Cheerleaders vs. Trainers Unquestionably, 2020 was a jarring year for startups. Whether you are a company dismantled by COVID or resilient to its impact, it affected your organization and placed undue strain on the founders of the company. Founders have had to not only worry about the viability and growth…

Democracy, capital markets and innovation cycles 4 years ago, I was on vacation with my wife. Trump had just been elected and we were escaping a frigid Chicago winter to relax on a warm beach. I’m not a casual beach reader and opted to read a relatively academic, twenty-year-old book…

Why keeping it simple is the secret to finding Product-Market Fit and raising your Series A The single hardest thing for any startup to accomplish is achieving Product-Market Fit. Product-Market Fit (PMF) is defined differently for every startup, but can most generally be described as the moment when there is…

Earlier this year, I penned a piece on why I’m NOT a B2B SaaS investor. I stand by my position that the landscape has evolved due to heightened competition across software companies, making it increasingly difficult to scale traditional B2B SaaS companies. The truth is, it’s never been easier to…

Originally published in VentureBeat on January 14, 2017 (http://venturebeat.com/2017/01/14/why-im-not-a-b2b-saas-investor/) People often categorize me as a ‘B2B SaaS’ investor, when in actuality I haven’t invested in a single SaaS company in years. Why? Because I think it’s really hard for a traditional SaaS company to be successful in today’s market. Given…

A large part of my day is spent meeting with companies that will likely never be a fit for our fund or my investment profile. There isn’t anything wrong with these companies (they often go on to raise money from other funds or angel investors), but they just aren’t a…

Today, I’m excited to announce that Eric Ong is joining Lightbank. Eric joins us from the west coast where he spent the last 2 years as a TMT investment banker at Deutsche Bank and returns to Chicago after going to Northwestern for his undergraduate degree. Eric is extremely impressive in…

Design, Decentralization and Democratization — The 3 Ds of Industry-Leading Software A decade ago, quality software solutions were a privilege reserved for the corporate elite, those who could afford multi-year implementations with swarms of resources to develop customized products. Customers would bring in large professional services firms to help with…

Trucking: The Next Unicorn Marketplace? With over $5.4B dollars poured into Uber over the last year, we are seeing more and more founders coming to us with an “Uber for X” pitch for their marketplace business. As frequent investors in (and builders of) marketplace businesses, we are thrilled to see…