Posts in Entrepreneurship

Driverless Will Affect Everything

A while ago, Benedict Evans had a really great blogpost about driverless cars and their effects on different things that you might not think about.  He is a VC for a16z and a great follow on Twitter.  For example, a …

Why Can’t A Country Do an ICO?

Yesterday I saw where Burger King issued it’s own cryptocurrency in Russia, WhopperCoin.  It didn’t surprise me.  When I first started thinking about cryptocurrency, I hypothesized that big companies would use it for their supply chain management and to lock …

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 …

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 …

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 …

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 …

Should You Always Wave the Pom Poms?

Yesterday at Fred Wilson’s blog, AVC, he talked about the backlash he was getting from a post on greed. In the crypto community, there is a lot of greed lately with the run up in value of several currencies.  There …

Can We Be Friends?

The other day I noticed Chicago Mayor Rahm Emanuel said Governor Bruce Rauner isn’t his friend anymore. Rauner had mentioned that even though they differ politically, he considered the mayor a friend.   I wasn’t surprised. My fear is that …

Entrepreneurial Blind Spots

Everyone has a blind spot. When I work with entrepreneurs, it’s sometimes easy to see what their blind spot is.  It’s harder to recognize it in yourself.  You have to work to uncover them.  It’s important to do that, because …

Do You Seed/Angel Invest For Wealth Accumulation? Or Not?

Have been reading Jason Calcanis book, Angel, lately.  I haven’t finished it. I plan on finishing it in the next couple of weeks and will write a review then.  Today, I caught the end of a Facebook Live gig, This Week …

This Law Is Going to Change

There was no way that I was ever going to law school.  It just wasn’t for me. In high school, I thought about it but knowing the lawyers I know I don’t think I would have enjoyed the occupation.  Some …