Dida Clifton

Disclaimer: This transcript has been lightly edited for clarity and readability. Filler words were removed, sentence structure was improved, and paragraphs were added while preserving the original meaning and conversational tone. Henry Harrison: Today we want to welcome to the show a very special guest, Dida Clifton—founder and owner of The Office Squad, a mother, a veteran, and a number of other remarkable things we’re going to hear about today. Welcome to the show, Dida. Dida Clifton: Hi. Thank you for having me. Henry Harrison: You bet. Let’s start with your business. You’ve been running it for over 20 years—maybe 23. You help entrepreneurs with what many people call the “back office,” which is instrumental to everything. Your company provides services beyond accounting, which is what some people think of first. How does that sound? Dida Clifton: That sounds good. I have a different philosophy. Accounting and taxes go in one bucket. What we do is full-charge bookkeeping—something that happens every day. In my mind, that’s operations. I don’t have an accounting background. We don’t do taxes, tax planning, or strategy. That’s a different world. In the military, I learned how to herd fighter pilots and run operations of a fighter squadron. That taught me systems and procedures. I took a little bookkeeping business and realized entrepreneurs needed a lot more than bookkeeping. So we created a place where they have everything in one location. It’s remote in the sense that you can work with us remotely, but The Office Squad is not remote. Everyone is in one building under one roof with a manager. We have bookkeepers, light accounting—which is end-of-month—administrative services, live phone answering, receiving mail, and all that stuff you used to buy and piece together. In our hybrid world, you can have all of that somewhere else, and it costs less than one employee. Henry Harrison: Do clients stay with you a long time? Dida Clifton: Yes. I like to say we’re picky and sticky. It took a long time to figure out who was a good fit and who understood our mission. Once they become a client, it takes about three months before the light bulb comes on and everything starts clicking. Clients stay on average five to seven years. I have one who’s been with me almost 16 years, and a couple more that are 10 to 12 years. Once you have a good fit, you want longevity. And in our case, you don’t just have one employee—you have 13 people in the squad right now. So you have 13 people who are loyal and working for you. Henry Harrison: You’re not working in the business in the traditional sense every day. That must have been an evolution—building a team that runs it well. Dida Clifton: I think I learned that in the military. You can’t be the only person doing what you do. There’s always backup. In the fighter pilot world, they have a wingman. In business, we built the same concept—backup for whoever’s doing what. I started with a small home business called “Dida’s Virtual Assistants and Bookkeeping.” As it evolved, I always made sure there was a backup. When I decided to step away and be more of the visionary, I trained someone else to take over my responsibilities. A year or two later, my husband walked in from his civilian job and said, “I want to move to Texas.” I said, “I think we can do that. I can run it remotely.” We moved to Texas. Now we live on an airport with the runway in the backyard, and he’s a very happy camper. Henry Harrison: You’re building a franchise model now. What lessons did you learn that you’re trying to help franchise owners avoid? Dida Clifton: When people ask what they get from buying a franchise—beyond profitability—I say: you get to learn faster, better, and smarter than I did. It took me 23 years to get here. With the franchise model, you can do it in one or two years. I started from home and joined the local Chamber of Commerce in Las Vegas, then sat back and expected it to work for me. It doesn’t work like that. You have to participate. You have to network. You have to get out of the house and go to events. So if you sign up for the Chamber, BNI, or whatever, it won’t work unless you show up and do the work. That’s a major lesson. Henry Harrison: In the franchise model, is your team supporting franchise owners? How does it work? Dida Clifton: The goal is for a franchise owner to do what I did: grow a squad that works without them. It took me a long time to learn how to hire and train the right people and build systems so they knew what to do. Now it’s all documented and built. A franchisee can start in the business—maybe they’re a bookkeeper—or they can hire a bookkeeper. They sell, network, and as it grows, they become further and further removed from day-to-day work. They can move to another state and still have a squad that runs the business and writes them a paycheck. Henry Harrison: More time for flights with your husband, hikes, travel—whatever matters. Dida Clifton: Sometimes. We went to Waco last month to do the Magnolia thing. Next weekend we’re going to Big Bend. I don’t love flying just to fly in circles and come back. But if he’s taking me somewhere fun, I can do that. Henry Harrison: You also planned this with family in mind. You’re a mother, and the more strategic the business, the more freedom you have. Dida Clifton: Yes. When my kids were little, they went everywhere with me. My youngest’s first job was collecting business cards at events. Now she’s my CMO and helps run the office in Las Vegas. She’s going to make me a grandma in December. I’m doing a franchise convention in Austin in November. I can grow the franchise and still fly to Vegas to visit my daughter and, soon, my granddaughter. And I had a really good business coach who helped me stay focused on the goal of retiring my husband. Before I knew it, we were there. She reminds me: when you think you’re not doing enough, look back at what