Game On! (Well, Sorta…Maybe?)

Monday, in a mostly expected move, the Supreme Court struck down a federal ban prohibiting sports betting. The move opens the door for states to legalize sports wagering under their own terms, with analysts expecting several dozen states to flood in, likely as early as Memorial Day in the state of New Jersey. Enthusiasts embraced […]

Double Clicking Arteen’s Marketplace Calculator

Earlier this week, Arteen Arabshahi at Fika Ventures released his Marketplace Calculator, which is a framework his firm uses to assess two/three sided businesses, with network effects. In general, I think these frameworks can be dangerous in that they commoditize a nuanced process, but I actually thought Arteen’s was nicely done, simple, and appropriately weighted […]

Thank You: On Leaving Chicago Ventures

The last six years have been the most exciting, important and fundamental of my life. Over that period, I graduated from business school, was blessed with three beautiful children with my wife Shira, and purchased my first home, amongst other major life events. But throughout it all, there was a constant presence – my second […]

The Future of Government (A Primer on Masternodes)

Happy new year everyone! As many readers know, I’ve been actively writing about and investing in the cryptocurrency sector since early 2013. And 2017 was obviously been a pretty extraordinary year for the space. Over the past few months, there’s been so much noise about bitcoin in the mainstream media, that I haven’t felt I’ve […]

Unboxing Stitch Fix’s S-1

The following article was initially published by TechCrunch on October 23, 2017 When Zulily went public in 2013, it sparked a resurgence of interest in an otherwise lagging e-commerce market. Quickly trading up to reach an $8B market cap – valuing the company at over 10 times revenues – Zulily became the poster child of the flash […]

Why the Midwest Needs Silicon Valley’s Respect

The past couple of months have brought several visible pieces on the opportunity and strengths of Midwestern startups, and underserved ecosystems in general. From Dear Midwest: Stop Trying to Compete with Silicon Valley to The Midwest’s Healthy Fear of Failure Beats Silicon Valley’s Fail Fast Manta to my own piece that I authored with Samir […]