Transcript: Why Small Businesses Hit Growth Ceilings and How to Break Through Them

Episode: The Covert Code Podcast

Host: Anna Covert

Guest: Rob Aquino

Anna Covert [00:00:03]: Aloha. My name is Anna Covert, and I’m coming to you from my battleship here on the beautiful island of Oahu.

Anna Covert [00:01:02]: This week on The Covert Code, the topic is why small businesses hit growth ceilings and how to break through them. My very special guest is Robinson “Rob” Aquino, CEO of JBS Corp and Entrepreneur Books, author of The Small Business Money Game: Hidden Strategies That Turn Survival into Scale, which is hitting shelves on June 30, 2026.

Anna Covert [00:01:36]: Rob comes from a deep background in all things finance. He’s been a CFO, financial advisor, wealth strategy management consultant, and founder, so he really understands why small businesses hit growth ceilings.

Anna Covert [00:01:50]: In his upcoming book, he shares the Breakpoint Framework, which provides real-world examples and understanding for entrepreneurs to better understand their numbers, overcome limits, and scale with intention. Thanks so much for being here today.

Rob Aquino [00:02:06]: Thank you, Anna, for having me. I’m excited to talk.

Anna Covert [00:02:09]: To kick us off, we like to begin our story with the little Rob CliffsNotes version of how you got from where you were to where you are right now.

Rob Aquino [00:02:18]: I like to say I grew up in small businesses. Both my parents were entrepreneurs. All of my aunts and uncles growing up were entrepreneurs, and we primarily had bodegas. We grew up in New York as Dominican-American immigrants, and the bodega was the place you went for everything: coffee, breakfast, lunch, dinner, and household goods.

Rob Aquino [00:02:58]: My mom raised us primarily by herself, and she was operating businesses. That meant no clocking in and out, no nine-to-five. Half my childhood was inside a business in a bodega.

Rob Aquino [00:03:18]: I worked inside JBS while I was in high school at my stepfather and brother’s accounting firm. I decided to study accounting because it was what I knew. I studied finance and accounting, went into wealth management with Northwestern Mutual, learned how to build a business, and naturally worked with entrepreneurs as my ideal client profile.

Rob Aquino [00:03:42]: I did a lot of estate planning, retirement planning, and M&A activity, helping entrepreneurs whose whole net worth was their business figure out how to liquidate effectively and go into retirement. My brother had been recruiting me for many years. COVID hit, and that changed everything for us. I’ve been here for about six years now, really scaling the firm.

Anna Covert [00:04:01]: You’ve done some incredible scale. I was reading your bio. Was it 500% growth? How did you get there?

Rob Aquino [00:04:08]: We’ve 5X’d since I’ve been working with my brother. A few ways we got there. I think this is a common misconception in scale: you don’t get to growth by adding. You get to growth by subtracting.

Rob Aquino [00:04:25]: When I came to JBS, we had about 15 services. We did tax prep during tax season, and off season we did almost anything you could do with an administrative team and air conditioning in the summer. Translation services, audit cases, sales tax, payroll services, and at one point we were a travel agency.

Rob Aquino [00:04:56]: The first thing I started doing was removing everything that wasn’t tax. Enhancing our focus, understanding pricing strategy, the market, bottlenecks, and the thing bringing in 98% of the revenue. We were able to double that relatively quickly.

Rob Aquino [00:05:15]: Then I realized the real market demand was B2B. People wanted to understand their books, do corporate tax returns, start businesses, and get support. We started that product from zero, and now it represents about 40% of the business.

Anna Covert [00:05:34]: That’s incredible. Congratulations. When did you decide now was the time to write this book?

Rob Aquino [00:05:48]: I’ve always wanted to write books. Ever since high school. My mom and I had a conversation when I was a sophomore or junior. She said, “Son, I hope you make a lot of money someday because you like a nice lifestyle. Whatever you study in college, I’m not going to choose for you, but pick something that earns well.”

Rob Aquino [00:06:22]: She didn’t know this, but I was sitting there thinking I wanted to be a writer. When she said that, I thought, “Writers don’t make money.” So I studied accounting because I knew the tax business was there.

Rob Aquino [00:06:50]: When I went into wealth management, they gave this 21-year-old writer access to wealth management tools and retirement planning. I joined the FIRE movement, which stands for financial independence, retire early.

Rob Aquino [00:07:12]: The premise is: why work 40 years to retire 20 or 30 years if you could work 10 or 20 years and retire for 40? The caveat is you have to save 50% or more of your income.

