Posts in Start Ups

A Short Thought About the Chicago Startup Community

Last night I was invited to speak at WeWork on Kinzie in Chicago for Startup Grind.  It was a lot of fun.  The presentation was from 7-8, I got there at 6.  I was there speaking with entrepreneurs until 10:30. …






The Valuation Game

One of the things I learned early when I started investing was that valuation in the Midwest was typically a lot lower than it was on the coasts.  The reason for that was basically supply and demand related.  On the …






How Do You Get A Job in Venture Capital?

This question comes up every time I speak at a college.  There is a romanticized version of venture capital out there that VCs are super wealthy and all you have to do is pick winners.  Everyone thinks it’s pretty simple. …






The Amount of Venture Debt is Increasing

My whole life, I have watched macroeconomics.  It is the “dismal” science.  But, as a futures trader, you could make some money by paying attention to macroeconomics and trying to piece together what you thought would happen.  A lot of …






Do Teams Have to Agree On Everything?

One thing that a lot of people don’t realize is that C level teams, or partnerships don’t agree on everything.  There is a misconception that everyone is in lockstep.  Great organizations are not always in lockstep.  It’s actually better to …






When Stuff is Fake

There is a lot of discussion of fake news these days.  Welcome to the world of entrepreneurship.  A lot of people follow the “fake it till you make it code”.  I think it invites trouble.  There is a big difference …






A New World In Commercial Real Estate

When we were raising our fund, I still made a couple of angel investments.  One of them launched their platform yesterday.  Build Truss is going to disrupt the commercial real estate market. The low end of the commercial real estate …






Is It A Tool or a Platform?

One of the toughest things about analyzing companies is figuring out if they are tools or platforms. In B2B Fin Tech, one of the things we are seeing is the unbundling of big entrenched vertical silos. Bloomberg, FIS, Fiserv, Envestnet, …






Where Can You Find Me?

For the next few weeks, I am going to be hanging out a lot at Nextspace River North in Chicago. We recently lost our space manager there and need to hire a new one. My wife and I worked there …






What About Blockchain and Custody?

A lot of people are wondering what the killer app will be for blockchain. I see a lot of potential in various areas. One of them is custody. What do I mean by that? In finance, equity is transferred between …






A New Blog For the Under Represented in Tech

Learned about a new blog, Citizen N Four,  that is going to talk about the problem of under represented people in tech.  It’s a problem that has been floating through the tech community in different ways.  Here is a link …






What Do You Do When You Lose? Or Win?

When you are selling, inevitably one of your filtered targeted leads won’t buy.  Sometimes, someone will buy and then drop off.  Other times, you will have a satisfied customer that keeps buying over and over again. It’s important for the …






The Way to Run A High Impact Sales Meeting

When we think about meetings, we usually moan.  Meetings generally suck.  As a matter of fact, when surveyed people all across the world thought only 5%-10% of the meetings they were in were productive.  5%-10%!! How many meetings do you …






Happy New Year

People love to make predictions and resolutions at the turn of the year.  I was never much for that. But, this year there are some things I want to change and it’s going to involve conscious effort on my part. What …






Closing The Deal

Apropos that I am writing a blogpost on New Year’s Eve about closing.  There are a lot of theories on closing.  Back in the days when all the major corporations taught “IBM Selling Skills” to their sales forces, there were …






The Proposal-The First Part of the Close

Recently, I have been blogging about the selling process.  The last part of the selling process is “the close”.  I know that the old adage is “always be closing”.  That’s not really true anymore.  If you are always closing the …






Objections In The Sales Process-Handle Them And You Are Awesome

One part of the sales process that is always hard is objections.  When you are selling to a potential customer, they always come up.  If you can’t handle them, you cannot sell.  For entrepreneurs, being able to take care of …