagues brainstorming new business ideas, or weekend coffee shop jam sessions talking strategy and corp dev
Personal* - Pushing myself to learn new things (anyone want to play tennis?), writing this blog on off hours during the week, or making my way through the stack of car parts in the garage queued up for the newest project
Or even familial* - Doing dishes, blowing the never ending leaves that find their way into my backyard despite no trees ACTUALLY LOCATED in my backyard, or sunday evening huddles with the family – providing overviews of our weeks, our intentions, and how we can set each other up for success today, tomorrow, and in the years to come.
(*I’m sure I could list more here, but you get the idea)
It’s all work.
It all FEELS like work.
But you know what? I love it.
Every minute of it.
Open up my Google drive and its filled with (digital) scratch paper – business plans, personal goals, long term financial planning excel files – archeologic records of a to-do list that only increases by the day.
I’ve always loved the grind. Not in the “toxic tiktok entrepreneur ‘buy ten homes and then take out a line of equity on each to buy 10 more’ videos” kind of grind – but in the “always be thinking, improving, making you, the people around you, and your situation better” kind of grind. I derive much (if not all) of my own meaning – and worth (both personal, professional, familial, and net) – from this grind. The constant want to improve upon oneself, to grow, to learn – to wake up a better version of yourself than you were the day before.
“Find what you love and you’ll never work a day in your life”?
Yea right.
I think about this phrase fairly regularly – and just how antithetical it is to those I’ve met who have truly found what they love – just how antithetical it is to me, and my life.
Find what you love and you’ll never work a day in your life?
Nope.
Find what you love and you’ll work harder than you ever have before.
See, the problem with the original phrase is it presupposes that the moment you feel like something is work it must mean you don’t love it.
“Oh man, my job felt like work today – I must not love what I’m doing – time to quit!”
But in actuality, what you love will PUSH you to work.
Think about something, anything (outside of work) that you KNOW you love, a hobby, sport, skill, whatever it may be.
Now think about whether that thing you love has ever felt like work.
If you’re doing it right, I bet it feels like work a lot more often than it doesn’t. Doesn’t mean you don’t enjoy it, but doesn’t mean it ain’t work.
Truth is, our meaning as individuals is defined by what we do. What we give back to our community, to our greater society, to history. Not our jobs – our work. The work we put into ourselves, the work we put into our relationships, the work we put into our hobbies, our personal pursuits.
And the beauty of it is – this work is all different - what we love is all different. Thats what makes our life, our work, and the work we do with others so interesting and compelling - those differences, those unique things we find that we love (because someone has to love revenue accounting and it absolutely isn’t me).
Some of us find those things early in our lives (a friend of mine knew he wanted to be a dentist when he was In the sixth grade. THE SIXTH GRADE. Not only did I not have any concept of “a career” in the sixth grade but I’m pretty sure my answer would have been astronaut or major league baseball player if you had asked me back then)
Whereas others of us spend decades searching, exploring multiple paths, before finding that thing we truly love.
And whether you arrive at what you love early, late, or somewhere in between - the very fact you’re out there doing it (prior Neatworking callback), trying to find it, is the important part - because you just never know - sometimes you’ll find what you love in the most unexpected places.
Enter our Neatworking connection for this week: Chris Hoffman (Founder and CEO of Equity Admin Co. also known as “Cap Table Chris” for those who follow him on Linkedin)
Chris and I have long since forgotten how we met, either through the multiple fundraising rounds at Hired, or Poshmark’s IPO, but either way - Chris has been a trusted advisor and friend to me and the businesses I’ve supported for years, and I got the opportunity to spend some time with him the other week discussing work, life, and just what it means to, as Chris puts it “love captables”
(I mean who LOVES captables? The only captables I love are the ones that I’m listed on, tbh)
Ready to get to work? Let’s go!
