A well known figure in the Boston entrepreneurship community, Peter Boyce, often referred to as PB2, has been building communities around startups since high school. After launching HackHarvard and co-founding Harvard Ventures, Peter co-founded Rough Draft Ventures with help from General Catalyst. His driving force? The opportunity to help others achieve.
Nowadays, Peter is building startup communities for student founders and investors in Boston and New York through Rough Draft Ventures. The support from General Catalyst and his team has given students around the country the opportunity to connect, learn, and build the next generation of student-led startups.
Nina Stepanov: Tell me about your background. When did you first realize you were interested in VC?
Peter Boyce: I was inspired by the New York entrepreneurial ecosystem and how close-knit the community is. Organizations like New York City Night Owls foster community among people that work full-time jobs by day and moonlight as entrepreneurs. Pursuing an idea comes with a lot of risk, and navigating these challenges alone can make it feel incredibly lonely. When you’re figuring it out with other people, however, these challenges become a source of excitement and inspiration. This is the energy I wanted to foster at Harvard.
At Harvard, my friends and I started HackHarvard, a student organization to provide mentorship and guidance for CS majors. We brought the flavors of an accelerator program into the university environment. HackHarvard allowed me to connect amazing people from around Boston: founders, VCs, alumni CEOs, and contribute to the success of some of these companies that started out as projects.
NS: How do or did you keep up with it all? What motivates you?
PB: Working on these initiatives and programs has personally been insanely fulfilling. When I’ve built something that changes even one or two people’s lives, it gives me incredible energy. It’s not enough for me to just pursue things that are self-fulfilling; I strive to build things that help others by changing the set of resources that they’re able to access.
NS: You worked at Bad Boy Entertainment, a major media and entertainment company founded by Sean “Diddy” Combs. Why did you pursue that?
PB: I spend a lot of time thinking about how to engineer serendipity and my time at Bad Boy was a great lesson in that. I met the VP of Business Development of Bad Boy Entertainment at a business plan competition and he invited me to visit the office. That would have been a story in and of itself, but I ended up joining their team.
NS: How did you end up at Skillshare and what kept you there for all of your roles with the company?
PB: I met the CEO of Skillshare through my friend Rob Go at Boston-based VC firm NextView Ventures and was super-charged by him. Some of the best advice I have received came from one of my mentors, Chris Sacca, who told me the best way to spend my time was supporting a founder or CEO that really inspires me. So that’s what I did.
I loved Skillshare’s mission behind education, learning skills and teaching skills. I’m addicted to working on projects that add value to other people’s lives.
NS: Tell me about starting Rough Draft Ventures. How did General Catalyst got involved?
PB: I got to know the team at General Catalyst, as I became involved in the Boston startup community. They were instrumental to the work I was doing at Harvard even before Rough Draft. They are dedicated to helping amazing young people who are passionate about computer science and starting companies. When I was gathering students together late night to work on startups, GC would help plug in notable local founders as speakers or mentors (and buy the pizza!).
My senior year, I felt like I had time for one more project to help my peers and help the startup ecosystem. I noticed that all of the teams we’d been mentoring on campus often needed a little bit of capital but had to rely on business plan competitions, checks from friends and family, or ended up raising a round of funding and dropping out. Our thinking was, there should be an accessible, student-friendly way to get capital and mentorship in building a community of peer founders. I was dedicated to making it happen and being able to collaborate with GC to build Rough Draft Ventures was incredible.
NS: Rough Draft Ventures is growing, what’s next for the program and what role do you play now?
PB: Right now we’re focused on building the community in both Boston and New York. We expanded our community building in New York this past fall.
There are a few things that we are exploring with RDV right now:
We’re going deeper with universities. We ask ourselves, how do we work more closely with the administration and students? Whether that’s joining forces with the MIT StartLabs team or The Engine, there’s always new collaboration opportunities.
We’re spending a lot of time building resources for our portfolio companies. We ask ourselves, how do we help them get more mentors and better access to resources? The first 90-180 days for a lot of these companies is pretty crucial and we’re focused on putting together the first set of those resources to support our founders in getting to the next level.
Finally, we’re looking to incorporate more universities and students into our ecosystem.
Addressing all of that will give us the confidence to start building RDV out even further.As for my role, I oversee the program. I set our vision and priorities. I help coach the portfolio founders as they build companies for the first time and then I get the distinct pleasure of collaborating with my team members, Natalie Bartlett (Boston) and Denali Tietjen (New York). We work together to create the next generation of resources for our founders and expand our university community.
NS: What stage of investments do you primarily target?
