Table of contents
Conversations about money often focus on tactics and numbers, but rarely do they peek behind the curtain of successful businesses to understand the human side of financial decision-making. In this candid roundtable discussion, three remarkable entrepreneurs share how they’re redefining success on their own terms:
Keila Hill-Trawick: Founder of Little Fish Accounting
Aja Evans: Financial therapist and author of Feel Good Finance
Angel Gregorio: Founder of Black and Forth and The Spice Suite
But first, we kicked things off with everyone’s favorite money anthem (yes, we’re talking about songs that reference money).
Entrepreneur Q&A: Defining financial success
Square: Before we get into it, tell us what you do, and because we’re talking about money, your favorite money song.
Keila Hill-Trawick: I run Little Fish Accounting, a boutique CPA firm serving service providers with one to two owners and small teams. We do everything from year-round tax support to fractional CFO services. For my money song, Lil Wayne, “A Millie.”
Aja Evans: I’m a financial therapist and the author of Feel Good Finance. I work with clients on their relationship with money. My song is Rihanna, “B* Better Have My Money.”
Angel Gregorio: I own Black and Forth, a strip mall I redeveloped that provides affordable commercial space to Black women salon owners. It also houses my spice shop, The Spice Suite. These spaces make up a dream incubator housing retail, a community business school, farmer’s market — all are free for participants. My money song is “Bossy,” by Kelis.
Square: I want to start with money failure. When have you learned a money lesson the hard way?
Hill-Trawick: Early on, I would’ve hired faster. I was so busy trying to be profitable, I underestimated the time savings [hiring] would’ve made. Entrepreneurs get stuck in this cycle of, “Should I hire now? Should I wait till we get more clients?” I would’ve hired, and then gone out and got the work.
Gregorio: I wish I had made the financial investment in an accountant sooner. I played the QuickBooks1 game for too long. I was trying to manage it myself. I thought I was minimizing costs. When I hired a real accountant, I realized I could’ve been making much better decisions. An accountant isn’t just about bookkeeping — they help me forecast and understand how to spend, how to save. Also, when it was time to purchase my commercial property, I needed to have a history of credit, and I didn’t have it. Growing up, we didn’t talk about money. I was scared of credit because I was taught to be scared. I was able to get approved, but I felt like my journey was harder because fears around money held me up when it was time to do something big.
Evans: I made the mistake of pulling out my retirement at my first job — it was only $700 at the time, but it was a long time ago. It was like an untouched account — not, “Hey, girl, what would this [$700] look like in 30 years?”
Square: Many of us grew up hearing debt is bad. Those fears carry over as business owners. Aja, how do we work through that?
Evans: Everything we’ve learned about money starts when we’re kids and we’re listening to the people around us — parents, aunts, uncles, at school, from the media. That information impacts our relationship to money. Angel identified and realized the people around her had a fear of debt. The second step I would say is to ask, “Does that money belief still apply to me and my situation?”
Square: Let’s talk about scaling yourself. Keila, how did you figure out that hiring was worth the investment?
Hill-Trawick: It was figuring out what success looked like for me — and it was both the money and the time. I was exhausted, I was working all the time. The first thing was getting my life back. Part of the math was how much can we afford now to hire somebody? And part of it was how much space would we have to get more clients, if I weren’t here doing all of the work? If I’m responsible for [all of the] bookkeeping and preparing tax returns, it’s difficult for me to have discovery calls, to onboard people with care, to get the right clients for us.
Square: Sometimes it can feel productive to do everything yourself, but it’s actually blocking your ability to scale. I also think we’re circling around this idea of separating yourself from your business.
Gregorio: I don’t know that I separate the two — it’s a matter of merging them in a way that’s healthy. My business success is tied to my personal identity because it’s what I deem purposeful: I support community. Providing free space for Black women and for farmers, offering community business school classes, the work that I do in jails and with young people who are impacted by mass incarceration.
