Tomorrow Americans will vote in the 2026 midterms. Whatever your politics, you have likely noticed the ads. According to the ad-tracking firm AdImpact, political ad spending and reservations for this cycle reached a record $11.21 billion a week before Election Day, already more than the entire 2024 presidential cycle, and the firm has projected $11.6 billion by the end of the cycle.
Negative campaigning feels like a modern invention. It isn't. The playbook was written in 1800, and the story of the man who wrote it is one of the most useful lessons I know for anyone who runs a company, raises capital, or competes for customers.
The first hatchet man
The presidential election of 1800 pitted President John Adams against his Vice President, Thomas Jefferson. The two had worked together on the Declaration of Independence. By 1800 they were leaders of rival parties, and the campaign became one of the nastiest in American history.
Jefferson kept his own hands clean in public. Behind the scenes, he supported a Scottish-born pamphleteer named James Thomson Callender. According to Monticello, Jefferson helped Callender in three ways: he helped him find work, he bought his pamphlets, and he gave him money outright. In 1799, Jefferson authorized a $50 payment for copies of Callender's forthcoming book, The Prospect Before Us.
That book accused Adams of being "mentally deranged," of planning to crown himself king, and of grooming John Quincy Adams as his heir, as PBS American Experience summarizes it. Its most famous line called the President "a hideous hermaphroditical character, which has neither the force and firmness of a man, nor the gentleness and sensibility of a woman" (Monticello via Google Arts & Culture). After seeing the work, Jefferson wrote to Callender that it "cannot fail to produce the best effect," according to Slate. The same account notes that Jefferson did not sign some of his letters to Callender: "You will know from whom this comes without a signature."
Callender's resume should have been a warning. He had already gone after Alexander Hamilton, exposing the Reynolds affair, and he had attacked George Washington himself (Printing Museum). He worked for his own grievances and whoever was paying.
The invoice comes due
Adams's administration answered with force. Callender was convicted under the Sedition Act in 1800, sentenced to nine months in jail and fined $200 (HistoryNet). Jefferson won the election, and two weeks after taking office he pardoned his pamphleteer.
Callender expected more. He wanted to be postmaster of Richmond. When Jefferson declined, Callender went to work for a Federalist newspaper, the Richmond Recorder, and revealed that Jefferson had subsidized the campaign against Adams (PBS American Experience). Then, on September 1, 1802, he published the charge that Jefferson kept an enslaved woman, Sally Hemings, as his concubine (Library of Congress), a story that followed Jefferson for the rest of his life and well beyond it.
Jefferson had tried to keep his distance through intermediaries and unsigned letters. It didn't work. The man he had paid to say what he would not say himself ended up holding the most damaging information about his patron.
What the General already knew
George Washington, who suffered his own share of forged letters and rumors, had copied out the remedy as a teenager. Two of his Rules of Civility speak directly to 1800:
Rule 49: "Use no reproachful language against anyone; neither curse nor revile."
Rule 65: "Speak not injurious Words neither in Jest nor Earnest. Scoff at none although they give Occasion."
Rule 49 is about the attack. Rule 65 is about the response, even when the other side "gives occasion," meaning it started the fight. In the 1800 story, both sides broke both rules. Jefferson paid for the reviling. Adams answered with prosecution rather than restraint, and the Sedition Act became a liability for his own party.
In Timeless Civility, I sum up Washington's rules on gossip this way: don't slam people who aren't in the room. Gossip "is like a bad NFT; once it's on the internet, you can't burn it." My personal policy is to talk about people, in person or online, only in ways I'd be proud to have read at my funeral.
Why this matters on a balance sheet
Most founders will never hire a pamphleteer. But the Callender pattern shows up in business all the time: a whisper to a customer that a competitor is "about to run out of money," a pitch deck that spends more time attacking the incumbent than proving the alternative, an agency or consultant told to "go negative" so the company's name stays off it, anonymous reviews, or a departing executive described in terms nobody would put in writing.
From a CFO's chair, these are not just questions of manners. They are risk decisions, and they usually price badly.
1. What you outsource, you still own. Jefferson's intermediaries and unsigned letters didn't create distance. They created leverage for someone else. When a company pays a third party to say what management won't sign, it takes on a counterparty with information, motive, and timing it doesn't control. That's a contingent liability, even if it never shows up on a balance sheet.
2. Attacking a competitor signals a weak case. Investors and buyers listen for what you can prove. A founder who spends ten minutes on a rival's flaws has spent ten minutes not showing retention, unit economics, or a credible path to cash flow. Sophisticated capital reads reproachful language (Rule 49) as a sign that the differentiation isn't in the numbers.
3. Answer provocation with records, not retaliation. Rule 65 assumes you will be provoked. When a competitor, a critic, or a former employee takes a shot, the strongest response is usually documented facts delivered calmly: audited figures, customer references, a clear timeline. Adams's overreaction outlived the insult that provoked it.
4. Silence inside the company invites rumor. Gossip fills information vacuums. During a raise, a reorganization, or a missed quarter, people will tell themselves a story if leadership doesn't. Regular, plain-spoken updates from the finance team are among the most effective rumor controls a company has.
5. Today's rival may be tomorrow's partner, acquirer, or customer. Adams and Jefferson stopped speaking for more than a decade. They reconciled through Benjamin Rush, corresponded for years, and died on the same day, July 4, 1826. Markets are smaller than elections. The competitor you disparage this year may be across the table in a merger, a supply agreement, or a co-investment. Diligence teams read old press releases, reviews, and emails.
The Callender test
Before any message about a competitor, critic, or former colleague goes out, internally or externally, ask five questions:
1. Would I sign it? If it can't carry your name, it shouldn't carry your money.
2. Can I document it? If the claim rests on rumor, it's gossip, however it's labeled.
3. Who holds the leverage if it leaks? Count everyone who knows you asked for it.
4. Does it strengthen our case or only weaken theirs? Only the first one builds value.
5. Could I live with this target becoming our partner, buyer, or customer? If not, rewrite it.
The vote that lasts
Whoever you vote for tomorrow, the ad flood ends tonight (hopefully). The reputations companies build or spend don't reset on a schedule. Jefferson won in 1800, but Callender's second act became part of his legacy. Adams lost, and the Sedition Act became part of his.
Washington's advice still holds, in the boardroom as well as at the ballot box: win on the record, not the rumor.
John Mortenson is the founder of Straiteis Consulting LLC and a fractional CFO who works with founders and mid-market leadership teams on capital strategy, financial planning, and operating discipline. This post is adapted from his manuscript, Timeless Civility: Updating George Washington's 110 Rules of Civility for a Modern World.
