When firms talk about innovation in accounting, they often start with technology. But in my conversation with Nick Pasquarosa, founder and CEO of Bookkeeper360, it became clear that technology was never the starting point for his firm. It was the result of listening closely to small business owners and building systems to solve their most persistent problems.
Pasquarosa founded Bookkeeper360 in 2012, long before cloud accounting was the norm. What began as a door-to-door side hustle helping local businesses reconcile their checking accounts evolved into a nationwide cloud accounting firm serving nearly 1,000 small business clients with a team of more than 75 professionals across 26 states.
“I started this in high school,” Pasquarosa tells me. “It really started with an interest in helping small businesses stop running their business off their bank account balance and [instead] giving them timely, accurate books so they could make real-time decisions.”
5 Advis-ROR® Takeaways
Innovation starts with listening. Bookkeeper360 focused on real small-business pain points before building technology and systems to support better decision-making.
Advisory scales through systems. Workflow, data, and process engines allow firms to deliver consistent advisory value without relying on individual heroics.
Remote-first enables growth. A distributed model expanded access to talent and reinforced a cloud-based operating mindset early on.
AI supports, not replaces, advisors. Tools like Bolt help surface insights and answer routine questions so professionals can focus on client conversations.
Leadership must evolve. As firms grow, leaders shift from daily operators to strategic builders who trust teams and clarify long-term direction.
That focus on small business decision-making, rather than on compliance alone, shaped the firm’s growth. Even as Bookkeeper360 scaled nationally, it remained a fully remote firm, well before COVID made remote work commonplace. Pasquarosa described the shift to a fully distributed workforce as a blessing in disguise, expanding the company’s access to talent and reinforcing a service model that was already built around cloud collaboration.
As the firm grew, so did Pasquarosa’s role. Initially, he was very hands-on, deeply involved in day-to-day bookkeeping, tax work, and client meetings. Over time, he built a leadership team, some of whom have been with him for more than a decade, allowing him to focus on more traditional CEO responsibilities such as strategy, culture, and long-term vision.
“I started as the first bookkeeper, boots on the ground,” says Pasquarosa. “ As the business scaled, I’ve been able to move into a more strategic position overseeing the technology roadmap, culture, branding, and partnerships.”
That evolution was supported by outside peer communities such as EO (Entrepreneur’s Organization), YPO (Young Presidents’ Organization), and Hampton. Pasquarosa emphasized the value of learning from leaders outside the accounting profession, noting that challenges in leadership, communication, and growth often translate across industries.
“It’s about surrounding yourself with like-minded people that strive on getting better,” he says. “Even if they’re not in your industry, there’s a lot to learn from shared experiences.”
Technology eventually became a core differentiator for Bookkeeper360, but only after years of operating as a traditional service firm. The company began as a QuickBooks Desktop practice, transitioned to cloud platforms like QuickBooks Online and Xero, and only later invested in building proprietary technology such as BOLT (Business Optimization Learning Technology). BOLT is a proprietary AI-powered chatbot whose purpose is not to replace advisors but to extend their reach.
“I realized there was no really integrated solution to give clients a convenient, modern way to manage their finances,” Pasquarosa said. “While we were providing services and killing it as a firm, I believed we could deliver a better customer experience by building our own technology.”
Nick Pasquarosa
Pasquarosa
Nick is the Founder and CEO of Bookkeeper360, a company revolutionizing small business accounting. By leveraging cutting-edge technology and personalized services, Bookkeeper360 simplifies back-office management, reporting, payroll, tax solutions, and advisory services. Since founding the company in 2012 while pursuing his Master’s in Taxation at St. John’s University, Nick has led the team to support thousands of businesses nationwide, earning recognition from NerdWallet, Forbes, Inc. 5000, and CPA Practice Advisor. A recognized innovator in the accounting field, Nick has served as a product advisor to industry leaders such as Xero, Bill.com, Gusto, and FreshBooks. His contributions to the profession earned him a spot on CPA Practice Advisor’s “20 under 40” influencer list. Nick is also deeply passionate about entrepreneurship and community leadership. He is the President-Elect, Finance and Governance Chair of the Entrepreneurs’ Organization (EO) Long Island Chapter, a member of Hampton, and a Young Presidents’ Organization (YPO) Long Island Chapter member. Nick’s charitable endeavors include serving as a board member and past President of the Northeast Region of Canine Companions, a nonprofit dedicated to providing support dogs at no cost to individuals in need. A proud Long Island native, Nick enjoys spending time with his wife, Josephine, and their son, Christopher. Outside work, he explores new technology, connects with fellow entrepreneurs, and indulges in his passions for travel, food, and skeet shooting.