Hill-Trawick: When people come to Little Fish, we have a conversation that there’s a team. I can’t possibly serve everyone by myself.
Evans: It’s hard to separate myself because, in therapy, there’s a saying called “self as instrument.” Who I am as a person is an instrument in conducting therapy. When you’re an entrepreneur and your business is paying your bills, it’s difficult to take those two things apart. When my business is doing well, I’m stabilizing my finances for my family. That’s why money is emotional — people will tie their net worth to their self-worth. I’ve only been able to disconnect with time and understanding that I don’t want to burn out.
Square: What about systems and habits — what has worked for you?
Evans: Saving for taxes in a separate account that I don’t even have a card for. I don’t see it, I don’t touch it. Also understanding that if the business made more money, it doesn’t mean I need to take more money. The business is its own entity of financial health.
Gregorio: The Profit First model helps me budget and make informed decisions. Money comes into my revenue account, and then I make deposits (on the 1st and 15th of every month) into my other accounts — operating, inventory, taxes, marketing, and profit. Sometimes I want to order new product and I’m like, “Slow down, you only have this amount in your inventory account.”
Hill-Trawick: A separate tax account is the first thing we recommend for clients, because that money doesn’t belong to you. I don’t want it to feel like it’s being taken from you. I made the decision to have an outside accountant manage our books. I knew I would put us last because I’d be focused on clients.
Square: That’s powerful. Even though you can do it, it’s better to have someone else do it. Switching gears, how are you approaching culture and community in your businesses?
Gregorio: I created my business model 8 years ago. I had been allowing Black business owners to pop up at the Spice Suite free. A couple of businesses wanted to keep coming back. I decided to have them run the shop for me so I didn’t have to be there as much. The first girl agreed to it, and from then on I decided I would bring other Black women along this journey and embody cooperative economics. Now I have 23 “Spice Girls,” that’s what we call them. I decided to call that business model Black and Forth, which is going back and forth with Black business owners to sustain a brick and mortar location. I’ve been using this model exclusively to run my business.
Evans: I want Black women to talk about their money. When I began this work, there wasn’t a space for us to have vulnerable conversations [about money]. I wrote a book because you can go to the library and get it for free, or pick it up for twenty bucks. I don’t want us to feel bad about our money.
Hill-Trawick: First of all, Angel, did the pinnacle of all the community things — it’s incredible. My goal is that Little Fish is a safe space for women to work. There’s overworking, undermining, condescension for women in [accounting]. We get people who were working 60 hour weeks or couldn’t take time off. We’re trying to reimagine the model of working at a CPA firm that doesn’t take your soul.
Square: For our final topic, there are tariffs, political, and economic headwinds. SBA (Small Business Administration) funds have been slashed, the Minority Development Business Agency has been crippled in its operations and its ability to extend grants. It could be easy to be fearful as business owners. What’s one thing that’s keeping you going?
Evans: Now more than ever, securing financial stability. An emergency fund is important. Have some money that you don’t need every month that’s liquid, that you can use just in case something happens.
Hill-Trawick: Investing in real relationships. We need community in big ways right now. It starts by sitting, talking, making phone calls, actually having conversations about what people need or what they’re running into. How can we address real issues in our own neighborhoods? Making time for that is important.
Gregorio: Ride the waves. There will always be ebbs and flows in life, business, and money. When times aren’t great, that’s when you ideate, dream big, put things on paper, and do administrative tasks toward the next phase of your business. Look at this as an opportunity to slow down and get things done.
Find the business model that works for you
Success in business isn’t just about the bottom line — it’s about creating sustainable models that serve both profit and purpose. Whether it’s Hill-Trawick’s mission to reimagine the accounting industry, Evans’s work to have more transparent conversations about money, or Gregorio’s revolutionary Black and Forth business model, these entrepreneurs show us that there’s no one-size-fits-all approach to building a thriving business.
