Compiled by Monica Bay

Meet Matthew Osman, 26, CEO of Deftr—which launched its first prototype in July. Osman is a Fellow at Y Combinator. On July 21, Osman was scheduled to present a demo at the July CodeX meeting, but had a last-minute conflict, so CTO Jacob Rosen substituted for him (and did a great job).  [Updated to correct my error saying he was presenting at CodeX! —Monica Bay.]

 

Home base: London, U.K. & Cambridge, Mass.

Citizenships: U.K.

Social Studies
Website: thedeftr.com
Twitter: @thedeftr
Facebook: https://www.facebook.com/thedeftr/

Education: University of Oxford, B.A., Philosophy, Politics and Economics, 2012. Called to the Bar of England and Wales, 2015, (but not practicing).

Past significant jobs: Assistant Vice President, Pearl Diver Capital, a $1bn structured credit hedge fund.

What problem does your startup solve? How does it help users? Lawyers frequently need to analyze a corporation’s structure and explain it to clients in plain English. The most effective approach is to transform the dense, text into comprehensible graphics. Unfortunately, even with existing software, that still requires manual work. Deftr automates the entire process—enabling the user to build a chart effectively and quickly. The end result is a win-win: clients can easily understand the structure (while they save time and money) and the lawyers can focus on high-level, analytical work (saving time and earning more money).

Audience:  Deftr addresses both corporate law departments and law firms. Initially, it is most useful to lawyers who are involved in corporate, securities or tax law.

 

What does it cost? Our prototype basic version is free.

Patents? We have two patents pending.

 

Why did you name it Deftr? It’s named after the Ottoman Empire’s tax registry. It was the first truly global and dynamic tax registry—updating constantly—not just land holdings but all taxable assets across a patchwork of different communities and local taxation systems. It also kept a record of transactions/relationships to assets that would affect a tax profile (marriages, gifts, debt transactions etc.)  It seemed like a pretty cool thing to be named for. It helped that my surname is Turkish in origin.

 

Do you have funding?  We received a Y Combinator Fellowship (around 7,000 applicants for 60 places). YC Fellows receive $20,000 and advice from the YC community for eight weeks, to go from an idea to a startup. Companies that have started there are valued at $65bn and include household names like AirBnB, Dropbox, Instacart and Stripe. We have also received investment from angels in the U.K, and U.S.

What is your biggest challenge re: the start-up? Convincing people that the legal industry can and must change.

What do you need right now? In six months? In a year?
• Now: Feedback from potential and actual users.
• Six months: A scalable sales and training process.
• One year: To be used by at least 50 of the Am Law 200 law firms.

What have you learned that you wish you knew five years ago? Nearly everyone is making it up as they go along.

 

Who most influenced you? The life of P.T. Barnum teaches the importance of a
little showmanship—he could sell water to a drowning man.

What two people are/were your most important mentors? Neil Basu: my former boss who encouraged me to pursue entrepreneurship.   Andrew Williams: the man who encouraged and supported my legal education in the first place.

What book changed your life?  Godel, Escher, Bach by Douglas Hofstadter.
It showed me the deep connections between art, mathematics and the mind.

What advice do you have for other entrepreneurs? Pick a co-founder very carefully. Get it right and it’s a dream but get it wrong and you’re dead in the water.

 

What are you afraid of? Clowns.

What’s your favorite vacation destination, and why? Majorca, the largest island in the Balearic Islands archipelago in the Mediterranean. I went there as a child. I remember I once saw the King Spain in a restaurant—but thinking about it now I think it may have just been an old Spanish man.

Favorite musician or group: Talking Heads: David Byrne is the musically equivalent of David Lynch.

Favorite food: Xiaolongbao—a type of soup dumpling from Shanghai.

Favorite quote: “Ever tried. Ever failed. No matter. Try Again. Fail again. Fail better” —Samuel Beckett

What’s your mantra? Keep Doing.

Aside from family members, who would you want sitting next to you if you got stuck for 3 hours on the tarmac in a 737? Tom Stoppard—a master of wordplay, has a very dry wit, and would probably have a hip-flask full of whiskey on him.

 Compiled by Monica Bay,  CodeX fellow and a member of the California bar.  Twitter: @MonicaBay  Email: mbay@codex.stanford.edu.

Cover image: Clipart.com