Talk to Chris about equity and his face lights up - a reaction few experience when they’re faced with a (very likely) messy private stage cap table with one-off equity grants, founder’s friends that “just happen to have been an early C-level employee AND have custom grants” (because of course they do), and more missed and cancelled grants that one auditor could catch in a lifetime (not at all speaking from personal experience here).
And I know first hand just how hard it is to find someone who truly loves equity.
Equity managers are few and far between.
And good equity managers?
Well they’re rarer than, boy, I don’t know how to even articulate how rare they are (According to Google search, Kyawthuite is the rarest thing on earth. A mineral only found in Myanmar (Burma?) - and with only one crystal EVER, found in the Mogok region of Myanmar, known to exist. Caltech's mineral database describes it as a small (1.61-karat) deep orange gemstone that the International Mineralogical Association officially recognized in 2015 - learn more about Kyawthuite and - be the coolest person at your next party, social get together, or networking event when you drop this knowledge on the crowd - here)
And although I’ve never gone hunting for Kyawthuite in Myanmar, I have had the pleasure of hunting for a number of equity managers in my time (Chris always had cooler things to do than work with me, apparently), and I think for the last position I posted I had approximately THREE applicants - TOTAL.
THREE.
I know I made a revenue accounting joke earlier, but at least there are thousands of good accountants.
Good equity managers?
Kyawthuite.
Which is why if my son ever asks me what I think he should be, I’m not going to say doctor, lawyer, or engineer - nope. I’m going to tell him to go get his equity manager’s cert from Santa Clara University and then he can inform the next job he applies to that whatever salary they already had in their head to double it, and then he’ll negotiate from there.
Pure Kyawthuite.
So - enough about rare earth minerals and me pre-selecting my child’s career path - what about Chris? How did he get into this niche field?
Turns out - completely by accident.
He had no idea this existed in school, neither did I, and very likely - neither did you, Neatworking reader (because if you thought my friend saying he was going to be a dentist in sixth grade was weird imagine if he had said he wanted to be an equity manager when he grew up?) and somewhat stumbled into it after applying to a job at private company cap table manager powerhouse, Carta.
Upon joining Carta Chris jumped into their managed services division (my words, not sure what they actually called it) - working on a one on one basis with CEOs, CFOs, Controllers, and even General Counsels (hey, like me!). Cap tables weren’t just excel spreadsheets and corporate docs to Chris, they were windows into the business, opportunities to work directly with founders, executives, watch their corporate journey, be a part of what they were creating, and share in their success.
What a cool gig.
And one Chris found was, unfortunately - fleeting.
Carta announced it was winding down his division, and with it - the very thing Chris loved.
So what does one do when they’ve found the thing they love, and aren’t able to do it where they’ve been doing it?
You go do it somewhere else.
Even better?
You go it yourself.
So that’s what Chris did. And he wasn’t even shy about it - informing Carta directly of his intention to hit the streets himself, stand up his own equity management services company - and since no one else wanted to (none of the THREE other equity managers, apparently) - Chris had the opportunity to carve out his own niche, create an opportunity for him to do what he loved, and do it his way. And so he jumped.
“It was terrifying” notes Chris.
And to add to that - decided to make the jump while he was on paternity leave with his (second) child. And remembering what paternity leave was like with my (first, and only) child, the fact that Chris had the mental capacity to make such a life changing decision during one of the most stressful, sleep deprived, moments of his life is (hopefully) a testament to just how much he loves this stuff.
Chris remembers his first few days after making the jump out on his own. The fear that he couldn’t do it - that he wasn’t good enough to make it work.
“I had that fear every single morning I woke up.”
But a funny thing happens when you’re doing something you love - you start to believe, in yourself, your abilities, in what you’re doing.
“A switch flipped…No way (I’m not good enough).” said Chris
“I can do this.”
And so he did.
And he worked harder than ever had, at what he loved.
From starting at Carta in 2018 with no idea what a cap table was, to running his own cap table company five years later. Loving every minute of it. Working every minute of it.
