Toil We Must
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Toil We Must

This was originally published in Investing 101, a weekly newsletter about the art and science of building and investing in tech companies. To receive Investing 101 in your inbox each week, subscribe here!

When I left home for the first time and was living on my own I started reflecting on my life growing up with my parents. When I thought about my parents I started to have quotes and phrases come to my mind that represented what each of my parents had taught me.

For my Dad the thought immediately came to mind:

"If a task once begunNever leave it till it's done.Be it the labor great or smallDo it well or not at all."(Paul H. Dunn)

Funny enough the idea of “anything worth doing is worth doing well,” is credited to a father writing to his son. My Dad's Dad was a forest ranger and my Mom's Dad was a chicken rancher. While hard work runs in my family I'm the beneficiary of hard work after the fact. My grandpa's worked the land so that my Dad could crunch numbers so that I could do… whatever it is I do. But it's certainly not chicken ranching.

I've wanted to think through the reality of hard work when it comes to startups and venture, and how you balance that with an increasing emphasis on mental health and quality of life. I kept collecting snippets on the idea thinking I would write about it eventually. And then a venture funding announcement brought it top of mind for me this week.

The Culture of Hustle

But first? Some background. The evolution of our relationship with work has evolved dramatically in what feels like a very short period of time. We've gone from "Greed is good" to "Rise and grind" to "It's just a job."

Nothing has taught me more about the changing relationship people have with work than corporate TikTok. Countless videos about companies mistreating their employees, expecting them to work overtime, creating a toxic culture that leads to waves of employees quitting.

Reddit and TikTok have countless motivational resources for the practice of "quiet quitting," which is a definitely a misnomer; it’s not quitting its people doing the baseline of expectations. Erica Pandey at Axios articulates the core idea:

"The idea is to work to live, instead of living to work — stay on the payroll, but focus on fun, fulfilling activities outside of work."

The divide feels particularly poignant across generations. My friend Rex, who I jokingly refer to as a Gen Z scholar, shared an interesting tidbit that was shocking to me as a Parks and Rec fan. Most Gen Zers don't like the character of Leslie Knope. She's a peppy motivated workaholic that can't stop making binders.

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Instead of "work for the sake of work," the younger overlap of Gen Z and millennials are reemphasizing a different focus for work.

"[This] doesn't mean we're lazy and don't want to work hard. We want to work for a company we care about, and for a boss we respect. And we don't see the point in clocking in super early and clocking out super late if it's only to show face."

This isn't a "young people don't know how to work" paradigm. There is an important nuance in balancing hard work and quality of life. But some important questions came to my mind:

  • Should your work-life balance change depending on whether you're working a big company 9-to-5 or building a startup?
  • Does hard work (aka 'grind') automatically indicate toxic culture?
  • Are you responsible for finding your fulfillment? Or is your employer?

The Drama in the Oven

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In case you haven't seen the talk of tech twitter this week a company called Oven announced a $7M venture round from Bucky Moore at Kleiner this week and put out a job posting for engineers. The above tweet was how they described what to expect.

For some people it was a real trigger.

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The responses fall into two camps:

(1) Building startups is hard; why is this controversial?

(2) This is the kind of toxic hustle culture that is killing everyone and everything

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I'm serious, read the quote tweets (there are 1,000 of them.)

This really hit a nerve for a lot of people. And there is an entire socio-economic web to unravel here around distrust in institutions, income inequality, mental health, and labor expectations. I'm not qualified to address pretty much any of that.

But I can't deny that this is an important issue. And it's not enough to brush it under the rug saying "I don't understand why this is so controversial." For me, as Kyle Harrison, I'm trying to strike the balance between (1) I don't think this company did anything wrong; building a startup IS a grind. But (2) I do understand why this is a trigger for some people. People who have worked hard and felt unseen, unappreciated, and taken advantage of.

For anyone building a company, hiring people, or funding companies that will then hire people: this is an important discussion for you to pay attention to.

Putting The Build in Building a Company

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This hard work vs. work-life balance dynamic flares up between two types of people, who I'll call Devotees and Balancers.

Devotees: People who want to sacrifice for the thing they're working on, sometimes even sacrificing sleep, personal relationships, mental health. They make a choice to deprioritize those things in favor of dedication to the thing they're building.

Balancers: These people are just as capable of building. But they acknowledge the importance they want to place on balance in every aspect of their life (work, education, relationships, health). And they're not willing to sacrifice that balance in favor of the thing getting built.

Neither of these groups are bad. They're simply people that prioritize their lives very differently. But, as we find ourselves doing in pretty much whatever cultural circles we're drawing these days, they often villainize each other. Devotees consider Balancers to be lazy snowflakes and Balancers consider Devotees to be either dictatorial robber barons (if they're in charge) or mindless zombies (if they're not).

Startups Are Hard

One key reason startups are uniquely hard is because they represent a different kind of work. Some day I'd like to go into the nuance of building vs. maintaining, but the key point here is that most startups represent the wizardry of building something out of nothing. That is hard to do. And to do it very well is harder than the average job.

