From Syndicate to Payout: My Investment in Writer.com

A 2.15x return, 23.8% IRR, and a few lessons from backing the right founder

Author

Bryan Hunsinger
September 03, 2025

In October 2021, I invested in Writer.com through WR Fund I, a syndicate on AngelList led by Awesome People Ventures. It was a fast-moving deal (24-hour turnaround) co-led by Julia Lipton, and backed by a strong lineup of investors including Insight Partners, Lenny Rachitsky, Packy McCormick, Ankur Nagpal, and others.

Writer had a compelling vision: an AI writing assistant built for teams, not just individual creators. While many tools focused on novelty, Writer aimed to help companies standardize clear, on-brand communication across marketing, support, documentation, and training.

Why I Invested

What stood out:

  • Founder-market fit: CEO May Habib had previously built Qordoba, saw its limitations, and pivoted to something much larger.

  • Early traction: $1.5M+ ARR within a year, 17% MoM growth, and customers like Intuit, Twitter, Pinterest, and Deloitte.

  • Massive tailwinds: Writing is one of the last major business functions to be automated, and Writer was positioning itself as the category leader.

The Return

In May 2025, amid strong AI market momentum, the fund sold ⅓ of its position in Writer at the Series C price, returning 2x cash-on-cash on that portion. The other ⅔ remains active and invested.

That partial exit resulted in a total return to me of 2.15x on my original investment, with an annualized IRR of 23.8% over a 3.5-year period.

Lessons Learned

  • Speed + conviction pays off: I had 24 hours to make the decision. The combination of founder strength, metrics, and investor confidence helped me move quickly.

  • Syndicates are powerful: AngelList enabled me to participate passively in a high-quality deal I wouldn’t have found otherwise.

  • Partial liquidity is smart: Getting some capital back early helped de-risk the investment, while still keeping upside in play.

Writer continues to grow, and I’m optimistic about its future. But even this early liquidity event is a great reminder: well-timed early-stage investments, even small ones, can quietly generate solid returns.

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