The Away Debacle: Is Judgment the Answer to Leadership Accountability?

Like many in the startup ecosystem, I read the recent article on the cultural challenges inside unicorn startup Away with shock and disappointment. I felt tremendous grief for the employees. I also sensed a pattern at hand in tech, a pattern that keeps repeating: Uber, WeWork, Away. And I wondered: while the leaders are culpable, might our rush to judgment be preventing us from addressing the systemic issues that encourage this kind of behavior?

Leadership accountability is a phrase we reach for quickly in moments like this. But what does it actually mean, and are we using it correctly?

I have a 7-year-old son named Marco. As a parent, I’m surprised and disturbed by the binary model of the world that seems forced upon him at such an early age. Media creates a paradigm where there are only two kinds of people in the world: the good and the bad.

My son is full of questions about how the world works. I find myself struggling to parent in an era of divisive politics, global warming, and jaw-dropping economic disparity.

No answers come easily.

One perspective I try to foster thoughtfully in my son is that there are no bad people. No one is born bad.

Even those you find most difficult to understand, or who most rub you the wrong way, are the way they are for a reason.

Most people are doing the best they can, at the moment, with the resources and information they have at hand.

The Mob Mentality Trap on Social Media

As I read through the Away article with that worldview informing my interpretation, I felt empathy for everyone involved. Yes, including Away CEO Steph Korey.

I’m certainly bringing my own biases into this. I spent the last 7 years as the CEO of a venture-backed company. I’ve written openly about my own struggles with putting growth ahead of culture and sustainability. But even setting my own bias aside, I strongly believe that empathy, not rage or mob mentality on social media, is the most appropriate response here.

It’s too easy to simply rip apart the Away founders. It’s lazy.

Many of the public responses that are rippling across Twitter are fueled by schadenfreude.

There’s little we love reading about more than the fall from grace of someone whose success made us feel less than.

I’m 100% culpable here myself. When I read of another founder’s company succeeding strongly against a meaningful mission, my first emotion is too often jealousy. I feel less than. When I have the opportunity to read about such a founder shitting the bed in a public way, I feel better about myself.

But where does that leave me? Where does it leave us?

The mob mentality trap is seductive precisely because it feels like accountability. It looks like we are holding power to account. But outrage cycles on social media rarely produce the systemic change that would actually protect employees or prevent the next Away.

I’m not arguing that we absolve Steph from her responsibilities. We shouldn’t.

As founding CEOs, when we take on venture capital and hire dozens or hundreds of people to work in our companies, we take on tremendous power. That power should be held to account.

But calling Steph a bad-apple and moving forward with our pitchforks to the next public enemy turns a blind eye to the complexity of the system and culture that supports this kind of dynamic.

Why Leadership Accountability Goes Deeper Than Blame

I read that article with great empathy for all involved. Like others, I felt tremendous empathy for the customer support team. I’ve had bosses who dumped their anxiety and fear on me and other young employees. There’s no excuse for that.

I also read it with empathy for the customers. I have an Away bag and love it. It’s a wonderful product that’s been to a dozen countries with me.

But I also read with empathy for Steph and Jen. It’s easy to point at founders and think they should know better. That they are only in it for the money. That they are putting their own interests and greed ahead of the team. And undoubtedly the equity positions and financial upside is vastly different for a founding CEO and a customer support rep. But I spend a lot of time with founders, and very few are driven at their core by economics.

Most Founders Are Not Bad People

Most founders are carrying some strong sense of iniquity they’ve born since childhood.

You don’t attempt something as impossibly hard as scaling a venture-backed company because you are greedy.

If you’re greedy, there are much easier ways to make a lot more money. Most founders are trying to prove, at a very visceral level, that they are enough. That they belong. That they are worthy of love and acceptance. That they can do something that matters in the world.

These are very core human needs.

Anxiety and Fear Drive More Bad Leadership Than Greed Does

When I read Steph’s Slack messages, yes I felt the shock and revulsion that’s been expressed across Twitter. But I also felt empathy and sadness.

Her comments didn’t strike me as being driven by malice or greed, but rather by anxiety, fear, and desperation. I know from my own anxiety, fear, and desperation, in my early days leading Twenty20, that I could have easily been writing such messages at 3 AM.

