You founded MassLight in 2000. Your team has grown to over 50 people–and partnered with many startups. Describe the origin of your vision for MassLight.
At the time we founded MassLight, we were trying to build a more engineering-friendly software consultancy. As we grew, we began to realize that many of the processes we put into place were even more useful when working with startups.
You established MassLight’s Build-for-Equity program in 2016. What inspired you to offer capital - and engineering solutions - to pre-launch and post-launch startups?
We began angel investing around that time. And, through talking to founders, came to realize that there were many non-technical founders who could be incredibly successful, but lacked engineering capacity even more than capital. They had industry knowledge, contacts, vision and the ability to sell. There were thousands of accelerator programs out there, including super famous ones like YC and Techstars, but none of them provided engineering teams.
What’s a risk you’ve taken as a founder that you’re proud of?
The shift from traditional software consultancy to build-for-equity model. Our build-for-equity work is largely category-defining. We take risks on startups with a level of commitment and investment that no one else does at the same scale.
What has been the most rewarding part of partnering with startups?
Our relationship with the founders of our portfolio companies. Our relationship is very different than in a fee-for-service consulting engagement. We are true partners with the founders. We sit in the trenches together. We know the business in an intimate way that most investors never will. We sweat the small details, we help close the sale, patch the 3AM outage (hopefully very rarely!). We don't see any return until the founders do. It's incredibly gratifying work.
You’ve been meeting with partners all morning and it’s time for some fresh air. Where do you take a break?
I like to walk around the city. See the buildings, cafes, people, and activity. It's how I take a break, clear my mind, and meditate.
Name a surprising skill or experience of yours that influences how you build and invest in startups?
Listening. A lot of my job is just listening to employees or founders. Sometimes they want to vent and sometimes talk through a problem. There's an interesting phenomenon we call "rubber duck debugging." By describing a hard to solve bug, you often solve it immediately, after spending many hours working on it quietly and unsuccessfully. The other person doesn't have to say anything, it's the act of talking out loud that helps. So often I'm like a rubber duck CEO.
What qualities in partner startups resonate with you?
A vision for solving an industry-wide problem in a large market, a contrarian or creative approach; and an ability to close sales.
As a founder, CEO, and investor, what’s a piece of advice you would give early-stage founders (or aspiring entrepreneurs?)
You matter more than your idea.