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2020 was a defining year for the InsurTech ecosystem as a confluence of factors brought startups & tech-forward insurance companies into the spotlight. COVID-19 forced companies across the insurance value chain to accelerate digital transformation efforts to effectively operate in the new world. This catalyzed the adoption of new products across departments and ushered in a wave of IPOs with Lemonade, Root, GoHealth, Clover Health, and several other big InsurTech startups going public.

We first met Ryan (ThreeFlow’s co-founder and CEO) just as Equal was getting started. The company had been known as WatchTower Benefits (as it was up until yesterday) and was introduced to me by my long-time friend and Equal LP, Shawn Ellis of NFP. Shawn was CEO of a benefits company we had incubated at Lightbank and is amongst the most forward-thinking minds you will find in the benefits industry. Shawn knew that we were on the hunt for solutions that could enable transformation of the brokerage process, rather than attempting to disrupt it by disintermediating brokers. Having worked with companies like Riskmatch, we believe brokers are critical to the value chain and were searching for the next platform to enable the industry.

I first met Ali nearly 5 years ago. He was finishing his senior year at the University of Illinois and was referred to me by Spencer Lazar, who was a VC at General Catalyst at the time. Ali had spent his summer working with the team at GC and Spencer had suggested that I get to know Ali given that we were both in the Chicago area (I was at Lightbank at the time). We had no intention of hiring anyone at the time but were blown away by Ali’s intelligence, maturity and intellectual curiosity. We offered Ali a position to join us full-time as an Analyst, presumably upon graduation. Ali countered, he wanted to start immediately. He was so eager to join the venture community that he dropped out of college to join us, reasoning that he’d learn more as part of our firm than he would in the classroom and that he would finish up his degree online later.

We are living in perplexing times. At the dawn of a new decade, we’re witnessing political, societal and economic polarity, unlike anything that we’ve seen in recent years. Technology, once heralded as a force to “make the world a better place”, is now being vilified across circles of politicians and the populous. A contentious divide has developed between technology hubs and the rest of society as we increasingly lay witness to a world of technology “have” and “have-nots”, what some refer to as the “digital divide”. With that, we are seeing virtually every category (and the incumbents entrenched within those categories) attacked by an onslaught of digital upstarts, creating unprecedented amounts of both transformation and displacement.

We’re excited to kick-off a new initiative at Equal Ventures to work with experienced Operators to explore opportunities for building and launching new ventures. Over the course of the program, we’ll provide a select group of operators to diligence a few market opportunities together and connect them with other high caliber operators and executives. We’ve written about the areas we consider our ‘Majors’ in a recent post on some of our Key Investment Areas. However, we welcome applications from operators with interests across other sectors and areas as well.