I was recently asked to interview for a series of profiles on leaders doing exciting new things in the business world. For reasons I won’t go into here, the article was never published – but I wanted to share my responses.
On my background:
I grew up on the bleeding edge of the poverty line as one of 5 children in a single-income family. My father, a Vietnam vet with undiagnosed PTSD, worked as a handyman for a city government. While we could have qualified for food stamps and free school lunches, my parents were too proud to accept help and so I spent most of my childhood hungry. I was also functionally blind until I was seven years old when my teacher realized I badly needed glasses. Being able to see made a big difference to my academics, and I went from the Special Ed track to the Gifted track literally overnight. When I graduated high school I had the grades and test scores to go to any college I wanted, but couldn’t afford the application fees – let alone tuition – so I struck out on my own.
By 23 I had served on the boards of two national nonprofits and had my third album go viral (before “viral” was even a thing) on the various file sharing networks – earning me a lot of underground recognition and no money. I had also toured and hitchhiked across the country and back twice, performed in front of crowds of thousands, dropped out of community college three times, eaten out of dumpsters to avoid starvation, and briefly ended up homeless. That same year my dad was diagnosed with PTSD and I suddenly had a ridiculously small stipend from the VA to go to college. I leaped at the chance and graduated at the top of my class four years later. In my last year of college I started a small business building websites after teaching myself coding fundamentals, and paid my way doing that (between protests for social justice and the environment and shows with my band) until I joined my first startup at 30.
I spent the next 13 years at startups of all kinds, working my way up from front end developer to Head of Product. I was often one of the only people from a working class background and always careful not to mention my age. As a white man people just assumed I belonged there – as long as I didn’t tell them anything about my actual life and lived experience. It was exhausting, but I am grateful for the opportunity. The money I earned gave me financial security for the first time in my life, I met some amazing people, and I learned a lot about business that I am now putting to good use.
At 42, I launched my company – Manzanita Cooperative – with the mission of addressing the twin crisis of food insecurity caused by climate change and habitat loss caused by farming. My experience with hunger as a child makes the looming crisis of food insecurity in a changing climate very personal for me.
Today I am happily married with two kids and live in unincorporated coastal Mendocino , wedged between the forest and the ocean. It’s nice.
How did you become a leader:
I’ve found myself thrown into leadership positions whether I wanted them or not my whole life. Even when I was early in my career I found myself thrown into leadership roles that my title did not justify because I was the only person willing to say “this thing is broken, here’s an idea for how we can fix it” and then follow through on that idea and deliver results. Leadership doesn’t begin with a title and it isn’t limited by titles. It’s an activity – not a position. I strongly believe that people who can’t lead without authority should not be trusted with authority.
As for becoming a founder, after working in startups for years I realized many of them make the same mistakes over and over again. I decided I want to make creative new mistakes instead, and that meant I needed to start my own company.
The most challenging part of leadership:
Leadership is fundamentally about trust, and so living up to that responsibility and being worthy of trust is the most important and challenging part. Humans are fallible and will make mistakes, but when my mistakes end up negatively impacting the people who have trusted me enough to be on my team, I take that very hard and am motivated to try harder, work harder, in the future.
Ultimately, it comes down to accountability. I am a big believer in 360 degrees of accountability. As I work with my reports to set their goals and metrics each quarter, I make a point of asking them what they need from me in order to do their best work. I use that feedback to set transparent objective kpi’s and metrics for myself as a leader, and create mechanisms where they can safely give anonymous feedback on my performance at the end of the quarter. That’s a consistent practice for managers at all levels of teams I lead, and I’ve seen it have dramatic impacts on performance and trust.
This is, of course, wildly unusual within the business world. I believe it should be the standard.
How do you structure your workday:
Sleep cycles (chronotypes) are at least partly genetic and my particular chronotype means I am most productive in the morning and then again from around 8pm to 2am. It’s 1:40am right now as I write this. There’s a ton of scientific research out there showing that pushing people outside of their chronotype – for example by forcing a night person to be in the office from 9-5 – causes a whole host of negative impacts. So I don’t. Unless there’s a non negotiable logistical reason for someone to have to work specific hours, everyone at Manzanita who works remotely is free to work on the schedule that makes sense to them and they are measured based on what they achieve.
I usually wake up around 9 and dive into work immediately, pausing for a quick breakfast/lunch around 10:30 or so. I work until 2, when I go pick my son up from kindergarten. We come home, spend some time reading together and do his Cello lesson, then I get my daughter from her after school program and do reading practice and a violin lesson with her, make dinner, do some dishes, and then turn the kids over to my wife for a couple hours so I can have downtime or (often) work some more before I do bedtime with them at eight. I spend a few hours with my wife, and am usually back working again from ten to a bit past one.
Of course, sometimes I need to be up much earlier and sometimes I work much later, but this schedule puts my family at the center of my day, which is where they belong. In the long term, all any of us are is a memory and I want to be a good one. Ten years from today none of our co-workers will remember if we stayed late at the office, but our kids will. There’s also hard data showing that productivity drops through the floor when people are judged based on hours in an office instead of what they produce. I think the world would be a much better place if people got their priorities straight and made time for the truly important things in life.
