The Investor Can’t Execute

When it comes to early stage startups, success is determined by execution.  If the team can get the job done, they continue to ascend the mountain.  If they don’t, they go out of business. A lot of venture capitalists and …

9 Trillion Gallons of Rain

Houston got hammered by Hurricane Harvey. 9 trillion gallons of rain. Wow. Alligators on people’s doorsteps. Already, people are going to help. The Cajun Navy is already there.  Grocer H-E-B already lined up trucks and is on the way. I …

How To Gain Context on a Sales Phone Call

When we do diligence on a company, one of the most critical things is the selling process. We analyze that process closely to see if the team can execute, and if it’s repeatable. We also analyze it to see if …

Chicago Fin Tech Event on Sep 13 at MakeSpace

When Kenny and I started West Loop Ventures, we had three things we wanted to accomplish.  Obviously, making money for our LPs and ourselves was a goal.  But the two other goals were different. One of them was to educate …

Congratulations to Lost Arts

If you aren’t in Chicago, you probably don’t know about Lost Arts.  It’s a special kind of co-work space started by one of the founders of Kickstarter, Charles Adler.  It is turning one year old on August 31.  That’s a …

Some Common Sense Economics

The economics geniuses will be out at Jackson Hole this week to discuss the world’s economy.  I love what my friend Yra Harris wrote: In July, Barry Ritholtz posted an interesting article by Alan Jay Levinovitz in Aeon Essays titled, “How …

Truss Takes it To The Next Level

One of the last independent angel investments I made was into a company called Truss.  They were solving a very difficult problem in commercial real estate.  If you have tried to find space of 10,000 square feet or less, it’s …

Getting Children Hooked on Technology

There is a big movement for governments to get kids hooked on technology.  While I appreciate the initiatives it’s important to realize not every kid is going to get hooked.  People are different and they need to be free to …

Taking Care of Your Own Field

Sometimes, you take stuff for granted.  Things happily get done and you don’t notice.  You just show up, and go about your business.  I was thinking about this as I power washed a deck yesterday for a few hours. At …

Book Review: Jason Calcanis “Angel”

I read the book by Jason Calcanis on angel investing.  If you are going to angel invest, it’s a good read.  If you are angel investing, it’s still a good read.  If you are an entrepreneur and you are going …

A Sensible Discussion on Race

I have avoided posting on my blog about what’s happened in America over the past week.  Safe to say, I am not on the side of any white supremacists.  I am also not on the side of anyone that wants …

Should You Pay Deal by Deal, or Total Fund?

There are more than a few ways to organize a fund waterfall. Fund waterfalls are how all the investors get paid. The return comes in, and then all the distributions happen. There are different ways to structure waterfalls, but the …

Rainy Day

This summer up north in Minnesota they have had a lot more rain than usual.  It’s lead to a lot more mosquitoes than usual.  Mosquitoes are the state bird here.  We have been doing a lot of work this summer. …

YCharts on the Inc 5000

Excited to announce @ycharts has been named #1158 on the @inc5000‘s annual list of the fastest-growing private companies! #Inc5000 pic.twitter.com/tR2Suv0kcl — YCharts (@ycharts) August 15, 2017 YCharts has been named to the Inc 5000. It’s the best stock and ETF …

Chicago And Food

I go back and think about the first meeting we ever had of Hyde Park Angels, the angel group I spearheaded, in April of 2007.  It wasn’t a pitch meeting, but a “meet us” meeting at the Gleacher Center in …

Remote Work, Can You Do It?

I have followed the remote work movement ever since I spoke with Sam Rosen and Pat Griffin at a breakfast in January of 2012.  That conversation lead to investments in Deskpass and into Nextspace.  Nextspace didn’t make it but Deskpass …

Why You Need to Learn How to Follow in Order to Lead

In Major League Baseball when a rookie comes up, they have to carry bags and do other menial stuff.  It’s part of ritual hazing that goes on.  It’s also a part of learning to be a pro.  Having respect for …

The Google

If you are in tech no doubt you heard about the engineer who was fired at Google for writing a ten page document on employment practices and the corporate culture.  Many women felt it was especially sexist and demeaning. Here …