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Don’t get me wrong. I acknowledge the privilege in that work. Working in tech to build startups has produced millions of millionaires. I wish that teachers and nurses and parents were appreciated enough to be made millionaires. That's a different battle to fight. But the reason so few startups workout is because they're really freaking hard to succeed at.

Brie Wolfson wrote a very good essay about her time working at Stripe. She acknowledges the work was both challenging and rewarding.

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The response to her article was similarly quite divisive. Some people loved the idea of working towards a bigger vision. Some people saw it as a greedy company having a negative impact on the lives of their employees.

"There’s no way around it: the culture was demanding. I spent many late nights working. I cried more than a few times after feeling like I let a user or a colleague down. My heart would beat out of my chest before heading into an exec review. Once, my manager asked me to reconsider the vacation I had been planning because my team needed me. “If you go, who will cover your work?” I looked around at my colleagues who were also regularly working 15-hour days and decided to stay put. I’m proud of that choice. Call me masochistic, but I have to admit that it felt good to care about anything that much. And, to be around people who I know cared that much too.  Lately, I can’t help but feel like Silicon Valley has lost this culture. I don’t hear people talking about work this way anymore. Maybe that’s for the best. Maybe it isn’t."

People read these descriptions of difficult life choices and intense work environments and they see it as exploitation. But these people are adults. They're choosing the kind of work they want to do. I worked at Amazon in their finance department. I only lasted 6 months because I was more bored working 32 hours a week making charts than I had been working 80 hours a week on a startup. But the important takeaway? There are people who work hard at corporate jobs. There are people who want to not work that hard. Everyone's situation is unique and that's okay.

I don't see anything wrong with the way Oven framed what the work at their company will be like. If that isn't a fit for you that's okay. I doubt they think you're less of a person. And a lot of the comments on the tweet said things like, "oh apparently this isn't a safe space for a pregnant woman." Or "I see they never want you to see your kids again?"

Maybe one of the biggest problems with the internet is we post what we think we see and then cite ourselves as the evidence that that thing is reality.

"To every thing there is a season." In the midst of big life changes like having a baby or dealing with a sick family member; that may not be the right time to work for a brand new startup. (Again, that’s okay! That doesn’t make you less of a valuable person.) For those who join a company ready to work hard, and then suddenly find themselves in difficult life situations? It's dependent on the humanity of the employer to handle that situation delicately. If they don't? Then let's drag them for that. But saying "this will be hard work" doesn't automatically make them guilty of every possible negative workplace behavior.

I have 3 kids. I love spending time with them. I spent 4 years building a company when I didn't have kids. I've worked 80+ hours a week when I did have kids but I have a phenomenal partner I don't deserve and we made that decision together, and then she made it possible for me to work that way. Working hard is a choice; not a consequence.

So if toxic work culture isn't just saying, "this is hard work," then what is it?

What is Toxic Culture?

I want to definitively and unequivocally reaffirm that toxic culture does exist.

In Brie's essay she talks about crying "because she let a user or colleague down." That's one thing. But if you're crying because you've been screamed at. Or verbally attacked on a personal level. Or forced, at the threat of termination, to forego things like funerals or weddings or the birth of a child? That's toxic. Brie missed her vacation because she chose to. Not because her manager demanded her fealty, or threatened her.

There is a very real wave of workers demanding their own quality of life, and I think that's good. There are employers who demand overtime, give no praise and constant complaint, offer no promotion or economic upside, and treat their employees like computers they can smack when they move too slow. Let the powers of capitalism demolish those employers. Let them be unable to ever hire anyone ever again. Those cultures are toxic. And TikTok is a group therapy session helping empower people who shouldn't have to put up with that.

But somewhere along the line we morphed "bad working environment" and "hard working environment" together and transferred the sins of the former to the latter.

Let's look at that rage-inducing tweet again. (Although I now find myself spiraling into an existential quandary as I act like an academic doing a close reading of cultural artifacts (aka tweets.) But there's no time for that. Back to the grind.)

Pay attention to the wording of Oven's tweet:

"If work-life balance to you means a lot of time spent not working, it's probably not a good fit right now."

Some people say work-life balance, others focus on work-life integration. The important reality is that more people have to define for themselves what they are and are not okay with. Reminding everyone that, as grown-ups, we get to decide what we do with our lives. What do we think work-life balance means? Because work-life balance could still include working 80+ hours a week. And that decision doesn't have to be an attack on anyone else's decision.

Many of the comments in the tweet are, in essence, saying things like, "Oh so you're saying that if I only want to work from 11 AM to 2 PM so that I can focus on becoming a certified scuba diver, then I don't deserve to work for you?"

Yes. That is specifically what they mean.

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That doesn't mean you're a bad person. If anything, you're a more interesting person than me because I'm not a certified scuba diver. But a company like Oven is putting out into the world a belief they have: "we want to work hard to accomplish something that is worthwhile."

If that's not your bag? That's okay. We are each responsible for our own fulfillment.

Fulfillment For Who? And From Who?