Rob Aquino [00:07:30]: I thought I would work hard, retire at 40, and then write. About a year and a half ago, Harper phoned me and asked if I had ever thought about writing a book. I said yes. We talked about it, and he asked about my business process. That’s how The Small Business Money Game was born.

Anna Covert [00:07:47]: What was the book you wanted to write?

Rob Aquino [00:07:49]: It’s a book that tries to synthesize and study the philosophy of success. I want to spend my life researching where the barriers are personally and sociologically, not just financially. That will require probably a decade of research before I start writing.

Anna Covert [00:08:16]: That sounds fun. What do you think are the most common reasons small businesses hit a ceiling?

Rob Aquino [00:08:33]: There are two easy ones nobody wants to talk about. The first is that the hardest thing a person can do financially is start and grow a business because you’re in this paradox: to get to the next level, you need more resources, but to get the resources, you need to be at the next level.

Rob Aquino [00:09:08]: Of all the entrepreneurs I’ve worked with, resourcefulness is the common trait I see over and over. You have to get it done with what you have, even though it’s nearly impossible.

Rob Aquino [00:09:25]: The second is that a lot of people starting businesses today have been romanticized into thinking starting a business is easy, lifestyle-based, or the obvious way to go. Many figure out the hard way three, five, or ten years in that it isn’t the case.

Anna Covert [00:09:45]: You have to be comfortable failing too. I work with entrepreneurs launching brands, and I’ve seen industries shift quickly. Solar is one of my specialties, and with changes to the federal tax credit, many small businesses are having to pivot. Tell me more about your framework.

Rob Aquino [00:10:22]: I love the wave analogy. I use waves and ocean as a way to think about the market, like this vast open ocean.

Rob Aquino [00:10:45]: People build their boat on shore. When you’re building a business, you have all these ideas, and it feels good in the bay. Then you go all in, leave the job or hire the person before you can afford them, and enter the open market.

Rob Aquino [00:11:20]: Then you realize things get stormy. There are other boats out there and they’re big. If you get too close, they can capsize you. You realize the boat you built on shore is too small to carry the resources you have, so you have to manage that boat while building another one in the ocean.

Rob Aquino [00:11:50]: That’s a lot like strategic planning in business. Most people don’t realize when the boat gets too small and they need to build a bigger one. People also learn how to grow, hire, build benefits, and create compensation plans, but no one prepares them for when it’s time to shrink.

Anna Covert [00:12:46]: We have to talk about AI. How is AI impacting your framework in both positive and negative ways?

Rob Aquino [00:12:50]: I’ll start with the negative so I can end more positively. People feel like they’re going to get disrupted, but no one really knows how.

Rob Aquino [00:13:08]: In the SMB landscape, clients may think they can be more self-reliant now. Maybe they don’t need bookkeeping support or marketing services. They’ll probably do some things they shouldn’t do and later realize they made mistakes.

Rob Aquino [00:13:40]: In the meantime, that may create a cash flow squeeze. Larger incumbents may also try to compete because it is cheap enough to do so.

Rob Aquino [00:13:58]: But I was at lunch with banker partners, and it was interesting to see clients leaving big banks that have acquired smaller firms and going back to relationship bankers because they want to work with a human. In many ways, I think it will be positive for human relationships. The boring stuff will get automated.

Rob Aquino [00:14:20]: What I worry about is the recurring dream of people’s AIs talking to each other. You send me an email using AI, then I use my AI to respond. Are we even talking at that point?

Anna Covert [00:14:34]: That’s really interesting. It could be a sci-fi movie.

Rob Aquino [00:14:38]: I wonder how decisions are going to get made. If I’m pitching services, am I pitching you or am I pitching a large language model? I’m trying to do more physical work, in-person work, and Zoom work instead of endless back-and-forth email.

Rob Aquino [00:15:12]: On the positive side, AI will lower the barrier to entry on many products and services. It will allow small teams to compete with large players. Over time, my theory is that we won’t really need 10,000-person companies, and that’s good because it may bring humanity back to capitalism.

Anna Covert [00:15:39]: I think it may happen faster than 30 years with the way AI is growing right now.

Rob Aquino [00:15:46]: You may be right. The more consolidation that occurs, the harder it is for the economy as a whole to do well.

Anna Covert [00:16:02]: What are some of the other Breakpoint Framework tips that can help people today?

Rob Aquino [00:16:09]: I’ll walk through the first couple steps. Across about 3,500 clients, I’ve had access to sensitive data: tax returns, bank statements, P&Ls, balance sheets, and so on.

