How Real Leaders Drive Real Change
Courage, Productive Distress, and the Power of Community
We talk a lot in startup and corporate land about “corporate values.” We put them on websites, paint them on walls, and weave them into recruiting pitches.
But when the pressure hits — when a major customer crosses a line, when a board pushes for decisions that feel off, when the market rewards behavior that contradicts what we say we stand for — many leaders discover something uncomfortable about themselves.
I was thinking about this during a talk with Rachel Cohen, the young lawyer who resigned from the fifth-highest grossing law firm in the world over its capitulation to threats from the Trump Administration aimed at retaliating against firms for positions taken against Trump in the past. [If you don’t know the background story that led to her resignation, I’ve added a quick synopsis as an endnote to this post.]
Rachel was our keynote speaker at our annual HiPower conference. At the event, she shared her story — a journey that has been defined by her commitment to not compromising on her core values. And while all of this might feel far from the world of startups, you’ll see that the lessons are remarkably transferable.
What Rachel learned about courage, distress, and community are exactly the muscles that founders and leaders need to practice if they want to build companies that don’t crumble when things get really hard – as they always do.
This three-part series delves into how founders and executives can build better businesses by following some of the principles Rachel has applied along her journey.
We start with Courage.
Part 1 – Building Courage Into Your Operating System
Courage doesn’t arrive all at once.
Despite what the movies teach us, courage is not a single, cinematic moment of clarity. It is something practiced long before the world asks us to use it.
Rachel Cohen’s resignation from one of the world’s most powerful law firms when they failed to uphold the rule of law wasn’t a spontaneous act of defiance. It was the culmination of years of smaller acts of courage. It had been built into her personal operating system.
Earlier in her career, she had stood up to pressure to water down an article she authored that was appropriately critical of the private prison industry.
When she was told to take down measured, balanced public statements because they were “inconvenient,” she stood her ground.
Each of these actions required her to tolerate discomfort. And each strengthened the internal operating system that she looked to to define her.
By the time her law firm capitulated to political threats, she had already practiced living the person she said she was. For Rachel, courage had started to become muscle memory.
There’s a lesson here for leaders, founders and executives who believe company values and culture matters.
Your true values are revealed by the actions you take and the decisions you make under pressure.
A venture capitalist once told me that there are two kinds of founders:
those who want to build a company because they think it will make money,
and those who want to build a company because they want to solve a problem that matters.
The VC only invested in the second kind — because only they maintain the backbone required to navigate the pressure they will face along the journey.
To build anything of significance successfully – a business, a community, a country – you must start with a mission and a belief system.
But your mission and belief system get eroded through hundreds of smaller decisions you make under stress. Those decisions look like this.
Leadership that once believed “our employees are at the core of our success” begins quietly rotating out high-paid employees for lower salaried ones under the pressure of driving more profits, lowering compensation to all but their own ranks.
A company that once celebrated product quality starts cutting corners because safety slows down profits.
A business that once touted customer trust creates new revenue streams based on use of personal information by burying privacy changes in unreadable agreements.
Every decision like this widens the gap between the stories leaders tell their employees and the reality their employees face.
Which brings us to the core leadership question: Why should leaders care? After all, Rachel’s old firm still exists. It still makes money.
Because leadership is not defined by who you pay. Leadership is defined by who follows you.
When you make promises and then break them, people stop following. They may continue working with you. They may tolerate you. They may even profit alongside you. But they will not follow you—not into uncertainty, not into innovation, not when you need them.
When you act outside of the values you promised to your community, you aren’t leading them. You are just using them.
It takes courage to lead. It takes courage to keep your promises.
The gap between the story you create about yourself and your actions is the gap in your courage.
To build courage into our operating systems, we must practice courage in the “small” moments so that we can find it when the stakes are existential. We can do this by:
Building rituals that force us to confront uncomfortable information: attrition reviews, deal post-mortems, “red flag” reviews on major decisions.
Designing culture and policies assuming hard decisions will come.
Asking: “If pressure increased 10x, would we still act in alignment with what we say we believe? Or would our values be the first thing to go?”
Values-driven companies don’t come from better slogans. They come from leaders who build courage into their operating systems.
And when you repeatedly close the gap between your self-story and your actions, something powerful happens:
People start to believe in you.
And then they follow you—through uncertainty, through hardship, and through the kind of transformational work that requires a courage practiced long before the work is required.
ENDNOTE: In March, 2025, in order to avoid being targeted by President Donald Trump for prior associations with his political enemies, Skadden, Arps, Slate, Meagher & Flom LLP, preemptively “settled” with Trump and agreed to pay $100 million towards free legal work to causes supported by the Trump Administration.
In a public statement in March of 2025, a representative of the law firm stated “We entered into the agreement the President announced today because, when faced with the alternatives, it became clear that it was the best path to protect our clients, our people and our Firm… This agreement does not change who we are.”
And yet, fundamental aspects of who they were did change shortly following the deal it struck with Trump.
The firm canceled all future events for its employee affinity groups.
Its legal foundation altered its application criteria to remove language related to racial justice.
It scrubbed much of its past pro-bono work that might have offended Trump from its website.
The whole point of having values is that they guide you during times of crisis. What became apparent in the spring of 2025 is that many law firms, many universities and many corporations hadn’t been honest about what their values really were.
