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Startup trek, episode 18: Coming of Age

Updated: Mar 10, 2019

Season 1, episode 18: "Coming of Age"

Lesson: how you fail says more about you than whether you fail

This post is part of my ongoing quest to watch every episode of Star Trek: The Next Generation and pull one startup, entrepreneurship, tech, or investing lesson from each.

Wesley takes the Starfleet entrance exams with three other candidates. Wesley, the youngest at 15 years old, would have to take first place in the exams to be accepted into the Starfleet Academy. But instead of being cutthroat about the competition, he befriends and helps the other candidates. He talks one candidate, Mordock, through a stressful moment in one test and Mordock completes it, getting the second-fastest completion time in history. It's a classy moment for Wesley. Ultimately Mordock gets the highest score of the group with Wesley coming in second. Mordock tries to vouch for Wesley, saying that he should be the one to move ahead into the Academy, but the test administrators don't change their choice.

Meanwhile on the Enterprise, an old Admiral friend of Picard's shows up and puts the crew under investigation. No one knows why, and the chief investigator is a really obnoxious, mousy pain in the ass. Riker gets all alpha and puffed-up about it. The investigator brings up strange occurrences in past missions, which adds some nice continuity to the show by referencing other episodes in this season. But while these situations may appear to be failures at first glance--e.g., the locals sentencing Wesley to death in "Justice," or Picard having hallucinatory flashbacks of a Ferengi spacefight in "The Battle"--they end up being triumphs showcasing Picard's composure under pressure.

One such "failure" happens while the investigator watches on the bridge: a student who failed the Starfleet exam steals a shuttle and tries to run away into space, not wanting to confront his father. The investigator initially criticizes Picard, asking how the Enterprise's security setup allowed someone to make off with a shuttle. But when the shuttle malfunctions, Picard talks the kid into pulling off a death-defying maneuver that saves his life with seconds to spare, and even the investigator is impressed.

The episode ends with a conversation between Wesley and Picard. Wesley is dejected about failing the exams. Picard gives him a pep talk, saying it's more important to compare yourself against your own capabilities than against external standards or others' expectations:

Wesley: "I failed you, and I failed the Enterprise."
Picard: "Ridiculous. Did you do your best?
Wesley: "Yes."
Picard: "When you test next year--and you will test next year--do you think your performance will improve?"
Wesley: "Yes."
Picard: "Good. The only person you are truly competing against, Wesley, is yourself."

The binary question of whether Wesley failed the exam isn't what matters; it's more important that he did his best, he behaved in a way that was admirable (e.g., helping the other candidates), and he'll keep improving.

Picard also reveals that he failed his own first attempt at the entrance exam. It's a cool moment of humility and empathy for this larger-than-life figure in the ship's captain to admit to Wesley that he's not perfect either. But he did get it on the second try.

Wesley Crusher: failing with class.


There's a mythos in startup land around failure. You hear phrases often like "failure is good," and "fail hard, fail fast, and fail often." Of course, everyone wants their companies to be successes. But given that most startups are objectively "failures," if we define that as "they don't become really valuable and don't return money to their investors," you can see why failure is a part of startup existence. Some estimate the startup failure rate to be as high as 90%.

Startups are risky creatures. So in a mode of existence where most people and companies fail (despite it feeling like everyone describes themselves as "killing it" constantly), how you fail matters a lot. Did you do your best? Did you do it with grace and integrity? Were you honest with your investors, and did you treat your employees well? No one expects a perfect track record, least of all us investors--making bad picks is part of our job description.

Thus we end up backing founders multiple times who have "failed," at least on paper. They didn't build massive businesses. They didn't find product-market fit. They couldn't scale. Whatever the reason, it didn't work. And yet we happily back these founders multiple times.

I was on a call recently with the board members of one of our portfolio companies and we were talking about making a job offer to a senior-level VP. This VP had never been part of a company that was a massive success, but my partner, Jeff Fagnan, vouched for him strongly anyway. One of the board members didn't have experience with this VP and asked, "Why would you continue to back this guy if he's never been part of a big success?"

Jeff responded that there are any number of reasons why these companies didn't work out beyond this one person's control, but the first hand data he had on the VP was all positive. This person was a known quantity and he was dependable. Markets fail, timing sucks, and companies have tons of interrelated things going on, but this person did his best. It's hard to say whether this VP could have pushed these past companies to be successes if he was truly an A+ operator. Probably not, though. Market forces are just too big.

The other board member asked Jeff if there would ever be a point when he'd lose faith. "I expect one failure and maybe even two," he said. "This is the world of startups. I can even accept three times given probability theory, but by the fourth time I don’t want you anywhere around because you're likely not exceptional or simply bad karma. Not on my ship."

In sum, as investors we would (and do) back founders and operators multiple times who have "failed." Success is hard to find and define in a startup. It matters more that you fail with integrity. If having a win at a startup was a requirement of being hireable or backable, we'd have a tiny pool of people to work with.


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