Ryan
Alshak

A $650-an-Hour Problem Nobody Was Solving

The math never made sense to Ryan Alshak. He was a corporate litigator at a law firm where his time was billed at $650 an hour. His clients paid that rate because they trusted him with complicated, high-stakes problems that required sophisticated thinking. And then, at the end of each day, he would sit down and manually reconstruct every six minutes of what he'd done - writing it out by hand into a timesheet system that hadn't meaningfully changed since the 1970s.

He had a very simple thesis: machines should remind humans what they did at work, not the other way around. The entire timekeeping industry - which touches $1 trillion in professional services billing annually - was built backwards. High-value humans were doing low-value administrative work on behalf of the software that was supposed to serve them.

In 2018, Alshak walked away from law and founded a company he called Time by Ping. The product was straightforward in concept and brutally hard in execution: an AI system that passively tracked what professionals did at work and automatically converted that activity into accurate, billable time entries. No manual logging. No end-of-day reconstruction. Just continuous, intelligent capture - and more time for the actual work.

What he built required solving two deceptively hard problems simultaneously: accurately detecting and categorizing work activity across dozens of digital tools, and then translating that activity into the specific narrative format that law firms and accounting firms use for client billing. The first is a data engineering problem. The second is a natural language problem. The combination is why nobody had solved it before - and why nobody could easily copy what Laurel has built since.

Goodbye Ping. Hello Laurel.

For four years, the company operated as Time by Ping. The name hinted at the product's core mechanic: a gentle reminder, a digital tap on the shoulder. But as the company expanded from law into accounting and consulting - and rebuilt its AI platform with four times the accuracy it had at launch - the name stopped fitting what they were becoming.

In 2023, Alshak renamed the company Laurel. The name is deliberate: in ancient Greece, the laurel wreath was the symbol of victory, achievement, and earned distinction. For a company whose mission is to return time to the world's highest-achieving professionals, it lands differently than a product name about pings and notifications.

The rebrand coincided with a genuine platform rebuild. The new Laurel launched with expanded features - delegate support, reference mode, revamped timers - and an AI model that had been retrained with dramatically more data from more professional contexts. Accuracy improved by a factor of four. The product stopped being a timekeeping assistant and started becoming a time intelligence platform.

The expansion into accounting and consulting wasn't just a market play. It was recognition that the underlying problem - professionals losing revenue because they can't track their own time - existed in every professional services category, not just law. Accountants at Big Four firms were losing billable hours the same way litigators were. Consultants at McKinsey were doing the same manual reconstruction at the end of every day. Laurel's total addressable market grew considerably when Alshak zoomed out from legal tech and saw what he'd actually built: an enterprise AI platform for time intelligence across professional services.

$100 Million. And a $510M Number That Surprised the Market.

The Series C, announced in June 2025, was a statement round. $100 million, led by IVP, with participation from GV (Google Ventures), DST Global, and a roster of strategically meaningful names: Kevin Weil, President of OpenAI; Alexis Ohanian, co-founder of Reddit; Vladimir Fedorov, CTO of GitHub; and Hans Tung from Notable Capital. The round also included a $20 million tender offer, allowing employees to take some liquidity.

The valuation - $510 million - reflected numbers that surprised even observers who'd been following Laurel closely. In the twelve months before the round closed, Laurel grew ARR by 300 percent and usage by 500 percent. Those aren't incremental gains; they're a step-change. The company had crossed $10 million in annual recurring revenue entirely through founder-led sales, with Alshak himself staying on the front lines of customer acquisition to capture product-market feedback directly.

What Seven Years of Building Actually Looks Like

Ernst & Young is a client. Grant Thornton is a client. Multiple top-five law firms are clients. These aren't early-adopter wins from a scrappy startup willing to discount its way into contracts. These are institutions with procurement processes, security reviews, and compliance requirements - institutions that chose Laurel on the merits of accuracy and ROI.

The product works because the underlying technology is genuinely hard to replicate. Laurel's AI sits across the digital work environment of a professional - email, documents, calls, calendar - and builds a complete map of how time was actually spent. It then uses that map to generate billable time narratives in the specific format each firm requires, applying client billing rules automatically. The AI is not just detecting activity; it's interpreting the meaning and value of that activity in the context of professional services billing.

Time as Meaning, Not Metric

Ryan Alshak is not a founder who keeps his company mission at arm's length. The philosophy behind Laurel runs deeper than a pitch deck slide about market size and billable hours recovery. For Alshak, time is not an operational problem. It is an existential one.

When Laurel was three months old - still called Time by Ping, still pre-revenue - his mother was diagnosed with terminal brain cancer. In their first meeting after the diagnosis, her first words to him were: "I'm sorry." He moved back to Los Angeles to be with her. She passed away on June 21, 2018, weeks after the company closed its seed round.

What that experience did to his understanding of time - of minutes and their weight, of the difference between minutes spent on administrative busywork and minutes spent with the people who matter - became inseparable from what Laurel is trying to do. The company's stated mission, "returning time to the world," is not marketing language for Alshak. It is personal.

This orientation shows up in how he talks about building a startup. He is openly skeptical of founders who wait for conditions to be perfect. "Dance in the rain," he has said. "Don't wait for the storm to pass. Enjoy the lows. Those are the fun parts." He advocates for full authenticity at work - "you are one person, and the way that you are at home is the way that you are at work" - and for staying on the front lines of customer relationships rather than retreating behind process as a company scales.

"If your path is paved, you're living somebody else's dream," he told Legal Tech Founders. For a former corporate litigator who walked away from a well-defined career to build something that had never existed, the line reads less like a motivational poster and more like a lived principle.

The Alshak Quotebook

Why the $1 Trillion Legal Industry Must Rethink Time

From Courtroom to C-Suite

The Specifics That Actually Tell the Story

• His company's Twitter handle is still @timebyping - a preserved artifact from the founding era, before the rebrand to Laurel.
• He studied Political Science at UC Berkeley before going to law school at USC - not a traditional path for someone who ended up building enterprise AI infrastructure.
• The name "Laurel" is a direct reference to the laurel wreath of ancient Greece - the symbol of victory, achievement, and honor. For a company that returns billable time to professionals, the metaphor is earned.
• He achieved $10M+ in ARR entirely through founder-led sales, staying on the front lines of customer acquisition well past the point most CEOs hand it off to a sales team.
• His Series C investor list includes the President of OpenAI, the CTO of GitHub, the co-founder of Reddit, and the founder of Salesforce's investment vehicle - an unusual concentration of operator-investors who understand both enterprise software and AI infrastructure.
• He writes personal essays on Medium about time, purpose, and the experience of building a company through personal loss - not a common format for enterprise software CEOs.