Ben Borodach has lived on both sides of the venture table. He has raised capital, built companies, advised at the policy level, and now he is modernizing something most founders avoid on purpose: the American tax system.
Ben is the CEO of April, the first company in 15 years to build a nationally chartered tax engine. That single detail tells you what kind of operator he is. He is not chasing “quick wins.” He is building infrastructure.
In our conversation, Ben laid out a blunt truth that every CEO needs to internalize.
“This is a business at the end of the day that’s mainly about long-term outcomes,” he told me. “And mainly about exceptions.”
That is not just a tax company reality. That is leadership reality.
Build The Roadmap Once, Then Bring Everyone With You
April is not a simple software story. Tax is seasonal. It is regulated. The documentation is incomplete. The edge cases are endless. Ben described years of learning through failure, hitting walls, and discovering that what the IRS or a state says on paper is not always how the system behaves in practice.
So how do you keep a team motivated inside a problem this messy?
Ben’s answer was discipline and transparency. April uses one roadmap across the entire company.
“We give the same roadmap to everybody,” Ben said. “It’s the same roadmap we give to investors, that we give to the board, that we give to our management team, that we give to the rest of our team. We even give it to our customers.”
That choice matters. It keeps people aligned when the work is slow and the milestones are not always revenue-shaped. It also keeps expectations grounded in reality instead of fantasy projections.
Ben was explicit about the trade he made early.
“We told our investors and our customers in the early days, we’re not going to make a lot of money,” he said. “And we told our customers, we’re not going to charge you a lot of money because we understand you’re taking a leap with us.”
That is how you keep credibility when the journey is long.
The Real Investor Pressure Is About Immediacy
Every CEO knows the pressure. Bigger targets. Faster growth. Prove it now.
Ben has raised hundreds of millions of dollars across his career and $80 million for April. He has seen how incentives can push founders into short-term thinking, even when the business demands long-term execution.
“A lot of the incentives in the industry don’t actually anchor to that,” he said. “They anchor to a short-term group think and they anchor to immediate results, immediacy.”
Then he did what strong CEOs do. He reframed the conversation using reality and history.
“I think we forget that Apple and Google and Tesla and some of the greatest companies of our generation were not overnight successes,” Ben said.
If you are building something with a real moat, the timeline is different. The milestones are different. The risks are different. You cannot fake your way through that with a spreadsheet.
Ben put it in a way I wish more boards would repeat out loud.
“If you can do that so easily, then so can your competition,” he said. “And why are you able to do it so easily?”
That is the CEO question. Not “how do I show more growth next quarter?” but “what makes this hard to copy?”
Work Backwards From The End Game
Ben described a first-principles approach that applies to any CEO building something durable.
He starts with the end outcome, then works backwards to define what success must look like along the way. Some milestones will be revenue-based. Many will not. In regulated infrastructure businesses, the early years are often about capability, coverage, and proof.
He also acknowledged the truth that founders hate.
“At some point the bill comes due,” Ben said. “You raise $80 million. The bill does come due and you have to pay it.”
That is the maturity test. You can be patient without being complacent. You can be long-term without being slow. The job is to know which one you are being in each season.
Scaling Yourself Is Not Optional
At one point in the episode, I brought up a statistic I have seen play out repeatedly: within a five-year period, a large percentage of CEOs get replaced. One of the core reasons is simple. The company grows. The CEO does not.
Ben gave an unusually honest view of what that looks like on the inside.
“The only truth is constant change,” he said. “If you’re doing it right, then you’re growing. So things are breaking.”
Then he went deeper. He talked about what limits top performers more than anything else.
“The number one reason that top talent struggles is because they’re unwilling to deal with their own personal limiting factor and they project it onto other people,” Ben said.
That is a CEO mirror. If you are constantly blaming the market, your investors, your team, your partner, your competitor, you might be avoiding the harder question: what is happening inside you that is shaping how you lead?
Ben also shared something many CEOs experience but rarely say publicly: the personal cost.
He described becoming impatient, getting hard on himself, and feeling the toll on his health. He also went through major life events while building April, including losing his father and welcoming a third child. He had to reset his relationship with work, his routine, his diet, and his discipline.
That is not a side story. That is the job.
If you want to stay CEO through scale, you must evolve at the same pace as the business.
AI Is A Force Multiplier, Not A Business Model
April’s mission is to embed tax intelligence into everyday financial decisions, across banking, wealth management, payroll, and more. Ben was clear that AI made April possible, but he refused to treat AI like a slogan.
“AI looks much more like cloud,” he said. “It’s something that makes good businesses much better. It doesn’t really make you have a business.”
That distinction is one every CEO should steal.
April uses AI in several ways:
- A proprietary system to automate tax codification with high accuracy
- Code-assist tools to accelerate engineering productivity
- Customer support automation that handles about half of inquiries in real time
- Document parsing and analysis, such as converting W-2s and 1099s into usable structured data
Then Ben dropped a metric that should make every operator pay attention.
“Our run rate [grew] nine X last year,” he said. “Our OpEx only grew about 8%.”
That is the promise of AI when it is tied to business value, not hype. Better output. Better efficiency. People redeployed into higher-leverage work.
And Ben made the CEO point I agree with completely: you cannot treat AI like a side project. It will reshape culture, hiring, measurement, and how you build.
What You Should Take From This Episode
If you are building something complex, regulated, or infrastructure-heavy, the short-term playbook will hurt you. Ben’s approach is a clean alternative:
- Anchor the company on long-term outcomes, not short-term noise
- Make milestones explicit and non-revenue milestones legitimate
- Tell the same roadmap story to your board, your team, and your customers
- Use AI to increase speed and accuracy, but tie it to customer value
- Scale yourself by dealing with your own limitations first
This is what durable leadership looks like.
Final Thoughts
If you want help clarifying your strategy, strengthening your leadership cadence, and building an execution system that holds up under growth, reach out and let’s talk.
I am Glenn Gow. I coach CEOs who want to scale their companies and scale themselves without losing control of the business, their health, or their direction.If you want the full context, including Ben’s perspective on managing investor expectations, building moats in complex markets, and using AI to codify the tax code at 20X industry pace, listen to the full episode of The Scaling CEO featuring Ben Borodach.
