Posts in Entrepreneurship

You Cannot Chase A Trade

One of the things common in trading and investing in companies is emotion.  There is the thrill of the chase.  It can consume you.  Sometimes, you get so involved, you ignore common sense and toss it to the wind.   …






The Voice Will Change Everything

Yesterday while the NCAA games were going on I was judging a Capital One/Amazon Alexa hackathon.  The theme was fin tech.  It was pretty cool.  Hackathons rarely put real companies together.  But, occasionally they do.  The biggest thing they do …






Lots of Failure

I think that startup CEO’s can learn a lot from the four act drama that just played out in Washington DC.  Learning from failure is an important concept.  In the startup world we are told to embrace failure, or ignore …






Voice Over Trading

I learned how to trade in the open outcry era.  We used our voices.  The people that were the most aggressive won.  Sometimes it meant having a big body.  In certain pits, traders were pretty beefy.  I remember slamming my …






The Founder Equity Split

Michael Siebel of Y-Combinator wrote an excellent blog on equity splits among founders.  I love some of the points he made and they cannot be underestimated.  The conversation about splitting equity will help you have a conversation that helps founders learn …






The Blockchain, Cryptocurrency and Trust

Trust is one of the more fleeting things in human society.  It’s why lawyers exist.  Think about whom you really trust in the world.  Think about how many people that you do business with in your life that you would …






The Practice Gym

It’s NCAA time and people are bemoaning their busted brackets.  Mine is broken, damn you Iowa State and damn you Big Ten.  A friend of mine knows a lot about busted brackets, and busted psychology.  I met Tom Heitz when …






The Big Data Blind Alley

My friend Notre Dame Law Professor Laura Hollis turned me on to a new blog. I was scrolling through it and his post on gambling caught my eye.  In it, he talked about a system he discovered for betting on …






FinTank Chicago

Thursday evening, George Vukovich revealed FinTank in Chicago.  I was fortunate George let me speak for a minute or two at it and then shoved off to a HPA meeting.  Financial Services are core to Chicago’s DNA. In 1848, someone created …






The Blockchain Road Will Go Through Chicago

Been sitting on this news for a bit.   One of the hardest things to sell in startup land is what Chicago is about.  I have had people look at me and wonder why they should have any money on …






ROI on Entertainment Spending

When things get tough inside companies, one of the first budgets to get hacked is entertainment. It’s an easy hack. One of the reasons it’s an easy thing to cut is there is virtually no data-driven metrics around it. “Hey …






When Things Screw Up, Tear It Down

Startups at seed stage execute on a hypothesis.  They either think they see a problem they are solving and fill the gap, or they create a new market that didn’t exist before.  No matter what they do, they often struggle …






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 …