That belief led to the development of an in-house engineering team and a fully integrated client platform spanning mobile and web. The platform includes dashboards, file management, scheduling, chat, and performance insights designed to reduce friction for small business owners.
“The truth is every small business needs a CFO,” Pasquarosa says. “But not every small business can afford one.” BOLT was designed to provide CFO-level insights at an accessible price point, with the option to escalate more complex questions to human advisors.
The most common questions BOLT helps businesses with revolve around cash flow and revenue. These are two areas that consistently keep business owners up at night, according to Pasquarosa. By analyzing seasonality, expense growth, and correlations between revenue and marketing spend, the system helps surface trends that would otherwise require hours of manual review, he explained
On the firm side, AI is also being used internally to support advisory conversations. After the month-end close, Bookkeeper360’s systems analyze client financials and surface insights for staff to review before meeting with clients.
“Historically, an accounting manager might have to download financials for 20 clients, analyze trends, and create agendas manually,” Pasquarosa said. “Now AI runs the analysis and informs our internal staff of what’s going on, so they can focus on the conversation.”
That leverage, he noted, helps firms deliver consistent value without burning out staff or relying on heroics to impress clients month after month.
Bookkeeper360 has also built a comprehensive internal practice management system covering workflow, capacity, profitability, and documentation. While the platform is currently used only in-house, Pasquarosa said the firm may eventually license it to other firms or keep it as a core part of its operating advantage.
Looking ahead, Pasquarosa sees AI as a force multiplier for both advisory services and firm operations, not a replacement for human judgment.
“Our goal is to increase leverage and improve how we serve small business clients,” he said. “Technology gives us the ability to do more, but the relationship still matters.”
TRANSCRIPT
(Transcripts are made available as soon as possible. They are not fully edited for grammar or spelling.)
[00:00:00] Narration: Welcome to AFO Wealth Management Forward, a podcast powered by Arrowroot Family Office that’s at the intersection of accounting, wealth management, behavioral finance, technology, and entrepreneurship. We help accounting firms and financial advisors grow their practices by going beyond the numbers, learning from industry leaders and subject-matter experts to discover the secret to their success. A podcast that highlights everything from the transformative power of AI to embracing the human-first approach of behavioral finance to help you understand the psychological and emotional relationships to money and meaning. Here is your host, Rory Henry, director at Arrowroot Family Office and author of Holistic Guide to Wealth Management.
[00:00:44] Rory Henry: All right. Hello, everyone. I have another great guest joining me today. He’s the founder and CEO of Bookkeeper360, a firm that simplifies back office management, reporting, payroll, tax solutions, and advisory services. He’s been recognized by Forbes, NerdWallet, and CPA Practice Advisor. Without further ado, let me introduce my friend, Nick Pascrosa. Nick, welcome to the show.
[00:01:06] Nick Pasquarosa: Thank you, Rory. Pleasure to be here. Thanks for having me today.
[00:01:09] Rory Henry: Yeah. I’m happy to have you on here. I know we have a number of topics we could probably touch on with AI, we can touch on practice management, and everything going on in the accounting space, but before we get started and dive in here, why don’t you give our audience a background yourself and what led you to create Bookkeeper360?
