Tales from the front:
my mistakes,
and lessons learned
of breaking into VC
About Me

The Importance of Celebritization, Part II

An emerging trend over the past decade has been the celebritization of leaders and influencers across nearly every vertical, hobby, and interest group imaginable. No longer are athletes and actors the only celebrities in the public sphere. One easy example – Swedish gamer Felix Arvid Ulf Kjelberg aka “PewDiePie” has over 30 million subscribers to his Youtube channel – more followers than Ashton Kutcher, or even Ronaldo.

In my view this is attributable to two main factors: (a) the rise of reality TV which has created recognizable personalities in hundreds of interests, ranging from food to polygamy and (b) the proliferation of single purpose interest groups across the web (discussion forums, content communities, etc), which cultivates credible influencers in a highly concentrated category.

It is the latter phenomenon, of digital celebrities – sometimes mere screen names – that has always fascinated me. In what I consider to be THE landmark e-commerce study, a 2012 Battery Ventures report found that celebrities were downright useless in influencing behavior, but that friends and family won the day. However, the report presumed that “celebrity” meant Kim Kardashian or Brad Pitt. What if you became so closely connected to celebrities that they felt like friends or family?

This is precisely what several of our portfolio companies at Chicago Ventures are doing. Here a couple of examples:


Florists are artists. Many have Masters in Floral Arts and create dazzling displays. But due to their reliance on the wire services  (1800Flowers, FTD) for business, they were relegated to de facto back office employees. Bloomnation inverted that. In creating the platform, they put the merchant first with content rich profiles that offer deep personality profiles of who you’re dealing with.

Second, they believe that florists need more opportunities to both feel and actually be important. To…

The Importance of Celebritization, Part I

When I joined CardRunners in April of 2007 I recognized our company had a dilemma; although our content producers represented dozens of the smartest minds in poker, none of them were “famous,” or TV poker celebrities. Instead, our content authors were predominantly college kids or hard working young adults who had turned their card smarts [...]

Food 3.0 & The Instacart Anamoly

This blog was originally posted on VentureBeat on July 19, 2014 Instacart, currently the most well funded and fastest growing startup in the emerging food space, is an anomaly. The evolution in food startups – from the scheduled warehouse deliveries of the past decade to the highly curated, on-demand prepared food companies currently proliferating the [...]

The Bitcoin Ecosystem: Strengths & Opportunities

This past weekend, I had the opportunity to give a 30 minute talk at The North American Bitcoin Conference in Chicago about my thoughts as a VC on bitcoin economy. As many of you know, although Chicago Ventures has not made a formal investment in the bitcoin space, myself and some of my colleagues have [...]

On the Importance of Customer Service

I’m writing this blog from 35,000 feet in the sky on a United flight from DCA to ORD, originally scheduled to arrive at 9pm, currently tracking somewhere close to midnight. Our outbound flight to Washington was equally delayed around 3 hours. We even boarded the flight before being forced back to the gate. Total flying [...]