He Raised $80 Million To Build An AI-Driven Tax Platform To Enable Users To Plan And Manage Their Taxes Throughout The Year
Some founders are shaped by success. But Ben Borodach’s journey is forged by the lessons of failure, reflection, and the relentless pursuit of doing it better the second time around. The co-founder and CEO of april, he learned extensively from an early stumble.
Ben went on to master the inner workings of enterprise systems and returned a decade later to build one of fintech’s most ambitious platforms. He went on to raise an impressive $80M for his company.
Early Curiosity and the Spark of Entrepreneurship
Born in the Bronx and raised in New Jersey, Ben grew up in a bustling home as the eldest of four. His parents were both lawyers, so naturally, the plan was to follow in their footsteps. But a curious mind and an affinity for problem-solving took him elsewhere.
At NYU, a pivotal class changed everything. The course Ready, Fire, Aim, taught by venture capitalist Larry Lenihan of FirstMark Capital, emphasized building before overthinking. It came with a twist. The winning student received $12.5K in seed funding from the professor’s own salary. Ben won.
Building His First Startup and Learning the Hard Way
While still in college, Ben co-founded Publish, a marketing and content automation platform that aimed to bridge the gap between CRMs like Salesforce and the dynamic web. At the time, Ben and his cofounder were sophomores at NYU and Rutgers, respectively.
The duo was doing marketing and website consulting for small businesses. They were learning about building websites and what businesses needed to drive leads. This was 2010, when HubSpot and Marketo were defining inbound marketing, and the idea of personalized B2B content was still novel.
The idea behind Publish was to render content, primarily in the B2B space. Think webinars, eBooks, podcasts, white papers, and more, dynamically serving up the content to the customer base.
Backed by FirstMark Capital and New York Angels, the young founders raised $250K, a significant seed round at the time. The New York Angels was also interested in backing the company that two students were running out of their college dorm rooms.
Yet, like many first-time entrepreneurs, the co-founders soon discovered how little they knew about scaling.
“We didn’t understand how to go from MVP to production, or how enterprise contracting even worked,” Ben recalls. “We got a big corporate interested, and when they asked for a contract, we didn’t even know what that meant.”
Instead of burning more investor money, Ben and his co-founder shut down the company, a decision driven by humility rather than pride. That failure taught him two core lessons: how hard startups really are, and how much he loved building and scaling technology.
A Decade of Learning Inside the Machine
Determined to fill his knowledge gaps, Ben did something unconventional for a tech entrepreneur. He joined Deloitte Consulting, diving deep into the world of finance, insurance, and payments. It was, in his words, a “masterclass in how business is actually run at the highest level.”
As Ben recalls, the position gave him unparalleled access to the world's leading financial executives, as well as the largest insurance and payments companies. He also gained a first-hand look at the problems they faced and the challenges that they had in running operations.
At Deloitte, Ben became the go-to person for solving complex innovation problems across Fortune 500 companies in sectors such as insurance, wealth management, and banking. He quickly developed real expertise within financial services.
This was where Ben learned to navigate enterprise structures, understand regulatory challenges, and observe the friction that slowed transformation, especially in financial services. He was more interested in customer or direct-to-consumer apps. But corporate life was only one chapter.
Valuable Lessons Learned in Entrepreneurship
As Ben reminisces, he could have gone on to build another startup or become a product manager. But being an entrepreneur is the ultimate exercise in humility. We tend to idolize highly successful entrepreneurs and place them on pedestals.
It’s crucial to remember that behind their success stories are tons of failures. They reached the pinnacle of success by digesting failures, reflecting, pivoting, and moving forward. Recognizing failure is key to succeeding the second time, as Ben points out.
He considers himself a self-diagnosed systems thinker who admits to his shortcomings and sets out to cover the gap. Thus, Ben learned enterprise sales processes and requirements, as well as how to build relationships with enterprise buyers.
He is grateful for his time at Deloitte and for the way they invested in young professionals.
