Optimize for Failures Not Successes: Lessons for the Legal Industry from a Hacker at ILTACON 2017

Topics: Artificial Intelligence, Corporate Legal, Government, ILTACON 2017, Justice Ecosystem: Technology, Law Firms, Legal Innovation

LAS VEGAS — One of the most exciting presentations at this year’s International Legal Technology Association annual conference (ILTACON) was the presentation by Pablos Holman on innovation and lessons from the world of hacking, entitled Innovate or Die Trying: From the Mind of a World-Renowned Hacker.

Holman, currently working at Intellectual Ventures Lab (which he described as dedicated to inventing solutions to the world’s biggest problems), captivated the audience with tales of an environment vastly different from most law firms — one where the focus is on optimizing failures instead of optimizing successes.

Holman described hacking as involving a discovery process fundamental to invention — one of innovation. Whereas most of us in legal might look at a new gadget and try to figure out how to use it, hackers instead look at new gadgets to figure out what else they can make it do or what they could build from its parts. Holman notes that without that discovery process, you never get anything new. In a line striking fear into spouses of DIY home improvement aficionados everywhere, Holman noted: “No one ever invented anything new from reading the directions.”


I expect 10,000 failures and 1 success. But I optimize for failures, not success.


While Holman spoke quite a bit about Intellectual Ventures Lab’s current long-term project of developing different laser guns to try to eradicate mosquitoes in Madagascar in order to radically reduce rates of malaria, those who have seen Holman’s TED Talk were likely familiar with that part.

But Holman noted that computer modeling malaria-testing in Madagascar provided the team with the ability to test their inventions thousands of times before doing it the real world: “We can make so many more educated choices than ever before; this is what we’re doing for epidemiology, and we will do in every industry.” The ability to collect so much more data due to increased sensors, bigger networks to transmit that data, and massive computers to analyze it all is changing the way we think about computers. Holman noted that when we talk about Big Data, we’re really “just talking about a different way to make decisions.”

In contrast, Holman noted that the ubiquitous Excel spreadsheet epitomizes Small Data — it gives a lot of information but doesn’t tell you why or what it means — while Big Data gives you a better and more complete answer. To more cheers than groans from the ITLACON crowd, Holman predicted Excel will never be used to invent anything interesting again and noted that can be a very uncomfortable place to be for all those of us using Excel on a daily basis.

ILTACON 2017

Pablos Holman

Truly understanding “disruptors” and why they have been so successful in so many industries was key to Holman’ message. He noted that the popular disruptors we know today (i.e., Uber or Airbnb) occurred when a computer was used to change an industry. He also observed that the disruption occurred because successful industries generally have become successful by evolving an immune system and protecting their success by eliminating all threats. So instead of Uber’s founders approaching taxicab companies and pitching them enterprise software, they just started from scratch building a parallel industry or business.

Indeed, this ability to scrap all existing ideas and try something new is the essential ingredient that Holman argued has made Silicon Valley so successful and impossible to replicate. Holman noted that many have claimed their intention to open Silicon Valley in Europe or Singapore or somewhere else but he has yet to see that succeed, mainly because no one else is ready to embrace failure in the same way Silicon Valley entrepreneurs and technologists do. “Be okay with the failures.”

Holman also described how he is planning for 10 years out right now, experimenting with things for which the needed technology does not exist yet, so he’s constantly wrong: “I expect 10,000 failures and 1 success. But I optimize for failures, not success.”

Part of the reason the technology industry is so successful today and is “eating the business world up” is due to its embrace of rapid iteration, he said, adding, for example, that Facebook is in such a state of continuous and constant deployment that everyone in the conference hall at that exact moment was likely on a different version of Facebook. “The beauty of this is that it’s way more efficient than anything humans have ever done.”


No one ever invented anything new from reading the directions.


The software and tech industry are essentially in a constant state of A/B testing, “steering toward success through rapid iteration,” he said. In the 1980s, Microsoft developers would spend 18 months writing new code, produce it on a floppy disk, shrink-wrapp it, and ship it to stores to which consumers travelled to buy it. Each box contained a small postcard on which buyers could handwrite software bugs they uncovered and mail that back to Microsoft. But today Holman can get up in the morning, write up code that is launched at lunchtime, field complaints and emails about bugs all afternoon, then launch a patch before heading to dinner. Physical items in other industries (like shoes or cars) Holman explained, still have an 18-month development cycle, assembly line production, etc., so they can’t keep up. But “in every industry it’s a long deliberate march towards rapid iteration and that is the way towards success,” he added.

He concluded his talk by noting that not everyone should quit their jobs and become innovators. But he encouraged the legal professionals present to find the people and companies who are good at it, and foster relationships with them. He also encouraged the audience to be okay with “the crazy [stuff] they’re doing in Silicon Valley” as well as their failures.

Holman cited his public success despite his many invention failures: “No company I ever worked for still exists — why am I the one up on this stage?”

What remains to be seen is whether the legal industry is ready to take this message to heart. Are law firms, in-house departments and technology vendors ready to try new things that may not work? Are we all ready to optimize for many failures in the hopes of achieving success from just one new idea?