[00:01:27] Nick Pasquarosa: Sounds great. Rory, again, and the listeners, thanks for watching. My name is Nick. I’m the founder and CEO of Bookkeeper360. Bookkeeper360 is a nationwide cloud accounting practice, and we’ve developed proprietary technology that helps serve the needs of small businesses across the country. We specialize in, obviously, in certain bookkeeping, taxation, financial advisory, and back office products for small businesses. It started as a hustle and side hobby that I was just doing door-to-door in my local community. I started this, what became Bookkeeper360, back in high school. The name was not what it is today, and it really started with an interest in just helping small businesses balance their checking account, stop running their business off their bank account balance, and give them timely, accurate books that they could make real-time business decisions and just be better and be smarter. It transformed from a local small business that I was going door-to-door to a nationwide team. We have about 75 team members across the country now supporting nearly 1,000 small business clients.
[00:02:37] Rory Henry: Yeah. Speaking about all those team members and all the businesses you support, obviously, we’re moving into this virtual world. I think you stated that you went from an in-person model to now a fully remote environment. Can you talk about that shift and where you see things moving forward here?
[00:02:53] Narration: Yeah.
[00:02:54] Nick Pasquarosa: We were forced to make that shift, probably like many listeners and firms when COVID happened. Prior to that, we had headquarters out of Woodbury, Long Island, New York. We were a team of about 25, 30 at the time. We were still servicing all of our clients remotely with Google Meets and Join.me at the time, I think it was called. Then it was a forced shift on us, which was actually a blessing in disguise in some ways because it also expanded our horizon and where we were able to source really great team members. We went from just being a New York business to a nationwide business where we now have team members in nearly 26 states. It was definitely just the different dynamics from how we operated as an entity. However, we’ve been servicing small business clients remotely for many years.
[00:03:44] Narration: Yeah.
[00:03:45] Rory Henry: How has your leadership shifted from maybe some of those early days to now in this environment that seems like there’s just technological advances that are transforming the way we do business? I know working with folks remotely is something that is a challenge as well. How do you think your leadership has changed over the course of the last five years here since moving to a virtual-type platform?
[00:04:12] Narration: Yeah.
[00:04:13] Nick Pasquarosa: It’s a really great question, Rory. I think my leadership has changed as my role in the organization has changed. Whereas I started as I was the first bookkeeper, boots on the ground, doing the bookkeeping work, my background’s in taxation. I have a master’s in tax. I could be a CPA, but just never sat for the exam. I was very much in the day-to-day operations of the business, doing the accounting work, meeting with customers, doing the pain points. I was very tactically involved with the business. As the business has scaled, I’ve been blessed to build a leadership team, which some of my core people have now been with me over a decade. That’s allowed me to elevate into a more strategic position in the organization where I oversee the technology roadmap for the business, the culture, the high-end branding, the big partnerships. We run on EOS, which has been a really great platform to help us communicate and get all our ideas on paper and get rocks and to-dos and all that stuff in a cadence of meetings. I wouldn’t say I’m perfect. I’m in groups like YPO and EO and Hampton to continuously improve my leadership style, but it’s something I’m always trying to improve each year.
[00:05:21] Rory Henry: Yeah. Are there any tips that you can provide for our audience that you’ve learned in EOS or YPO? Hampton’s obviously something new. If you want to talk to the audience, I’m sure they may know about YPO or EOS, but if you can talk about what Hampton’s is?
[00:05:36] Nick Pasquarosa: Yeah. These are all entrepreneurs’ communities where you can be paired with like-minded individuals that are not necessarily in your exact business, so you’re not competing with them. It’s not like you are going to give away some secret sauce that you’re going to be like, wow, I wish I didn’t tell someone that because my competitor’s going to steal that from me. What I’ve learned is that even there could be someone in a forum, so I’m in a forum with a CEO of a big nationwide school. There’s a lot of things she talks about in her role and her challenges and opportunities that are translatable for things that I’m going through, maybe I’ve gone through or things I will go through in life. It’s all about my journey of leadership has been constantly just surrounding yourself with like-minded people that strive on getting better. Even though they’re not in your exact same industry, there’s a lot to learn from people and shared experiences and whatnot.