PB: At Rough Draft Ventures, we back student startups at the earliest stage; investing up to $25k in funding to help get teams get off the ground.
General Catalyst has approximately $3.75 billion in total capital raised. We make early-stage and transformational investments.
NS: What are the top traits you look for in terms of backing a company or founder?
PB: We try to gauge how fast founders learn, which is important today as markets and products are changing so quickly. We also look for the ability for founders to recruit, rally teams, work tirelessly and see the vision of the company through.
Some of the best founders/CEOs should hire people that make you think, “I can’t even believe this person is working here, I can’t believe they got this person to join the company.”
Additionally, I look for clarity of product vision as well as clarity around the vision for the future while factoring in that things are going to change. Having perspective and long-term orientation is important and stems from deep-rooted conviction.
The best teams give you a feeling that they’re going to accomplish what they’ve set out to do no matter what. They’re thinking, “We’re going to do this, with or without you.” It’s all about that ambition, drive, and ability to learn.
NS: What sectors of technology, industries or trends are of interest to you?
PB: I personally spend a lot of time thinking about the travel industry. A lot of our behaviors and relationships with travel are changing, more and more millennials are using new tools related to travel. We’ve backed two companies at RDV who are taking on this industry: Getaway House and Freebird.
I also think about the future of design and the way software is created, specifically in understanding how the ways in which we create software and design experiences are changing. I also spend a good amount of time thinking about the way brands are built online. A great example of that is a company we invested in at GC called Outdoor Voices.
NS: What excites you about the current market in Boston and NY?
PB: In Boston, the density of universities and student talent is insanely powerful. Some of the best people in the world consistently spend time getting educated here, at the best universities in the world. I’m excited about what can come out of Northeastern, Tufts, Olin and the broader ecosystem of young entrepreneurs. The Forbes 30 Under 30 event hosted in Boston this past October, which we participated in, is a testament of how strong the ecosystem is here.
With New York, I’m excited about a lot of the industries that are creating talent and opportunity for technology and software to reinvent major industries like ecommerce and financial services. Companies like Cadre and Mark43 are examples.
NS: What companies in Boston, outside of your portfolio, do you find interesting?
PB: In Boston, I love Robin, founded by Sam and Jack Dunn. They’re amazing young entrepreneurs creating infrastructure that's helping a lot of other companies be more productive. Another one is PillPack. One of our early RDV team members was the first hire there and we’ve enjoyed watching the company grow. Adelphic Mobile founded by Jennifer Lum is a great company as well that was just acquired. Jennifer is a champion of the Boston tech community.
NS: Who do you admire or who has been the greatest mentor for you?
PB: I’ve been lucky to learn from a tremendous amount of people in my career. It’s important to choose places to work based on who you get to work alongside of and learn from.
David Fialkow and Joel Cutler, co-founders and managing directors of General Catalyst, represent such amazing leaders in the venture community. I also just think that working alongside them, I get exposure to all these skills and experiences that are hugely helpful for me. Fialkow is super rare energy and he’s an amazing mentor.
I also consistently come back to the people who mentored me over the years. Bijan Sabet from Spark Capital wrote one of my favorite blog posts where he outlined all the people who took a chance on him as an investor. It’s not one or two people, it’s a whole chapter of people who mentored me.
NS: Outside of your day to day work, what are your personal interests or activities?
PB: I spend a lot of time traveling. I enjoy learning about different cultures and meeting new people. It’s worth remembering the perils and challenges that people used to go through to see other parts of the world. Now everything is a plane or train away. I come away with fresh perspective each time.
I also read a lot. I don’t watch television, but I try to read as much as possible. Books are awesome in that they’re like life cheat codes.
NS: What was the last concert that you went to?
PB: There’s a group in LA called Soulection, an artist collective of sorts that was started by a then university student. He created a weekly radio show and would find emerging artists from around the world to feature their music from SoundCloud. It turned into an amazing community on SoundCloud and now beats #1. They did a show in NY a few months ago that I went to. The founder who started it had this dedication to finding emerging artists and pulling them together in this next-generation collective / label / studio community. This was an aggregation of two things that I love: music and entrepreneurship.
NS: Are you involved in any charitable organizations?
PB: One of the programs I’m involved with is iMentor, a program that connects high school students with mentors to help with the process of applying to college, getting internships, and the like. I get to go back to an area near where I grew up in the Bronx to spend time with high schoolers and have the opportunity to help a young person make decisions and navigate all the things that later in life we forget we had to face. It’s insanely fulfilling. I love supporting this organization.
Images courtesy of Rough Draft Ventures, General Catalyst and Peter Boyce II.