An Inside Look with Codeship: Bob Mason, Director of Project11

Bob Mason is a Managing Director at Project 11, a tech seed stage fund that invests and advises in early stage startups. Prior to starting the fund, Bob co-founded Brightcove, a B2B online video service. We recently had a chance to sit down with Bob and discuss his experience founding Brightcove, mentoring entrepreneurs, and taking a holistic look at a business.

An Inside Look with Codeship is a regular series providing an insider's perspective on founding and building a tech company. Each session, we chat with some of the most exciting voices in tech and ask them where they've been, where they're going, and what we could all be doing together. You can read all Inside Look interviews here.

You’ve gone through several iterations as a technical founder and an entrepreneur. Can you tell a little bit about your current role and the projects you have going on?

I’m a Managing Director at Project 11 Ventures, an early stage software and tech seed fund in Boston. Along with my partners Katie Rae and Reed Sturtevant, we look to lead very early investments and remain very active with the founders. Previously, we managed the Techstars Boston program; prior to being an investor I was the co-founder and CTO at Brightcove, a B2B online video platform and honed my skills as a software engineer at ATG, another enterprise software firm.

Let’s start with Brightcove. What problem did you want to solve when you started the company?

I've always been interested in interactive media. I built media projects throughout high school and college. Coming out of ATG in 2004, I wanted to get back to my roots around interactive media. I started seeing all that was going on with video. It's hard to think back a decade, but Tivo was coming on the scene, DVRs, Microsoft Media Center. There was a resurgence around video. YouTube didn't exist yet. Doing online video typically would have cost millions of dollars and required a very strong engineering team.

So when I met my co-founder Jeremy Allaire, an EIR at General Catalyst, we clicked on this vision that video could be as ubiquitous as text on the web. Jeremy was the former CTO at Macromedia, which at the time managed the Flash platform. One of the key things that Jeremy had done before leaving Macromedia was to get a video codec in the Flash runtime. He understood how the Flash runtime would get updated across the globe. From that we knew that in about 18 months, 98 percent of all the computers in the world would have viable video playback capabilities.

That was the foundational element of the company. It was our combined passions around the possibility and future for online video, understanding this technical insight to be able to build a new type of online video platform. And leveraging the early precursors of cloud-based technology, our goal was to make it as easy as possible for any professional organization in the world to launch an online video channel.

What was a big challenge you didn't foresee that you encountered early on?

Trying to understand your core customer, how many iterations of the product you have to go through, how you get the right economics for the business to work. Like many startups we wandered in the desert for a few years trying to figure that out. We were very fortunate to have amazing investors in General Catalyst and Accel Partners. They supported us the whole way through that process, but it's tricky, to give yourself the ability to say no, so you can have the right amount of focus. We were certainly not perfect, made many mistakes, but eventually, we were able to build a really vibrant B2B business around online video.

How did you make the move from working on a product to working in investment?

For many years, I was so heads-down, focused on building our own company. But back in 2011, a friend of mine invited me to a Techstars Demo Day, and it happened to be the first demo day of my now-current business partners, Katie and Reed. I was floored by these interesting businesses and amazing founders that were telling compelling stories.

So, while I was still full-time CTO at Brightcove, I started mentoring and advising early stage companies. I really enjoyed amplifying the intention of others. Increasingly, I started seeing it as a way for me to be able to spend more time around intellectually curious, high-energy people. So, when Brightcove was exiting its IPO, I was thinking about my own transition, and Katie and Reed invited me to go deeper with Techstars. So I started advising teams fulltime, started making investment decisions with them, and did that for a couple of years until last year, when we stopped managing the program and we launched our own seed fund.

What was the biggest surprise helping other founders through Techstars?

When I started doing it fulltime, I thought it would be like a student-professor relationship; I'd hold office hours, people would come to me, and we’d work on some problems. Something silly like that. What I quickly realized, particularly at the early stage, in the first year or two of a company’s existence, the way you add value is being there at the random, serendipitous moments, by helping them think through problems and ask really important and hard questions.