Working at Team8, the Israeli Venture Fund
Eventually, Ben joined Team8, an Israeli venture fund founded by former intelligence officers. Here, Ben worked with Nadav, who had a thesis. Nadav strongly believed that strengthening cybersecurity and solving highly challenging technical challenges needed more than just adding venture capital.
What was needed was to bring together the world's largest platforms—like Microsoft, Cisco, and Citibank—and have them invest in a single platform. This platform would allow entrepreneurs to think beyond just building for the next 6 to 18 months. It would attract talent to solve technical snags.
Thus, Ben joined as the chief of staff and led corporate strategy for the robust go-to-market platform. He helped scale the firm from a $40M AUM fund to a family of 4 to 5 funds with about $1B AUM across multiple funds.
His four years at Team8 taught Ben two enduring lessons: to think at a massive scale and to build with long-term horizons. “You can’t iterate on a Fortune 500’s infrastructure,” he says. “You need to de-risk in stages and think in years, not months.”
Ben learned that Fortune 500 companies need a different build model that breaks risks into smaller components and addresses them one at a time. This was a crucial learning that he would leverage when building april, his next venture.
In retrospect, Ben conceded that he was never really passionate about cybersecurity, and he saw hacking as more about slowing organizations down. However, he could see how the largest of them was dealing with tons of complex patchwork, which was very inspiring for Ben.
He wanted to unlock business productivity, not play offense and defense against the bad guys. Team8 gave Ben exposure to Nadav, a general, and Admiral Rogers, who ran the NSA and became an operating partner in the company. Furthermore, Doug McMillan from Walmart would regularly visit the office.
Founding april: Fixing the U.S. Tax Experience
Out of Team8, Ben spun his next big idea, april, a fintech startup aiming to entirely reimagine how Americans do their taxes. For decades, U.S. taxpayers had only two options: an accountant or legacy software like TurboTax.
april addresses the totality of the tax experience for 170 million American households and 32 million small businesses that pay $3T in taxes annually. Ben wanted to optimize that huge problem by building the first national tax engine in 20 years. It was his superpower to think big.
It took Ben and his cofounder, Daniel Marcous, three years to build april, the national tax engine. They started with the IRS and a couple of states and scaled to other states, fintechs, and organizations.
These entities were already building on top of april’s infrastructure pilots and initial rollouts. This strategy enabled Ben and Daniel to de-risk the model and technology. Since Ben spun april out of Team8, the company has become an investor and is now a board member.
Finding the Right Co-Founder: A Match Built on Values
Ben describes finding Daniel Marcous as “co-founder dating.” Ben recognized himself as more of an operationally minded and business-oriented person. He needed to partner with a technologist.
Ben was looking for someone who shared his views about the world and his grit to take on the problem of this magnitude. He needed a cofounder who was a good person, would work hard, and could challenge him while complementing his skill sets. He was looking for the right fit.
During the pandemic, Team8 helped him connect with technologists who shared his vision. What sealed the partnership wasn’t just skill alignment, but philosophy. At the time, Daniel was the CTO of Waze and Google Israel, “a very prolific data scientist, and a wonderful person,” as Ben says.
The duo each wrote lengthy “manifestos” about what they believed in, the world, and how they envisioned making the venture successful. They edited each other’s writing until there was no disagreement left. This approach became the cornerstone of a four-year partnership.
“That’s how we’ve run april ever since,” Ben says. The pairing worked. Daniel became the product visionary, excelling in taking ideas from “minus one to zero,” while Ben focused on scaling, partnerships, and strategy.
The april Business Model
As Ben explains, the genesis of april is taxes, which is a very painful activity for Americans across the board. Currently, it's siloed, retrospective, and once a year. Ben wanted to embed tax directly into the financial tools people already use--banking apps, payroll systems, and digital wealth platforms.
april is a platform that integrates tax considerations into financial decisions. It’s the most connected tax software in the world. Ben markets the product as a white label version of TurboTax to the largest banking, wealth management, and payroll platforms in the US.
