Started trading stocks with his mom's social security number in middle school…
Built a six-figure business from his parents' basement before finishing high school…
Now manages $3.4 billion in client transactions annually.
That’s the scrappy journey Hampton member Nick Pasquarosa took to build Bookkeeper360, a $10M+ accounting empire transforming how small businesses handle their finances. In this exclusive Hampton interview, Nick reveals:
- The Craigslist hustle that landed his first clients before he even started college
- How rejecting the traditional hourly billing model disrupted the accounting industry
- Why ordering 360 Taco Bell tacos became an unexpected client acquisition strategy
- The jaw surgery complication that nearly bankrupted the company at its most vulnerable moment
- Why turning down $30M in venture capital might have been his smartest business decision
If you're wondering how to bootstrap your way to eight figures while competing against VC-backed giants, Nick has some words of wisdom for you:
Hello! Who are you and what business did you start?
Hi, 👋 My name is Nick Pasquarosa, and I’m the founder and CEO of Bookkeeper360.
Bookkeeper360 is an accounting solution that helps small businesses eliminate the headaches of managing their finance department so they can focus on growth and free up time for personal life.
At Bookkeeper360, bookkeeping is just the start! We offer a complete financial service suite— year-end tax preparation and planning, payroll, fractional CFO support, back-office services, and technology consulting. While we began as a service-only firm, we’ve evolved into a tech-enabled firm with proprietary AI-powered software that delivers real-time financial insights and seamless communication with your dedicated accountant, and we have a mobile app coming out soon. Our platform integrates with Xero, QuickBooks Online, and Gusto Payroll, all backed by our U.S.-based in-house engineering team.
We’re proud to serve over 1,000 clients nationwide—covering nearly every state in the U.S. In 2024 alone, we oversaw more than $3.4 billion in client transactions, and today we’re a $10M+ business.
We specialize in supporting service companies, retail/e-commerce, technology ventures, real estate brands, and more. Our typical client is in the startup or growth stage, with up to $30 million in revenue. We’re an ideal fit for growth-minded entrepreneurs who understand the importance of solid financial reporting but lack the time or expertise to handle the books on their own.
What's your backstory and how did you come up with the idea?
I’ve always been passionate about numbers and dreamed of becoming a finance professional. I started trading stocks in middle school using my mom’s social security number. I made a lot but also lost a lot, which taught me I wasn’t cut out for the rollercoaster of daily market swings.
My mom, an entrepreneur and interior designer, needed help creating invoices in bookkeeping software, so I took an accounting class in high school. Around the same time, we launched an eBay business (this was before Shopify), and I was responsible for everything from creating listings and promotions to handling the finances—often during my high school classes. That experience led me to enroll in a college-level accounting course in high school. I’ll never forget my teacher emphasizing that accounting is the language of business. At that moment, I knew I’d found a field that truly sparked my interest.
In my senior year of high school, I landed a job on Craigslist as an administrative assistant for a financial advisory firm. That opportunity led to part-time tax work with a CPA in the same office and some basic bookkeeping for the firm’s clients. Feeling inspired, I decided to incorporate and start my own company. My first office was my bedroom in my parents’ basement, where my desk took up half the space.
I found several of my first clients on Craigslist, and through word of mouth, I generated a six-figure income before even heading to college. Looking back, I sometimes wonder if I should’ve skipped college since I never sat for the CPA exam. I graduated from St. John’s University with a Master’s in Taxation Accounting—though I never attended a dorm party or got the typical college experience because I was consumed and focused on building what would become Bookkeeper360.
There was never a grand plan for Bookkeeper360 to become a nationwide firm with clients and team members scattered across the country. The true ‘aha’ moment came when an entrepreneur from Brooklyn—someone I’d never met—called and asked me to handle his books. I offered to drive out to meet him, but he said he didn’t even have an office and worked out of Starbucks. Five minutes later, he sent me his Chase bank account login and emailed his tax returns, lighting the spark that ultimately fueled my ambitions.
Take us through the process of building and launching the first version of your product…
In the early days at Bookkeeper360, we focused on what small businesses needed for critical decision-making, how much they could budget for outsourced services, and which technologies would make everything more efficient.
One of our best decisions early on was partnering with Xero Accounting Software. Before Xero, we relied on remote desktop servers running QuickBooks Desktop, which was clunky and often unreliable—so much so that we spent more time fixing printing issues than discussing finances. Xero’s cloud-based model and multi-user support allowed our team to collaborate with clients anytime, anywhere—completely transforming our workflow. We quickly became one of Xero’s top bookkeeping partners and resellers nationwide, and we were honored to receive their Top Partner award in two separate years. As a bonus, we got plenty of Xero swag to fill our office!
