April 18, 2016

[Investor Q&A] Ryan Moore of Accomplice: A Proven Track Record of Success

Ryan Moore has been an active investor in the Boston tech scene since 1999. He's currently a Partner at Accomplice, where his investments include DraftKings, InsightSquared, Plastiq, LovePop, clypd, OwnerIQ, and lots of other high growth companies. He was also a co-founder and general partner at Grandbanks Capital, where he invested in several successful companies like Enpocket, WHERE, Vela Systems, and Nexage. 

Learn more in my Q&A with Moore below.

Keith Cline: Tell me about your background. 

RM: I grew up north of Philadelphia in Bucks County. I went to public school and was the youngest of three. We were raised by a single parent, my father. I was an athlete in high school and wanted to continue to play college football, and despite its proximity, Princeton was the right fit for me both academically and athletically. I wanted to study business, and given that Princeton was a liberal arts school, I chose economics because it was the closest proxy to a business curriculum.

Why did I want to go into business? I’ve always had a love and knack for numbers and math. Therefore, I actually thought finance and accounting was interesting.

Ryan and his wife on the sidelines at Princeton last fall, as his 1995 Ivy Championship team was honored during a game.

KC: What did you do for work right out of college?

RM: I moved to San Francisco and joined an investment bank named Robertson Stephens, one of the original emerging growth investment banking boutiques. After 22 years on the East Coast, I wanted something different. I wanted to have an adventure and felt San Francisco was for me.

KC: How did you get into venture capital and join SOFTBANK Capital Partners?

RM: Three years into investment banking, I realized I didn’t like it. I was out there in what would come to be called the first internet bubble, and I was a big believer in learning by doing. I felt like venture is a skill that’s learned by applying. Softbank was one of the more prolific and active VC firms in late '90s. They had an opportunity to join as an associate, so I seized it.

KC: What prompted you to move on and become a Co-Founder and General Partner at GrandBanks Capital?

RM: When I was at Softbank, they had a smaller office here in Boston. I moved here in 1999 to work in that smaller office so I could get more exposure. About a year or a year and a half into it, the partner I was working really closely with, Charlie Lax, decided he wanted to go raise his own fund. I felt that I could either go to business school or learn by investing. Charlie offered me a partnership spot in the new fund. I was 27. Time to take risks, I thought. So I went over to join him, and that fund became GrandBanks Capital.

KC: You were at GrandBanks Capital for over eleven years.  Can you talk about your investment and exits while you were there like Enpocket, WHERE, Vela Systems, and Nexage?

RM: Early on as a young partner, my thesis was pretty simple: invest in people 10 times smarter than myself. Fortunately, I found a few of them. The first was Mike Baker, the CEO and co-founder of Enpocket, which Mike drove and ultimately sold to Nokia. Through GrandBanks, I met Alan Phillips, who founded WHERE. Alan and I recruited Walt Doyle back to Boston from Mapquest, and Walt drove the growth of WHERE, which ultimately was acquired by Paypal.

KC: Do you have any interesting or fun stories to share from the web 1.0 bubble years?

RM: Unique would be the way I describe it. The role the IPO market played in financing in web infrastructure buildout was incredible.

KC: Why did you decide to leave GrandBanks and join the team at Atlas, now Accomplice?

RM: In the Spring of 2011, after WHERE was acquired by PayPal, I started thinking about joining a larger platform. I had known Jeff Fagnan since our SoftBank days of the '90s and kind of grown up with him in the industry and had a great deal of trust in him. Plus, I was motivated by the challenge of rebuilding of a franchise. Jeff and Fred Destin at the time had created a fair bit of momentum with what was a differentiated approach to venture. I loved the idea of challenging the status quo and felt Boston was ripe for some innovation in venture.

KC: What are the top traits you look for in terms of investing into a company or founder?

RM: I have to love the market they’re operating in. I have to believe that they’ll be successful, whether they’re capitalized or not. I don’t care about pedigree. I care about tenacity and character. If I’m sitting across from someone, I’ll get into their background a little bit to find something that galvanizes them to me as a person. They have to have some story of adversity, because they’re in for it. Their ability to cope defines their success as an entrepreneur, because they’re always starting out as the underdog. I love the underdog.

KC: What sectors of technology, industries, or trends are of interest to you?

RM: I think entrepreneurs, the good ones, are like water: they find a way through in an interesting market. This is a cliche answer, but we’re at the stage of investing where we’re all about the people.

KC: What is the current fund that you are investing from?

RM: Accomplice I. $212M. Tech only.

KC: Which investments are you involved in at Accomplice?

RM: DraftKings, clypd, Blispay, OwnerIQ, Plastiq, Crew, Joist, LovePop, MOO, and Globoforce.

KC: You have been a very active investor in the Boston tech community since 1999. What excites you about the Boston market and how has it evolved since you’ve been in the venture capital industry?

RM: I am most excited about the current crop of founders that are building companies - large sustainable businesses that will be here for the next 50 years. Led by Niraj Shah from Wayfair, Brian Halligan from HubSpot, or Jason Robins at Draftkings  - all of them likely had opportunities to sell early but wanted to build large independent businesses.

One healthy evolution I have witnessed is venture capital's willingness to back first-time founders and let the founder lead. In the past, we replaced founders too quickly. You cannot replace a founder’s energy or passion. It's vital to a company’s success.  

KC: Which companies outside of your portfolio in the Boston area do you find interesting?

RM: Lots of great ones in Boston – CarGurus, Placester, Localytics, and Maxwell Health are a few.

KC: Greatest misses. What companies have you passed on that you wish you hadn’t?

RM: Too many to even list.

KC: Who do you admire or who has been the greatest mentor for you?

RM: I admire any founder. I don’t think the average person appreciates the courage it takes to found a company and to put it all on the line. I’d also be remiss if I didn’t mention Charlie Lax. He was an important mentor for me in my career. And of course, my father. He raised three kids all by himself. I miss him every day.

KC: Outside of being a VC, what are your personal interests or activities?

RM: I love being a father and husband, even more than I thought I would. I try to work hard and love spending time with my very understanding wife and my young daughters. For fun or exercise, I like to play basketball, head to InnerCity Weightlifting, or go running on the esplanade. Boston is beautiful. You don’t realize how much until you run it.

Ryan with his two daughters.

KC: What was the last concert that you went to? 

RM: I have two daughters under 30 months old, so you’re catching me at a very lame moment in my life. The last concert I went to was Sesame Street Live. No joke.

KC: Are you involved in any charitable organizations?

RM: Given that I’m a founder of Accomplice, I’m involved with TUGG. My favorite TUGG nonprofit is Innercity Weightlifting. Shoutout to my trainer Eric Flores Powell.

Ryan with his wife at Super Bowl 50 attending the NFL Honors event.

Keith Cline is the founder of VentureFizz. Follow him on Twitter: @kcline6.