From Being Fired to Launching Two Successful Startups

Inspiring Stories of Our OwnersMay 10, 2018 4 min read Ziggy is curious

This woman entrepreneur is proof that even when life knocks you down, there’s always a way to get back up and shine even brighter

Rachel Wynn is a tenacious, poised, and creative professional in the communications field and is the Founder and CEO of both Starlight Social and Solopreneur Circle. Wynn earned her degree in Business, Media, and Communications from Gettysburg College and has extensive experience in sales, event planning, and community management. She’s a savvy go-getter with a passion for collaboration with other entrepreneurs, connecting colleagues with opportunities and resources, and empowering women to start their own business and balance household emotional labor. Wynn currently lives next to Meridian Hill Park in Washington, DC with her husband, David, and dog-child, Rufus.

How did you decide to start your own company?

I was fired from a large coworking company and no reason was ever given, which was incredibly frustrating, and humbling. It became clear to me that allowing corporations to determine my future financial wellbeing wasn’t going to cut it. I decided to start a business so that I could be in control of my economic destiny and carve my own path to success and freedom.

I honestly had no idea what I was doing, so I relied on Google as I determined what service I could provide in exchange for monthly payments. Once I settled on social media, 10 short days after the worst day in my professional career I registered for my LLC and started Starlight Social!

That’s a great way to bounce back from a difficult moment. What do you know now that you wish you had known when you started your entrepreneurial journey?

The biggest thing I wish I had known was the power of getting a service-based business on auto-billing. If you have an agreement in place with monthly payment, there is no reason why you shouldn’t require ACH or credit card information to be submitted for automatic withdrawals.

Entrepreneurs don’t have time to chase money down, so it was a huge game-changer when all of the sudden I had a stable, monthly income I could count on which got my business into a much more strategic place.

[Editor’s note: Visit Alice for more on accounting tips and tools.]

Describe a perfect day.

Here is exactly how I’d map out my perfect day:

9:30am: Wake up and snuggle with my dog as I read a book in bed
10:00am: Take my dog for a walk
10:15am: Review tasks for the day in my bullet journal while making tea and breakfast
10:30am: Go to desk and check email
11:00am: Check in with my team on Slack and assign tasks
11:30am: Eat my biggest “frog” of the day
1:00pm: Eat lunch and check email
1:30pm: Knockout rest of tasks for the day
6:00pm: Close out work, determine tasks for next day, and plug in phone to workspace
6:30pm: Light candles, switch to evening lights, and make/eat dinner with partner
7:30pm: Tidy up condo and relax, usually Netflix
11:00pm: Drink EmergenZzz, get in bed to unwind, read, or write
12:00am: Go to sleep

Wow. Love the detailed schedule! What is something most people don’t know about you?

I was home-schooled until the age of 13! There’s definitely a stigma around homeschooling, but my parents wanted to provide the best possible education for my brother and me, so my mom taught us while my dad, and current business adviser, worked.

I do feel as though this alternative upbringing impacted my entrepreneurial drive, creativity, and desire to enjoy life “outside of the box” and in a space where flexibility and freedom were valued. Plus, getting the extra time with my mom and brother were awesome!

That does sound like it would be a great opportunity to bond with your family. You’re part of our Alice community. What has Alice helped you with the most?

The webinars and articles online have been incredibly helpful resources as I grow and lift other women as I climb! The most impactful experience has definitely been attending the Circular Summit. I can’t wait until next year since I made a ton of fantastic connections!

[Editor’s note: sign up for free on and check the box to receive our weekly newsletter for updates on Circular Summit 2019 and Alice’s free webinars]

We’re glad you find our webinars helpful! Is there a specific resource that is at the top of your list and you recommend to Alice users?

Entrepreneurs should check out Solopreneur Circle, an inclusive, collaborative, and affordable group for women that meets in DC, VA, or MD on a monthly basis and provides support, resources, and coworking dates to create a community of trusted business besties.

I’m also fairly obsessed with productivity tools and Amazing Marvin is changing my life! Anyone looking for a behavioral science based to-do platform should check it out.

At Starlight Social we just hired our fifth remote team member, a Social Media Intern, and I’m excited to share that my Social Media Director, Sydny Atwood, is going to be taking on more of a leadership role in the company since we’ve been steadily growing.

With a bit more time freed up, I plan to further streamline our business processes and work on a new venture! Later this year I’m launching a Washington, DC based workshop, currently titled “The Balanced Boss,” to empower women as they transition from the traditional office to full-time self employment, a somewhat murky and confusing time for new business owners!

I’m super excited about the topics I plan to cover, which include how to craft your unique and ideal work day, setting up systems and routines for productivity, how to protect and reclaim your time, and education about emotional labor and navigating household division of labor conversation with your partner.

Connect with Rachel on Instagram and Twitter.