From early on, we chose to bundle our solutions offerings and provide transparent pricing so business owners could easily budget for our services. This gave them a clear understanding of what they were paying for. Bookkeeper360 was the first to introduce bronze, silver, and gold value-based pricing plans, allowing clients to choose between quarterly, monthly, or weekly bookkeeping updates.
Traditionally, CPAs and accounting firms billed by the hour, leaving business owners with unexpected charges months later. Our transparent pricing approach fueled much of our early growth. Over time, we refined our packages to be more flexible. Clients often called or emailed saying, ‘I want your monthly bookkeeping package—the Gold Package.’ In less than half an hour, we had their banking access, prior tax returns, and the first month’s fees processed, and then we were off to the races.
From 2012 to 2017, we expanded our offerings to include payroll and HR admin, back-office support, fractional CFO services, and tax preparation and planning. We leveraged third-party technologies like Gusto and Bill.com, which integrated seamlessly with Xero and QuickBooks Online.
In 2018, after attending Xerocon’s annual conference—where we accepted our Partner of the Year award—I had another ‘aha’ moment on the plane ride home. It hit me that clients didn’t just need reconciled bank and credit card accounts; they needed real-time reporting and insights that told a story, empowering them to make smarter decisions. That realization sparked my drive to develop the Bookkeeper360 software.
Since launch, what has worked to attract and retain customers?
Looking back, there’s always something a founder wishes they had done differently. Still, we’re proud of where we stand today—supporting thousands of small businesses across various industries over a decade. We’ve had the privilege of working with some incredible brands and entrepreneurs, and we truly believe we’ve helped them along their journey.
We discovered early on that offering great service at a fair price naturally attracts referrals. Since we bootstrapped until 2022, reinvesting profits into software development rather than flashy marketing campaigns, we learned how to stand out by letting our work speak for itself. We also set ourselves apart by offering month-to-month contracts, which give clients the flexibility to leave with just 30 days’ notice—creating a low-risk way to try our services.
Our mix of services lets clients begin with basic bookkeeping and then seamlessly add tax, payroll, back-office advisory, and other accounting solutions as they grow. Focusing on our clients’ evolving needs has consistently paid off, inspiring us to build a mobile app so they can message their dedicated accounting team right from their phones.
Happy staff means happy customers. In our very first office, I had my own private space, but by the time we moved to a larger office for 40 employees, I chose not to have an office at all. There was no door, no barrier—just an open, collaborative environment. This decision was about fostering a culture where anyone could walk up to me at any time, helping build the strong team dynamic we have today.
Here’s a glimpse of our Woodbury, Long Island, New York office and snapshots of the fun activities that energized our team over the years. We’ve always believed that a strong cultural strategy creates an environment everyone wants to participate in.
One of our favorite annual traditions—back when we had a physical office—was our Cinco de Mayo celebration. We’d order 360 beef tacos from Taco Bell (yes, we had to call in advance so they knew it wasn’t a prank), and we challenged ourselves to finish them all. Other CPAs and accountants in the building couldn’t resist the fun and started asking to join the festivities each year—some even referred clients to us over the years. Never in a million years did I think a taco party would generate business for us, but luckily for us…it did!
How are you doing today and what does the future look like?
Today, we’re a $10M+ business with low client acquisition costs and rising gross profit margins—thanks mainly to our technology, which boosts our team’s efficiency and improves the client experience. Our virtual team of 100 CPA’s and professionals supports over 1,000 small businesses nationwide, and in 2024, we processed $3.4 billion in client transactions.
We’ve always run the company lean and don’t tolerate unproductivity—our culture naturally weeds it out over time. Over the years, we had multiple opportunities to raise more than $30M in venture capital but turned them down. Maybe that’s kept us from hitting $50M+ in revenue, but we’ve managed to scale while maintaining a healthy work-life balance for our team—and I’ve retained control as founder.
We’re up against ‘capital-raising giants’—competitors who’ve secured over $160M at valuations in the hundreds of millions and billions. Unfortunately, some have imploded, only reinforcing my commitment to a steady, fiscally responsible approach. It might not be the flashiest path, but it’s how I plan to win this race.
The future at Bookkeeper360 looks bright, and our team can’t wait to launch our new mobile app in just a few weeks. Let us know if you’d like a heads-up when it’s ready!
Did you ever have an “oh shit” moment where you thought it wouldn’t work?
In 2014, I had triple jaw surgery to correct an underbite, which meant my mouth would be wired shut for weeks. For someone who thrives on communicating with people, that alone was challenging. Unfortunately, I faced a post-surgery complication that required spending five hours a day in a hyperbaric chamber—right when we had just expanded our Long Island office and taken on a significant rent bill, equal to about 10% of our revenue at that time. We needed the space to grow, but the timing couldn’t have been worse.
