Enough With the Award Shows Already

[I originally authored this blog in early 2018 and elected not to post it at that time. Over the past two years, unfortunately, nothing has changed. If anything, hosting organizations have gotten more aggressive at using “award shows” to project their fundraising needs onto unprofitable startups, bleeding them of valuable capital, and distracting them from […]

The Mentorship Delusion in Secondary Markets

I was listening to Steven Galanis, CEO of Cameo’s, interview on the Tech in Chicago podcast last week and one thing in particular stuck out to me: his emphasis on seeking out world class mentors and his consistency in honing in on particular pieces of advice that became global priorities for the business. Specifically, he […]

Kraft Heinz and Why The D2C Revolution May Be Bigger Than You Think

Late last week, Kraft-Heinz, one of the largest global food conglomerates reported disappointing earnings, admitted to an SEC investigation, and wrote down the value of a couple of its iconic brands. The market responded by dumping their stock 30% – the single largest daily drop in its history – wiping out ~$15B of market value. […]

Kraft Heinz and Why The D2C Revolution May Be Bigger Than You Think

Late last week, Kraft-Heinz, one of the largest global food conglomerates reported disappointing earnings, admitted to an SEC investigation, and wrote down the value of a couple of its iconic brands. The market responded by dumping their stock 30% – the single largest daily drop in its history – wiping out ~$15B of market value. […]

Dressing Down the FarFetch IPO

Earlier this week, UK based FarFetch filed to go public, with media experts expecting an ultimate public market valuation above $6B. You’d be forgiven if you actually didn’t know much about FarFetch – it’s largely been a non US focused story to date. But you’d also be remiss if you didn’t study the business: at a $1B+ […]

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. […]