Roosevelt’s Arena: Today’s CEOs face dust, sweat, and torched Teslas
In the spring of 2021, the co-founders of Basecamp, a software company known for its project management tools, decided that political discussions had no place in their internal communications. The decree came down like a guillotine: no more debates about elections, no more arguments over social justice. The backlash was swift — employees quit in droves, and the press jumped in, with The New York Times documenting the exodus as a tale of corporate overreach.
A few months earlier, Brian Armstrong, CEO of Coinbase, the cryptocurrency exchange, had taken a similar approach. He urged his staff to leave politics at the door and offered severance to those who couldn’t comply. About sixty employees — around five percent of the workforce — accepted the money and left, while critics condemned the move as a suppression of dissent. Both companies, in their pursuit of focus, stumbled into a firestorm.
Elon Musk, the undisputed titan of technology, has entered a different kind of battle. Appointed by President-elect Donald Trump to co-lead a growing Department of Government Efficiency — DOGE, a reference to Musk’s cryptocurrency interests — his arrival in Washington has sparked not only debate but outright rebellion.
Teslas are being vandalized in parking lots, dealerships are being picketed, and cars are being set ablaze in isolated bursts of anger. Threats against Musk’s life have emerged, serving as a grim reminder of the stakes when business and government collide.
In recent days, left-wing favorite California Governor Gavin Newsom sent prepaid phones to a hundred tech CEOs, preloaded with his personal number, only to face a wave of skepticism from the media and many in his party: Why associate with the Silicon Valley elite?
There are countless more examples, but the pattern is clear: when business leaders enter the public arena — or even flirt with it — the atmosphere fills with recrimination. Employees rebel, customers bristle, and the media sharpens its knives. This is enough to make any executive hesitate, questioning whether the reward is worth the effort.
Let us present another perspective on this issue — one where a leader doesn’t shy away from chaos but embraces it. Theodore Roosevelt, in a speech that decorates many business leaders’ walls, articulated it best: “It is not the critic who counts, not the man who points out how the strong man stumbles.... The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood.” For business leaders peering over the parapet today, the question isn’t whether they’ll be liked — it’s whether they’ll have the courage to step in at all.
The aversion to mixing business and governance is understandable. Business thrives on clarity — profit margins, market shares, quarterly reports. Politics, by contrast, is a swamp: murky, tribal, and unforgiving.
Criticism in politics often only gains traction when there are elements of truth. Let’s look at the following:
When Basecamp and Coinbase prohibited political discussions, they weren’t merely avoiding distractions; they were protecting their cultures from the turmoil that arises when opposing ideologies confront each other.
Musk’s involvement in Trump’s administration, which vowed to reduce bureaucracy, suggests a touch of self-interest — his companies depend on government contracts and regulatory support.
Newsom’s burner phone strategy, an attempt to connect Sacramento and Silicon Valley, risks alienating the very base that propelled him. The critics are justified in their concerns: power, when concentrated, tends to favor those who already possess it.
But to stop there is to miss the point. Life isn’t a popularity contest, though it’s tempting to live as if it were. The alternative — shying away from the arena because the crowd might jeer — is a recipe for stasis, a slow drift toward irrelevance.
Roosevelt’s words carry a sting because they’re true: the arena isn’t kind. It’s a place of bruises and missteps, where every move invites scrutiny. Basecamp’s founders lost talent; Coinbase’s Armstrong lost goodwill. Musk’s Teslas are paying a literal price, scratched and scorched by those who see him as a usurper. Yet the arena is also where history gets made, where the timid don’t tread.
Business leaders who engage with it — whether to streamline bureaucracy, resolve internal conflicts, or form a new alliance — aren’t guaranteed success, but they are guaranteed to face challenges. To do otherwise — retreating and polishing one’s image until it shines — is to squander the little time we have in life to make a difference.
And that, Roosevelt would argue, is the only thing that counts.