Rob Aquino [00:16:35]: I found correlations across industries and company sizes. I identified seven breakpoints that take businesses from zero to $25 million in revenue. I call them identity layers.

Rob Aquino [00:16:55]: In the beginning, you’re the salesperson and founder. You’re trying to get someone to buy something from you, and that takes you to about $100K.

Rob Aquino [00:17:10]: From $100K to a quarter million, you face the decision of whether to stay a solopreneur or build a company. From $250K to $500K, you face the hiring challenge. You need to hire real technicians, salespeople, delivery people, and product people.

Rob Aquino [00:17:35]: Now you have to become a recruiter. You had to learn sales, then build a company, and now recruit. The learning never stops. People get stuck at the role they can do themselves.

Rob Aquino [00:17:50]: Two things occur: they can’t become the operator, CEO, or shareholder, or they don’t know how to hire that person. The combination of those things is where most people flatline.

Anna Covert [00:17:59]: I can see that. It reminds me of the Peter Principle and asking whether you want to stretch.

Rob Aquino [00:18:15]: I work with high-income W-2 people who decide they’re so good at something that they’ll start a business. Then they wonder why people don’t want to buy from them or why it’s hard to sell.

Rob Aquino [00:18:40]: They thought because they cooked well or knew computers well that they could convince people to enter a service engagement. That’s a whole separate skill. They don’t see that they’re a rookie again and have to learn this new skill.

Anna Covert [00:19:20]: It’s easy to decide you don’t want to look at the credit card statements or finances. We do a lot of technology consulting and often find companies paying for software they don’t even use.

Anna Covert [00:19:57]: How do you help people understand their numbers?

Rob Aquino [00:20:10]: People are scared of their books and finances. Much of the early book focuses on your relationship with money. I call it the money game because I try to simplify things.

Rob Aquino [00:20:38]: Have you played Monopoly?

Anna Covert [00:20:42]: I love Monopoly. I was a Monopoly queen.

Rob Aquino [00:20:58]: The Small Business Money Game was an idea that came to me in 2014. I called it the Monopoly Theory. I told my brother Alex, “Isn’t it crazy how much the real world is like a large game of Monopoly?”

Rob Aquino [00:21:20]: We have a central bank. We have players making luck-based rolls. A lot of this is luck, but it’s also what you do with the luck. Depending on where you land, you still have to buy and negotiate.

Rob Aquino [00:21:43]: Monopoly has a fascinating history. Lizzie Magie invented and patented it in the early 1900s as The Landlord’s Game. She built it to teach about the downsides of capitalism, particularly concentrated land ownership.

Anna Covert [00:22:25]: That makes sense. Once you own a strip or corner, that changes everything. I liked the red and orange corner because it was cheaper to buy and build on.

Rob Aquino [00:23:03]: You’re a master Monopoly player. Statistically, if you buy orange or red, you’re likely to win. Not just because of return on investment, but because those are the most likely places for people to land.

Rob Aquino [00:23:40]: Monopoly is luck-based but also skill-based. You picked up pattern recognition. We all start with the same amount of money and income in the game, but inequality shows up quickly. Why? Because while luck matters, skill matters too.

Rob Aquino [00:24:38]: In the official rulebook, the bank technically cannot run out of money. If the bank runs out, you cut pieces of paper and write amounts on them. That is like quantitative easing.

Rob Aquino [00:25:40]: If you take Monopoly principles and apply them to the fact that life is an infinite game, it is virtually the same game.

Anna Covert [00:26:10]: Someone basically stole the game and renamed it Monopoly?

Rob Aquino [00:26:19]: There was a long lawsuit. There were two versions of Magie’s game: a cooperative version and the monopolist rules. The monopolist rules became the commercial version.

Anna Covert [00:27:26]: Now there’s every version. I’m a traditionalist. I like the classic one.

Rob Aquino [00:27:42]: I grew up playing games. Have you ever played Acquire?

Anna Covert [00:27:57]: I have not.

Rob Aquino [00:27:59]: You’d like that one. It’s trading stocks and things like that.

Anna Covert [00:28:23]: My dad played Acquire and backgammon. He was from New York.

Rob Aquino [00:28:29]: Chapter two is titled Starting from Go. In Monopoly, we all start at go and with the same amount of money. In life, we know it doesn’t work that way.

Anna Covert [00:29:00]: My dad owned Aspen Ski Tours, which eventually became Ski.com.

