§ 06Insights
Notes from the partners.
What Lev and Oleg are seeing in legal tech: the founders, the companies we back, and where AI is changing legal work. First shared on LinkedIn, kept here in one place.
§ 6.2All posts
From the archive.
Lev Loukhton
A Concurring Opinion: Who Actually Discovers the Winners?
Mega-funds have “access to the winners.” Did they find them first, and does it matter? Across 29 major outcomes in legal tech, cybersecurity and B2B insurtech, a generalist mega-platform was in the earliest institutional round of just 5.
Venture11 min read
Lev Loukhton
The Pint and the Corgi
The real question is not whether AI shrinks the legal market. It is whether the Legal Capability Frontier keeps moving faster than commoditization can catch it.
AI & the law6 min read
Lev Loukhton
“What should I build instead?”
One of the key factors we take into account when assessing investment opportunities is founder-problem fit: “Why should this founder be the one to solve this problem?”
Founders2 min read
Lev Loukhton
“High bandwidth” is being replaced with “safe bets”
“Tech beta” and “kingmaking” are real strategies. Oleg Loukhton and I are seeing it in our corner of the market.
Venture1 min read
Lev Loukhton
Who the hell am I to argue with Bill Gates?
I agree with the diagnosis. I am less certain about the prescription, because there is a question that precedes it: which institutions do we actually want to preserve?
AI & the law9 min read
Lev Loukhton
The Dwarf, The Dragon, The Ludens and Marble
When the machines can do almost everything that can be done, and can do it better than humans, what will we do because we still want to do it ourselves?
AI & the law6 min read
Lev Loukhton
Searching for the King of Kings
Agamemnon, Elon Musk and the AI wars. We should be rather careful about assuming that, having found a king, we have found the kingdom.
AI & the law4 min read
Lev Loukhton
Legal Tech Investing for Angel Investors Part 4: From Paradox to Kelly
From whether to invest to how much: what the Kelly criterion says about sizing a check, and where it stops being useful.
Angel investing4 min read
Lev Loukhton
Part 3 About Legal Tech Investing for Angels: Saint Petersburg Paradox
A coin-flip game with infinite expected value that no rational person would pay much to play, and what it says about the price you pay to enter a round.
Angel investing5 min read
Lev Loukhton
Why Venture Capital Returns Look Like Nothing Else You Have Invested In — Part 2: The Power Law and The J-Curve
Roughly 6% of investments generate approximately 60% of total returns. A three-company angel portfolio is a lottery ticket purchased with the confidence of expertise.
Angel investing5 min read
Lev Loukhton
Venture Math for Legal Tech Angel Investors - Part I
Approximately 90% of startups fail, but lawyers tend to apply that statistic linearly. Why a two- or three-company portfolio is far riskier than it looks.
Angel investing3 min read
Lev Loukhton
Legal Tech for Angel Investors - Part I
Ten things we look at when an angel asks, “Can you help me assess this legal tech startup?” Domain expertise is a must.
Angel investingFounders3 min read
Lev Loukhton
GrayHair Venture Partners: FAQs for legal tech founders
Our focus, how we decide, why a warm intro carries essentially zero weight, and why “ghosting” is not part of our DNA.
Founders2 min read
Building in legal?
If the product you are building has a use case for legal, we would be interested in taking a look at it. No warm intro needed.
Founders: no warm intro needed. Ghosting is not part of our DNA.