Student Startup Series: Lily Herman ’16

In this series, we interview Wesleyan students and recent alumni who have founded businesses, nonprofits, and social enterprises. Our first post features Lily Herman ’16, a freelance writer, editor, digital strategist and founder of Rogue Sunday. She’s also the founder of Get Her Elected, a network of over 2,300 people offering skills like writing and graphic design pro bono to more than 230 progressive women candidates running for U.S. political office. She sits on the Patricelli Center for Social Entrepreneurship Advisory Board. Read other Student Startup stories here.


Herman during her TEDx Wesleyan U Talk

Lily Herman ’16
Major(s): Government, Sociology

Tell us about your startup:

I started Rogue Sunday, a digital strategy and marketing firm that specializes in editorial strategy and content creation; social media strategy/execution and audience engagement; and PR and media outreach. In particular, we work with individuals and brands that are making the world a better place. Often, that means solving some of the biggest problems with new solutions and perspectives.



Why did you decide to create your startup?

Rogue Sunday came about really organically. In addition to my own writing, editing, and other digital media work, I’ve been doing strategy and marketing projects for other people since I was a freshman at Wesleyan. As any entrepreneur knows, you can’t really scale past yourself, and the potential workload got to a point where it was too much for one person. That meant I either needed to turn down work or expand my business to get more help. Obviously, I chose the latter! Now, Rogue Sunday consists of eight other team members.


If you started it as a student, how did you juggle it with everything else?

I didn’t start Rogue Sunday as a student, but I did start another venture, The Prospect, as a Wesleyan student, and running that previous organization while balancing collegiate responsibilities and my other work gave me a lot of practice for how to keep a lot of projects in the air at once. I learned many great lessons in finding a schedule that works for you, being honest about your workload, and knowing how to recharge so that you don’t feel overwhelmed.

How did you choose your legal structure and what was it like incorporating?

Another blessing of starting The Prospect in college is that I’d already gone through the process of learning about legal structures and incorporation with that venture, so doing it this time around was a lot easier. An LLC made sense given my stake as the sole owner and operator of Rogue Sunday.

What was your biggest challenge and how did you overcome it?

Rogue Sunday’s team is entirely remote, which means it requires a lot of communication and balance to make sure everything gets done the way we need it to and that we’re constantly keeping each other in the loop with what’s going on. In the worlds of client work and with digital media, things change quickly, so you always need to talk your team through it. Being a manager is difficult as is, but there are unique struggles that come with managing a team that isn’t in a physical office space with you and may have different schedules.

What advice would you give to your younger self?

My high school drama teacher used to end every Friday class with “if it feels wrong, it is wrong,” and I’ve always stuck with that mantra. When you’re an entrepreneur just starting out, it’s easy to want to take every single opportunity, even if you know deep down that it’s not a good decision. After making lots of mistakes and not trusting my gut, I’ve learned the importance of knowing when to say no and when to take a risk.