Boards: Venture Evolved on Strong Suit Podcast

I recently was a guest on the Strong Suit Podcast, discussing habits of successful and unsuccessful boards of directors. I compressed learning from 16 years and 750+ board meetings into 22 minutes! Enjoy. Strong Suit 090: Leading VC Gives You a Peak Into the Board Room

Another Lesson of the Cubs’ Victory

I’ve been a Cubs fan for 20 years. It’s the first team I adopted when I moved to Chicago after college. I realize that’s not a lifetime, but I’m emotionally invested. It is for this reason that the World Series run up was thrilling and scary all at the same time. It’s magnified because I […]

Revenge of the Nerd

This story is about a good friend of mine who wished to remain anonymous given the content of the story. We wrote this story together. Enjoy. It was an unusually crummy weather day in 2005, and my wife and I decided to go to a movie. As we were exiting our parked car to go […]

Revenge of the Nerd

It was an unusually crummy weather day in 2005, and my wife and I decided to go to a movie. As we were exiting our parked car to go into the theater, my wife inquired if she had to bring along her big purse. I’m always amazed on the occasions that I have to lift […]

Why Origin Invested in Tock

The Start In 2014, Nick Kokonas wrote a manifesto highlighting that if restaurants used tickets instead of free reservations, restaurants could dramatically reduce no-shows, optimize their supply chains, improve working capital, and eliminate staff answering the phones to take reservations. It made so much sense– the world SHOULD work that way, but it does not. […]

Why Origin Invested in Tock

The Start In 2014, Nick Kokonas wrote a manifesto highlighting that if restaurants used tickets instead of free reservations, restaurants could dramatically reduce no-shows, optimize their supply chains, improve working capital, and eliminate staff answering the phones to take reservations. It made so much sense– the world SHOULD work that way, but it does not. […]

The Melting Liquidation Preference

I’ve been through two severe market declines, both in 2001 and 2009. Public market volatility at the beginning of 2016 gave birth to a lot of “doom and gloom” posts on VC blogs. The public markets have recovered, but the scare earlier this year seems to have resulted in more conservative cash planning within early […]

The Melting Liquidation Preference

I’ve been through two severe market declines, both in 2001 and 2009. Public market volatility at the beginning of 2016 gave birth to a lot of “doom and gloom” posts on VC blogs. The public markets have recovered, but the scare earlier this year seems to have resulted in more conservative cash planning within early […]

A Post on Post-its, Cheap Art, Lasers and History

I am not much of a student of history. I do, however, believe it’s important to honor the previous generations for the contributions and sacrifices that give rise to the current generation. I’ve always liked Newton’s quote: “If I have seen further it is by standing on the shoulders of giants.” The history of Origin Ventures is […]

A Note on Notes: Hidden Costs of Convertible Notes

It’s been really exciting to watch the explosion of startup activity the last three years. This expansion has been characterized by technology infrastructure shifting from fixed cost to variable, proliferation of seed funds and accelerator programs, exit markets opening and other factors. A byproduct of this increase in seed investment activity is the wide use […]

The Pitch

Yesterday, I had the chance to participate on a podcast called The Pitch. It was started by a serial entrepreneur and angel investor Sheel Mohnot that I know from my investment in FeeFighters. The podcast features entrepreneurs pitching their seed companies and investors reacting to the investment. Yesterday was only the second episode, and the […]

Venture Evolved on WBEZ: The Chicago Venture Market

I was recently interviewed by Niala Boodhoo on the Tech Shift, a radio segment of the Afternoon Shift program produced by Chicago’s NPR station, WBEZ. It was a lot of fun to meet Niala and Melba Lara in person after hearing their voices for so many years. We discussed the state of venture capital in Chicago […]

How to Lose Credibility in your VC Pitch

I’ve sat through a lot of startup pitches over the years. I estimate at least 4,000, probably more.   The truth about VC investing is that it is as much about selection as it is about elimination. A huge percentage of a VC’s time is with companies that do not turn into investments. So how do […]

Do Not Take this Software Era for Granted (Pt. 3)

This is the third (and last) post in a series. Consider reading the first and second posts. Before there was the Internet, there were bulletin board systems (BBSes). Like the Internet, the BBS world had an underbelly. There was a hierarchy of people in the dark corners, a social order that I found fascinating. Up until […]

Do Not Take This Software Era for Granted (Pt.2)

This is part two of a series. Read the first post here. In the late 1980s and early 1990s, there was a predecessor to the Internet called bulletin board systems (BBSes). Enthusiasts used modems to call other computers that hosted BBSes. Those that knew how to navigate it and who were willing to break the law could […]

Do Not Take this Software Era for Granted (Pt. 1)

We live in an amazing era of software. We walk around with powerful networked computers in our pockets/purses where we can wirelessly download millions of software titles, most for free, in under a minute. While most people can appreciate how insanely cool this is, I think there is an important secondary effect. An aspiring software […]

You Might Owe Your Job to a Veteran

I had the privilege of attending a launch lunch for the Bunker Incubator earlier this week in Chicago, thanks to my friend and US Airforce vet Todd Olhms. The Bunker is an accelerator for veteran-owned businesses that has started in Chicago but has quickly spread to seven cities. Among its many purposes is to create […]

Tips on Negotiating a Termsheet

Last year, OpenTable founder and all-around great guy, Chuck Templeton, asked me to put together a talk on negotiating termsheets for participants in his Impact Engine program. Although Chuck thought he was asking a favor of me, I found the process of organizing my thoughts on negotiating termsheets (and in general) a personally useful exercise. Below […]

Why I Joined Origin Ventures

In June, I made the difficult decision to leave one of the Midwest’s finest venture capital firms, OCA Ventures. I began my career in venture capital at OCA in 2001, when I started as an intern. I will be forever grateful to the mentors, partners, support staff, founders, management teams and friends that made working at […]

How To Bend the Arc of Your Career to VC

I am still learning the formula of what makes a great venture capitalist. In an examination of other successful investors and my own numerous deficiencies, I’ve composed a theory that the best venture capitalists are a Jack/Jill of all trades and a master at a couple. Here’s how to bend the arc of your career […]