Business Spotlight with Ashley Quinto Powell from myVA Rocks

Kory Dogs
January 14, 2025

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In this episode, Ashley Quinto Powell, founder of myVA Rocks, recounts how she transformed early business challenges into the creation of a successful virtual assistant agency. Starting with a costume jewelry venture that didn’t succeed, Ashley’s career evolved through consulting roles and eventually led to the creation of myVA Rocks in 2021. The agency now employs 60 virtual assistants and provides crucial support for solo entrepreneurs and growing businesses, allowing clients to focus on scaling without the burden of administrative tasks.

Throughout the discussion, Ashley reflects on the lessons learned from her entrepreneurial experiences, including the importance of testing ideas, embracing coaching, and staying resilient through challenges. Looking ahead, she is excited about the launch of Rock Solid VA Academy, a school designed to train virtual assistants and create economic opportunities, especially for caregivers and women re-entering the workforce. Her story is a testament to the power of perseverance, mentorship, and a solid support network in growing a successful business.

 

Podcast Transcript:

Kory Dogs: This is Coach Kory Dogs from ActionCOACH, and I’m excited to welcome Ashley Quinto Powell from myVA Rocks today. Ashley is a serial entrepreneur, national speaker, and author of Executive Motherhood: The Art of Having It All Without Doing It All. She’s also the founder of the virtual assistant agency, myVA Rocks.

Ashley has delivered talks on motherhood for TEDx, AnitaB.org, the University of Chicago’s Polsky Center, and more. She lives in Madison with her husband and two children. Her business, myVA Rocks, aims to transform how people work by providing exceptional support to their clients while creating flexible, joyful work for their team. They connect top talent with a growing, diverse clientele who often start small but quickly expand their virtual assistant rosters once they realize the impact of this support.

Something unique about Ashley? There’s a children’s book about her—not many people can say that! In her downtime, she enjoys spending time with her family and training her dog. What she’s most proud of is her team at myVA Rocks. She describes them as the most talented, generous, and uniquely awesome group of people she’s ever worked with.

With that, it’s my pleasure to welcome Ashley Quinto Powell to the show. Hello, Ashley!

Ashley Quinto Powell: Hi! Thank you so much for having me.

Kory: No problem. Let’s dive into the questions. First, tell us a bit about your personal story—where you were born, where you grew up, family, hobbies, that kind of thing.

Ashley: I’m originally from Chicago and started my first business in my early 20s. It was a platform for costume jewelry, but it was a total flop. That was almost 20 years ago, though, and since then, I’ve had quite a few businesses and corporate jobs. Now, I’m in Madison, Wisconsin, working on a business I truly love.

Kory: Awesome. What about hobbies?

Ashley: I enjoy artsy stuff like making models and painting. But, honestly, with two kids—ages nine and eleven—my main hobby is being their taxi driver.

Kory: Yes, I can relate. Those days are behind me now. Next question: what’s a funny story your family tells about you that you’d be willing to share?

Ashley: There are plenty of funny stories! Lately, my kids have figured out that I’m the CEO, and they’re fascinated by it. My daughter occasionally says, “My mom’s the CEO. Whose mom is a CEO?” It’s adorable.

As for a particularly funny story, I’ll share one about myself. I love galas, especially participating in auctions. We’ve ended up with quite a few random golf packages, theater evenings, and weekend getaways. One of my favorite things is to scare my husband by almost winning live auctions every time we attend a gala!

Kory: That’s fun! Thanks for sharing. Next question: Tell us how myVA Rocks came about, and at what point did you feel confident you could do it?

Ashley: Well, I wouldn’t call it confidence, but I certainly had hubris when I ran my first business—and that didn’t go well. I invested so much time and money in an industry I knew little about, but looking back, I’m grateful. That failure pushed me into tech and gave me a solid foundation for the next step in my career.

After that experience, I was really hesitant to have all of my income—and my family’s livelihood—rest entirely on my shoulders. I often said I’d always have something on the side, but someone else had to ensure that paycheck hit my account every Friday. Ironically, I’ve learned that others can mess that up, too.

It wasn’t until 2018 that I felt ready to truly strike out on my own again. Like many small business owners, it was a white-knuckle experience. I had two kids in private school, a stay-at-home husband, a mortgage in Madison, and rent on a Chicago property. There was a lot of pressure, but also a lot of energy and great ideas behind it.

I’ve heard entrepreneurs, like Kate Spade on How I Built This, say that pressure is crucial. She mentioned that if she’d had a day job while starting her line, she might not have succeeded. I understood that pressure was necessary—that businesses deserve a real chance to stand on their own.

Kory: So, after the first attempt didn’t work, you decided to try again. You juggled everything—husband, kids, and responsibilities—and built myVA Rocks into what it is today.

Ashley: Well, to be fair, myVA Rocks wasn’t my initial business when I went solo. I first co-founded a wedding registry startup for art, serving as its Chief Revenue Officer. To keep money flowing, I also did a lot of consulting, mainly focusing on revenue generation for software development firms and marketing agencies.

In 2018, I realized I didn’t love being a CRO for the wedding registry but really enjoyed consulting. Over time, myVA Rocks emerged from that consulting work. I also started networking groups and even launched another jewelry line.