With me out of commission, our team felt leaderless, our bank account nearly went into the red for several months, and everyone worried. As a subscription-based business, we were always relieved when the first of the month rolled around and revenue posted. Still, it was a challenging time that almost brought us to bankruptcy.
Focusing on small wins daily kept me motivated. Over the years, I’ve shared this story with other founders, and it’s clear that persistence—and celebrating those small victories—eventually leads to remarkable outcomes.
In addition, I’ve had my share of head-butting with some of our earliest investors, which proved distracting. My advice to any entrepreneur is to make sure you and your investors are aligned, especially if you plan to reinvest profits instead of distributing them. Fortunately, we’ve moved past those issues. We now have a small group of investors who believe in our team and mission, and we don’t have any institutional investors on our cap table—yet.
Where do you see untapped opportunity in the market? What business do you wish someone else would build that would make your job easier?
There’s an incredible opportunity to offer strategic, meaningful coaching to business owners. Often, once founders reach the $2–3M revenue mark, their operations become far more complex. We plan to go deeper by helping entrepreneurs and operators understand their financials, manage cash flow, create brand value, and eventually prepare for an exit and life-changing financial impact.
Our industry still waits for a company or a solution to automatically code and reconcile bookkeeping, debits, and credits. That breakthrough would allow Bookkeeper360 to focus on higher-value services and cultivate strong client relationships. I’ve watched dozens of firms raise tens of millions of dollars to solve this challenge, only to fail. Many of those companies—names withheld—aren’t around anymore or on the verge of extinction.
What platform/tools are absolutely crucial for your business?
- Of course, the Bookkeeper360 App Software!
- Xero and Quickbooks Online, Gusto
- Google Suite, ClickUp, Slack, Grammarly
- Chase Bank, American Express, Ramp, Bluevine
- A2X, Cin7, Chargebee, Stripe
- Hubspot, Github, Cursor
What have been the most influential books, podcasts, or other resources?
- Turning the Flywheel by Jim Collins
- The Speed of Trust by Steven Covey
- Scaling up by Verne Harnish
- Traction by Wicman (we run on EOS)
- E Myth by Michael Gerber
- The Accounting Podcast by Blake Oliver and David Leary’
- How I built this with Guy Raz Podcast
Advice for other entrepreneurs who want to get started or are just starting out?
Ditch the 10-page business plan and condense it to one page—you’ll revise it plenty of times anyway, and pivoting is normal for any startup. Focus on something you’re passionate about that genuinely makes life easier for others. It’s not just what you do, but how you do it. You don’t need to reinvent the wheel to launch a business; just solve someone’s problem more efficiently.
As your team grows, if you’re ever uncertain about a process or strategy, tackle it head-on. Don’t be afraid of direct conversations—especially when working remotely.
Raise capital strategically and only for specific initiatives—like driving efficiency, boosting margins or cash flow, or scaling a proven product. There may be thousands of ways to fund a business, and millions of dollars sitting in private equity’s bank accounts, but strong operators are far less common. Fundraising can quickly become a major distraction, so stay focused on what really matters: delivering an outstanding client experience.
Can you share a specific example of how being part of the Hampton community has helped you achieve a goal or tackle a challenge?
The Hampton community is a group of forward-thinking individuals who openly share experiences with the goal of collective improvement. It gives entrepreneurs access to resources that often go unspoken. If I have a marketing question, someone in our community will offer insights from a software or skill they’ve mastered.
A few months ago, I had lunch with Joe Speiser, CEO of Hampton, and we discussed various scaling and fundraising strategies. When I mentioned considering a private equity investor, he strongly advised against it, echoing my internal concerns. Hearing his perspective—especially since he’s built and exited businesses and earned those extra gray hairs—was incredibly reassuring.
Hampton is filled with bold, bright entrepreneurs who thrive on helping one another become better leaders. They genuinely want success for everyone in the community.
Where can we go to learn more?
- www.bookkeeper360.com
- https://www.linkedin.com/in/nickpasquarosa/
- https://x.com/nickpasquarosa/
- We’re Hiring! See our open positions here https://bookkeeper360.com/careers
Personally, I find being the CEO of a startup to be downright exhilarating. But, as I'm sure you well know, it can also be a bit lonely and stressful at times, too.
Because, let's be honest, if you're the kind of person with the guts to actually launch and run a startup, then you can bet everyone will always be asking you a thousand questions, expecting you to have all the right answers -- all the time.
And that's okay! Navigating this kind of pressure is the job.
But what about all the difficult questions that you have as you reach each new level of growth and success? For tax questions, you have an accountant. For legal, your attorney. And for tech. your dev team.
This is where Hampton comes in.
Hampton's a private and highly vetted network for high-growth founders and CEOs.