Recent leadership lesson:
My working definition of an ethical person is someone who says what they mean, means what they say, and does what they say they’re going to do.
Ethics aren’t about what you do when it’s easy, they’re about what you do when it’s hard. Especially when they come at the cost of your career aspirations or bank account. And while a lot of people talk about ethics, far fewer actually have them. Finding the people who do and hiring/promoting them is at the core of good team building.
Favorite Leadership books::
I honestly learned far more about leadership from participating in grassroots organizing over the course of decades than I have ever learned from a book on the topic – and I’ve read most of the trendy ones at this point.
The trouble with books on leadership written for a business setting is that they all assume hierarchy and asymmetrical power relationships. That’s not really leadership – it’s paying people to do what you tell them. I’m overstating a bit for dramatic effect here, but the problem is a real one. Leadership is about inspiration and accountability and when people are dependent on someone else’s opinion of them for their livelihoods, they self censor. That means in organizations where power only flows from the top down, leaders can easily find themselves surrounded by people who only say what they think the boss wants to hear. In other words, unaccountable hierarchy is the enemy of information flow, and information flow is essential to effective decision making.
Organizing volunteers, by contrast, is based on inspiring them with a shared vision, something worth going the extra mile for because it’s the right thing to do. The fundamentals of that approach – collaborative decision making, cooperative goal setting, nonviolent communication – are all applicable to the workplace and the best leaders make use of them to create safe and collaborative communication where data-driven dissent and opposing viewpoints are valued. This is very hard to do well and requires real trust, but it’s absolutely worth it.
Over the years I’ve developed my own framework which I call Redwood Culture. Redwoods are the tallest trees in the world, but instead of having deep tap roots they have shallow roots that spread out wide and grab onto the other redwoods around them – they literally hold each other up.
I believe healthy organizations are the same way, and so in addition to the normal Agile rituals and goal setting described above, I do circle sessions with my team at the end of each sprint. We discuss what went well, what we can improve, and each person is prompted to pick a colleague to thank or acknowledge and then pick a skill or set a goal they want to focus on for the next sprint. We end by reviewing last sprint’s goals and talking about progress made. The practice of expressing gratitude and setting goals in a structured way has transformative impacts on team cohesion and attitude.
I may write a book on the topic one of these days. If my company succeeds the way I hope it will, maybe people will even want to read it! We’ll see.
My most important takeaway is simple: if you want to be a leader, be someone worth following.
Final thoughts:
One of the hardest things in the startup world the last couple years has been watching so many intelligent and talented people struggling to find work as companies have gone through round after round of layoffs. I’ve seen people with decades of experience unable to land new jobs until they lose homes, marriages, and more; or give up and retrain into other industries.
I’ve been in this industry long enough to realize that the best asset any of us have in our careers – and the only asset we get to take with us – is the network of colleagues and friends we build over the years. Especially now when record-breaking layoffs are shaking the tech startup world to its foundations, it’s worth making the effort to help friends and former colleagues who are struggling in whatever way one can. Even if it’s just to lend an ear or a shoulder. As the song says, we all need somebody to lean on.
We should help each other, not out of any sense of obligation, but because we know that in this modern economy bereft of real leaders, layoffs can happen at any time and no one is safe. Because there is real joy in celebrating a friend’s success when they find a new position. Because helping each other makes us human.
Far too many “leaders” in our industry have never worked at a company where they weren’t the boss because they started their companies right out of college (or instead of college) with money from wealthy parents, or jumped straight into upper management based on connections instead of earning it. No one wants to acknowledge that fact, but it’s true. Folks like this have never experienced the precariousness of wondering when the next round of layoffs will come or staying in a job you hate because your wife is pregnant or you have a medical condition and you need healthcare. The empathy deficit that this creates is real and dangerous. People who do not recognize their own privilege and the asymmetrical nature of the power relationships that surround them are simply not capable of making decisions rooted in empathy. And so they lay off the people who built their companies in order to boost share prices in the short term, not thinking or caring about what that means for the human beings on the receiving end. It is truly sadistic indifference to the suffering of others.
This is why the Bylaws for Manzanita Cooperative allow anyone in a Leadership position – up to and including me – to be removed at any time by a vote of no confidence by the people they lead. We also have a clause in our bylaws that no dividends can be paid for 1 year after a layoff. Changing those rules would require a 2/3 majority vote by all members of the Cooperative. I wanted to be very sure that even after I retire and am no longer part of the business that this company will retain the ethics I’ve tried to bake in, and that the sort of people who should never be trusted to lead a business like ours will find it unappealing.
Real change in the business world requires structural change – not just nice words. The only way that happens is if more people from working class backgrounds start companies, and structure them as worker-owned cooperatives that give team members a real democratic say in how the company is run. That’s what my co-founders and I decided to do and I’ve had no cause to regret it. It’s a poor way to become a billionaire, but in my book anyone who succeeds at amassing that sort of wealth in a world with so many people in need has fundamentally failed as a human.
At the end of the day real leadership isn’t self-aggrandizing and it doesn’t hoard the rewards of success. It’s an act of service done with the intention of lifting up the people around us and helping them be the best versions of themselves.