Built by founders, for founders.

Before I was a lawyer, I was a founder.

I know what it feels like to lie awake at 3am thinking about burn rate. I know the excitement of landing your first big deal, and the panic of realizing you might not have the legal infrastructure to close it. Every decision could extend your runway or cut it short.

I also experienced something that shouldn’t be part of building a company: I dreaded every interaction with my own lawyer. Not because they weren’t competent. Because the whole experience was broken.

The invoices read like ransom notes. Thousands of dollars for basic tasks, when I was budgeting every dollar to stay alive. I never knew if the next bill would be $2,000 or $20,000, so I couldn’t plan. I stopped asking legal questions, because a five-minute call cost $200. And I waited weeks for routine documents while my competitors moved.

All of it had one cause: the billable hour. It’s a business model that rewards inefficiency, punishes communication, and injects uncertainty into the moment you need clarity most. It is out of step with how startups operate.

So in 2008 I made a decision. If I couldn’t find a law firm built for founders, I’d build one.

The firm I wish I’d had

Westaway runs on one idea: transparent pricing. We don’t charge by the hour. We scope the work, set a flat fee, and stick to it. That one shift changes everything.

• Reasonable fees. Legal help that doesn’t wreck your runway.
• Cost certainty. You know the price before we start.
• Open communication. Call us without the meter running.
• Startup speed. We’re paid to finish, so we move as fast as you do.
• Tech-enabled. Flat fees reward efficiency, so we built automation and AI into the practice. Routine work gets done faster and more accurately, and our lawyers spend their time on your company.

Over eighteen years the team has grown, but we’ve stayed focused on building systems that scale. That’s how a lean firm delivers quality, consistency and speed, with no bureaucracy between you and the lawyer who knows your company.

Eighteen years in

From bootstrapped indie hackers to unicorns, we’ve worked with more than a thousand founders and closed over $1 billion in deals for them. Fast Company has named us a World Changing Idea and one of the Most Innovative Companies in the world; Inc. named us a Power Partner. And our clients don’t just tolerate their lawyers. They like working with us. Don’t take my word for it: read the 100+ five-star reviews.

When you’ve sat in the founder’s seat, you get it. You need a legal partner who solves problems, not one who creates them. That’s why I started Westaway: so legal speeds you up instead of slowing you down.

If you’re building something ambitious, we’d love to build it with you.

About Kyle

Kyle Westaway is a startup attorney. Since 2008 he’s helped early-stage founders scale their companies smarter. He is admitted to practice law in New York.

He’s the author of Profit & Purpose: How Social Innovation Is Transforming Business for Good and a contributor at Forbes, where he writes about entrepreneurship. He also writes two popular newsletters, Weekend Briefing and Founder Fridays.

Kyle has taught at Harvard Law School and Cornell Tech for a combined ten years.