Raising $80M and Navigating the Market Swings
Armed with a bold vision and a clear strategy, april raised $80M across three rounds, including a recent $40M Series B led by QED Investors. But the road wasn’t smooth. As Ben learned, entrepreneurship that involves venture capital is a rule of exceptions.
Founders have to be willing to take leaps and to enumerate them. When pitching to investors, they must iterate on their conviction in making their products work and in evaluating their success. With april, Ben realized that building the tax engine involved crossing technical and regulatory hurdles.
The april platform was the first of its kind in 10 to 15+ years, and the software and company had to get approval in every US state. Furthermore, they had only one shot per year to do it and then prove it. Aside from regulatory approvals, they also had to prove to customers that april could work.
Proving Traction and Customer Engagement
Investors and customers wanted to see april’s track record and traction, including acceptance rates and resolution rates over multiple years. From a business model standpoint, there was also a risk that digital banks, payroll companies, and others would not adopt these capabilities or pay for them.
Over the next three years, Ben and Daniel proved that their target customers were willing to engage and derive value from it. They showed that digital banks were attracting more deposits on their platforms and wealth management companies had higher LTVs.
The duo also proved that small business platforms generated millions in fees. Their customers didn’t just refer their business to an accountant; they were open to engaging in a more wholesale SaaS arrangement with april.
The company raised its first $40M at the peak of the 2021 fintech boom. And then the market cooled.
Remember to unlock the pitch deck template that founders worldwide are using to raise millions below.
Investors wanted instant revenue, not multi-year infrastructure builds. “We had told everyone we were going to spend three years building before revenue,” Ben recalls. “That wasn’t fashionable at the time.”
The discipline paid off. april grew from zero to its first million in revenue, then 9x growth the following year, validating the long-term thesis. Ben gives a shout-out to Edie and Nigel, who he calls “amazing team members,” who made things happen at april.
Lessons in Redemption and Growth
For Ben, the journey from his dorm-room startup to leading a high-growth fintech isn’t just about success; it’s about redemption. He considers self-doubt a significant factor. As he points out, at different phases of his journey, he needed patience and finesse, which weren’t his strong suits.
Ben considers himself better suited to be an entrepreneur for the middle and later stages of his founder path. The parts that really challenged him at the early stages were the minus one-to-zero and the zero-to-one transitions. Now he is well beyond the one point.
In some ways, Ben is relieved to be moving beyond the gate because now he’s “dealing with a business that’s in the market and competing every day to win market share.” And that's obviously what he loves as an entrepreneur— and why he’s in the game. It’s an inventive process.
Ben credits Daniel with being the inventor who shaped the partnership. Daniel excels at taking things from minus one to zero and enjoys the process. Although Ben tries to contribute, that part of april is entirely Daniel's. The duo has benefited from being great partners, as Ben points out.
The Vision Ahead: Tax as an Always-On Financial Engine
In Ben’s view, taxes aren’t just compliance; they’re one of the biggest untapped data assets in the economy. Americans pay over $3T in taxes annually, yet most lack real-time visibility into how tax affects their daily financial decisions.
As Ben points out, the single largest check or the largest or second-largest expense of the year, for most individuals and businesses, is their tax bill. And taxpayers lack optimization for it. People rely on bankers, advisors, and CPAs for help.
But it’s time to move toward consolidated software platforms that will primarily serve taxpayers, augmented in some cases with human assistance. These platforms will recognize what humans need and optimize for them.
april’s mission is to make tax intelligent, embedded, and personalized. Imagine your bank, brokerage, or payroll app automatically telling you how to optimize your cash flow, save more, or prepare for, say, stock sales. All of this is now powered by real-time tax intelligence.
“Tax should be the backbone of every financial platform,” Ben says. “If you know someone’s tax situation, you know almost everything about their financial life.”
april is about bending the curve on one hand—how tax manifests itself and how decision-making is presented to the customer—so they're actually getting more dollars back in their pockets. Most importantly, the platform adapts to individual customer needs.
