Why Seed or Early Stage?

One day I was talking to another investor.  He said, “Why do you invest at seed, it’s so f*&6ing hard.”  I laughed.  For him it was hard.  He was incredibly busy doing other things besides investing in startups.  I think …






World Events and Fintech

A lot of folks are trying to figure out what Brexit means for Fin Tech.  London is a huge financial center and has a great Fin Tech community.  I think it’s a waste of time trying to figure out the …






Breaking It Down

The other day, I showed how my partner Kenny and I came to our investment thesis.   It took more than a blogpost.  We have been discussing it for a long time.  I wanted to break it down a little …






With All The Pomp And Circumstance

On this day in 1826, both John Adams and Thomas Jefferson died. Both knew it was the fourth.  Adams said the fourth should be celebrated every year with fireworks and all the pomp and circumstance.  It should be a joyful …






Some Interesting Data-How We Found Our “Why”

Data doesn’t give you passion.  Data doesn’t execute.  Data doesn’t do anything but if you interpret it correctly you will make better decisions.  I thought this data was interesting and I wanted to share it with you. I often tell …






Focus on Sales

The first VC ever in Chicago was Bob Geras.  Over lunch we were chatting and he told me the best way to get bottom line revenue is increase top line revenue.  We laughed.  Of course it is-and of course startup …






You Better Like People

One thing I learned early in the trading business is it wasn’t about the numbers.  It was about people.  Fighting for trades was one thing, but you had to build relationships over time to get those trades.  Sometimes there was …






Centralized VS Decentralized

I found this video interesting because it goes against my general opinion. It’s easy to say she is talking her book. That’s the cynical view. But, she makes some interesting points on servicing the back end of the transaction. I …






Should You Stay In College, or Go To College?

Over the past of the last year, I have read about a lot of people pulling out of college or not going to do a startup.  Peter Thiel has his experiment with “Thiel Scholars”.  He gives talented kids money, puts …






Don’t Fake It

Jaw-dropping from today’s Lending Club filing: pic.twitter.com/YHaPTj22c0 — Tracy Alloway (@tracyalloway) June 28, 2016 Saw this roll across my Twitter feed. Lending Club ($LC) must be in trouble. Their demise won’t be good for tech stocks. It sort of reflects …






Chicago Aldermen Tell Startups to Go Away

As expected, Chicago alderman passed very stringent regulations and taxes on ride sharing and on AirBnb.  They will justify their decision citing fear, and the broken city budget.  As a Lyft driver told me last night, “They seem to be …






Post Brexit

I wanted to let the dust settle a little before I commented or thought really hard about Brexit.  Volatile events like that have after shocks as well, and we haven’t seen those yet.  As you are reading stories  and opinions …






The Black Knight Strategy Doesn’t Work Long Run

Some people will remember this scene and many won’t. If you haven’t seen the movie Monty Python and the Holy Grail, download it and watch it. It’s funny. 100% satire. When you are a startup, it’s all about survival. We …






Government Can’t Stamp Out Great Ideas

A long time ago, I was on the CME/PAC. Often, legislators from Washington DC would come to CME and tour the floor. After the tour, we’d get to meet them, take our photos with them, and talk frankly about business …






#Brexit

Today Great Britain votes on Brexit.  I saw some stuff on “how to insulate your portfolio from Brexit”.  Truth be told, there is no way to do that.  It’s a binary event that will probably cause a quick market move, …






Learning From Winning

In startup circles, we talk a lot about failure.  Companies fail.  It’s a fact of life.  It sucks as both an investor, an employee, and as a founder.  When I was on the trading floor they used to say 90% …






StreamLink Software Can Save Governments Big Money

A while ago I invested in Streamlink Software via Bill Campbell.  He is a member of Hyde Park Angels and was the deal lead.  HPVP also invested in the deal.  Streamlink is based out of Cleveland, OH.  I am sure …






Heuristics. Sometimes They Lead to Bad Decisions

Humans think in heuristics.  They create a process, and they follow it.  It’s any approach to problem solving, learning, or discovery that employs a practical method not guaranteed to be optimal or perfect, but sufficient for the immediate goals. Heuristics …