Part I
Rob got lucky.
In the early 1990s, RRBB owned four computers for a staff of around 30. Rob Quick called them “lunch boxes.” Each computer sat sixteen inches wide, nine and a half inches tall, with a small screen that popped off the front.
Those computers weighed thirty pounds, and Rob lugged them through airports, to client sites, plopped them in the back seats of taxis, and he says the only reason he went to the gym was to not show up sweating to meetings after carrying them around. Rob lived 45 minutes from the office, and would drive down and back Monday morning before work to get a computer for his client visits that day. If four others beat him to the computers, he was out of luck. They were under lock and key, and it was first come, first serve.
As a young auditor, those computers changed his life. But when laptops came out, Rob walked into a partner’s office and asked for one. He compared it to the calculator. Eventually, we’ll all have one, he argued.
The partner agreed, and Rob never carried the lunch box again. When his peers saw, they asked for the same, but the firm gave them interest-free loans they had to pay back over time. Rob grins telling that part of the story. He’s always been early.
Rob Quick, Partner
•••
There is an old drawer in Rob’s office in Somerset, New Jersey that seems to hold the last quarter century of the history of American accounting.
In it sits a red well filled with green ledger paper and 13-column spread. When Rob pulls out the red well, he handles it much like I would handle an old yearbook. He flips it open, thumbs through the files, laughing and shaking his head. He talks about carrying the lunch box with an audit bag full of red wells in the humidity of a New Jersey summer. He talks about Alice, the data entry lead at RRBB some 25 years ago. He talks about a young Dave Roth, who even back then struggled to take orders from anyone.
Rob has been at RRBB for 32 years, and led most of the technology transformations at the firm since then. Each new wave of technology - the computer, the laptop, the software - when it arrived led to the same fear.
The machine is going to take our jobs.
In some ways, I think that prediction has been correct. Alice, when she left RRBB, predicted they would need to backfill her role or data quality and organization would fall apart. The firm didn’t, and today the firm is as much a data firm as it is financial services.
Dave Roth has heard that same fear for three and a half decades. Dave is RRBB’s CEO and former managing partner, and he joined the firm in November 1987 at $16 an hour when it was a two-office practice his fiance worked at. The firm was about 20 people then. Tax returns were done on green four-column paper or filled out by hand on input sheets, which were mailed to a central service, keyed in by strangers, and mailed back. If one number changed, Dave put the sheet back in the mail and waited weeks for the updated return. The audit practice ran entirely on paper and red wells. When the first PCs arrived, Roth remembers them as “the size of a vending machine,” and says the feeling in the profession was that the computers had come for everyone’s job.
Some jobs disappear, yes, but Dave doesn’t see it as a one to one replacement. More often, he’s seen it change the job, move the work somewhere else, or expose a different problem entirely.
Dave is a bit of a maverick. He slicks back his hair, dresses well, and talks more about the Knicks and golf than he does finance. His side project is reinvigorating a golf club he purchased in Jersey, and I get the distinct feeling he would’ve been an entrepreneur no matter what field he built his career in.
Dave Roth, CEO
Dave was never a technologist. He will tell you he doesn’t understand coding or software, but he’s never been scared of technology. He is and was the talker, and he reasoned even early in his career that if you can bring in business, there’s never a question of your job security and never a question of who does the work.
One idea from Dave stuck with me. He says it’s not that people fear technology, it’s that people fear the unknown. The roles that will be gone are obvious while those that will appear are difficult to predict. When the computer entered accounting, everyone could see the central mailing service was going to struggle. What people didn’t predict is that hundreds, if not thousands, of tax and audit software companies would rise to take its place.
“Watch,” Dave says, “The same fear is always the fear that’s been there all along.”
•••
It would be convenient to tell this as an unbroken march of technology, tool after tool, each one welcomed after brief resistance.
But somewhere between the laptop and today, Rob brought a tax accounting software to RRBB that he thought would revolutionize the firm. At the time, client documents arrived in no order at all, and preparing a tax return meant hunting through piles of unorganized documents for every number. Rob says he was forever grateful to be focused on audit watching his colleagues go through tax prep.
His software would sort every document into the sequence of a tax return. It even attempted to fill in the return itself, though that part was a bit rough, about 70% accuracy.
“It doesn’t do 100%,” people told him. “We still have to check everything.”