We never run someone else’s business. We're just there to prod them along and ask questions based on our experiences so they can figure out the answer that’s relevant to their particular situation. That was the biggest insight to me. Simply being around, immersing yourself, and doing that in a mechanism that allows for serendipity to occur.

You’ve said you have a passion for good code and design but you don’t consider yourself necessarily a hacker or a maker. How did you navigate that conclusion as a technical founder?

I am a software engineer by training. Coming out of college in 1994, I stumbled into the startup world and ended up working as a Senior Software Architect at ATG for ten years.

Brightcove was founded in 2004, and in the first few years of my role as a CTO, I certainly continued to write code, but more and more, the company really needed me to focus on the role of product leader: establishing our strategy, what we should build, why we should build it, and so on. A few years into it, I was getting pulled more and more away from code.

I realized at a certain point that I wasn’t a hacker in the sense that I no longer enjoyed coding as its own endeavor. Coding increasingly wasn’t as important to me, but because I had spent so many of my years building challenging, scalable systems, I have a real appreciation for the art of code and have worked with some amazingly talented coders. I understand the value their art brings to a company. I think that insight helps me make better business decisions. As an investor, it helps me connect with some startup founders in a way that may be challenging for others because they don’t understand what it means to be in the barrels of a really complicated system.

What was one of the hardest lessons for you to learn in your career?

As a software engineer, often your value as a person is related to the quantity and quality of code that you write. So when the company or your personal interests are pulling you away from that, you really try to understand if you're a good contributor -- am I still a productive member of society?

Your first inclination is to fight to get back to writing code, which is fine, but recognize the huge value you can contribute holistically to the company. At the end of the day, the critical things to make a company successful are understanding the business needs, the sales strategy, the marketing, how you're going to tell your story, and finding product market fit. In some ways, the engineering is just supportive of these initiatives. Some of the hardest problems to solve in a company are not found in engineering. Having people focus time and energy on those is hugely valuable.

How are you and Project 11 giving back to the community?

We're big believers in an open startup ecosystem, and beyond our continued engagement with Techstars, we create businesses and support programs that add value to this ecosystem. For example, several years ago Katie and Reed founded a program called Startup Institute which is an immersive educational experience for those who want to contribute to the startup economy in engineering, design, marketing, and sales. Folks that are not founders but they want to be part of a startup. It's a boot camp for individuals where they can take control of their careers, really get engaged, and find job opportunities within the startup ecosystem.

Similarly, last fall we started a program called N2 which was a one-day event to build better bonds between corporate executives and the early-stage startup community. So, if you're an executive in the corporate world, how do you really know what's going on in the startup world? Startups are already working in your future. So we held a one-day event where we brought and curated startup founders in the Boston area and senior corporate executives from across the U.S. We had a day of conversation around really interesting topics that are affecting our society. It was really fun to get these two worlds, that generally don’t mix, together for the day. We're planning our next event this October.

Are there any problems facing the tech industry and the tech community that you're working on or that keep you up at night?

Talent. Oftentimes there is a calculation that it's a zero sum game, that the only way to get the right talent is to pull people from elsewhere. We need to look at ways to nurture and encourage more people to be entrepreneurial. We need to encourage more people that fit nontraditional career paths and bring them into the startup world. It’s a broad problem. We need to do more to include universities, local governments, venture capital, and the startups themselves to find the solution.

If you could go back in time to before you started, what advice would you give to yourself?

I would continue to tell myself to do less.

I've always envisioned myself as a problem solver. In some ways, if you can solve lots of problems, this enables the business to focus on breadth and not depth. It’s so important to focus on what you're not going to do. That, for me, is something I continually try to refine. Of all the possibilities and all the different things I could be doing right now, what am I not going to do so I can really pay attention?

Thanks, Bob!