Waking up an Indentured Servant to My Own Company

In October of 2016, I attended a CEO bootcamp in Colorado. Basically 5-days of group-therapy. The folks present were all CEO’s of successful venture-backed startups ostensibly screened from a longer list of would-be attendees. One of the crazier but more life-changing exercises we did during the week was called a Clearness Committee.

Clearness Committees were pioneered by the Quaker community as a way to help individuals within the community find clarity about a particularly difficult decision. The structure is simple; the impact is profound.

The individual in quandary sits in the center of the circle and is surrounded by supportive community members. He or she gives a brief synopses of the decision to be made. The community members then proceed to ask the individual open-ended questions about the decision.

I’m usually one to dive in to such witchcraftery out of a sense of curiosity and adventure. Plus I was carrying a weighty question that fall.  So I raised my hand and volunteered. The quandary I brought to the group went something like:

I feel lost in what I want to do with my company and my role.

The questions asked were wide-ranging:

• When is the last time you felt energized as a CEO?

• Why did you first start the company?

• How might you know if it was time for you to leave the company?

• What’s keeping you in the CEO role today?

• What do you love about your role?

• What % of the time do you feel happy at work?

That last one was a doozy. I realized I was deeply unhappy in my role. I was burned out and needed a change.

The Clearness Committee worked. I flew home to LA that Sunday with total clarity that I needed out of my company and out of my current CEO role as soon as feasible.

Even with that clarity, it would be two and a half years before I would finally make that change.

Two and a half years!

We finally sold Twenty20 in April of 2019.

I spent 30 months in a state of fatigue and burnout.

Looking backward, there was tremendous irony in the reality that the more successful my startup became the more trapped I felt

I had started the company 5 years prior out of a desire to really experience life. Part of what drove me into the chaos of startup life was a deep fear that if I lived a ‘normal life’ and had a ‘normal job’ my life might pass me by. My fear of normalcy was far deeper than my fear of diving into building a venture-backed startup.

The irony wasn’t lost on me. The company I created as my escape-hatch from a normal life became the source of my own indentured servitude.

I wish I was an isolated case.

Realizing how very un-alone I was in my experience

Since exiting the company, I’ve turned my attention to coaching startup leaders full-time. It began as a part-time exploration of what it might be like to intentionally help a handful of founders while I sorted my next startup. But I’ve been astonished at the need.  Not for more shitty life-coachy types who leech off the tit of venture money, but for experienced startup operators who have done their own deep work and can show up as real partners for other leaders.

I’m a newbie to this coaching thing, but the need has been staggering already.

Yesterday alone, I heard the following from 4 different founders:

• My company just raised $100M, and I want to quit. What do I do?

• We’ve launched in two countries. I want out but don’t want to leave the team unemployed.

• I’ve been at this six years. I’m tired. But I don’t think we can sell.

• I know I need to grind, but I can’t find my way back to the focus I used to have.

One day, from four different founders!

Burnout is rampant in the startup community, and nobody is talking about it.

How can you?

You’ve convinced professional investors to entrust you with millions of dollars. Tens or hundreds of employees have changed their lives to follow you on this journey. Exits are few and far between, and nearly impossible to engineer when founder-burnout is the primary driver.

What to do?

Welcome to the land of no easy answers.

How to Handle Burnout

The setup

Most CEO or leader types aren’t entrusted with the role because they tire easily. Most of us have lived most of our lives as the one who would place other's needs ahead of our own and who simply will not quit.

I’m astonished when I dig in to the family-of-origin stories of founders how often they share the experience of ‘early promotions.’ Times in their families of origin where they were required to step into adulthood earlier than might be natural.

In my case, my dad was emotionally absent and struggled with drug and alcohol addiction, so from the age of 10 or so my mother began turning to me to fill the friend and partner role my dad left absent.

Thus, at 25, the CEO role felt a natural fit for me. I’d already spent 15 years shouldering the challenges of adults.

This set up can be quite functional in the early years of being a leader. In my case, I was a natural at juggling the needs and interests of employees, investors, advisors, and partners. I could weave and address the needs of dozens of people as long as you didn’t challenge me to also include the one person whose needs I couldn’t voice: me.  

I hadn’t practiced noticing nor articulating my own needs in 20+ years. I didn’t know how.

When a leader builds a team or company with an eye toward taking care of everyone else, even at their own expense, it’s a recipe for burnout.

Fatigue vs. Burnout

I’m not talking about fatigue or tiredness. We all get tired sometimes. After a tough month or a busy quarter, we’re ready for a break. Shut off the laptop, take a vacation with some friends. Lay on the beach awhile.

Vacations solves fatigue.

It doesn’t do shit to address burnout.

Burnout is the big scary weightiness that’s sitting their at your desk waiting for you your first day back from that sunny beach escape. And it’s likely grown not shrunk.

Burnout grows during times of spaciousness because the spaciousness clears our vision and gives us perspective, and that perspective further informs us that something is wrong. That something much change. That the way we’ve been living, working, leading, while it might have functioned well for years, is not going to work anymore.

This is the state I often find founders in when they come to me to discuss coaching.

The good news is that finding a real partner who can hold space for the exploration of burnout is the first step in real change. The bad news is there’s no easy fix for burnout. And solving the misalignment causing the pain might require changes you’re unable or unwilling to make.

In my case, those changes took 2+ years of grinding toward a sale. For others, it can mean  the end of a marriage, a role, the sale of a home, or any myriad of other difficult but necessary life changes.

But first, let’s talk about alignment.

