Rachel Wynn on Starting a Successful Business & The Importance of Knowing Your Worth


About her

Name: Rachel Wynn

Degree: Bachelor’s in Business, Media, & Communications

Career title: Founder + CEO

Q: Tell us a bit about yourself, your academic background, and how you started your career/corporate journey?

Rachel: I grew up in Miami Shores, Florida and was home schooled until my family moved up to St. Johnsbury, Vermont, so that my brother and I could get a solid high school foundation before college at a prep school 45 minutes south of Canada. I graduated in 2008 from St. Johnsbury Academy and went to Gettysburg College where I planned to major in Sociology.

After realising that statistics were 100%, not my strength, I decided that I wanted to be a communications major which was something my College didn’t offer as a small liberal arts school with 2,600 students. I took a leap and decided to design my own major at Gettysburg’s Interdisciplinary Department where I combined classes in business and management, creative writing, and media. Basically, I’ve never fit well into a box which is something that certainly comes out later in my career!

After graduating in 2012, I moved to Washington, DC (VT was too cold and Miami was too hot) where I started a two-year saga of jobs that included software sales, technical recruiting, general recruiting, event planning, and community management. Nothing felt quite right and I wasn’t willing to settle on a career that I didn’t love.

Q: At the age of 25, you started your own Social Media Business, Starlight Social, to help businesses gain an online presence and increase their website traffic and engagement. What inspired you to start your own business?

Rachel: It was actually a colleague named Ken Graham who inspired me to start a business! In June of 2015, I was fired from a large co-working company with no reason given and after only-positive performance reviews. I was devastated but went from sad to angry fairly quickly since I couldn’t believe a company could toss a loyal employee out without explanation or feedback. Plus, what if I had kids or were taking care of parents? Suddenly I was jobless and frustrated since I’ve always been a type A overachiever and getting fired was a “stain” on my record.

Five days after I was dumped I met with Ken who suggested I start a business based on what I learned in school. To be honest, I laughed because who was I, a 25-year-old without an MBA or concrete math skills going to run a business? But then something clicked. Why not? At the co-working space I had witnessed tons of young millennials around me launching start-ups, so why not take control of my economic destiny by becoming my own boss of a communications business?

Ten days after I was fired I researched how to start a business in the District of Columbia, got my LLC, and launched Starlight Social. I truly had no idea what I was doing and kinda learned as I went, slowly raising my social media rates as I became more confident in my skills and services. Three years later I’m proud to say that we’ve doubled our company revenue each year, I have an incredible new business partner named Sydny Atwood, and a team of four fierce women who all contribute their unique skills to my social media company.

Q: Starting a business can feel quite overwhelming. What advice would you give to young women who want to take the step, but still feel quite doubtful about becoming an entrepreneur?

Rachel: This is a great question because in October of 2016, at a Blogalicious conference, I had a second career epiphany: wouldn’t it have been nice to have a group of trusted peers to help guide me through starting and growing a business? Wouldn’t it be awesome to have a support circle where we could get REAL with each other, share our wins and lows, and hold each other accountable to goals? The first iteration of Feminist Founder: The Circle was founded with a few other business besties I had recently made.

So ultimately, I have a social media company that’s growing fast and providing me with income stability, but my true passion is helping women find the confidence within themselves to start businesses and then help them along that twisty journey to make the path just a bit more smooth. This fall I’m super thrilled to be launching another wing of my personal brand, Feminist Founder: The Workshop where I’ll be empowering women to find balance in their careers, but also learn how emotional labour can hold their careers back and what steps they can do to create a more equitable household with their partners.

Also, another important tip when it comes to choosing your business partner, make sure that both your qualities and strengths equal each other out. The best business partnerships consist of the ‘Get things done’ individual, who mostly works in the background, making sure that important tasks are carried out. And the ‘Face of the company’ individual who mostly focuses on representing the company and building a strong outside network.

Q: What are some of the challenges you have experienced in your career journey? And how did those challenges help shape your career so far?

