Q: You left a $300,000 partner-track attorney position—what made you feel confident in betting on yourself?
AK: I didn’t necessarily feel confident in betting on myself at first. What drove me to leave was my frustration with being disrespected at work and the concern that my race and gender would impact my ability to reach my professional goals. I didn’t want my future to depend on anyone else’s biases. I realized that staying in that system was a bigger risk than going out on my own. Plus, with a successful career and a high salary, I knew I was worth more. So, leaving to build my own business felt like the safer bet in the end.

Q: You recently made the Inc. 5000 list and ranked in the top 10% of all companies on that list. What strategies did you implement to grow your revenue 10X from 2020 to 2023?
AK: From 2020 to 2023, our company saw major growth, landing us at 370 on the Inc 5000 list. The key to this growth was playing a bigger game—investing in marketing and focusing on how to get more people to know about us. We ramped up our advertising, showed up more on social media, and leaned into video marketing. At the same time, we solidified our backend operations, making sure our systems and team could handle the growth. We hosted regular events, both virtual and in-person, and launched new initiatives like direct outreach and our book, Speak Your Way to Cash®, to build our brand and engage our community.

Q: There are a lot of uncertainties with the economy, especially for business owners. What should every entrepreneur be doing right now to increase their sales?
AK: To boost sales, you should be hosting webinars and pitching directly. Regular online events, whether on Zoom or another free platform, give you a consistent way to showcase your offers—weekly or monthly. This ensures people know exactly what you do and how they can work with you. Without these, you risk missing out on sales simply because potential clients aren’t aware of your services or how to engage with your business.

Q: You work closely with your husband in your business. How do you balance both your personal and professional relationships? How did you know you could successfully work together? 
AK: I knew we could work together because of our strong personal and professional history. We’ve collaborated on ministry projects, hosted events, and ran a nonprofit, the Kirkwood Foundation, where we helped students explore high-paying careers. My husband has always been a steady, trustworthy presence in my life. I’ve seen him at his best and worst; and he’s seen me at mine. His strong character, commitment to our family along with trust and a shared vision made me confident in working together effectively.

Q: As a successful entrepreneur, lawyer, mom and wife, how do you maintain balance in your life? 
AK: I don’t aim for a perfect balance in life; instead, I focus on managing different seasons. Sometimes I need to dive deeply into work, while other times I prioritize home life, relationships, or health. To maintain my well-being, I have non-negotiables: playing tennis 2-3 times a week helps me clear my mind and get sunlight, which is crucial for my mood. I also make time for daily prayer, which provides spiritual grounding. When I feel off, I assess what’s missing—like tennis or prayer. I’ve learned that understanding my needs and taking breaks when necessary is key to sustaining my productivity. I communicate my needs with my husband and plan, accordingly, ensuring I take time off when needed to recharge.

Q: You are a global traveler and take an annual sabbatical with your family—how does this influence your perspective as a business owner? 
AK: For me, the sabbatical I took in 2023-2024 was life changing. I spent six weeks focusing on myself, my health, and my family, and it was incredibly refreshing. Waking up without the pressure of work made me realize how essential it is to take mental breaks because that work that I do involves a lot of mental energy. This experience was so valuable that I’m committed to making sabbaticals an annual part of my wellness plan.

Q: You frequently launch new services, programs and host live events as a core sales strategy. In fact, you recently hosted multi-city, sold-out events across the U.S. for entrepreneurs seeking to enhance their sales techniques and scale their businesses. What advice would you give to someone looking to attract more clients through events? 
AK: A successful launch involves several key elements. First, you need to be clear on what you're selling. Once that’s defined, structure your entire schedule to ensure attendees have all the information they need to buy by the end of the launch. But the most important part isn’t the event itself—it’s how you market it. Your marketing should attract the right audience with the right message before the event even begins. If the wrong people attend, you won’t achieve the sales you need. While launching can be complex, these are a few foundational tips to get started.

Q: You are recognized as a LinkedIn Top Voice due to your innovative approach empowering women with expertise to start at the top of the market. Your bestselling book, Speak Your Way To Cash®: How to Start at the Top of the Market Instead of Working Your Way Up from the Bottom, teaches entrepreneurs how to land 5- to 6-figure corporate contracts. As a former attorney, what legal steps should companies take to protect themselves, especially when entering into corporate contracts?
AK: First, it's crucial to own your business and personal brand names. I own trademarks for Ashley Kirkwood, Speak Your Way to Cash®, and many others—over 40 in total. Trademarks are essential because they give you the right to sell, license, or lease your intellectual property without doubts about ownership. Second, always have contracts in place with everyone you work with—vendors, contractors, even volunteers—to ensure clear ownership of what’s created. Finally, if you're working with corporations, make sure you have an LLC, contracts, trademarks, and insurance in place. These steps will protect your business legally and position you for success.

Q: What is the single best piece of advice that you were given when you decided to become an entrepreneur, and what advice would you share with others who desire that same path or are budding entrepreneurs?
AK: My best advice would be to start by being authentic about who you are and what you stand for. Don’t shy away from making decisions that align with your core values and principles, both big and small. Be clear on what you're offering, and make sure your marketing attracts the right audience with the right message. Lastly, surround yourself with like-minded individuals who can support and encourage you on your entrepreneurial journey. It might feel uncomfortable at first, but as you stay true to your values, you’ll find that it not only enhances your work but also empowers those around you.

Q: Can you tell our audience one of your most memorable moments of your career?
AK: It was when my husband joined the company full-time in February 2021. It was something that had always been a dream of mine. For us to be working in the business together, full-time, is probably one of the best days of my career.

Q: At the start of your career, what do you wish you had known? 
AK: I wish I had known that I needed to plan for bigger goals from the start. I think I set my goals way too small just to replace my $300,000 law firm salary. If I had set a goal of building a $25 million company, I would have approached things very differently including how I structured the business, the hiring process and even the vigor with which I promoted the company.

Q: Which woman inspires you and why? 
AK: My mom inspires me because she instilled values in me as a child that I still hold dear today, such as confidence, conflict resolution, and how to balance a successful career while prioritizing family and honoring God. I admire many people for their work ethic and career achievements, but I often don’t know who they truly are behind the accolades. What makes my mom's inspiration so special is that I’ve seen the behind-the-scenes of her life, and I’m still deeply inspired by who she is.

Q: After high school, where did you feel your career path would take you?  
AK: After high school, I thought my career would take me to law and it did. So, that is still a big part of my journey, and I still own a law firm. I thought I would be practicing law, but I did not see entrepreneurship, Speak Your Way to Cash® or being a CEO of my own company. I always thought I would be a lawyer, be a partner at a law firm or maybe even be on the Supreme Court. That was one of my goals. I clerked in law school for a federal court judge, really enjoyed the process and just always dreamed that one day I would be a federal judge. 

Q: What's your advice for women in male-dominated fields?
AK: I would say to find women that you admire in those fields and use them as proof that you can do absolutely anything in that field. Also, never feel bad about speaking up for yourself, but choose wisely which wars you want to fight. Finally, make sure that you are developing allies early.

Five Things About Ashley Kirkwood 

1. What's your favorite family tradition? 
Sunday dinners and Sunday walks.

2. What’s your favorite thing to do in your free time? 
Play tennis.

3. Who is the most fascinating person you’ve ever met? 
Dr. Dennis Kimbro.

4. What was the last book you really got into?
“Black Fortunes,” the story of the first six Blacks who went from slavery to becoming millionaires.

5. What’s the most amazing adventure you’ve ever been on?
It was my sabbatical. My husband and our three-year-old went to Ghana, Thailand and Bali for six weeks.