[00:06:27] Rory Henry: That’s the beauty of community. I know there’s a number of communities in the accounting profession that people can share ideas and challenges, but when you are able to go outside of your industry and get others’ input, I think that’s incredibly valuable. I’ve been talking about lately, my friend, Dr. Megan Lurtz talks about do-it-yourself is kind of bullcrap and that we all need coaches, we all need a team, we all need accountability partners to help us move forward here in business and in life.
[00:06:56] Nick Pasquarosa: Yeah, absolutely.
[00:06:57] Narration: Yeah.
[00:06:58] Rory Henry: All right, let’s shift because I know you talked about technology and you work with platforms like Xero, Build.com, Gusto, FreshBooks, Ramp, and others. Can you talk about the integrations that you guys have and how you’re thinking about technology and the roadmap here for BookKeeper360?
[00:07:16] Nick Pasquarosa: Sure. When we started BookKeeper360, I’d be lying to say if we had any software development in our playbook. We started first as a traditional firm, boots on the ground, doing RDP on QuickBooks Desktop. That’s where our roots are in 2010, 2012 era. We evolved and we started using cloud apps like QuickBooks Online and Xero, which are the two GLs that now we support. Until about 2019, 2020, we were predominantly just a cloud-based firm that was utilizing tech, no tech development whatsoever. I held some product board seats on some companies and was very familiar with APIs. Growing up, I always had a love for technology. I was the kid in high school with a Palm Pilot taking notes and I was actually turning on and off the TV with the IR sensors when they still existed. That’s who I was. I was always messing around with technology from a very early age. I realized that there was no really integrated solutions to give clients a really convenient, accessible, modern way to manage their finances. While we were providing services and we were killing it, we were a multi-million dollar firm doing a lot of service revenue, I said it would really be awesome if we can make a pivot and start developing our own technology because I believe that we could deliver a better customer experience. That’s been at the core of everything we’ve done. That’s really what motivates us, what connection that has transformed and built the technology. Today, we have an engineering team in-house. We developed an iOS, Android, and now web app. We also have a practice management suite, which is how our team exclusively manages the workflow of our firm as well. Our customers log into that portal. It provides them everything from dashboards so they can understand their cash flow. They can see their year-over-year business performance. There’s an integrated file manager with Google Drive. They can conveniently schedule meetings with their dedicated team. They can chat with their team. It’s really just an all-encompassing solution for that small business owner. It’s one app that gives them access to a bundle of services and things that they have to do. It’s been a game-changer for us to help streamline the back office of small business clients.
[00:09:30] Rory Henry: I think you stated somewhere that you’re building that through Bolt AI or using that as the AI tool to build out these workflows and build the app. Is that correct?
[00:09:40] Narration: Yes.
[00:09:41] Nick Pasquarosa: The most recent announcement, we just announced in December of 2025 this year, that we just launched and went to market with Bolt. Bolt is our own proprietary chatbot. Bolt can do a lot of analysis and you can ask it questions. It integrates with a handful of the LLMs where we’re sending the data in a trusted manner to the LLMs. We’re asking a series of questions. The data from the financials are being sent in a very much formatted way that the LLMs can interpret it and then it can answer questions like, how much money do I have? What’s my cash burn? How’s my revenue trending? What expenses are growing faster than revenue, et cetera? To help the small business, because that’s the core of what we believe in, we’ve always wanted to pair them with accurate information that they can make timely decisions. The truth is that a lot of small businesses, my belief is that every small business needs a CFO. However, not every small business can afford a CFO, especially full house. Even fractional at times is pretty costly and they just can’t afford it. Our vision for Bolt was to be able to provide fractional CFO level insights for small businesses for a affordable price. Then we have access to a CFO team for more concierge type assistance and more complicated projects and things like that.
