Carlease and Lightbank 2 Years in the Making


Bill Pescatello

Today we are excited to announce our investment in, and while we generally do not write about investments when we make them, we thought Carlease was a great example of what we look for at Lightbank and what we think about before making an investment.

We first met two years ago, when they were looking to raise a Series A round. Providing the promise of leasing a car without ever stepping into a car dealership, Carlease had an innovative idea and a material footprint in Chicago. While there was a lot to like about the business, there was significant technical debt, little reinvestment in the business, and needed additions to its management team. Due to these issues and our inability to get the ownership we needed to get involved, we passed on the investment, but could not stop thinking about this opportunity in our backyard. Despite these fixable faults, Carlease had a history of profitable growth and a model that was working. We felt confident, if we spent the time, added the talent and capital it needed, we could help build something extremely valuable, but without the right ownership, we just could not enact the changes and resources the business needed.

While it looked as if we may have missed our chance to invest in Carlease, an opportunity emerged 6 months ago to acquire the entire company. This buyout changed everything for us. While it may have been outside the box for most traditional venture firms, we have always been different and have alway embraced these types of opportunities. In buying out the company, we could get the ownership we needed, really double down, and roll up our sleeves.

Making the opportunity even more attractive, we partnered with two Lightbank founders (Kayne Grau and Justin Mahlik) who recently sold their auto startup DRIVIN, and together we pulled together an impressive syndicate of leading online auto operators to invest alongside us, and added a proven leadership team headlined by CEO Andy O’Dower and VP of Product Clay Johnson.

As we look to the future of Carlease, we see a massive space ripe for disruption. There is a lot more work to be done with Carlease, but this is a quintessential Lightbank deal. We are working hand in hand with founders and partners who we know well and are confident we can make a real difference. Time to to get to work!