Steve Osborne

Supported by Greenhaven Road Capital, finding value off the beaten path.

Steve Osborne is a former NYC detective, speaker at The Moth, and author of The Job. Osborne’s book should be a graduation gift candidate. When young people finish school and begin work I’d hand them this book and say, find something that makes you feel and think like this.


1/ Find a job where you say, “I love this fucking job.”

“I really liked the Ninth. I really liked the salty cops that worked there and the station house that was crumbling around us. But more than anything I liked the neighborhood. It made you feel alive, and it made me feel like a cop.”

“I got to work early, found a safe place to park my car, and walked into the precinct. I had that spring in my step that said I was happy to be here. It may sound crazy but I didn’t want to be home curled up in bed, or out at a party somewhere.”

Osborne hated waking up at 4:30 but he loved the work.

Mike Reiss wrote that after leaving The Simpsons, “I couldn’t stop writing.” Tyler Cowen said, “I view myself as a prisoner of my passions so that helps me to be very motivated to do what I do.” Charlie Munger, who said, “The more you know about some topic, the more passionate you will get,” is aligned with Steve Martin and Cal Newport to be so good they can’t ignore you.

PassionSkill (1)

How? Reps.

2/ Reps and understanding.

“The trouble with rookies is, once you learn a little and start to get the hang of things, you get cocky.”

Osborne admits he was like this.

“In my overenthusiasm to catch the perp and make a nice collar, I never planned on the likely event the train would come. Now, I only had a few seconds to think of something before I became a hood ornament.”

“I realized (later that day) that in police work having balls is a great thing, but having brains and common sense is what keeps you alive.”

With reps, Osborne learned how to spot a drug dealer.

“They’re always walking, constantly moving, but they never seem to go anywhere, and they watch everything and everybody – just like cops do.”

And reading graffiti.

“To normal people, graffiti looks like some nonsense written by a two-year-old child with a crayon, but to the trained eye it contains a wealth of knowledge.”

Reps led to what Ben Horowitz calls “earned secrets.” These lead to win-win situations.

3/ Create win-win, avoid lose-lose. For Osborne, a streetfight was a lose-lose proposition. Winning meant paperwork and time on something (likely) inconsequential. Losing meant being punched, stabbed, or shot How does a cop avoid that? “The reason we start yelling like maniacs is to shock the shit out of you.”

Warren Buffett looked for opportunities he called “two strings on a bow.” If an investment increased in value, Buffett’s stake would increase. If an investment decreased he could take a controlling stake and adjust the companies course. Buffett was like a pirate. If the captain did his job well, the profits would be shared by everyone. If he didn’t, then the crew would vote a new captain in and chart a change of course. That new captain would be Buffett.

Win-win is also theme in Scott Adams’s book Win Bigly.winbiglywin

4/ Opportunity costs.

“We could all collar up the first five minute of the tour, but then there wouldn’t be any cops left out on the street.”

After a homeless woman took a piss on his car, “I thought about chasing her – but why? What the fuck for? I didn’t want to catch her…And if I did catch her, then what? Tie up a sector car for a couple hours while they sat on her at the Bellevue psych ward? We only had three sectors working that night, and crime never stops in the Ninth. It would be a total waste of manpower.”

Opportunity costs can be difficult to tabulate…

…but Osborne succeeded.


Thanks for reading.

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