Medium Rare Bracketology

By: Chris O’Brien

Have you ever been entrusted to create a playlist?

Any kind of playlist. Background music for a dinner party. A collection of soft rock hits for the dentist. Grinding music for a sweaty dance party.

Each setting has a list of ol reliables. For example, there has never been a documented case of “Get Low” failing at a dance party. Same can be said for “All I do is Win” or Usher’s “Yeah”.

But you can’t loop the handful of reliables for two straight hours. Eventually you have to go a little riskier. Not a problem at first. You add Beyonce, Ke$ha, Justin Timberlake, Jay-Z and the playlist still looks great. Only problem is you don’t feel like you’ve made your own personal stamp. The list is too generic. You gotta think outside of the box.

That’s when things get weird. Sometime around 3 a.m. you take a good hard look at the following songs:

  1. Thong Song
  2. Who Let the Dogs Out
  3. Total Eclipse of the Heart
  4. Mambo No. 5
  5. Sweet Caroline
  6. Party in the U.S.A

I have seen all six of these songs work and I have seen all six of these songs fail miserably. Sweet Caroline can win over an entire baseball stadium or kill a dance party. I witnessed Mambo No. 5 clear out a basement of 80 people like it were a bad fart. I have seen Party in the U.S.A get booed and I have seen Party in the U.S.A. get an introvert to dance on a bar.

These are the songs, and there are hundreds more, that can make or break a playlist. When they connect, you’re a genius. When they fail you’re an idiot.

Just like–and here comes the loose transition to college basketball–your March Madness Bracket. This year the race is wide open. I’m two weeks away from seeing a bracket and I already feel like I’ve screwed up my picks.

Just a few minutes ago I watched Penn State beat Ohio State, Arkansas win at Kentucky and Duquesne win at Saint Louis. Yesterday I was contemplating Saint Louis to the Final Four, now I’m contemplating how to pronounce Duquesne!

This year my plan is to over-plan. I am preparing in advance, hoping to make some sense of this year’s tournament picture before I see the bracket. These are my Reliable Picks:

  1. Florida
  2. Kansas
  3. Syracuse
  4. Duke
  5. Arizona

Low chance of losing before Sweet 16, high chance of making the Final Four and if they do get upset, most of the people in your pool will go down with you.

My next group is the 16 teams I feel good about taking to the Round of 32 and almost feel safe putting in the Sweet 16.

  1. Cincinnati
  2. Louisville
  3. Wichita State
  4. Villanova
  5. Creighton
  6. Michigan
  7. Wisconsin
  8. San Diego State
  9. Michigan State
  10. Kentucky
  11. Virginia
  12. Memphis
  13. Ohio State
  14. UCLA
  15. New Mexico
  16. Oklahoma

Could they go further than the Sweet 16? Absolutely. But picking them would give me a little heartburn.

So the logical thing for me to do, I have 21 teams above, I should wait to see the matchups and try to get 16 of them to the Sweet 16. The problem is:

1) March Madness is never that simple

2) There are 16 teams, the “Bittersweet 16”, that are itching to be the bracket busting equivalent of the Thong Song. That sentence gets weirder each re-read, but what I’m trying to say is these 16 teams are a couple of beers and some roster searches away from looking like Final Four contenders.

They also have a high risk of losing in the first round. Or being selected to the N.I.T.

They are the teams you kick yourself for not having the guts to have picked further or ban yourself from ever picking again after they lose by 10 to some team from the MAC.

Over the next 16 days I will focus on one team a day and bring some confusion/clarity for you to consider later when the bracket is released. There are at least 275 better sources of March Madness advice than what you will receive here in my Medium Rare Bracketology, but who knows, maybe one of these 16 teams will turn out to be the sleeper pick that your bracket needs. Or they may ruin your bracket. Time will tell.

For now, here are the 16 Bittersweet teams in alphabetical order. Click the team for their article or head back to the ‘Medium Rare Bracketology’ tab above for the list.

Florida State, Gonzaga, Iona, Iowa, Iowa State, North Carolina, Oklahoma State, Saint Louis, SMU, Stephen F. Austin, Texas, Toledo, UCONN, UMASS, VCU, Vermont.

Did I forget a team? Should any of these 16 teams be moved up a category? Does anyone have game film on Stephen F. Austin? Let me know. Message or tweet me @MediumRareBooks or send me an email 


Low Expectations Perfect for Building a Winning Streak

Going through customs at the Miami airport is a surprisingly decent experience.

Anyone else with me on this one?


The surprising truth here is I am actually telling the truth. No sarcasm, no satire. Ashley and I went through Miami customs yesterday and the line was always moving, the workers: friendly, the process seemed, dare I say, efficient.

Which went against everything we had been told. “Miami customs are awful” “An absolute bear.” “Arrive two hours early just to be safe.” 

Maybe our expectations had been set so low that any bit of customer service would seem 10x better than it really was, or maybe the Miami Airport happened to be on their A-game, who knows, what matters is their losing streak ended and they got a couple tally marks in the win column.

If you created a product, delivered a service, made a set of cold calls and the reaction was overwhelmingly negative, be it from your boss, your customers or even just negative thoughts in your own head, it’s not the end, it’s the beginning.

Downside – The expectations regarding you have been lowered.

Bright Side – Lowered expectations does not mean lower potential.

Examine the negative reviews. Fix the flaws. Begin converting opinions. A winning streak is never more than one good day away.

Production Dollars are Advertising Dollars

I am on a website placing an order, but the continue arrow isn’t working. The page isn’t loading. Great, now there’s an error code. My session has timed out. What session? Does that mean everything I’ve been working on is just… gone… off floating somewhere in outer space?

I call the customer service line. I’m lucky, the hold time isn’t too long and I’m connected to a living breathing human being. He tells me to refresh the page. No luck. He asks me what internet browser am I using.

Most people use either Internet Explorer, Safari, Google Chrome or Mozilla Firefox. The browser “Opera” has lately been gaining momentum. I tell him which browser I’m using and the customer service rep replies:

“Our site doesn’t always operate well with (said browser) we recommend you try (better browser) or (2nd best browser) and then the page will load correctly.”

The reason companies dump millions of dollars into marketing/advertising is to reach this exact moment, one person telling another, “That product doesn’t work, try this one, it’s much better.”

If your programmers tell you they need two extra weeks and $50,000 more to fix a minor glitch in the system, this isn’t just a production cost, it’s a marketing cost. Same with the engineer asking for more time to fix a flaw with the car. Or the writer wanting to totally rewrite her book two days before you were set to announce the upcoming release date.

Saying no makes sense. There are deadlines to keep and the product is still good enough. A 94 percent is still technically an A.

The problem, though, with pushing forward despite the flaw is you leave the door open for someone else to make something better. The customer will eventually find out.

If you are already over budget in production costs, move money over from the advertising budget. Reasoning?

If I find out the product doesn’t work, there is not an advertising budget big enough to convince me otherwise. However, if the product does work, but I haven’t heard of it, I’m just one free recommendation away from being hooked.

My name is Chris O’Brien. I wrote a book called Medium Rare. The short elevator pitch: self-help advice in the form of a comedy. Available on Amazon.