After months of arguing, Rob finally got the partners to approve the software, but just for the auto-sorting. The tool converted the skeptics overnight. Rob recalls the same people who had told him we’re not doing this walking into his office saying, “Wow, why didn’t we do this before?”
“Get out of my office before I punch you in the face,” Rob says, laughing. In New Jersey office culture, this seems to mean, ‘I’m glad you’re enjoying it.’
There was, however, another problem. The software required someone to scan every document and upload it into the tool. Otherwise, the software had nothing to sort.
The scanning became admin work, and the admins didn’t want to do it. They already ran the office, coordinated partners’ calendars, and essentially made sure the office didn’t fall apart. The scanning, especially during the rush of tax season, would add hours to their days.
The admins simply stopped doing the scanning. A couple weeks later, the initiative was dead, everyone but Rob forgot about it, and the firm returned to the old way of preparing a tax return.
As Rob tells the story, I started to think about what went wrong. Many technologists, and plenty of founders and investors I’ve worked with, think technology is the hard part. They are almost always wrong. The challenge comes from people, and from years of habits and beliefs that have to be shifted before any new technology can come to exist as part of a new workflow. The admins weren’t won over, so the tax software died.
Nothing about this story matches the fear of technology replacing our jobs. The people the software threatened, the tax preparers, jumped at the technology once they finally tried it. The group who killed the initiative were never threatened at all. In fact, it would have expanded their responsibilities.
The firm’s history is less a story of computers replacing practitioners than of practitioners repeatedly learning what a computer can’t do on its own. Which is why I wanted to meet Susan DiPaolo.
•••
Susan stands behind her desk in Somerset. “If anyone knows this firm’s history, it’s her,” Dave Roth told me. For more than 22 years, Susan has been at RRBB, and it seems she has her hands in every aspect of the business.
Susan DiPaolo, Manager of Firm Administration
Her career is not as linear as Rob’s or Dave’s. Before RRBB, her career took her from Hawaii to New Jersey to St. Croix. Along the way, she worked as a legal and executive assistant, taught fitness, and managed the maintenance department for an airline in the Virgin Islands. “I've done everything,” she told me. “It introduced me to a lot of different cultures and a lot of different people, and it gave me a different perspective on things. I've had such broad exposure that I think I see things a little differently, and I can pretty much work with anybody.”
She landed at RRBB almost by chance in 2003. The firm reached out to the employment agency where she worked about a part-time role in its M&A department, and a couple couple weeks later Susan spent her mornings at the agency before walking upstairs to work with RRBB in the afternoon until, in 2004, the firm hired her full-time.
A few years in, she watched the firm go paperless and she remembers the mood as “a little bit of fear.” Was it going to work? Would clients accept it? What happens to all the paper?
When she started at RRBB, processing a single tax return meant a physical file inches thick, a room full of archives and copies, and the logistics of running a full mailing operation. Like Rob, she pulls reams of old files from her drawers and off her shelves, almost as mementos of days not long past.
Today she processes a return in 10 or 15 minutes. This step comes after returns are signed and sealed, ready to go to the IRS. She uses a mix of four or five different programs to do it, which she seems to say both as a complaint and as a compliment. Even with all those steps, the technology saves her days of time and is faster than anything the profession has ever had. When a client asks for last year’s tax returns, she used to need to dig through files, make a copy, and mail it to them. Now she finds them on her computer and sends them across in a few minutes.
What strikes me about Susan is her ability to adapt. Throughout this story, I’ve focused on the technology changes that have come to RRBB. We’ve talked about the people who liked those changes, and the roles that no longer exist. Susan is interesting to me because her original roles are some of those. Yet today, it takes her a while to list everything she’s doing for the firm.
Her responsibility and influence have only grown. “I’m really working in, I would say, six functional areas in the firm,” she says. “It’s a lot. But I've been doing it so long, I don’t even think about it, honestly.”
In January 2026, RRBB closed its Maplewood office and combined it with the Clark office. Susan managed the whole transition. Maplewood still kept paper copies of everything, no electronic files at all, so Susan hired a company to digitize the records.
Rob points out why RRBB is so focused on getting technology right today.
“Things moved slower when I was coming up. Accounting firms tend to move very slow. I named five things in about 30 years,” he says. “Now that feels like it’s happening every six months.”