[00:11:06] Rory Henry: I think I’m hearing you saying, Bolt and the AI is able to take in all the data and then the small business owner can query the AI to receive answers. If they want things to be escalated to an actual human, they would then get someone at that point to review things. Is that correct?
[00:11:26] Nick Pasquarosa: Exactly. Bolt stands for Business Optimization and Learning Technologies. That’s something we’ve trademarked. That’s our own thing. We pair that with our service team that can deliver more customizable and more human-to-human type of relationship type services as well.
[00:11:41] Rory Henry: I mean, this is relatively new. What are some of the common themes that you’re seeing as far as queries to the AI and the financials? What are most of the small business owners looking at when it comes to asking the AI about their business?
[00:11:57] Nick Pasquarosa: The two biggest things that we see that have been the pain points for a long time have been around cash flow and revenue. Those are the two drivers that keep businesses up overnight, we find. Before we even developed the technology, we asked our team and we asked our customers, what keeps you up at night? We had a good feeling that these are the things that people were talking about, so then we just tucked those common service questions and we developed the technology to automate the delivery of those answers then, if that makes sense.
[00:12:33] Rory Henry: Yeah. Let’s just, for example, can you give me an example of what a potential output would look like for how do I increase revenue? Is there an example that you can provide, Nick?
[00:12:49] Nick Pasquarosa: Things like how would I increase revenue would essentially do analysis of seeing the seasonality trends of your revenue. It would explore if there was new products or new general ledger categories that were added throughout times of the year that they could say have given you the creative revenue growth. It will do seasonality. You’ll see if you had new product launches and see what’s changed over the period. It can also analyze your revenue versus your marketing spend. If you see your revenue is increasing, let’s say 20% year over year, but your marketing spend is staying flat or maybe there’s some correlations that sees, hey, a pickup in marketing has transformed to a pickup in revenue, it can create those types of correlations and communicate that to a small business owner.
[00:13:31] Rory Henry: Are you also able to look at industry benchmarks and analyze the industry as a whole or is it keeping confined to the financial data that’s being inputted?
[00:13:42] Nick Pasquarosa: We do have the benchmarking features. Those are the things that is on the roadmap for 2026 and beyond that we will be investing more in. We do need to work on better benchmarking, but that’s something that we’re scratching the surface on that. But there’s a lot more that we can go deeper with that, which is something that we have our eyes on.
[00:14:02] Rory Henry: Yeah. And then as far as the practice management capabilities here, now, are you selling this to other accounting professionals or is this something that’s just being used in-house right now?
[00:14:11] Nick Pasquarosa: That’s a really great question. So our journey with practice management started back in about 2014. Prior to us developing our own technology to manage our practice, which is an eight-figure practice today, we were using Salesforce and I was a Salesforce architect. I developed a lot of custom objects and workloads and it was pretty much point and shoot, very easy to do.
[00:14:33] Rory Henry: I was doing the same thing around the same time, Nick.
[00:14:37] Nick Pasquarosa: Yeah. It worked. It was great, but it was still a clunky interface, we felt, and it also became really expensive to scale. The infrastructure is really expensive. So we set out, it was about a three-year journey. It was longer than we would have hoped, a few road bumps along the way, but we got there. And we’ve developed the entire practice management suite that does everything from flight management, capacity analysis. We have profitability, time and billing, integrated with the file management, customer tasks, internal tasks, SOPs, month-end closed processes. So you name it, it does it now. And we use it internally. So we’re the only customer of the product itself today, but we’ve showed it off to a few friends in the industry and the feedback has been phenomenal so far. And we are currently evaluating whether we want to productize it as its own product and license that to the accounting community or just keep it close to the heart and keep it just part of the secret sauce that we use to operate officially.
[00:15:39] Rory Henry: Yeah. I mean, it just seems that AI here is really becoming a force multiplier for firms like yourself just to be able to give better insight on the businesses of clients. And then on the personal financial planning side, I’m seeing the same being done over for wealth management, financial planning, be able to ingest all that data, analyze the data, get sentiment insight from the clients, and then give guidance to the practitioner to better serve clientele. What are you seeing? I know we talked about practice management. I know we talked about the Bolt AI. What are you seeing moving forward in the next couple of years here for the accounting professional in the form of technology and practice management for folks out there to run a profitable and growing practice?
