Glenn Gow, The Scaling Executive Coach and host of The Scaling Executive Podcast, sat down with Ben Borodach, co-founder and CEO of April, to examine what it actually takes to build a business designed to last — and why the incentives in venture capital work against that goal more often than not.
This episode is for CEOs building complex, regulation-heavy, or infrastructure-intensive businesses who are under investor pressure to show revenue before their product is truly ready.
Key Takeaways
- Milestone-based roadmaps, not revenue targets, are the right accountability tool in pre-revenue infrastructure builds — they keep investors aligned on what progress actually looks like before revenue can reflect it.
- The same roadmap Ben Borodach gives to April’s board, investors, and management team, he also gives to customers — radical stakeholder alignment that converted early adopters into partners willing to take a leap without charging them much.
- CEOs who fail to scale personally often do so for one reason: they project their own internal limitations onto the business, their partners, or their team rather than looking inward first.
- April grew revenue nine times in a single year while holding OpEx growth to 8% — a direct result of deploying AI across workflows without expanding headcount proportionally.
- AI is not a business model. It is infrastructure. CEOs who treat AI as a differentiator in isolation are making the same mistake as companies that declared themselves “cloud-based” and called it a strategy.
Why the Best CEOs Reject the Pressure to Grow Fast Before They Are Ready
April built the first nationally chartered tax engine in 15 years and the only one in nearly 20. That is not a product that could have been shipped fast. It required years of technical groundwork, regulatory navigation, and patience that the venture industry’s short-term reward structure does not naturally support.
Borodach’s rule is direct: when you are building a business with a real moat, the question “can you get revenue immediately?” is the wrong question. The right question is whether you are solving a real problem in a large and growing market at a moment of genuine technology shift — and whether your investors understand the difference.
“We forget that Apple and Google and Tesla and some of the greatest companies of our generation were not overnight successes,” Borodach told Glenn. “And they had many ups and downs along the way.”
CEOs who cave to investor pressure for immediate revenue in complex markets make a strategic error: they optimize for a metric that, if achieved easily, signals the absence of a moat. As Borodach put it, “if you can do that so easily, then so can your competition.”
How April Manages Investor Expectations: The Same Roadmap for Everyone
The tactic Borodach used to hold the line with investors is not a negotiation strategy. It is a structural one.
April gives the same roadmap to every stakeholder — investors, board members, the management team, employees, and customers. That single document describes milestones, not revenue targets. In the early years, the milestones were regulatory: what approvals did April need to clear? What state coverage did it need to achieve before scaling? What partner integrations were required before charging full price?
“In the first years, we’re going to only do federal and a couple of states, and we’re aiming to learn and prove that this can work,” Borodach explained. “And then the next year we scaled, had coverage in about 25 states. We started producing revenue. And last year was the first year we went national.”
This approach did three things. First, it set expectations with investors before pressure to grow could become misaligned pressure. Second, it gave customers — who were taking a risk on an unproven platform — a clear view of the roadmap they were betting on. Third, it told every stakeholder exactly what success looked like before any revenue was generated.
The principle: set milestone-based accountability before setting revenue-based accountability. Revenue is an output. Milestones are a proof of progress toward a sustainable competitive position.
April raised $80 million in equity capital across a seed, A, and B round. That funding gave Borodach the runway to honor the roadmap rather than compress it. But the funding only works as a tool when the CEO has already framed the terms of what it is buying.
How CEOs Scale Themselves: Look Inward Before You Project Outward
The second question Borodach addressed — how CEOs maintain themselves as effective leaders while the business outgrows its original form — produced the most direct answer in the conversation.
His starting point: “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.”
This is a harder problem than managing investors. Investors can be managed with a roadmap and a clear framing of timelines. A CEO’s internal limitations are not visible on a slide. They surface in decisions — in impatience, in inability to delegate, in the tendency to frame a personal frustration as a business problem.
Borodach describes his practice as looking inward before projecting forward. When he encounters friction in the business, his first question is not “why is this happening to me?” It is: “How am I not reacting correctly, or why am I reacting this way? Is this because my mind was trained? Has the business grown? Has the market evolved?”
In early 2024, Borodach faced a genuine personal breaking point. He lost his father. A third child was born. Regulatory approvals were taking longer than expected. He describes the combination as a moment when he had to reset — his relationship with work, his diet, his routine.
“Over 2025, I think I did that successfully,” he said. “I’m probably in the best shape of my adult life. I’m eating better. I have more discipline than I had, and that’s prepared me, I think, better for the next phase of growth that we have in the business.”
This is the practical version of personal CEO scaling: not a philosophy, but a deliberate reset of the habits that determine daily performance. The CEO who cannot reset when conditions change will eventually become the constraint the business works around rather than the leader it works through.
Glenn Gow’s observation is consistent with this: 60% of CEOs get fired within five years of investment, and the fundamental reason is that they do not scale themselves. They were the right person at the moment of investment. They failed to grow into the person the company needed once it scaled.
How April Used AI to Grow Nine Times While Holding OpEx to 8%
April’s AI deployment is not a strategy. It is a discipline applied across every function where it produces measurable efficiency gains.
