The Story Behind Truewind

When people ask why we named the company Truewind, I usually start by talking about sailing.

On a boat, the wind you feel depends on how fast you’re moving. But the true wind—the actual wind speed and direction—can only be measured from a fixed point. That’s the role accounting plays in business. It doesn’t just track movement. It offers an objective view of reality, so leaders can make smart, grounded decisions no matter how fast things are moving.

In a nutshell, that’s the idea behind Truewind. We build tools that give accountants a clear view, so they can help others navigate the waters ahead.

Why We Started Truewind

Tennison and I founded Truewind in 2023. We both saw the same problem: accounting was overloaded with manual work, but the real challenge wasn’t just about efficiency. It was about turning numbers into business context.

Accounting isn’t a checklist. It takes judgment. It requires understanding what a business is trying to do, and helping it get there.

Take this example:

• Two companies buy the same mug from a vendor

• The bank memo says “Hasami Natural Mug”

• If a venture firm buys it for internal use, it’s a general and administrative expense

• If a coffee shop buys that mug to sell it, it’s cost of goods sold

Same item. Same vendor. Completely different accounting treatment.

The missing variable is intent. “What does this business do? Why was this item purchased?” That kind of information lives in natural language. And until recently, we didn’t have the technology to make sense of it at scale.

What We’re Building

There’s a lot of hype around AI. But underneath it, there’s something real happening—and accounting is one of the places where it’s already making a difference.

For the first time, we can build tools that understand the why behind a transaction. Not just who and how much, but what it’s for, and what that means in context.

At Truewind, we’re building a copilot for accountants. An AI assistant that helps categorize transactions, reconcile accounts, and close the books faster with fewer errors. It learns how your firm works, adapts to your process, and gives you control over every decision.

The goal isn’t to replace accountants. It’s to empower them—to spend less time on repetitive tasks, and more on projects that call for their judgment, experience, and insight.

What We Believe

The best accountants don’t just close the books. They help their clients understand what the numbers mean, and what to do next.

That’s the future we’re building toward—where accountants are seen as strategic partners, not just service providers. And where software handles the busywork, so that teams can focus on strategy, collaboration, and better outcomes for their customers.

The tools that accountants rely on should match the weight of that responsibility. Accounting is how a business tells the truth about itself, and the systems behind it need to be built with precision, thoughtfulness, and care.

Where We’re Headed

We started this journey with the support of incredible investors. In 2023, we raised a $4 million seed round led by Fin Capital and Y Combinator. A year later, we raised a $13 million Series A, co-led by Rho Capital and Thomson Reuters Ventures.

Today, we’re proud to support over 30 accounting firms and more than 200 businesses. These companies aren’t just using Truewind; they’re shaping it. Their feedback, ideas and high standards have pushed us to make something better than we ever could on our own.

Looking ahead, we’re building for a future where accounting teams are faster, sharper, and better supported than ever. One where the tools match the complexity of the job. And where clarity, accuracy, and confidence aren’t a luxury—they’re the standard.

Interested in learning more about Truewind and our AI-powered solutions? Chat with our team to get started.