In Ben’s opinion, when we think about an agentic future or a self-serve personalized future, tax is a must-have behind every financial services provider. The future we imagine is one in which tax is embedded everywhere, particularly where the financial infrastructure powers it.
Advice to a Younger Self: Don’t Be So Hard on Yourself
If Ben Borodach could offer his younger self one piece of advice before launching a business, it would be simple: don’t be so hard on yourself. As someone who has always been his own harshest critic, Ben admits that his drive for excellence often came at a personal cost.
Over the years, Ben has pushed himself relentlessly, sometimes to the point of neglecting his own well-being. A health scare last year, when he lost a bit of vision in one eye, became a wake-up call. It forced him to reexamine how he approached work, health, and longevity as a founder.
“It’s a reminder that if you’re already doing everything you can, you don’t need to worry so much,” Ben reflects. “Make sure you enjoy life and the process along the way.” He encourages entrepreneurs to find balance early on, to prioritize what truly matters rather than equating effort with endless hours of work.
Redefining Work: Lessons from a Professional Athlete’s Mindset
With experience, Ben’s definition of “work” has evolved. Early in his career, productivity meant sitting at a computer until he was exhausted.
Today, he views his professional rhythm through the lens of a professional athlete, sometimes playing the game, sometimes training, sometimes resting, and sometimes strategizing.
Now, preparation extends beyond the desk: his diet, exercise, thinking time, and even informal activities like recruiting or networking outside the office all contribute to Ben’s effectiveness.
“You have to look at all of it as part of the equation,” he explains. “And that balance shifts depending on your career stage, the business you’re building, and your strengths.”
The Compounding Power of Experience and Efficiency
With maturity also comes efficiency. Tasks that once took Ben a week can now be completed in an hour. Where it once took a month of networking to reach the right person, today it’s often just a phone call away.
Ben likens this compounding effect to what happens at the highest levels, with founders like Elon Musk or Mark Zuckerberg, who can compress massive impact into minutes.
For Ben, success today isn’t about clocking more hours; it’s about maximizing leverage and clarity. The key, he says, is taking a wider view, focusing not on how long you work, but on how intelligently you work, and ensuring that your drive to build doesn’t come at the cost of living.
In Conclusion
Ben Borodach’s story is a rare blend of first-time failure, deliberate reinvention, and world-changing ambition. “I made every first-time founder mistake possible,” he reflects. “But the key is to diagnose your gaps, learn what you don’t know, and come back stronger.”
From building websites in college to redefining how 170 million Americans manage taxes, his journey reminds us that true entrepreneurship isn’t about speed; it’s about the stamina to keep learning, building, and scaling what truly matters.
Ben Borodach’s early startup failure became the foundation for a more disciplined, world-class approach to building april. · A decade inside Deloitte gave Ben rare mastery of enterprise systems, regulation, and financial-services complexity. · Team8 taught him to think in decades, not months, and to de-risk massive infrastructure challenges step-by-step. · april was built to reinvent the entire U.S. tax experience by embedding real-time tax intelligence into financial platforms. · Ben and co-founder Daniel formed a values-aligned partnership grounded in shared “manifestos” and complementary strengths. · april’s traction proved the power of long-term conviction, growing from zero to millions in revenue despite market swings. · Ben now prioritizes balance, efficiency, and well-being, urging founders not to be so hard on themselves as they build.
Original Version
Alejandro Cremades: Alrighty, hello everyone and welcome to the DealMaker Show. So today we have ah another guest, you know, another guest that, team again, you know, quite an inspiring conversation that we have in front of us. We're going to be talking about the good stuff of the building, the scaling, the financing,
Alejandro Cremades: You know, when things go well, when things go not so well, you know, so we're going to be talking. I always say that either succeed or you learn. So there's going to be quite a few lessons from, ah you know, the previous venture that he did. But right now, his current venture is a rocket ship. So, again, you know, we're going to learn about the founding story,
Alejandro Cremades: You know becoming co-founders with his co-founder, raising $80 million, bucks I mean, you name it. but So brace yourself for quite the conversation. So without further ado, let's welcome our guest today, Ben Borodak. Welcome to the show.