you’ve already accomplished, then plan the next step. Henry Harrison: That’s a great reminder. What other challenges or lessons stand out? Dida Clifton: Listening to advice. As entrepreneurs, sometimes we think we know it all. I tried profit-sharing setups where I thought I could grow with someone who wanted to do what I did. They listened for a little while, then said, “I can do this myself.” I was stubborn too. If I had listened to people who had been there and done that, I would have grown faster and with less pain. Henry Harrison: There’s a balance—confidence to jump in, but also listening to experienced people who can help you avoid mistakes. Dida Clifton: Absolutely. And honestly, The Office Squad exists because someone told me, “You can’t scale bookkeeping.” And I said, “Hold my beer.” Henry Harrison: A lot of entrepreneurs struggle with phones, scheduling, bookkeeping, admin—things that don’t directly make money but are necessary to run a real business. Dida Clifton: Exactly. People hire virtual assistants now, but most have a niche—marketing VA, bookkeeping VA, and so on. To get everything, you end up managing multiple people. In our model, anything that’s not phone answering or bookkeeping goes into admin. That includes dispatch and scheduling, talking to vendors, ensuring payroll taxes and sales taxes go out on time—because so many people ignore those until they get a letter. We pay attention to the small things that become big problems if you ignore them. Henry Harrison: And you’ve eliminated the “Susie is out” problem. Dida Clifton: Yes. I hate that. We cross-train. If one person is out, another can step in. It might be slower than Susie, but they know what to do and how to take care of the client. Henry Harrison: As a kid, did you like numbers and admin? Dida Clifton: My first job was as a cashier at a grocery store. I liked pushing buttons and making the cash register work. I remember when barcodes were introduced and thinking, “That’ll never work.” That’s how old I am. I liked QuickBooks and bookkeeping. And by the way, anyone can call themselves a bookkeeper—there’s no certification or license. Part of my mission was fixing the messes I kept seeing from people who “knew QuickBooks” but didn’t understand debits and credits. I didn’t know what I wanted to do as a kid, which is why I ended up in the Air Force. My father politely suggested I find something that would give me discipline. Henry Harrison: It worked. Dida Clifton: It did. I hated the first six weeks, but it turned out to be a pretty good deal. I was in for six years, joined as a 19-year-old right out of high school. I met my husband, got married, then followed him around for 23 years and raised two daughters. Entrepreneurs don’t sit still. I started a gift basket business, thrift shops—everywhere we went. I even started a thrift shop in East Germany right after the wall went down, because people didn’t know about garage sales or thrift shops. A kindergarten needed resources, and we built something to help. Furniture, toys, painting—it was great. Henry Harrison: So by the time you built The Office Squad, you’d already run a lot of “offices” through different businesses. Dida Clifton: You don’t realize it when you’re doing it, but yes. You have to look back. I started bookkeeping by volunteering, became treasurer of the Wives Club, learned QuickBooks, used it for my businesses and our household. When we got stationed at Nellis Air Force Base in 2001, I put the kids in school and thought, “Now what?” That’s when I started Dida’s Virtual Assistance and Bookkeeping. Eventually I stopped listening to people telling me the fighter pilot brand wouldn’t work. In 2017, I decided to do it my way. We went all in with The Office Squad and the Flight Club, and it’s done very well since then. Henry Harrison: How do clients experience the model? Are they saving money and getting better execution? Dida Clifton: Yes. We have a client in California where we replaced a full-charge bookkeeper and a controller. They pay about $6,000 a month, which is still cheaper than hiring both roles. We have an HVAC company where we answer phones, dispatch and schedule techs, and help with operations. The owner even rents a space in our office to work outside of home. She has her own bookkeeper and we don’t overstep—we just handle what we’re needed for. Henry Harrison: Tell people what “call sign” and “Dida” means. Dida Clifton: Like Top Gun—Maverick isn’t his real name. In the military, nicknames are common. For pilots it’s a call sign, and they actually use it when they fly. Eventually it becomes their name. “Dida” is my nickname, and it stuck. Henry Harrison: Thank you to you and your husband for your service. Dida Clifton: Thank you. Henry Harrison: If someone wants to connect with you—clients or potential franchisees—what’s the best path? Dida Clifton: There’s a Franchise button on the website in the top right corner. You can also email franchise@theofficesquad.com , which goes directly to me and the developers. If you’re looking to be a client, use Contact Us—Taylor, my daughter and CMO, will reach out. And if you’re near Austin on November 15th or 16th, I’ll be at the Franchise Convention at the Renaissance Hotel. Come see me in person. Henry Harrison: Clients can be in any state? Dida Clifton: Clients can be anywhere. Franchising has registration rules in some states, but for clients, yes—any state is fine. We work remotely with anyone. Henry Harrison: Fantastic. Anything you want to wrap up on? Dida Clifton: I think we covered the important spots. If anyone wants to know more, we gave the contact options. I really appreciate it. Henry Harrison: We appreciate you coming on Entrepreneurs, Business, and Finance. You’re definitely all of those—entrepreneurship, business, and finance. You can’t do finance if you don’t have the books. Thanks again. Talk to you soon. Dida Clifton: Thank you.