It was always an awkward conversation. As a New York City transplant to Chicago (for about six years), Chicagoans would invariably raise "The New York-Chicago rivalry" with me.
It's clear that President Trump watches a lot of tv. And it's clear he believes just about anything he hears on Fox News (which also helps explain why he connected so well with his supporters last year).
The most extraordinary moment of this year's Oscars wasn't when Warren Beatty and Faye Dunaway awarded Best Picture to the wrong movie. It occurred earlier in the broadcast when The New York Times ran an advertisement directly taking on Donald Trump and his relentless attacks on the media.
My firm fell into venture somewhat recently. Even though we started working with, and taking equity in, Uber during its Series A, we also started working with, and taking equity in, several dozen startups over the last 18 months and have only deployed capital four times. We're still relatively new to this world.
Immigration bans. Border taxes. ACA repeal. North Korea. Russian interference in elections. Yes, these are all important issues, regardless of where you stand on each of them. But Jesus f*cking Christ. The constant, nonstop fighting, wailing and screeching over each of them makes me want to lose my mind.
When I was 29, I was named Deputy Governor of Illinois. The job meant overseeing the budget, operations, legislation, policy and communications of the fifth largest state in the nation. I was totally unqualified. I also didn't know the terrain (other than going to law school in Chicago, I had no connection to Illinois).
No matter what your politics are, we can all agree that we're now living in one of the most tumultuous and emotional periods in modern political history. Add in a deafening eco-chamber on Twitter, a relentless and highly energized media, and advocates of every stripe now having a digital megaphone in their pocket, and it's not surprising that so many CEOs are anxious about dealing with this new political climate.
Many have wondered about what's really going on behind the scenes at the White House and the types of conversations that the public is not exposed to. Since we likely won't be gaining access to those conversations anytime soon, here is a theoretical conversation between Donald Trump and Steve Bannon for your entertainment.
You're in your 40s. You've got a spouse. Kids. Friends that you've accumulated over the last several decades. Current colleagues. Former colleagues. Current employees. Former employees. You've had some luck in business, which means you now have resources, relationships, advice that people want. But you don't have the time or emotional bandwidth to accommodate everyone.
Stephanie Keith | Reuters For the vast majority of Democrats, there's little to like about Trump's immigration ban. But beyond the traditional actions of protesting, rallying and filing lawsuits, there are also several ways to leverage the surge of opposition to the ban to their advantage (and with all of the fights coming up, they're going to need it.)
So you're Hillary. You're getting over the misery of the inauguration, and you're starting to figure out what to do next. You're not taking this running for Mayor thing too seriously, but you also think Bill de Blasio is a disaster so you're keeping half an eye on it.
The other weekend, my wife and daughter went to DC to join in the march against Trump's views and policies towards women. It was a great moment, but without sustained action, it's not likely to change much. My wife asked what people concerned about Trump should keep doing beyond marching.
There's an adage in politics that's been around for years: don't f*** with people's cars. While the right to drive where you want, when you want is not formally enshrined in the U.S. Constitution, for decades upon end, it might as well have been.
"Patience is a conquering virtue." - Geoffrey Chaucer Bullshit. Only two things in life are certain: birth and death. The rest is variable. There's no master plan for every person. There's no invisible hand guiding your every step. And the world is not responsible for your well-being (no matter how much your parents led you to believe otherwise).
Before investing, one of the first questions we ask any potential portfolio company is "Who are your natural predators?" In our case, we're looking at regulatory threats and the answer has historically been the entrenched interest in whatever industry they're disrupting. Taxi medallion owners for Uber, hotels for Airbnb or casinos for FanDuel, and so on.