WCW Spotlight: Lily Womble

Updated: Feb 21

Meet The Date Brazen! Lily is the CEO + Founder of this one-of-a-kind company that works with women to give them all the tools and resources they need to discover extraordinary love!


Lily is a LIGHT and when I first met her, she completely inspired me. Her view on dating, love and everything in between is honest, constructive and just, spot-on.


You'll definitely want to read what she has to share!


Questions and Answers:


Q: Are you most productive in the morning, afternoon or night? A: Morning Q: I stay motivated by .......  A: serving my clients well and seeing the results Q: My best friend would use these three adjectives to describe me….  A: empathetic, enthusiastic, unstoppable Q: Growing up, when I envisioned my career, I saw myself....  A: as a Broadway star, killing it onstage Q: If I could have dinner with one person (dead or alive), it would be...  A: Oprah Q: If I were a fruit or vegetable, I'd be....  A: An avocado. I make every salad exciting. Q: Give your best elevator pitch. In at least three or four sentences tell me what you do. A: I was a top matchmaker at the largest firm in the U.S., and after matching hundreds, I realized that with coaching, women can match themselves better than anyone else ever could. Now as the founder of Date Brazen, I get the privilege of helping women around the world build fulfilling, joyful and successful dating lives, becoming their own expert matchmakers along the way. Q: What motivated you to become an entrepreneur? Is having your own business something you always wanted? A: I've always been very entrepreneurial-- from starting a recycling club in first grade to creating a local nonprofit in high school, to building Date Brazen-- strategizing to create solutions to deep-seated problems has always gotten me out of bed in the morning.

Q:  How did you come up with your business idea? What inspired you? A: Before starting my company, I was one of the top matchmakers at the largest firm in the country. While working there, I saw a need in the dating landscape for a more holistic, long-term approach to women's dating needs. I started Date Brazen after matching hundreds and realizing that with coaching, women could match themselves better than any professional ever could. Now, my mission is to transform the dating industry by helping women build fulfilling, joyful, successful dating lives on their own terms

Q: What were you doing before this? How did it prepare you for the entrepreneurial life? A: I owned a cafe which is the hardest and most fast pace business you can be in. I learned a-lot about margins, taxes, employees, food costs, budgets, human resources, contracts, events, licensing, and everything under the sun that goes into owning a food business in NYC.

Q: How do you generate new ideas to stay relevant on the market? Is it important to innovate in your space? A: #1 piece of advice is to ask your ideal customers questions about their struggles and LISTEN to what they say. I come up with my best ideas and new products directly from what my clients are struggling with.

Q: What is one of your goals for the new year and how have you begin implementing it into your life already? A: My biggest goal for 2020 is Radical Visibility. I want to push past the bounds of where I think I "should be" to experience as much growth possible personally and professionally this year. I planned my Swipe with Intention national tour to lean into this goal. It's scary as hell, and it's already paying off.

Q: What would you tell your 18 year old self today? A: Girl, you're extra and it's perfect. Lean into it, keep creating stuff that you love, bless and release people from your life that don't get where you're going. This journey will be hard and it will be worth it. Q: What is your best advice for someone starting their own business? A: Invest in something like Marie Forleo's Bschool. It's how I learned all the basics necessary to build a strong foundation.

Q: For fun... describe your guilty pleasure.  A: Gilmore Girls. I go to the fan festival every year. It's nerdy and lovely. Q: Describe your perfect day.  A: Coffee with my partner, Chris, pancakes at a local Brooklyn brunch spot, a book store, an impromptu dance party, cooking a delicious meal and rewatching a favorite movie.

When I met Lily at the start of 2019 in January, I was in a cloudy and unsure mindset. Immediately, Lily's positive energy rubbed off on me.


She made me realize that, we don't need to have everything figured out. We can to lean into love, and let life take its course. We reconnected about 3 months ago and after reflecting on what happened over the course of the year, her words and advice back in January were truly so powerful.


Lily has a gift, and I highly encourage a coffee or conversation with her. You won't regret it, schedule a time to chat on her calendar!


Want to learn more about the Date Brazen? Keep up with her on social: Website and instagram


To read more articles from Neela, visit the blog!

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