Rob Aquino [00:30:01]: That’s a very innovative entrepreneur. He pivoted multiple times. You saw that in real time behind the scenes.

Anna Covert [00:30:45]: I started my first company when I was eight. It was a dog babysitting company called Canine Villas.

Rob Aquino [00:31:06]: One of the strongest correlations of successful entrepreneurs is that they sold something as children.

Anna Covert [00:31:46]: I was selling drawings to my parents. They weren’t getting them for free.

Rob Aquino [00:31:58]: We all form a relationship with money very early, often between ages five and twelve. The way we see money and value gets formed early.

Rob Aquino [00:32:30]: Many people grow up with scarcity and money fears. Part of the work is changing how entrepreneurs view money, because it’s not as scarce as they think.

Rob Aquino [00:33:25]: There is also the idea of bartering. People think money started as bartering, then paper and metals. But anthropologists have found that there was never a civilization that bartered at scale. Instead, the oldest writing we have includes debt covenants from Mesopotamia.

Anna Covert [00:35:02]: A lot of people don’t realize the Federal Reserve is not the government.

Rob Aquino [00:35:49]: One quote I open a chapter with is from Henry Ford. I’ll paraphrase: it’s well enough that Americans don’t understand money, fiat currency, and central banking, because if they did, there would be a revolution by tomorrow morning.

Rob Aquino [00:36:36]: Fundamentally, money has always been about trust. Whether you go back to 3000 BC or today, money is something we agree upon and trust until we don’t. Government imposes that trust, and banks help create and control the flow of money.

Rob Aquino [00:37:50]: If I had to condense what money is fundamentally, I think it’s the language we all speak.

Anna Covert [00:38:04]: It’s also frequency and energy. Money has to flow. If it doesn’t flow, it gets around the blockage like water.

Rob Aquino [00:38:45]: Investing is a form of spending that continues the flow, because ideally it comes back with return.

Rob Aquino [00:39:35]: Proximity to the bank is critical. If we were talking about a water source, the people closest to it would get water first and get more water. Banks control the flow of money, and people with strong banking relationships pool more capital.

Anna Covert [00:40:21]: What was one turning point in your career that changed your view of leadership and growth?

Rob Aquino [00:40:26]: COVID. Nobody understands where they sit in the ocean until the tide comes out.

Rob Aquino [00:40:50]: In March 2020, I was still an advisor. The stock market had its largest drop in the shortest amount of time, and I spent two weeks convincing clients not to sell their stocks.

Rob Aquino [00:41:20]: Then my brother had all these missed calls from small businesses asking what they were going to do. Federal relief required tax returns and financials, and many small businesses did not have either up to date.

Rob Aquino [00:41:50]: I had to decide whether to build my wealth management business or help my brother’s firm solve the bookkeeping and accounting shortage for the community. I decided to help JBS build a bookkeeping business so businesses could get grants, and I never looked back.

Anna Covert [00:43:15]: COVID was a growth opportunity for my business because I specialized in digital advertising. But we also lost clients in tourism and had to look to the mainland for more work.

Anna Covert [00:45:00]: I tried to refinance my house during COVID, and because I own my own business, the process took about nine months because banks wanted W-2s.

Rob Aquino [00:45:30]: Banks often don’t fundamentally understand entrepreneurs. Entrepreneurs are seen as risky until they are crushing it at $25 or $50 million plus. Then banks want to be their best friend.

Rob Aquino [00:46:00]: Accounting, banking, and money are languages. Entrepreneurs don’t always speak them. We help cover the gap by providing the reports and explanations banks need.

Anna Covert [00:47:22]: This has been wonderful. How can people get ahold of you, and what’s your book launch sequence?

Rob Aquino [00:47:30]: I’ll be doing more conversations like this. I have three young kids, so I’m trying not to do a physical book tour. The book will be available everywhere: Barnes & Noble, Amazon, Target. Our pre-order sales are doing very well.

Rob Aquino [00:48:12]: I’m also actively writing on Substack with a weekly newsletter where I continue the money game, not just the small business one.

Anna Covert [00:48:49]: Thank you so much. We’ll provide all of Rob’s links and his book in the channel below on YouTube. Please join me next week as I interview another industry expert on topics to help you succeed on and offline.

Anna Covert [00:49:10]: If you have not done so already, please subscribe to this channel. We are just shy of 200,000 subscribers, and that is because of you and your aloha. Continue to share this content if it feels compelling with your friends and family so I can get more great guests like Rob to share their wisdom and passion with us. I’ll see you next week in the pixels. Aloha!