Rachel: I think the biggest challenge has been issues with imposter syndrome. There have been countless times I feel like people don’t take me seriously because I’m young, but more so it’s my own fears that I’m not “legitimate enough” to be running a business, especially when I do something stupid like mess up my own bookkeeping.

This self-criticism and judgement is likely why a lot of women decide to stick with their regular jobs, it’s downright scary to take the leap to entrepreneurship and suddenly be missing the security of a consistent paycheck. My goal is to help women push past that fear because being self-employed has brought the kind of freedom that allows me to prioritise what I want out of my lifetime. In my opinion, that’s invaluable!

Q: What are some of the challenges you have faced in business or within your industry? And in which way do you help other young women who are faced with these sample exact challenges?

Rachel: Despite the great strides we’ve made, I still sometimes can’t help but wonder if being a woman is a factor in certain business situations. For example, I had a client ending their contract and was 2.5 weeks late on their final payment. When I followed up, yet again, he very flippantly said, “Don’t worry I’ll pay you back when I get back from vacation”, in August…likely 2-3 weeks later. I’ll never know, maybe this guy was just a jerk, but I couldn’t help but wonder: would he have been so casual to a man in this situation?

I had a choice at that moment, and thankfully I made the correct one which was to calmly say that no, that was not an option since the payment was already past due and that he needed to tell me whether he’d take option 1 and pay electronically, like he had been doing all along, or option 2 where he’d drop a check in the mail by the end of that day. He sent me a check and that was the end of that.

This was a crucial point in my business because I felt like it was unprofessional, and simply disrespectful, to give someone the run-around on money for work that was already performed. My solution was to look into a thing called “auto-billing” as a payment method and oh my goodness, my business has never been the same! Now I encourage all of my monthly service-based friends to get their clients set up on auto-billing since there is no reason not to. We have every right to request ACH or credit card information since that takes back control to the point where you can set things up to charge their payment info on the date in their contract.

The client doesn’t have to remember and you don’t have to waste precious time chasing down that paycheck! This business move changed everything because all of the sudden I knew how much money I’d have in my business bank account by a certain date. I had figured how to create financial stability in my business!

My advice to other women is this: Ensure that auto-billing is something you can set up (I use QuickBooks Online but I know you can do it in PayPal), request their payment info and store it securely, set the payment up in your system to auto-draw, sit back and watch the money magically appear in your account!

Q: In your opinion, what are some of the main skills every career girl should acquire to become successful, not only in their career but also in the workplace?

Rachel: The ability to push back on things and say “no” is an incredibly hard skill to foster since we don’t want to be seen as a “bitch” or “too aggressive”. As frustrating as that is, since men would be called “decisive” and “a strong leader” for the same situation, it’s something that all women need to learn how to do. That jerk client I mentioned was the first time I put my foot down and it shifted the way I saw myself. Along these lines, another example is charging your worth and charging late fees. When I first set prices on my services I was incredibly nervous since this is the one thing that’s a bit more difficult to learn from Google.

Women tend to undervalue and undercharge their work and I’ve been combatting that since day 1. The main advice I can give is to start high to leave room for negotiation and to also raise your rate for every single new client. In regard to late fees, this is the bane of existence for freelancers and the self-employed. I’ve always had late fees in my contracts for those who don’t want to elect into auto-billing, but here’s the thing: I never enforced it.

I’d send reminder emails on invoices, frustrated I couldn’t convince them to get on auto-billing, but I wouldn’t actually charge them the late fees they signed off on! What’s up with that? I didn’t want to be “mean”…Seriously, that how I felt. So that was me about two years ago. Now, I charge 5% DAILY interest on the monthly balance that’s overdue if they can’t pay an invoice by the 5th of the month. Heck yes, that’s a huge fee but it was done intentionally so that I could be paid on time for the work that we performed.

In fact, a few months ago I charged a client over $800 in late fees and when they came back at me, three weeks into this overdue invoice asking if we could compromise, I held my ground and said “no” because the terms were all clearly listed in our contract and I had already sent numerous reminders. As you may guess, they are now on auto-billing!

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