Technology transformation is weird like that. Often it doesn’t sweep through an industry, or even through a firm. Inside the same firm, you have people testing AI tax preparation while paper copies are still the go-to in certain offices. It’s not that the paper firm is ineffective, it’s just the way they and, importantly, their clients are used to working. The job still gets done, and done well. But the tech transformation remains uneven.
This is not as uncommon as I originally thought. Over the past couple of years, RRBB has acquired multiple smaller firms. “The smaller firms we’re purchasing don’t have the money to invest in technology,” Dave told me. There are firms all over New Jersey - and the United States - still operating in this way.
The machines are going to take our jobs. Is it different this time?
That summer, I took a train to Somerset to find out.
Part II
RRBB’s Somerset office sits about an hour outside of New York City. Two glass-pained wooden doors frame the entryway, and the reception area reflects that same style. Susan meets me there and gives me a tour of the office, which they renovated in late 2020. I settle into a conference room, and Amy Grant walks in. She shakes my hand, asks about this piece, and says, “We’re behind, right? We’re behind right now. I’m hoping we can hurry up.”
Amy is RRBB’s new COO, and I get the sense she lives life at one hundred miles per hour. Amy wears glasses and likes to talk with her hands. At this point, her eyes get big and, likely without her even realizing, both her hands are up in the air.
Amy Grant, COO
“There is a client need,” she says. “And the client need is the human touch. That’s actually what the clients have been complaining about. It’s one of the top reasons clients switch accounts.”
Over the last decade, the industry has seen a sharp downturn in the number of accountants entering the workforce. Bureau of Labor Statistics’ data shows 300,000 accountants left the profession between 2019 and 2022, and the supply of new accountants has fallen about 17% over the last decade to a 20-year low.
I like how Amy explains it.
“No accountant went to school and studied gruelingly for the CPA exam and said, ‘I want to put numbers in a box.’
I want to take a W-2 and enter that same exact number that was issued into another form in a computer, and then send that off to another highly paid professional so that they can double-check that I didn’t transpose the number.”
While she speaks, though, I’m thinking of Rob’s story about the software that worked but failed to gain adoption at the firm. It was many years ago, yes, but the same risk exists today. The firm has been operating, it’s been growing, by all accounts things are going very well.
Why would this time go differently?
•••
RRBB made one of the most consequential bets in the firm’s history about three years ago.
I FaceTime Dave Roth and he answers from his car, driving to visit a potential acquisition's managing partner. His voice is static, and I ask him about the decision to be the first firm to join Current.
“I use the word guinea pig,” he says, grinning. “But they don’t like that. I’m the experiment. That’s a better word… I wanted to be part of changing a profession. And get some money off the table, too.” A bigger grin.
For RRBB, joining Current was both a big risk and a big opportunity. As Dave puts it, “We took a chance on them. They took a chance on us. We’re in it together, and the new firms should thank us for enduring the mistakes so they don’t have to.”
Dave does not strike me as the type of person to voluntarily sign up to report to someone else. He is an entrepreneur, and I’m not sure he’d make a great employee. I tell him this, he agrees and gets into what made Current compelling to someone like him. He - and his partners - didn’t sell their entire firm. Current bought the majority of it, yes, but Dave and co. kept a good chunk of the firm. Dave stayed as CEO, and the firm kept the RRBB culture while getting Current’s backoffice support. If the firm grows, their value grows with it.
The original partnership didn’t include anything about AI. But in 2025, two things happened: Dave decided RRBB was going all in on AI, and Thrive Holdings partnered with Current. Dave sees AI as the next wave of technology in accounting, much like the computer and internet that came before it. But he knew he wasn’t the right person to lead that transformation, so he went on the hunt. A couple months later, Amy Grant joined RRBB as COO.
One of Amy’s first moves was to volunteer RRBB to pilot a new but unproven AI product from Holdings for the April 2026 tax season.
The experiment, as Dave says.
•••
In January 2026, engineers from Holdings and OpenAI visited RRBB’s office. They would regularly return over the next several months, sitting with RRBB’s accountants to understand the entire flow from tax preparation to completed return.
Remember, while this is happening, another RRBB office is transitioning from paper to digital.
I do enjoy this image. Amidst the talk of tokens and 10xing productivity coming out of NYC and San Francisco, eight engineers cram into a train car for an hour and a half to sit with accountants and together build a product they hope will be useful in the real world.
Rob seems to see tech adoption as a design problem. He introduced me to both Chris and Bobby, two fourth year supervisors on the audit and tax side, respectively. He calls them the firm's AI champions.