The reason you and I connected, Kory, is that I knew from the start that myVA Rocks had bigger potential. I partnered with ActionCOACH early on to build the business. While I didn’t need coaching for my one-person consulting firm, I knew I’d need it to scale myVA Rocks into what it is today.

Kory: Got it. So, tell us more about myVA Rocks. When did you start it? What do you do, and who’s your ideal client?

Ashley: I started myVA Rocks in May 2021 and officially spun it off from my consulting business that July when it became clear it was taking off. We’re a virtual assistant agency. Most clients come to us when they feel ready for their first employee but realize they’re not quite ready for that responsibility.

We currently have 60 virtual assistants and grow steadily each month. Recently, we launched a virtual assistant school to train aspiring VAs. We also do a significant amount of grant writing for nonprofits and handle a lot of social media.

Our clients are mainly consultants or solo entrepreneurs, but about 25% of our team supports entire executive teams. In those cases, one VA might work with three or four clients at the same company.

Kory: Alright, that’s a great model. Next question: can you share a story of someone who pushed or inspired you to believe in yourself and the impact that had on you?

Ashley: Well, without exaggeration, the coaches at ActionCOACH were instrumental in that early push. I had moments, especially during GrowthCLUB, where I thought, Wow, I think we’re making it—I think we’re doing it. I remember feeling astonished at that realization.

I also have an amazing support system of friends and family. My husband, who we call the GHOAT—Greatest Husband of All Time—is an incredible cheerleader. Whenever I face a crisis of confidence, he’s right there, encouraging me and telling me I can do it.

Kory: And speaking of GrowthCLUB, as a coach, it’s always rewarding to guide clients through the planning process and watch them grow. You were one of those clients. It’s amazing to see how far you’ve come since that first session where you were like, “What is this planning thing? How does it work?” It’s been great to witness your evolution. What’s been your biggest learning as a business owner?

Ashley: I approach everything with a design-thinking mindset. Comparing my first business to my current one, which is my seventh or eighth (and I’ve got nine and ten in the works), I’ve learned to run small experiments first. We always start with an MVP—a minimum viable product—to test concepts.

One of my key lessons is not being emotionally tied to a business idea. After my first venture, I committed to figuring out who the buyer is and whether they’re willing to pay. I’ve seen many business owners get caught up in thinking, I just know this will work, but until someone writes a check, you don’t have a buyer.

For example, a client once suggested I run small accountability groups. She laid out exactly how it should work, so I launched it with her input. But when I announced the program and price, no one signed up—not even her. That was a valuable lesson: unless people commit financially, it’s not a viable product. This approach helps me avoid clinging to ideas that might not work.

Kory: Well, having a strong mentor and peer group is essential. Now, let’s talk about challenges. Business has its ups and downs—COVID, for instance. Can you share a significant challenge and how someone helped you overcome it?

Ashley: It’s hard to pick just one! I’ve had some tough days. Coming from a family of entrepreneurs, I’ve seen my share of business challenges. My dad once told me about a day he calls “the blowout.” He owned a brokerage firm that traded on the Kansas City Board of Trade and accidentally cornered a market. It blew up, and it was a dark day. Now, he tells the story as a joke, but it took 25 years to become funny.

For me, running myVA Rocks involved tough lessons about understanding our clients. I remember one client who screamed at a VA over something. After analyzing the situation, I realized her business wasn’t profitable, and she was unfairly relying on the VA to fix that. That’s just not a VA’s role.

Since then, we’ve become selective about our clients. We now ensure their businesses are sound and that they can clearly define the processes they need help with to make their business profitable. When you’re new, it’s hard to turn away business, but this approach ensures both our clients and VAs succeed.

Kory: Awesome. What’s next for you and myVA Rocks?

Ashley: It’s definitely the virtual assistant school, Rock Solid VA Academy. We’ve learned so much about client care and how to serve people virtually. At the same time, there’s a real need for remote, flexible jobs, especially for caregivers and women returning to the workforce while balancing childcare. Creating those economic opportunities is really important to me. We’re excited to pull VAs from that pool—people trained in our methods and making it work.

Kory: Have you launched that yet?

Ashley: We’re currently in an internal beta, but it’ll go live for the public on July 1.

Kory: Alright, one last question before we wrap up: What advice do you have for business owners trying to go it alone?

Ashley: It takes a lot of grit. I’ve made it a priority to read nonfiction, and now, during strategy meetings, I often find myself recommending books. It’s easy to get caught up in busywork, but making time to think deeply about your business and work on it—through coaching, for example—is invaluable. For me, it’s been a game changer.

Kory: Alright. Would one more piece of advice be “get a VA”?

Ashley: Absolutely!

Kory: Okay, to wrap up: Any shoutouts? You’ve had a lot of amazing people in your life.

Ashley: Sure! My team is incredible. I’m lucky to have an amazing right-hand person, Sarah Hardy, our VP of Operations. Dr. Emily Elsner Twesme is leading our virtual assistant school. And, of course, my husband Sean deserves a shoutout, as do my wonderful parents, Jeff and Tony Quinto.

Kory: Thanks, Ashley. If someone wants to learn more about myVA Rocks, how can they contact you?

Ashley: Just visit myva.rocks and set up a call.

Kory: Alright. Thanks, Ashley. It was great talking to you and having you on the show.

Ashley: My pleasure. Thanks, Kory!