I’m an Accomplice for life (but part-time as of January)

Sarah A. Downey
5 min readJan 27, 2020
Illustration by Richie Stewart of Commoner Inc., www.richiestewart.com

TL;DR: I’m an Operating Partner at Accomplice as of January 2020. I’m a contractor, continuing to serve on boards, work with companies, run Rev Boston, develop content for Spearhead, and do a few other things for the firm. I’m a co-founder with my friend

of our new company, and focusing more on angel investing. The biggest change is that right now I’m not writing checks for Accomplice.

I’m still at Accomplice; this doesn’t mean I’m leaving. I’m now doing ~2.5 jobs; this doesn’t mean I’m available for hire. Or random coffees.

I’ve been at Accomplice for 5 years. I started as Director of Community in 2015, not in an investing role nor wanting one. I didn’t know anything about venture capital, honestly. I just loved working with startups, and that’s what I did.

After 1.5 years, the General Partners at Accomplice, Jeff Fagnan and Ryan Moore, brought me over to the investing side. Me, someone with zero finance background, who wasn’t even close to having the personal wealth to be accredited, and for whom the terms “cap table” and “syndicate” were still largely mysteries.

To say it’s been a learning curve is an understatement. I still don’t have all the answers, but after 30 angel investments, several investments on behalf of Accomplice, a few company boards, 5 Rev Boston cohorts, ~25 episodes of The Pitch podcast, hundreds of VC/tech blog posts, and countless startup crises seen and survived, I get it now.

Venture capitalist is my third career, after lawyer and startup marketer. Venture is 24/7. You have to be on all the time, trying to be everywhere at once, seeing everything, meeting everyone, doing everything, especially when it comes to finding new investments. There’s a constant pull to be in motion, but I want to slow down. I miss building things and going deeper so I’m taking time to do both. I don’t believe that you can be part time as a venture investor or as a founder, and I need to take some time to decide which is the optimal path for me.

What I’m doing from now on:

Working with Accomplice as an Operating Partner

Accomplice is always innovating and recently has been working on how to decouple the idea of a full-stack General Partner; that someone can add value all along the spectrum of company size and stage. That’s a myth. I think decoupling — letting people focus on their expertise areas only — is the future of venture, and thankfully it allows me the flexibility to try this new arrangement that allows me to continue with certain aspects of the business while removing others. That means serving on boards, working with select companies (like Ezra, ZOE, and Freebird), developing content for Spearhead, running Rev Boston, and doing a few other things for the firm.

Continuing angel investing

Yubari, the angel fund I co-manage, has done well: the first fund is around ~10x unrealized multiple already, and we’re investing out of fund two now. We’re writing $10k-$100k checks in pre-seed companies mostly in frontier spaces, like gaming, crypto, and digital health. Some early standouts include ZOE, Digits, and Hedera Hashgraph. Yubari is fun. It energizes me because it’s all about people, ideas, and markets.

Building Atrous (and our to-be-named Enneagram app)

My friend

introduced me to a personality typing system called the Enneagram back when we worked together at Ovia Health. I was skeptical at first; I thought it was some astrology bullshit (sorry astrology people, but not sorry). I’ve come to find it the most useful — I’ll go as far as “life-changing” — tool in understanding your and other people’s tendencies in order to anticipate conflicts and harmonies in relationships. It’s always running in my head when evaluating founders and teams and working through personal problems.

The Enneagram emerged near the 4th century but has gained recent popularity for understanding personal and team dynamics in companies, with VC firms using it to type their portfolio founders to celebrities writing about it in biographies (hey to fellow type Eight

👋🏻). Yet all of the online Enneagram tests and apps are severely lacking. People take the tests and come back with results that are simply wrong, which does a disservice to the model.

Thus now feels like the right time to build a data-driven, consumer-friendly test and app around the Enneagram, and Isabella (a former data scientist and VP of product who’s worked on both B2B and consumer apps) took the plunge to do it. We’re building it as a lifestyle business by design, so no plans to fundraise, ever, unless we get such insane traction that we revisit that decision. Funny that an investor would actively avoid raising money, right? Except most great businesses aren’t venture-scale and can handicap themselves by getting in debt to investors when bootstrapping would do just fine. We both want the independence and space to create what we believe in.

What I’m NOT doing:

Anything outside my job description at Accomplice

I’m a contractor and that means I’m going to be ruthless about anything that’s outside my job description for Accomplice. See above for the list of things I’m doing. The endless stream of requests/favors/coffee meetings/intros/random crap was my least favorite part about VC, so I’m nipping that shit in the bud as a contractor. Saying “no” to what drains you gives you the space to say “yes” to what energizes you. You don’t owe everyone a response. It took me too long to realize that.

Accomplice is all about tweaking the craft of venture: taking risks and trying new, crazy things that no one has tried before, from our seed-led strategy to truly generous founder investing programs like Spearhead. I’ve seen several evolutions of its model across five years and am proud to be a part of the bleeding edge of venture capital, not the lagging “old boys’ club” you see clinging to life nearly everywhere else. I’m following that lead and thinking about my own career to keep evolving. I feel better about it than I ever have.

I moved to Boston 10 years ago for a startup job I found on Craigslist with no idea what I was doing. Thanks to Accomplice for making a bet on me. I’m still here, just optimizing.

Illustration by Richie Stewart of Commoner Inc., www.richiestewart.com



Sarah A. Downey

Pro 1A. Operating Partner at Accomplice; founder/GP Yubari (angel fund); co-founder Blueprint Enneagram app; capitalist; esquire. I 🖤 weights, gaming, scifi.