Chris, who started at RRBB as a staff accountant, worked closely with the engineering team. He tells me, “The product was… not great the first time I tried it.” He describes rework and inaccuracies, and a growing hesitancy among his peers. Big promises had been made, but he hadn’t yet seen the results and tax season was fast approaching.
Chris keeps laughing while telling the story. He spent January and February skeptical, wondering if he’d ever use this product, then when April came around he was one of the biggest users not only at RRBB but across every firm that piloted Tax AI. “The rate of improvement was crazy,” he says.
“One month I didn’t trust it to do a simple W-2, then a couple weeks later I used it to prep a tax return for a Broadway guy with 25 W-2s.”
In simple terms, Chris went from preparing the return to reviewing it. I often hear tech people talk about ‘higher leverage’ activities, and in many ways that has struck me as fluffy, intentionally non-specific language. Here, for the first time, I felt I saw it happening. In previous years, Chris would pour hours into preparing a single return, which basically means pulling the right numbers from the right forms onto the right text input box, and repeating that process for hours. It is a painstaking process, and one accountants have grown numb to. I’m not sure they realize how brutal it sounds.
I asked Chris how he sees the role of staff accountants shifting. “Just in the three years since I’ve been there, it’s an almost completely different role,” he says. “People are growing a lot faster now, with more time to understand the whys and the risks rather than just punch numbers.”
In a way, this puts more pressure on people like Chris. From a purely mathematical perspective, faster throughput means he can service more clients, and more automation on the backend means a higher value on the client-facing front end. He needs to be more comfortable and more effective interfacing directly with clients than whoever was in his seat a decade ago. That person could largely hide behind a computer, Chris cannot.
I find myself thinking of Dave Roth’s influence on the firm. Specifically, about his risk taking personality and how that infiltrates the decisions being made, even when he’s not present.
I see it in the people most involved with today’s transformation. Amy lights up when speaking about the opportunity in front of them. To think big, “radical,” to think a 65-year old firm in Jersey gets to be on the forefront of how AI gets adopted into one of the biggest and oldest industries in the world. On the audit side, Rob echoes that sentiment, “I’m jealous of the younger generation, man. This industry is going to look so different.”
Compare this mood in the office to when Rob first tried to get through tax preparation software. Then, the partners approved the tool but let it die. Today, the vision is, to be honest, further along than most of the tools.
I ask Amy about this. “You have to set the stage,” she says. “If you want it to work, you have to be relentlessly positive. The hardest part of leadership is controlling the conversations you’re not a part of, and to do that you have to set the vision. You have to repeat yourself over and over.”
To come back to the idea of why this time is different, there is a willingness to experiment across the entire firm. I half-expected Chris and Bobby to sing a very different tune than the partners but, if anything, they’re more excited. “We’re halfway out of the trench,” they say, only part joking.
This is, I think, the formula RRBB has landed on for tech adoption: partner excitement at the top paired with champions to spread the tool amongst their peers through demos and trainings. Amy is the champion pushing for AI adoption across the entire firm, supported by folks like Rob and Dave, and the challenge will be empowering people like Bobby and Chris to be her champions within each of the firm’s departments.
Technology is rarely the hard part. The habits and expectations around it are.
•••
I leave RRBB thinking about a story Rob Quick told me.
His daughter is interning at the firm this summer. She’s a senior in accounting, and when the summer started, some people told Rob they had no work for the interns to do.
“I’m saying it’s bullshit,” he told me. “Have them play with the technology. They’ll learn something, and they’ll be the ones teaching us.”
This is the bet RRBB is making, even as it figures out how to make it work. The firm’s history offers no guarantee that this will be easy but instead something more useful; a long record of learning that the tool itself is not the full transformation, and to get the most out of it requires people and process as much, or more, than technology.
All three of Rob’s kids ended up in finance. His oldest son works at PwC, his middle son sells software at Ramp, and his daughter picked accounting. I sensed some unspoken pride as he was telling me this, and asked if he was glad they followed in his footsteps.
After a couple seconds of thought, he said, “We built it on our own time. We worked during the day, and we went out networking at night. It’s a different world. People want to be able to fit what they have to do for work in a day, and not have to do it at night.” There's no bitterness in his words. “I want all this younger generation to understand: it’s not the grind. It doesn't have to be the grind. The grind can be done by a computer.”