Late last summer I was feeling very fortunate. The small angel investments that Jon DeLuca and I made jointly in startups were making a visible impact. Our goal was to be one of the first checks and believers into humble and relentless founders. …

I love Mike Tyson’s quote as it relates to startups. Startups that have a plan, even if it’s short-term, will often face adversity. Your new hire decided to leave pushing timelines back The investment hasn’t yet come through enabling you to fund certain operations The marketing that you expected to…

This week we publicly disclosed our investment in MVMNT. The company helps shippers and carriers manage the full shipment lifecycle via one end-to-end platform. Chicago has a rich history of success in logistics with companies like Coyote, Echo, CH Robinson and newer folks in the tech space like Project44 and…

While we’ve only announced one investment at the time of this post, Subconscious Ventures has made 5 investments in startups with a 6th happening in the next week. Since our founding, that’s basically an investment every 6 weeks. One trend I have observed in this portfolio is that I can…

The early stages going from zero to one are so complex and tricky. You have an insight or an opinion that you believe to be true. Getting that insight into action can be daunting. There are SO many things to do. Even in a business that’s pretty straightforward like SaaS…

Several years ago I was in Europe for an event we held for Yello customers in EMEA. I was walking back to my hotel after dinner when I learned of an issue one of our large enterprise accounts was having with a critical integration. It was after 5pm eastern on…

Last week we publicly disclosed our first venture investment of our fund in EarlyBird. Their mission is to simplify investing and elevate gifting to enable a brighter financial future for the next generation. …

When we think about the folklore of startups that had tremendous success, we hear or read how their founding teams would pull all-nighters coding to get a release into production. This was life or death and the team needed: the flow to work to pitch investors on demo day a…

It took me 15 years to learn the difference between features and value. As a product-focused and customer-obsessed founder, each feature you release isn’t just something that you can check off on an RFP, it’s something you created out of absolutely nothing. It’s a smile for your customers, something the…