For Love of The Product

Although it’s rather topical to mock Silicon Valley for its “elevated” housing prices, shortage of UHaul vans, and celebrity investors, there are some things that the Valley undeniably does better than anyone else. One of those unique traits is to emphasize – almost to the point of idolatry – a focus on expertly designed and thoughtful […]

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 […]

On Being Early and Being Right

Over the past ten years or so, I have been relatively early to three highly nascent, wild wild west style industries: online poker, daily fantasy sports and bitcoin. In two of them – poker and bitcoin – I experienced significant professional and financial successes. In the other, daily fantasy, I lost my shirt. With bitcoin’s […]

You May Not Want to Tell Your Customers You’re the Cheapest

Last week, while speaking with a founding team building a new marketplace connecting buyers to suppliers, I mentioned offhand that it can actually be quite detrimental to actively advertise one’s platform as the cheapest. The insight took them by surprise and after some discussion, felt it was worthy of unpacking a bit in a post. […]

Anatomy of a Managed Marketplace

The following article was originally published on Techcrunch on May 25, 2017. Managed marketplaces (also known as end-to-end or full-stack marketplaces) have been one of the hottest categories of venture investment over the past several years. Recent examples of high-flying managed marketplaces include The RealReal, Opendoor, Beepi, Luxe and thredUP, which have collectively raised nearly […]

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 […]

How J.Jill’s IPO Could Help Define E-Commerce Valuations

You’d be forgiven for missing a small cap retail IPO last week in the midst of the global Snapchat mania. Last Thursday, without much fanfare, J.Jill, a nearly sixty year old former mail order catalog company selling women’s apparel, quietly went public at a nearly $900M enterprise value. And surprisingly, for the complex world of […]

Looking Out Towards 2017

2016 was a good but challenging year for me. It was a year in which I watched family members battle serious health issues, a year where I allowed myself to become distracted and reactive at home and at work, and one where my professional insecurities often got the better of me. But, like most challenges, […]

Why the Micro-VC Surge Will Drive Innovation Across the US

The following was co-authored by Ezra Galston of Chicago Ventures(@ezramogee) and Samir Kaji (@samirkaji) of First Republic Bank. Over the last several years much has been made of the opportunity, or perceived lack thereof in technology centers outside of the Bay Area and NYC. From Steve Case’s Rise of The Rest Tour, to Google for […]

Trump’s Rust Belt and the Hoofbeats of Technology

I am permitting myself one political/policy related post on this blog. I can’t help it. I am child of the beltway: my father served in the Clinton White House and I spent my early years on the floor of the West Wing doing 3rd grade homework. This piece takes no sides. It merely offers observations based […]

The First Time Founder Discount

Venture is a cyclical business. But in spite of dire bubble warnings, recent unicorn implosions, and a February 2016 nosedive in public SaaS valuations, the NASDAQ has now been on fire for nearly the past decade. In layman’s term, we’ve been on a (only slightly variable) linear up and to the right curve since 2009. […]

How Slack and Facebook Are Making Access to Information Less Democratic

Earlier this month Jonathan Libov, an Analyst at Union Square Ventures penned a widely circulated piece on the importance of paying attention to “fringe” technology and interests in the corners of the internet. He noted: “Fringiness, if you will, is in many ways vital to the business of venture capital. Sure, there is a large segment […]

The Hidden Challenges of Starting a Company in Secondary Markets

Fred Wilson’s much debated post, Second and Third Tier Markets and Beyond, sparked an important discussion about operating and investing in businesses outside of the Valley. Case in point: within 48 hours, the piece generated a heated Twitter exchange (including input from the one and only Bill Gurley), a Pitchbook analysis of the best M&A outcomes […]

Why Amazon Has Consumer Investors Bemused and Confused

Amazon’s recent entries into home services, food delivery, private label clothes & shoes, as well as a wide range of private label home items represent its most brazen efforts ever to attack the entire retail stack as well as penetrate seemingly defensible network effect businesses. Over the past couple of years, Chicago Ventures has made a number of investments in […]

The Increasing Cost of Consumer Startups

If you have the dubious distinction of spending as much time around consumer facing seed VCs as I do, you likely start or end every conversation with some variant of “what’s exciting you these days?” And for the first time in my nearly 5 years in venture, the answer for the past six months has […]

On Predicting The Future

“In the strict formulation of the causal law – if we know the present, we can calculate the future – it not the conclusion that is wrong, but the premise.” – An overview of the “Heisenberg Uncertainty Principle” from Uncertainty: The Life and Science of Werner Heisenberg It’s common parlance to suggest that venture capitalists are […]