Today we’d like to introduce you to Tiffany Winfrey.
Hi Tiffany, it’s an honor to have you on the platform. Thanks for taking the time to share your story with us – to start maybe you can share some of your backstories with our readers.
I launched my brand and web design business, T. Smiles Design in 2017. Just two years prior I was designing logos for $20, not knowing my worth, and up until January 2017 was making excuses on why I felt I wasn’t good enough for the market. Thankfully I had some amazing, supportive friends who saw the gifts in me before I did and knew how to push me. Amazing how often God sends people to confirm your path and leaves the rest up to you to move.
I remember like it was yesterday. I launched my business on my birthday, January 4th, 2017 still questioning myself, but something happened. Just that month alone I made my first thousand dollars. You couldn’t tell me anything after that! I took that as confirmation I was on the right path. Since then, my business has evolved tremendously, 2021 during Covid, I dropped the Smiles and rebranded to T. Winfrey Design.
I’m sure you wouldn’t say it’s been obstacle free, but so far would you say the journey has been a fairly smooth road?
It wasn’t always a smooth road; Lord knows I wish. I think the hardest moments for me weren’t when I had no clients or slow seasons, but rather when it was hard to show up.
For instance, just a year after launching my business, in 2018, I experienced a difficult breakup, quit my day job, packed up my 2009 Infiniti with whatever could fit, donated the rest, and moved from New York to Maryland. That was a hard, depressing, devastating year for me, and then trying to post on social media, show up, have consultation calls with a smile, man listen, the struggle was real. But, despite it all, I never wanted to quit.
Alright, so let’s switch gears a bit and talk business. What should we know?
In my creative studio, T. Winfrey Design, I work with women to create a powerful brand that establishes them as experts in their field and enables them to create wealth for future generations. I didn’t grow up with the idea of having my own business or generally having an entrepreneurial mindset, I’ve gained a lot of knowledge along the way.
What makes T. Winfrey Design unique is that, while it does specialize in logo design, web development, and brand strategy, the heart of my business actually consists of therapy sessions, crying sessions, healing sessions, and growing sessions because I’m not just here to design but to support women who are likely firsts like me—the first to graduate from college, the first to own a home, the first to own a business and is out here trying to build while maybe doing it alone.
What has been the most important lesson you’ve learned along your journey?
The most important lesson I’ve learned is to keep it moving. Despite disappointments, despite disconnections, despite things just not working as how you expected it to be, keep it moving. The path of business ownership has had its twists and turns along the way, including some thunderstorms and a few tornadoes but I always kept it moving. Sometimes in the wilderness is where we learn and from there comes an even bigger success we may not have even imagined.
I remember stressing one night over something crazy and the next day booked an amazing contract to brand an event on the west coast. Which eventually led to a loyal client and several referrals after that. Can you imagine, had I sat and wallowed too long in whatever I was going through and missed booking that client? So yes, definitely keeping it moving has been a lesson learned for me and forever my theme in everything.
Contact Info:
- Website: www.twinfreydesign.com
- Instagram: https://www.instagram.com/twinfreydesign
- Facebook: https://www.facebook.com/twinfreydesign

Image Credits
McCrae Multimedia
