This article was originally written in September 2015 When you're an entrepreneur, it's your job to take risks. If you're risk-averse or hesitant, you will inevitably fail as an entrepreneur, because the market can be cruel and unforgiving of even minor mistakes.

I spent this past weekend at Washington and Lee's Entrepreneurship Summit. Started in 2011, this year's iteration at my alma mater brought together over 100 current and aspiring alumni entrepreneurs from New York to California, and even Alabama. As part of the conference, I was asked to judge and mentor a student group's business plan on a panel with two other alumni entrepreneurs.

"You were pretty brutal in there," one of the other panelists remarked to me at the reception following the business plan pitch. My colleague went on to detail the number of ways I evicerated these poor kids' business idea, even commenting how he could see their hopes visibly deflate as I handed down my judgment. While he didn't disagree with my assessment, he appreciated my directness. He had been significantly more nuanced and subtle in his own inquiry than I had been.

I'm not one to parse words. I'm going to tell you like it is. Another colleague of mine once compared me to Joe Pesci in Goodfellas when I'm in the zone. I didn't take it as an insult, and it wasn't intended as one. It was an honest assessment of the impression that I can make. Regardless of whether that's the image I intend to provoke or not, it is one I have to be cognizant of. It can be a powerful asset in a tense negotiation, but it can also be a volitile liability if I'm trying to deliver constructive criticism.

This weekend, Joe Pesci Watson delivered judgment from on high, and the directive was terminal: this business was just not going to make it. At least not in its current form. I delivered the sentence susinctly; not because I'm cruel, but because I respected these college students as the adults they were. I didn't want them to waste their time on a pipe dream. With a couple of tweaks, their business could have legs, but as college students who didn't have the free time to devote to this business, it would have probably have taken them months, if not more than a year, of spending money and time before they realized their mistakes.

I liked to think of it as ripping off the proverbial bandaid. My fellow panelist saw it as a haymaker.

Which is why I think Simon Cowell was the best of all the American Idol judges.

For those of you still unfamiliar with the tv reality show, American Idol was a hit show until very recently. Based on Simon Cowell's Britain's Got Talent, American Idol featured aspiring singers hoping to make a break into the industry by broadcasting their talents (or lack thereof) in a judged competition where the viewing audience would vote for the winner. A performer would take the stage, showcase their selected song, and would receive feedback from a panel of three judges. The mix of judges varied from time to time, but usually featured industry veterans who often politely encouraged even marginal talent while making grand displays for the exceptional few.

And then there was Simon rowell.

Simon's default speed was brutality. If a singer was marginally talented, he ripped into them. "Go back home," was a common refrain. Even if a talented singer made a poor song selection or failed to control the stage, Simon was quick to note their shortcomings and usher in the next contestant. For this, he became the judge America loved to hate.

He also became the one to win over.

Good singers knew they would at least get courtesy applause from the other panelists, but Simon was the jewel. If you had the chops to make a blip on his radar, you could almost guarantee that you were in the top 10% among your competition. If you could make Simon smile, you had yourself a record deal. At the end of the day, the other panelists were window dressing solely to build suspense before Simon hammered the gavel.

Admittedly, Simon Cowell's on-screen persona was a measured amount of schtikt. The show needed a devil's advocate, a counter-balancing force to the audience's compulsion to pull for the contestant, no matter the talent level. While Simon was that counter-weight, it wasn't all act.

Thomas Sewell once remarked that there is no greater folly than to assign decisions to individuals that bear no responsibility for the success or failure of those actions. In economics, this problem is so pervasive, it has its own name and is the subject of entire classes in departments around the world: it is called moral hazard.

The revolving door of American Idol judges were moral hazards. These judges were salaried individuals whose primary motivation was the success of the show itself, not the talent it produced. If they could inject some "warm fuzzies" into the episode, they could go home and call it a job well done.

Simon was not in the same boat. A career record producer, Simon Cowell's label would ultimately be the one writing the checks to the show's winner. Simon knew, probably better than anyone on that stage, what it took to make a star, and he certainly was not going to saddle his company with a flash in the pan if he could groom a sensation. In that way, American Idol simply make public the process Simon had used for years to find talent that would sell records. The show was a means to an end, not an end in itself.

That American Idol became the cultural sensation it was was a surprise to all involved. Running for over a decade, it can easily be counted as one of the most successful shows in television history. No one plans for that success. Simon was hoping to leverage the show's audience to drive record sales, and, instead, the show itself became more lucrative than the records it was designed to push.

At its heart, the show was about a record producer trying to find his next cash cow. He only had room for one. Anything that could help narrow that field was welcome, even if it was as superficial as how a singer looked or the way they carried themselves on stage. Obviously, Simon went a step further than simply passing on a potential recruit and vocalized the specific reasons why he was opting out. While few disagreed with his often-humiliating analysis, Simon's critics focused on his delivery, challenging whether or not he should have even vocalized what was obvious to everyone watching.

Everyone, that is, except for the singer.

It's a strange truth about humans that we are impossibly incompetent at evaluating our own capabilities. Ironically, studies are increasingly showing that the least capable individuals are most confident in their skills, and the most competent are least confident in their own skill sets. It turns out, the more we learn, the less we think we know. The opposite is crippling true, as well.

A common question posed by American Idol viewers was why the least talented contestants even bothered signing up for the competition. After all, surely they knew how untalented they were? Chances are, they didn't. Chances are, no one ever told them how terrible their singing was. Chances are that the first time they ever received honest feedback on their capabilities was when Simon Cowell eviscerated them on national television and the resulting breakdown gained over 100,000 views on YouTube.

Meditative practice embraces a concept called "nonjudgmental thought." Essentially, during meditation, the individual will sporadically think of potentially stressful activities or upcoming deadlines. However, instead of seizing on the thought and bringing emotion into it, or even forcing the thought aside, meditative practice encourages the individual to view the thought objectively: recognizing that the thought exists, then allowing that thought to evaporate on its own. This mindfulness allows the mind to process the information without being overwhelmed by it.

Criticism might as well be a new 4-letter word these days. We are afraid to tell someone the truth, even when doing so might save them some larger future embarrassment. We're afraid of sounding rude or offending someone or putting something on them that we don't think they can handle. When Kristen and I were engaged and taking pre-marriage counseling classes, our counsellor summed it up this way: Withholding vital information from someone is not doing them a favor, it is a fundamental judgment that they are not capable of handling that information. In an instant, you've determined for another person that they are at once insufficient and incapable of handling their own insufficiency. You've demeaned that person without saying a word.

So I get called Joe Pesci. I've been called a bull in a china shop. I've been called intense, and often times, even an asshole. That's fine. I know that about myself. I'm an adult, and I know who I am. I also know this: I care more about making you a success then I care about what you think of me. That's an easy trade off for me.

Call it tough love, call it brutal honesty. I prefer to think of it simply as help, without wasting your precious time.