Working toward alignment

When talking with CEO’s about difficult decisions for their businesses, I nearly always start with ‘what do you want?’

Because of the common experience of the ‘early promotion’ I described above, most leaders I meet aren’t very in touch with their own desires. And they’ve been leading from a place of self-flagellation for some time with some success.

But it isn’t sustainable.

I believe that getting clear on what the founders and leaders  want in any situation, in addition to asking what’s best for the company, is critical.

Burnout and a myriad of other culture issues arise from lack of alignment.

Examples of when alignment is present:

• The company’s mission, vision, and values align with or compliment those of the leaders

• The company’s growth supports the lives the leaders and employees desire for themselves and their families

• The board and investors are bought-in to the way the founders and leaders want to build the business in support of their own desires and needs; this plan fits the needs of the investor's fund and LPs

• The team’s rituals create a container for common human desires (belonging, trust, partnership, emotional support, etc.)

Examples of misalignment:

• The CEO could give a fuck about the company’s mission (I found myself here 3 years before exit), it's a problem as you might surmise

• The company’s culture is in direct conflict with the employees’ sense of well being (sadly the default in corporate America)

• Company leadership can’t be honest with the board about their desires or experience (the default in Silicon Valley but deeply unnecessary)

• Investors want to ‘go long’ but founders want to sell soon

• The head of engineering would rather be spending his time making handmade furniture (real world examples abound)

In search of alignment

Solving fatigue is easy. Solving burnout is fucking hard.

Rest isn’t the solution. Alignment is the solution.

As you can see in the examples above, few cases of misalignment have quick fixes.

How do you ‘fix’ a CEO who doesn’t care about the company’s mission? Companies are run by humans, and humans change and evolve as the years pass. What can be done?

Firing founders is a toxic, nuclear solution. But what are investors supposed to do when they need a company to ‘go big’ in order to care-take the bets of their LP’s?

There are no easy solutions here.

For me, the change was massive and took years. Thank god for the coach, therapist, board members, cofounders, team members, and good friends who helped me along the way.

Two and a half years after getting clarity on ‘what I wanted’ (to sell the company or transition out as CEO), I got my wish.  I looked, but I never found a path to alignment that would keep Twenty20 on its core mission while keeping us independent and me in the CEO chair.

Avoiding burnout, or finding one’s way out of burnout, is achieved by finding and maintaining real alignment.

To avoid burnout in your work, your work must be in line with the difference you want to make in the world. The pace and flexibility of the work must support the relationships, hobbies, and healthfulness that you need in your life.

If you’re experiencing burnout, the solution begins with an honest exploration of what you need that you aren’t receiving. The work of finding the answer to that question is impossible to do alone. We simply aren’t made to process our lives’ hardest questions in isolation. The question is particularly difficult for those of us who, like most leader-types, have spent our lives pushing away our own needs and desires less they get in the way of the family or team.

But ask you must.

And these are dangerous questions.

If you wake up to find yourself an adult of 25, 35, or 45 with a team, partner, or children relying on you to be a stable force in their lives, these questions can really rock the boat. That’s part of the reason we avoid them until we no longer can.

For some, the answers are palatable. A CEO friend of mine recently realized his business afforded him great control over his schedule but that his sense of duty precluded his ability to enjoy that flexibility. Once realizing he could actually leverage his role to experience greater flexibility in his life, he started jogging in the morning after dropping the kids at school. A beautiful example of alignment achieved with minimal change. Last I heard, he was planning to use some his personal proceeds from the business top open a bar, a lifelong dream. That’s alignment, for him. And it's a beautiful thing.

For others, the answers can bring harder realities.

When alignment isn’t an option

As humans, we are notoriously bad at predicting our happiness level in hypothetical future scenarios. We think moving to a new town will free us from the lurking anxiety we face daily. That marriage will mean we never feel listless or alone.

Or that starting a successful business will provide a feeling of empowerment and freedom.

What happens when a venture-backed founder wakes up to realize she no longer wants to be CEO of her company? She can gut it out for awhile. Months. Maybe even years. But burnout will arise. And when that kind of misalignment is present, a shift in role, more vacation days, or work from home Wednesdays will not solve the real issue.

Of the founders I meet with in a given week, at least half are looking for a way out of their company.

I've written before about the common founder to founder conversation about 'when I finally get out of my startup.'

I made a lot of mistakes as a founder and CEO. I’ve written openly about most of them, and I promise to keep doing so. But one thing I got right was a determination to build a high-trust, high-functioning board. And the boardroom became a place where we told the truth and shared the hard things no matter the fear. So when I began to suspect I was needing to approach the end of my tenure as CEO, I shared the thought openly with the board. It wasn’t a decision yet, and I didn’t have a timeline, but I had an awareness. And I shared it.

I’m so very glad I did.

To my surprise, my board fucking showed up for me. God bless them. Your people just might too if given a chance.

Getting Support

When burned out, there is nothing worse than isolation. When you are feeling like there is no way out that keeps your family safe, your team whole, and your investors happy, keeping the fears locked away in your own head is both isolating and dangerous.

Tell someone.

Tell a founder friend. Tell a coach. Tell your partner. When you’re ready, tell your advisors and your board. Invite them in to the ‘problem’ before you find yourself needing to race for the door in search of solution.

You aren’t an indentured servant.

You’re just human. Trying to do the right thing, and experiencing pain around that effort.

You’re worthy of relief. Of support. Of a way out.

If you’re feeling alone in your leadership role today, I’d love to talk with you.

Helping leaders feel less alone is my life’s work.

Wishing you peace on your journey today.

Matt