3 min read

Into the White Space

After a twenty-year career working with some of the best entrepreneurs in Boston at companies like Ascential Software, ProfitLogic and Demandware, I am excited to step formally into my new role as an Executive-in-Residence (EIR) at Underscore VC with the goal of finding (or creating) the next big opportunity.

Why am I so excited about entrepreneurship?

One of the traits that I find most admirable in successful entrepreneurs is their unwavering need to enter the void — or the white space — in markets where few rules and patterns exist. For some, the structures and conventions of proven markets bring comfort, but entrepreneurs, in my observation usually find such structure to be uncomfortable.

They have the need to try something new, test new ideas, explore some new market, develop a new product, push conventions. They are restless creatures, prone to exploration, discovery, learning and advancing. If they are not at the frontier, they are not content. While they can see things for what they are, the most dominant reality for them is the future and what today can become. In the name of that vision, they work tirelessly with their head, hands and heart — to make it a reality.

The start of a new journey

As with any trip into the unknown, a compass is indispensable. Mine is simple with only a few points of demarcation.

1. Commerce

The landscape is undergoing tremendous and rapid iteration, driven by changing forces at both the corporate level (Amazon to buy Whole Foods? Say what?) and consumers who think digitally and natively.

For all of the progress in the commerce industry, from ecommerce as a peripheral business to ecommerce as the growth driver, from leaden on-premise commerce systems to nimble cloud-based services, we have only begun to realize the profound changes that are afoot.

What will happen when commerce weaves throughout a consumer’s digital engagement with a brand (and it’s all digital)? What will happen when commerce ceases to be defined by a website or point-of-sale system and becomes as effortless and intuitive as a conversation between old friends? What businesses will be born to make this possible? The ecosystem is buzzing with ideas, some of which will become tomorrow’s household names.

2. Team

Plenty has been written extolling the virtues of great interpersonal dynamics and how that sets the trajectory of a business. Based on all the years I have spent serving teams, I can say without a shred of doubt that there is no greater caliber of success then the caliber of the team.

Great teams in bad markets pivot again and again until they find a way forward. Great teams with product issues fix them. Great teams subordinate personal agendas to the greater good. Great teams recruit extraordinary talent and turn them loose. And having walked the startup journey with more than a few good teams, I can say there is no place I would rather be than right beside them.

These two guides first took me here to Underscore where the fit could not be better. The team is incredibly experienced and talented and puts people first. The investment thesis is compelling: Cloud Intelligence with a central focus on Commerce, Open Source and Cloud, supported by partners who have had a series of successes in the field at companies like Demandware, Acquia and Salsify.

To Underscore, team is central — primary actually — to their thesis on where to invest. They seek out great teams, help entrepreneurs build great teams and then surround them with deep support frameworks.

This is supported by key premises all designed to help stack the deck in the entrepreneur’s favor:

  • Insights gleaned from hundreds of startups on why some win and others don’t
  • A community of founders, operators, and industry experts who have walked the path before and genuinely want to help
  • An investment approach that focuses and sustains through the ups and downs and challenges of startup life and on achieving the long term potential of the entrepreneur’s vision

So, it’s onward from here — with a focus on team and on commerce — in full partnership with my colleagues at Underscore VC who believe deeply in both.