A Bugatti prompted a question about money for Barrett-Jackson’s Craig Jackson. In an earlier School of Hard Knocks interview, published March 3, 2025, he confirmed the car was his and agreed to discuss his business career.
Jackson had owned several businesses over the decades. Asked which had made him the most money, he answered, “The car business.” The interviewer then asked how much he made in a single year.
“Well, I did $80 million in one day,” Jackson replied. The exchange does not establish $80 million in personal take-home pay.
Looking back on school, Jackson called himself “a horrible student” and said he had ADD, which he felt had gone unrecognized at the time. He credited it with giving him creativity, vision, and energy. In business, he surrounded himself with calm, focused, driven people.
Across the Table
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Asked for his best sales advice, Jackson answered: “Always tell the truth, underpromise and overdeliver, and you’ll have customers for life.”
His father had been known for keeping his word. Even with attorneys and contracts involved, Jackson put it this way: “If I shake your hand, it’s a done deal.”
For the cars, that meant describing their actual condition. He acknowledged that not every car was perfect and recounted a visit to a customer’s collection in Dubai, where the buyer pointed out several cars purchased through his business.
“Your cars always come in better than the descriptions, not worse,” Jackson recalled the customer saying. The buyer’s confidence extended to purchasing cars sight unseen.
Beyond the Business
On taking chances, Jackson offered a baseball comparison: “If you don’t swing, you’ll never hit a home run.” He also connected the long hours entrepreneurs work with loving what they do.
The interviewer’s request for life advice brought the conversation to marriage. Jackson called choosing a wife the biggest decision of a person’s life and explained that a shared passion could keep a couple working toward the same goal.
He said his wife shared his enthusiasm for the business and its customers. “I have to drag her out of the office sometimes.”
A Few More Answers
Elsewhere in the video, a commercial real estate businessman put his best year at $3.75 million, specifying that he meant his own earnings. He connected his start in land sales to working on a ranch and farm in western Kansas, where he came to understand farmers. He advised building close relationships with a small group of repeat clients. In his field, he said, two or three could be enough.
Another interviewee, who described his business as a court-reporting firm, said his last case, involving Deepwater Horizon, generated $28 million. Asked for his best negotiation advice, he answered: “100% honesty. Period.”
Real estate investor Pace Morby put his best year at $15 million after taxes and other costs, while estimating his company did about $115 million that year. His advice for growing a business included paying well to attract strong employees and bringing in partners with different strengths. On sharing ownership, he said: “I’d rather have a slice of the pie than 100% of a grape.”