Posts in Entrepreneurial Ecosystems

No Occupation Is Immune From Automation

When I speak to students at Universities about entrepreneurship and what I am anticipating for the future, we eventually talk robots, artificial intelligence and machine learning.  Those three things are going to put a lot of people out of jobs. …






The Terms on a Term Sheet

One of the things we try to do at WLV is be very friendly to entrepreneurs.  A lot of people say that, but we really try.  For example, we try to give really honest feedback.  When some VC firms pass …






Billions In Value, One Pit

One of the things that is hard to pin down is how entrepreneurial Chicago is.  It’s really an entrepreneurial Mecca.  But, it doesn’t seem like it because the kind of entrepreneurship that has existed here doesn’t resemble anything on the …






Would I Want My Daughter To Work For Uber?

One of the things we used to joke about years ago was having daughters.  When I had my first daughter, my trader friends in the pit showered me with bar room humor.  “God’s way of getting even with you.”, was …






A Critical Point of Differentiation in Framing

There are a couple of quotes that I want to pull from articles that I read this morning.  The first is from WSJ editorial writer Bret Stephens.  Stephens is writing about the collapse of Western Civ in education; and how …






Competition Makes You Better

America was based on the notion of competition. As a culture, we are getting away from it. Everything is pre-planned. When I used to do television, often a producer would call me up to ask me questions before I went …






Including Diversity in Entrepreneurship

There has been a lot of talk about diversity in entrepreneurship.  I am all for it. I am also reminded of Thomas Sowell’s brilliant observation.  “The next time some academics tell you how important ‘diversity’ is, ask how many Republicans …






Work Ethic and Competitiveness

One of the things about Midwestern people that people find they like is their work ethic.  Midwesterners were farmers that broke the prairies.  That hardscrabble work ethic is ingrained in their DNA.  Former football commentator John Madden would describe them …






Square Up!

When I played a lot of basketball, I was a pretty damn good shooter.  I can still knock down free throws like it’s nobody’s business and shooting from 20 feet in I can tickle the twine.  My father was a …






The Down Round

Yesterday I interacted with Mike Moyer’s class at Chicago Booth.  It was a lot of fun.  There were lots of questions, but one of the questions was on valuation.  How does anyone go about valuing a startup company? It’s a …






CryptoCurrency and Freedom

One of the features of cryptocurrency that fanatics advocate is freedom from all government. I don’t think this is realistic. But certainly in extreme cases you can see where cryptocurrency can fill a need when government totally breaks down-or is …






Clearing is Centralized, and Concentrates Risk

One of the things blockchain might be able to do better is clearing.  Clearing of swaps especially.  Under Dodd-Frank, the government mandated a lot of swaps clearing.  Logically, this made sense.  I was initially in favor of moving plain vanilla …






Trump Loses on Department of Labor Law

“With or without regulation by the federal government, the principle of ‘clients first’ is here to stay.” – Jack Bogle When I read the Department of Labor was wading into financial regulation, my first inclination was dread.  I didn’t trust …






Set A Goal For a Meeting

Humans tend to spend a lot of time in meetings. Craig Wortmann found that humans waste a ton of time in meetings. Most people only think that 5% of meetings are even productive.   I have blogged about how to …






Want To Start A Bank? You Might Have a Chance Now

We talk about how easy it is to start a software startup these days.  It’s cheap.  Two people in a garage.  Of course, academic studies have shown despite the ease, starting an entrepreneurial business is on the wane.  There are …






The Series B Investor

There are a lot of VC investors that prefer not to mess with early rounds.  They would rather initiate the investing cycle at Series B.  There are a lot of logical reasons for this.  Their funds are too large.  Spending …






The Cashless Society

Experts have said it for years but it’s never happened.  Everyone has talked about a cashless society for as long as I can remember.  We are starting to see it come true, but it’s not cryptocurrency that is leading it. …