This matters for leadership accountability because if we misdiagnose the cause, we apply the wrong solution. Firing a suffering CEO and replacing them with another person operating inside the same broken system will not protect the next team of customer support reps.

What Real Leadership Accountability Looks Like

The important question here isn’t how we expel leaders like Steph out of the companies they founded. That may be a fine first step, but stopping there too quickly absolves all of us from the harder questions.

Those of us propping up the tech ecosystem with our labor, our attention, and our investment have our own responsibility to ask more difficult questions.

It Starts in the Boardroom

The tech ecosystem is beautiful and wondrous. It has been an engine for economic development and innovation unmatched in human history. But as the ecosystem matures, we have a responsibility to have open conversations about taking concerted steps toward sustainability. Sustainability not of the economic engine itself, but of the institutions and the human lives that make up those institutions.

If you’re an investor, advisor, or board member, please read the Away story as more than another cautionary tale of a CEO gone too far. Real leadership accountability begins with the governance structures that shape CEO behavior long before it becomes a PR crisis.

In boardrooms, use this story as impetus to talk in depth about the experiences employees are having in the company across the pay scale. Have an open and honest conversation with the CEOs and leadership teams in your portfolio about their own wellbeing also.

Be the person who checks in on a founder just to see how they are. With no other agenda than to know how they really are. Model the welcoming of humanity in work.

Employee Wellbeing in the Workplace Cannot Be an Afterthought

Take a human and strategic interest in investing in the sustainability and humanity of company culture. Ask your company leaders challenging questions about employee happiness, not simply fiscal performance.

Employee wellbeing in the workplace is not a soft metric. When leaders operate from chronic anxiety without support, their distress flows downward. The customer support team at Away did not deserve to receive their CEO's fear through a Slack channel at midnight.

The antidote is not simply removing the anxious leader. It is building organizations where leaders have access to the support, coaching, and honest feedback they need to lead well. You can read more about what that looks like in practice at The Hidden Cost of Anxiety in Leadership.

Moving From Outrage to Systemic Change

A sustainable conversation about leadership accountability is longer-term and more difficult than tossing out bad leaders.

Leaders acting badly are usually suffering. So are employees. So are their boards and investors.

The answer is to have open conversations among founders, among investors, and in the boardrooms of our companies about how we can relieve this suffering. How we can bring more humanity into our companies.

I, for one, believe those conversations must begin with a deep understanding of the experience each of us are having in our respective roles. And with deep empathy. For all involved.

If you are a founder struggling with the weight of leading a company, you are not alone in this. I've written about the deeper patterns at play in navigating founder burnout and the hidden cost of anxiety in leadership. These are not personal failures. They are systemic ones.

We are doing incredible things in tech. Let's be remembered as much for how we do the work as the accomplishments we achieve.

Wishing you peace on your journey today.

-Matt

Looking for support as a founder or CEO? If now is the time to consider CEO coaching, reach out here.

Frequently Asked Questions

What is leadership accountability in a startup?

Leadership accountability in a startup means that founders and CEOs take genuine ownership of the culture they create, the wellbeing of their teams, and the impact of their behavior, not just the financial performance of the company. It extends beyond reactive PR management to the daily choices leaders make under pressure.

Why does mob mentality on social media fail to create real accountability?

Social media outrage cycles focus on individuals rather than the systems that enable their behavior. When a CEO is publicly shamed and removed, the incentive structures, funding pressures, and boardroom cultures that produced their behavior remain unchanged. Real accountability requires harder, slower conversations inside institutions.

How does employee wellbeing in the workplace connect to leadership behavior?

Leaders who operate from unmanaged anxiety tend to transfer that anxiety downward to their teams. Employees absorb the stress of a CEO who has no outlet, no coaching, and no honest feedback loop. Investing in leader wellbeing, through coaching, peer support, and boardroom candor, directly protects employee wellbeing at every level.

What role should boards play in leadership accountability?

Boards carry significant responsibility for leadership accountability. Beyond monitoring financial KPIs, boards should regularly check in on CEO wellbeing, ask direct questions about team culture, and create conditions where founders can be honest about their struggles. A board that only engages during a crisis is a board that has already missed most of the accountability work.