Ben Borodach: Thank you so much for having me, I don't remember too much of that.
Alejandro Cremades: So originally born in the Bronx, but raised in New Jersey. Give us a walk through memory lane. How was life growing up for you?
Ben Borodach: it was It was more known as Riverdale, I guess, which is technically in the in the Bronx. And my parents moved to North Jersey when I was fairly young. I'm the oldest of four siblings, so it was a pretty crazy time.
Ben Borodach: I had two siblings, two years, ah both sequentially after me, so it was already always a pretty rambunctious time growing up.
Alejandro Cremades: That's amazing. And how did you get into like the whole thing of computers problem solving? I mean, was that something that you developed while growing up or or where did that spark from?
Ben Borodach: I was raised by two lawyers, so I always thought that I was probably going to be a lawyer because that's what I think other lawyers sort of instill upon you. And yeah at some point in my time at and NYU, I met this professor named Larry Linehan, who was a venture capitalist at First Mark Capital, which was, I think at the time, sort of one of the still probably one of the preeminent firms specifically headquartered out of New York. and he taught a class in the business school called Ready, Fire, Aim, and it was all about bill build first and ask questions later.
Ben Borodach: And so I took that class and won an astounding $12,500 as an investment, which was his salary, I guess, from the NYU business school and sort of parallel tracked my first company while attending university.
Alejandro Cremades: I mean, I remember ah Larry from back in the day. I mean, the guy was always like super well-dressed from head to toes. And he was saying that was something that i remember from Larry. That's for sure.
Ben Borodach: I don't think I've ever met a venture capitalist that dresses as well as Larry, that's for sure.
Alejandro Cremades: That's amazing. anything so So obviously, you know, like during this time is when you got started, as you were alluding to the first company. So that was called Publish. So give us give us some, you know, ah highlights on on perhaps what were the, you know, sequences of events there for you to get going with the company? You know how it all happened with FirstMark also backing you guys on what you were doing and then also, you know, what happened, you know, with the with with the with the outcome of the company.
Ben Borodach: Yeah, so we were very young. We were sophomores at NYU and Rutgers, where my co-founder was at the time. And we had this idea, we had been doing marketing, marketing and website consulting for small businesses. So we started to learn about building websites and sort of what businesses need to drive leads.
Ben Borodach: And this was sort of back in 2010, 2011, when CRMs were really blowing up HubSpot, Salesforce, Marketo and others. And we realized there was sort of a disconnect between the CRM and the content that was on the website.
Ben Borodach: And so the idea behind the company was to basically dynamically render content mostly within the B2B realm. So think webinars, eBooks, podcasts. other other white papers and and more dynamically serve up the content ah you know to the to the customer base. I think we would have been super successful had to be stuck with it. So we raised about a quarter million dollars, which back then was actually a seed round.
Ben Borodach: The New York Angels wanted to put more money into the company and we were kind of running this out of our college dorm rooms while telling our parents that we were sort of getting our degree, which we all eventually did get. and I think it was just a classic story story of making way too many first time mistakes. We didn't really understand how to go from an MVP to a production scale product. We didn't fully understand ah even what the enterprise contracting process would look like. So we finally got a buyer.
Ben Borodach: i think it may have been someone on the marketing team at Trinet or one of the other POs that was interested in this. And then they were like, okay, send me a contract. And we were sort of just not even exactly sure how to proceed. And so I think what it really inspired me you know with, and ultimately what we decided to do is just not take on more capital. So we ran it kind of on ah out of the dorm room for another year and eventually realized probably we didn't have what it took at that point. And so I think it gave me couple of really important lessons. One is,
Ben Borodach: how hard it was to build a successful startup company. And it actually took me about 10 years until I was willing to try it again because I had to go learn everything I found out that I didn't know. um And the second thing is how much I loved building and scaling technology.