Death bed regrets come up a lot when talking about the true purpose behind work. When people are approaching the end of their life they often point out their greatest regrets:

  • "I wish I'd had the courage to live a life true to myself, not the life others expected of me."
  • "I wish I hadn't worked so hard."
  • "I wish I'd had the courage to express my feelings."
  • "I wish I had stayed in touch with my friends."
  • "I wish that I had let myself be happier."

I believe in all of this. I had my first kid when I was 24 years old because I believe life isn't meant to be lived for myself. I take immense satisfaction in watching my children grow. When I see my son captivated by a Lego set I feel a deeper sense of pride than I feel in most of my own accomplishments. I don't want my life to be defined by the number of emails I sent.

But life is about progress, not stasis. In the words of my Dad, "anything worth having is worth improving." When I've thought about my parenting philosophy I often think about this quote:

"Whatever you are, try to be a good one."

When I share that perspective I often get similar responses to the comments to the Oven tweet (though much softer). "But that puts a lot of burden on your kids, it’s so hard to be the best at something."

But back to our close reading; I didn't say be the best. "Try to be a good one."

Certainly motivate yourself by striving to be the best. But in the end? There is a lot of fulfillment that comes from trying to be good at something. You have to define for yourself where that sense of fulfillment will come from.

For Brie (and a lot of people, including myself), work can be a big part of that fulfillment. This quote is a longy but a goody:

"I do think work can be a source of real meaning in life. But, we’ll only ever get out what we put in. And in the case of work life, it is kind of a collective decision. Once your neighbor starts signing off Slack at 3:30 consistently, it’s hard not to do the same. The path of least resistance is right in front of us, and we are taking it. I’m all for creating healthy boundaries that keep us satisfied and emotionally healthy—inside and outside of work. And of course I believe you can love something without it having to hurt. But I’ve never truly loved anything that didn’t move me to my core. I can’t help but wonder if all this effort we’re putting into keeping work at arm’s length is actually holding us back from being our best selves.A few months ago, someone complained to me that the new (very hot stuff) startup they were at had a “lgtm culture.” Upon inquiry, they explained that no matter what they do or how good it is, everyone just says “looks good to me.” “I know I should feel good about being a competent, trusted, contributing team member,” he continued, “and my new colleagues are so, so kind, but at the end of the day I just feel like no one has any standards.” He looked down at his coffee for a moment. “I’m afraid I’m never going to see my best work again.”I’m not exactly sure how we balance the realities of the world today with a working life that asks so much of us. But I do know leaning all the way out isn’t the answer. I hope we find the right way through it, together. We certainly need the support of our leaders to get there, but I know from experience that anyone, in any corner of an organization, can play a meaningful role in building the organizations we want to be in.And when we do, I think we’ve got a shot at transforming organizations into the incredible sources of community and self-actualization they should be.

Growth Is Good

I don't know about every other country but certainly in the U.S. we have a bit of an obsession with GDP growth. It's in the news all the time and we think about it constantly as a scorecard of national economic health. And it can be one important metric. But it shouldn't be such a guiding light.

"GDP measures everything except that which makes life worthwhile." (Robert F. Kennedy)

I consider myself a progressivist. I want more technology. I want more progression. I want to solve hunger and poverty, but I also want to go to different planets and virtual realities. I want everyone to find happiness and be their best selves, but to also have as much money and resources as they want.

So I'm (obviously) not one of the people that deride tech companies or hard work or a focus on building new things. I'm very much for it.

But I'm also a big believer in personal growth, not just economic growth. I want people to be happier and working more or working less is not the deciding factor of happiness. Building a resilient mind and a rewarding life; that's what leads to happiness.

So instead of focusing on "not working hard," I wish we would spend more time learning how to "do hard work well." How do people find work they love? How do people set boundaries for what they are and aren't okay with? How do they communicate those boundaries? How do they motivate themselves when they're afraid? How do they become more self-aware of what their body needs (sleep, a walk, sunlight).

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The principles of “quiet quitting” immediately sounded quite familiar to me when I first saw them laid out by Erica Pandey:

  • Work for a company we care about
  • Work for a boss we respect
  • Give us something to believe in

I thought of Charlie Munger’s 3 rules for a successful career:

  1. Don’t sell anything you wouldn’t buy yourself (you’ll feel much better when you’re selling something you actually believe people need)
  2. Don’t work for anyone you don’t respect and admire (a boss you respect)
  3. Work only with people you enjoy (easier to do when you’re working with people to build a company you care about)

Some combination of those things can lead to a much more fulfilling life, whether you’re working a lot or a little.

What Does This Mean For Venture Capital?

For those of you who consistently read my writing, I may have strayed a bit from the "art of venture capital" this week. But the relevance to me is more obvious than I've probably made it.

Startups see venture dollars as a part of their life source. The people who provide that capital are an important voice in the way founders build their companies. Certainly it's on every founder to dictate the culture of their own company. But VCs play a role in helping founders to be more thoughtful about their approach.

We can't, and shouldn't, deride hard work. Building something from nothing is hard. But we can embrace an element of humanity by helping people identify where their fulfillment comes from, and then helping them to find that in their role.

A good founder will hire a qualified person. A great founder will help all of their people become more qualified. More fulfilled. More capable. Great companies should make great people.