Join Hannah Konitshek, COO and Founder of Legal.io, as she shares how a hackathon transformed into an enterprise legal marketplace and network that connects thousands of lawyers with in-house roles, offers advice for founders on working with investors, and explains why the biggest risk is not taking a big enough swing.

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Key Insights

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1. Legal Tech Starts with Community

Hannah’s entry into legal tech began when she organized one of San Francisco’s first law school hackathons—hosted at Airbnb HQ. The event drew hundreds of students and legal innovators. “It was like finding the other ten people who were thinking about this,” she recalls. That spirit of community and experimentation became the foundation for Legal.io’s mission: connecting legal professionals and empowering them with better tools.
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2. Second-Time Founders Think Differently

Legal.io went through several evolutions—from a legal referral network to a marketplace for legal talent and ALSP services. The biggest lesson? Focus on distribution, not perfection. “First-time founders obsess over the product. Second-time founders obsess over distribution,” Hannah says. For her, the shift was about getting great tools into more hands, faster.
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3. The Biggest Risk Is Not Taking One

When asked how her risk tolerance evolved, Hannah put it simply: “You only get to live once. The biggest risk you can take is not taking a big enough swing.” In her world, the real failure isn’t an imperfect launch — it’s building something no one ever sees. Her philosophy: ship, learn, iterate, repeat.
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4. Conviction and Flexibility Are Not Opposites

Hannah believes great founders balance deep conviction with active listening. “You have to have conviction in your 10-year vision,” she says, “but be flexible about the steps.” The Legal.io team lives by the Bezos principle: build on what won’t change—people will always need peers, jobs, and trusted resources.
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5. Fundraising Is a Partnership, Not a Prize

Legal.io’s Series A, led by Tiger Global, was the result of finding alignment — not luck. “If investors don’t buy your thesis, no metrics will change their mind,” Hannah says. Her advice: treat fundraising as mutual due diligence. Founders should interview investors, ask about portfolio collaboration, and seek shared vision—not just capital.
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6. AI Will Accelerate, Not Replace, Legal Work

Legal.io is investing in AI to scale intelligent talent matching, helping more lawyers find meaningful work. “We can only talk to a fraction of people today,” Hannah says. “AI can help us make smarter, fairer matches at scale.” She predicts ALSPs and AI tools will handle routine work, freeing lawyers for higher-impact, human-centered roles.
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7. Focus Is a Founder’s Superpower

Quoting Steve Jobs, Hannah says success often comes from “the 99% of things you say no to.” For Legal.io, the next two years are about depth, not breadth—serving existing enterprise clients better and expanding its network through smarter technology, not new products.
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8. Closing Insight:

“You only get to live once. The biggest risk is not taking a big enough swing.”

For Legal Ops teams, that means taking bold bets on systems, AI, and talent models that redefine how legal delivers value—not just manages cost.

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