Ben Borodach: And so from there, I went to Deloitte Consulting, which was probably not the classical thing that a tech entrepreneur would do, but it gave me unbelievable access ah to the largest financial executives in the world, the largest insurance companies and payments companies, and and sort of the problems that they were facing on the one hand, and also sort of the the the challenges that they had in operationalizing those. And so it really gave me a masterclass in how business is run at the highest level within financial services. And I became the go-to person at Deloitte for answering challenging innovation questions um you know across insurance, wealth management, and banking. And so it allowed me to get sort of an unparalleled access and also develop a real expertise within financial services.
Alejandro Cremades: So talking about future here, let's say shift to the past to the lens of reflection. You know, let's say I was to um give you the opportunity of getting to a time machine and you arrive to the NYU campus and you're entering there, you know, the class where that younger Ben is at, where he is thinking about starting a company and you're able to give that younger Ben one piece of advice before launching a business. What would that be and why, given what you know now?
Ben Borodach: Don't be so hard on yourself. um and I And I think that's specific to me, but it's probably specific to a lot of my peers also. I think I've beaten myself up over the years and been very hard. you know hard I'm my own toughest critic, right? And I actually lost a little bit of vision in my eye ah last year and had to kind of like sort of like reassess some things in terms of just like how I managed my own health and you know played for the long run. And so I think it's just a reminder that if you're, it's like only the paranoid survive. If you're already doing everything and you know you're doing everything, then kind of you have nothing to worry about.
Ben Borodach: and And just make sure that you you enjoy enjoyed life and enjoy the process along the way.
Alejandro Cremades: And I think that's such ah so's an important thing because founders, especially at the ah on on their first business, they just go all in, you know, and they make so many sacrifices and especially on their health. I guess in this regard, you know, which is what you were alluding to, how do you think, you know, founders should be looking into this, looking into the real balance, looking into prioritize what matters? I mean, what have you learned, you know, in that that perhaps you can share with with folks that are listening right now?
Ben Borodach: Look, this is just you know my learning, and I think there's a little bit of you know provocation going on on on X and some other platforms. But look, I think I work just as hard as any founder, if not more. I think most of my family and friends would say that I'm working most of the time. But I think what work is and how you prepare for work is a little bit different.
Ben Borodach: Or I look at it differently as I got older. I think when I was younger, that meant sitting in front of a computer for the most hours that I could until I literally passed out. And I think as I've gotten older, I look at it through the lens, maybe more akin to the way that a professional athlete would look, right?
Ben Borodach: Sometimes I'm playing the game. Sometimes I'm preparing to play the game. Sometimes I'm working on endurance. Sometimes I need to take a step back. And so now whether it's my diet, my exercise, um my my space to think, my space to work, um and also doing things that are not necessarily...
Ben Borodach: work, um but maybe things that are sort of like in the middle, right? Recruiting, um meeting colleagues out of the office. And so I think you you have to look at at all of those things. And the balance is going to change based on where you're at in your career, based on the type of business you're building, based on your own strengths and weaknesses.
Ben Borodach: um But I think it's clear that as I've advanced, I can do things with more efficiency than I was able to do, right? Something that used to take me a week, I now know how to do in an hour. ah Something that I wasn't connection you know I didn't have as as many connections early in my career. so you know So I would have to take a month to network. Maybe now that person's a phone call away. you know And if you transition that all the way up to the greats like Elon Musk or Mark Zuckerberg, it's tenfold. right Those guys probably could do in in five minutes what would maybe take me an hour or or a month. I I don't know. so um I think that that constantly finding ways to maximize your efficiency um and get more more more punch for the for the time you spend is really important. I think you have to take a wider view than just like how many hours are you in the office and be realistic that that's not always going to be the thing that's most productive for you in business.
Alejandro Cremades: I love it. Ben, for the people that are listening that would love to reach out and say hi, what is the best way for them to do so?
Ben Borodach: My email is ben at getapril.com. Feel free to reach out.
Alejandro Cremades: My God, he easy enough. Well, Ben, thank you so much for being on the Dealmaker Show today. It has been an absolute honor to have you with us.