[00:16:26] Nick Pasquarosa: It’s a really great question, Rory. We are ready to develop some technology that assists in this fashion. So if you look at the traditional workflow of, let’s say, an accounting manager that’s managing, say, 20 small business clients, in order for them to provide insights, meaningful insights, they would have to download the balance sheet and the P&L for those 20 customers each month, do a historical analysis, find trends, come up with the agenda, have 20 meetings with those customers. And you have to wow those customers each and every time. You start proving that you’re not delivering new wow to the customer, and the customer feels that that leads to churn, that leads to lack of engagement, et cetera. So our technology, not only is our AI strategy, and our customers can access our AI through the customer portal, which is available on mobile, iOS and Android, and the web app, we also have AI technology in the back end, where we run analysis for every single one of the customers once we close the month-end books. So what that AI technology is doing is it’s going to the customer’s books, analyzing the financials, and informing our internal staff of what’s going on with the customer. So look at the exact kind of role I just shared with you. You’re an accounting manager, you have 20 customers, you kind of come up with those agenda points. Historically, you’re popping the hood on each of those, doing a lot of research, and then creating those. Whereas our team is now equipped when they come in, say, on the 15th of the month after the books are locked, AI runs, it creates insights. We’re still in a grading and validation standpoint, where we’re measuring them for relevance and accuracy, and then it’s learning that the insight was accurate, and then it’s essentially providing those insights to the staff internally, which then we can go explore and have those conversations with those customers. So it’s definitely enabling us as a firm to do more, and increasing our capabilities, and we’re about one year in with development on that specific feature, but we’re really focused on that in the long run to making sure we can just increase the leverage and better ways that we service our small business clients.
[00:18:32] Rory Henry: And this is flowing into the tax advisory component, the tax planning for folks out there. Is that currently part of the process, or is that on the roadmap as well?
[00:18:42] Nick Pasquarosa: So we have some internal products that are just available on the back end right now, which we use to identify clients that are probably going to be underpaid for their taxes, or they don’t maybe have a tax plan or tax planning even engaged or set up, and based on their business growth and all that. So we don’t have a tax planning product right now in the app, but it is something that is also on the radar for, probably won’t be available for this upcoming tax season, but certainly for the next one.
[00:19:10] Rory Henry: I love it. I love it. Awesome. Well, this has been great here, Nick. Is there anything else that you want to touch on here and share for our audience members?
[00:19:20] Nick Pasquarosa: I think we’ve covered a lot of it. We’d love to meet any firms that are interested in the technology. It’s something that we’re building a list of interested parties and firms that may want to license it. So if you find this interesting or your small business owner that wants to use the tech, we’d love to meet you. And you can find this at bookkeeper360.com.
[00:19:38] Rory Henry: Awesome. I’ll put that in the show notes. I appreciate you coming on, Nick, and I look forward to talking to you again. My pleasure, Robert.
[00:19:45] Disclaimer: Thanks so much. Thank you, buddy. Appreciate it.
All opinions expressed by Rory Henry on this website podcast interview are solely their opinions and do not reflect the opinions of Arrowroot Family Office, LLC, or their parent company or affiliates, and may have been previously disseminated on television, radio, internet, or another medium. You should not treat any opinion expressed by anyone as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of their opinions. Past performance is not indicative of future results.All opinions expressed by Rory Henry on this website podcast interview are solely their opinions and do not reflect the opinions of Arrowroot Family Office, LLC, or their parent company or affiliates, and may have been previously disseminated on television, radio, internet, or another medium. You should not treat any opinion expressed by anyone as a specific inducement to make a particular investment or follow a particular strategy, but only as an expression of their opinions. Past performance is not indicative of future results.