Borodach is specific about where AI operates inside April:
- A proprietary tax coding engine that functions like a custom-built version of Windsurf — a developer automation tool similar to GitHub Copilot — purpose-built to convert tax law into software executables. This engine increased April’s pace of tax code codification by approximately 20 times relative to the industry.
- An AI customer support bot that handles roughly half of all inquiries in real time.
- AI-powered OCR for document analysis, parsing uploaded 1099s and W2s into readable, processed files.
- AI layers embedded in existing SaaS tools, reducing time and cost without requiring net-new software purchases.
The result: April grew revenue nine times in a single year. OpEx grew 8% in the same period.
Borodach’s framing for what AI actually is — and is not — is precise: “AI looks much more like cloud. It’s something that makes good businesses much better. It doesn’t really make you have a business.”
The implication for CEOs is direct. A company that declares itself an “AI company” without a defensible underlying business has the same problem as a company that declared itself “cloud-based” in 2012. The technology is infrastructure. The business still has to solve a real problem better than the competition.
The discipline Borodach applies: before adding AI to any workflow, he asks whether it makes the company go better, faster, or cheaper. If it does not produce a measurable answer to at least one of those three, it does not get deployed.
Principles April’s CEO Uses to Build for the Long Term
| Principle | What it means in practice | Named evidence from this interview |
| Milestone accountability before revenue accountability | Define regulatory, integration, and coverage milestones as the primary success measures with investors, especially pre-revenue | April used federal-only coverage in year one, 25-state coverage in year two, and national coverage in year three — each milestone confirmed before charging full price |
| One roadmap for all stakeholders | Share the same growth plan with investors, board, team, and customers — radical transparency that converts stakeholders into partners | April’s early customers accepted below-market pricing during the platform’s unproven phase and then converted to full-price contracts on schedule as each coverage milestone was hit |
| Project inward, not outward | When business friction appears, ask first how your own reactions or limitations are contributing before attributing the problem to the market, team, or investors | Borodach reset his diet, routine, and relationship with work in 2024 after personal and business stress compounded — and credits that reset with preparing him for April’s current growth phase |
| AI as infrastructure, not identity | Use AI to make every existing function better, faster, or cheaper — not as a standalone differentiator | April’s AI-assisted tax engine, customer support bot, and document OCR together produced 9X revenue growth with 8% OpEx growth in a single year |
| Endurance is a moat | Choose markets and problems where the difficulty of the work is itself the competitive barrier | April’s years of IRS documentation, regulatory approvals, and state-by-state codification built a compliance infrastructure that kept competitors out — no rival has replicated a nationally chartered tax engine since April’s launch |
Quotes from This Episode
- “We forget that Apple and Google and Tesla and some of the greatest companies of our generation were not overnight successes. And they had many ups and downs along the way.” — Ben Borodach, CEO, April
- “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 Borodach, CEO, April
- “AI looks much more like cloud. It’s something that makes good businesses much better. It doesn’t really make you have a business.” — Ben Borodach, CEO, April
- “This is a business that’s about first principles. That’s about real problem solving and critical thinking. And I think if you do that and you follow a process, you’ll have great results.” — Ben Borodach, CEO, April
- “How am I not reacting correctly, or why am I reacting this way? Is this because my mind was trained? Has the business grown? Has the market evolved?” — Ben Borodach, CEO, April
Frequently Asked Questions
How should a CEO manage investor pressure to grow revenue before the business is ready?
CEOs building complex, infrastructure-intensive businesses must set milestone-based accountability with investors before setting revenue-based targets. Ben Borodach, CEO of April, used the same roadmap — covering regulatory approvals, state coverage expansions, and partner integrations — for investors, board members, employees, and customers. This alignment meant investors understood the timeline before pressure to accelerate could become misaligned. April raised $80 million in equity capital and held a clear multi-year milestone structure before generating meaningful revenue.
What causes CEOs to stop scaling themselves as their company grows?
The most common failure is the unwillingness to examine personal limiting factors before projecting problems onto the business or team. Ben Borodach describes the discipline as looking inward first: when friction appears, his first question is how his own reactions, habits, or blind spots are contributing. In 2024, facing personal loss, the birth of a third child, and prolonged regulatory delays simultaneously, Borodach executed a deliberate reset of his health, routine, and relationship with work — and credits that reset with preparing him for April’s current growth phase.
How do CEOs use AI to increase efficiency without losing the human value in their business?
AI works best as infrastructure applied to specific, measurable workflows — not as an identity or a differentiator on its own. April deployed AI across tax code automation, customer support, and document processing, growing revenue nine times in a single year while holding OpEx growth to 8%. Borodach’s decision rule: before adding AI to any function, ask whether it makes the company go better, faster, or cheaper. Functions where AI cannot answer at least one of those three do not get automated. Human capital is redeployed toward creative and relationship-intensive work where it generates more value than automation can.
CEOs Work with Glenn Gow to Build Companies That Endure and Scale
Glenn Gow is The Scaling Executive Coach — he coaches ambitious executives into the CEO seat and CEOs into successful exits. With 25 years as a CEO and 5 years in venture capital, Glenn helps leaders scale their companies by scaling themselves first. If this conversation was useful, you can apply for executive coaching with Glenn Gow or apply to be a guest on The Scaling Executive Podcast.
