Posts in Entrepreneurial Ecosystems

The Board

Fred Wilson wrote a post about convertible notes and SAFEs the other day.  I agree with what he posted 100%.  It’s always better to do a priced equity round than a squishy round.  I understand why squishy rounds happen, and …






The Age Old Question: Why Does a Venture Capitalist Invest?

My friend Chicago Booth Professor Steve Kaplan just published some research on why VC’s invest.  He and his collaborators surveyed 885 institutional venture capitalists. They found the quality of the management team is the reason they invested. Venture capitalists also say that …






Zero Barriers To Entrepreneurship

I am glad the Kaufmann Foundation is moving forward with this. In the last ten years, I have spent a lot of time with entrepreneurs. I can assure you, when people think about problems they think about inner cities. But, …






Advice For Employees of A Company That IPOs

Back in November of 2002, we completed our IPO process at CME that we started in 1997.  I thought I would pass on a little advice to Snap employees from my experience.  I suppose they are being hounded by wealth …






Chicago Fin Tech Hackathon

The Capital One DevExchange is sponsoring a Hackathon featuring the Amazon Alexa team. On Saturday, March 25th, 2017, teams from all over Chicago will gather for an all-day workshop and hackathon in celebration of the new Capital One Café in …






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 …