Founder and CEO, Samantha Kennedy, on Turning her Social Media Skills into Lemon Stripe


Please share a brief introduction about yourself and your business:

I am the founder and CEO of Lemon and Stripe, a social media management agency dedicated to helping our clients grow their audiences, engage their followers, and enhance their online presence in a way that’s aligned and authentic. Our approach is warm, straightforward, and genuine. We spend time getting to know each client to understand their company and goals, we study their industry and audience, and we create a custom connection-building strategy that masterfully represents their brand and draws people in.

What excites you about being an Entreprenista League member?

I have an amazing support system and circle of friends, yet I am pretty much the only one of us who’s an entrepreneur. When I’ve run into obstacles or need advice, I often don’t have anyone to turn to other than online trainings, forums, and YouTube. It can get pretty challenging and lonely. I knew I needed a community of entrepreneurs to connect with, a network of other women who understand what it’s like to run a business. I wanted a place to turn where we could support one another, so I was thrilled to find the Entreprenista League in my search for this kind of network.

What made you take the leap to start your own business?

When COVID hit in 2020, almost all of my work as a sign language interpreter literally disappeared overnight. For years, I had been helping friends and colleagues with their social media on the side, but I hadn’t really been charging for it. With no sign of my old job returning anytime soon, I figured it was as good a time as any to turn my social media side gig into a full-fledged business. So I did. Now I run that business full-time, have a roster of clients, and I just hired the members of my first team.

What was your background prior to starting your own business?

I actually had owned and run a business before this one. In 2011, I successfully grew my own sign language interpreting company from the ground up through a creative marketing strategy, a strong online presence, excellent communication, and the development of authentic connections with customers and my team. I started out as a company of one (me) serving one client. In a few short years, we were a team of over 50, serving hundreds of customers in multiple states, with a thriving and engaged social media following. Optimizing and expertly managing my social media accounts was a huge contributor to my success. Now, I dedicate my skills in business development to supporting other entrepreneurs in establishing a strong online presence that feels aligned with who they are, what they do, and why they do it.

Did you always know you wanted to be an entrepreneur?

I think deep down I always did, but I didn’t know it. I was never truly happy in any job I had, even when I genuinely loved the actual work. Looking back, I realize that it was the structure of a “job” that I didn’t like. I wanted freedom, flexibility, more creative license, and most of all the ability to call the shots and build something that was truly an expression of what I want for the world. And that’s something I could only get through being an entrepreneur.

Take us back to when you first launched your business, what was your marketing strategy to get the word out, and did it go as planned?

Given the circumstances, I had to put my business together in a hurry, so I had very little in the way of a marketing strategy. I didn’t want to be held back by perfectionism (a pattern of mine); I knew I just had to take big, direct action toward getting clients each day. So I named my business after two swimsuits I’d just bought, started answering ads for freelancers, and I had three clients before I even had a website. So even though I didn’t have a solid strategy (at all!), I had a clear goal, a lot of determination, and a pretty dire need driving me, all of which helped me succeed early on.

What is the biggest challenge you have encountered along the way and what did you learn from it?

I significantly undercharged for a good year and a half into my business. Because of this, I took on just about anyone as a client just to make ends meet, which ended up making my business feel like a constant struggle both financially and emotionally. It got so bad that I let all but two of my clients go for 6 months just to get some breathing room and a sense of sanity back. When I returned, I sent out my first 3-tier proposal that reflected what my services were actually worth, and the client chose the highest tier: three times what I’d ever been paid for my services before. At that moment, I learned that I need to give my clients a lot more credit and believe in their capacity to invest in themselves. I’d been doing them a disservice by believing I couldn’t charge what I was worth based on an assumption that they couldn’t afford it. I now charge what I know my services are worth and what I know I need to make my business viable. Even better, I only work with clients I absolutely love working with, so I’m energized by my business instead of drained by it.

What is the accomplishment you are the proudest of to date?

I am honestly most proud of the incredibly personal, mental, and emotional transformation that I have had to undergo in order to start, run, and grow two businesses from the ground up. Friends of mine who don’t own businesses say they don’t think they could do it because of how difficult it would be, but they are often talking about the day-to-day operations of business. That part is challenging, but the really hard work is the personal growth that comes with the necessary inner work of entrepreneurship: learning to value yourself, set boundaries, get broken down over and over again and build yourself back up stronger each time, stand up for yourself against attacks, love yourself enough to work hard, love yourself enough to rest and discover who you are like you never have before. I’m proud of the work I’ve done and continue to do. I know it’s not for everyone.

Do you believe in work/life balance? What are some of your best tips?

I don’t see work as separate from life; it’s a part of life, just like anything else. And there are times when some parts of life take up more time and space, and at other times they take a back seat. So for me, I have to look at what’s taking priority at this particular time, whether it’s this morning, this week, or this season and try to plan my time accordingly. Sometimes work does take up more space, and there’s nothing wrong with that. Sometimes, we take a big step back from work, and that’s OK too.

What’s a piece of advice you can share that you wish you’d known when you first started your Entreprenista journey?

I wish I had known (or understood or applied) that saying no to potential clients coming in with red flags or letting go of clients who caused daily stress for me was worth any loss of income.

What have you achieved recently that you’d like to celebrate with our community?

I hired an amazing team! Earlier this year, I said I was going to hire a group of people who were even better at what they did than I was. This past May, I found them, hired them, and I couldn’t be happier with them.

What’s next for your business? What can we expect to see over the next few years?

I plan to keep growing! My goal is to expand my team and free up some more of my time to create programs and resources that support other business owners on their entrepreneurial journey.

Learn more about the Entreprenista League and join today!

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