For those who truly love what they do, there is no work life balance, because those terms are one in the same.
Your work is your life. Your life is your work.
There is nothing to balance.
Does that mean you’re sitting behind a desk 24 hours a day?
Absolutely not.
But if you’re doing it right, all of the things you “work” on (yourself, your family, your career, your hobbies) bring you the joy, the love of the grind - that balancing that “work” against your “life” seems not just unnecessary, but an impossibility. If you’re doing it right, it all blends together - a life filled with passion, blurred at the edges of all the things you love, converging into a life of meaning - a life of work.
“Maybe everything should just feel like life.” says Chris - a statement more eloquently punctuated than any of my above preamble could have concluded.
Because when you find what you love, it really does just feel like life.
Ever sat around a “day counter” at work?
“Man, this is a grind, but atleast tomorrow is friday.”
Chris not only doesn’t count, he doesn’t even know.
“Man, this is a grind, but I don’t care what day it is.”
And maybe that’s a product of living and working in perpetual vacation mode in Lisbon Portugal? I dunno - I might have to try it out for myself one day - but whatever it is, its a state of being, a state of working, we should all strive for.
Not just in our jobs (because our “work” is much more than just our “jobs”) - but in our personal, familial, and communal pursuits as well. Find the things, people, experiences you love - and dive so deeply into them that time disappears, and the only thing left - is work.
There’s this book that’s a favorite of mine and my friend group (either shows how cool me and my friends are, or how lame me and my friends are - and I don’t want to know your thoughts on which one it is), and one which we reference fairly regularly, The Myth of Sisyphus, by Albert Camus (I’m actually surprised this is the first time I’m bringing this book up in Neatworking - maybe I’ve mentioned it before - but if you only read one book this year, make it this one)
But for those of You who didn’t study classical studies in college, don’t worry - I am here to use my effectively-meaningless-in-the-real-world undergraduate degree to bestow upon you the knowledge of antiquity the State of Florida paid for me to learn.
You see, Sispyhus was a king (aren’t they all), and Hades - King of the Underworld (see? all kings) wanted to punish him for cheating death twice, and the punishment Hades came up with? Rolling a boulder up a hill for eternity. Every time Sisyphus rolled the boulder up the hill, there it would go - rolling right back down to the bottom. Only for Sisyphus to go back down the hill and roll it back up again. And again. And again. Ad Infinitum.
Now - many (including Hades, clearly) may see this as a punishment. Labor forever. A continuous push up a hill, day after day, year after year.
But without this labor - what would we have Sisyphus do?
Camus asks this question in his book, examining the fundamental human need to attribute meaning to life, and the silence we get from the universe when we ask it to answer this very question for us - “what does this all mean?”
Ever stopped working? Just sat? Listened to the silence? That is the universe, being unreasonable - being absurd - providing you zero meaning to your own life that you do not provide for it yourself.
And therein lies Camus’ point (hence, that Sisyphus’ punishment was not a punishment at all, it was a myth - instead - it provided to Sisyphus meaning - for eternity)
Without work, without labor, without a boulder to push up a hill continuously, meaning sheds from life - leaving an absurd existence, an existence without purpose.
Camus notes, in his final passage of the Myth of Sisyphus: "The struggle itself towards the heights is enough to fill a man's heart. One must imagine Sisyphus happy"
And we don’t need much of an imagination to do so.
We all find our own boulders. Chris has found his. And his life is more meaningful as a result - even if that means rolling the same rock, up the same hill, day after day.
Because one day we won’t get to roll that boulder anymore - so while you get the chance to - roll the hell out of it.
Find what you love and you’ll never work a day in your life?
Nope.
Find what you love and work at it as hard as you can for as long as the universe will let you.
That’s what Chris would do.
That’s what Sisyphus would do.
And that’s what I’m going to do.
Happy rolling.