LegalTech Lowdown – TLTF 2023

There are at least a few journalists who will provide their thoughts on the TLTF Summit which is great but I want to provide a different perspective. I think it’s important to summarize the event using the lens of a legal tech founder and someone who’s worked in the industry for more than a few years. Everyone’s time is valuable, so I won’t bury the lead: the conference was excellent. It wasn’t perfect but no conference is. There were a few very small tweaks I’d make but overall it was one of the more enjoyable legal tech conference experiences I’ve had.

Let’s start with the time of year and venue of the event. This is an under-appreciated aspect of the conference experience IMO. I love the audience and content at ILTACON but I don’t love Orlando in August or the sprawl of the Disney property. LegalWeek is not my cup of tea any time of year and NYC in January and that Hilton don’t help the cause. TLTF, on the other hand, was hosted at the beautiful Marriott Turnberry Resort in the Fort Lauderdale area. It is an awesome property and South Florida in December doesn’t suck either. The rooms were beautiful and the staff were eager to please. The conference area was just a short 5 minute open air walk from the room. If you needed to head back to take a call or rest it was no trouble at all. I don’t know the exact count but there were just a few hundred attendees so a property like Turnburry was an option. However, a smaller property like it could never accommodate an ILTACON or LegalWeek sized crowd so we need to keep that in perspective.

Obviously, the content is a very important part and I’ll dive in to that next, but I want to say a quick word about the networking along with food and drink. In a word they were outstanding. Each night the cuisine seemed to have a cool ethnic vibe, there were lots of healthy choices and the drinks were top shelf. The quality and timing of the food and beverage was also on point. Each night after dinner there was an open bar and an outstanding venue in which to socialize. Networking was a big focus for event and the conference nailed it. In addition to the evening opportunities to socialize there were interesting (and a little whacky) formal networking events. There was a women’s lunch, a birdwatching session (network while birdwatching?), assembling bikes for charity and Texas hold ’em training. I attended the hold ’em training and met a bunch of people I interacted with the rest of the show.

During Zach Posner‘s opening remarks he emphasized the networking mantra describing the intent to create what Jim Collins describes as “who luck.” Who luck is when you come across somebody who changes your trajectory by investing in or betting on you in some way. By bringing investors and legal tech founders together under one roof for 3 days the concept makes a lot of sense. We aren’t trying to raise external capital at Infodash but we might one day so I came to TLTF to start to build the relationship with investors and watch start ups pitch. Honestly, I didn’t meet with many investors but I did see a lot of pitches and good content. I also got to talk to a lot of people I don’t normally have access to like Mark Dorman who’s the CEO of the newly independent Elite, Josh Baxter who’s the CEO of NetDocuments and Brian Liu who founded LegalZoom. I had great conversations with each of them and all three were very gracious with their time and fully engaged in the dialog.

Okay, let’s talk about the content. Here are a few summaries of a few of the sessions I was able to attend.

Summit Kickoff

Daniel Katz kicked off the week with the first day’s keynote and did a great job talking about the most popular topic on Earth right now: generative AI. There was an illustrator onsite creating murals for many of the sessions including Dan’s as shown above and his slides are available here. There were lots of facts and dates in the presentation on things like gen AI legal use cases and a “Year in Review” which listed 11 important dates over the last 12 months. I’m not going to regurgitate all of them here as they’re available in the slides. After the presentation, Damien Riehl came on stage and he and Dan sat down for a fireside chat on the topic of AI. They discussed LLM copyright issues in depth and addressed some of the ethical concerns around using AI in a legal context. The two also talked about Steve Schwartz who is the NY lawyer with 30 years experience who is famous for all the wrong reasons for filing a legal brief with the court that was written by ChatGPT and cited cases that didn’t exist. Dan and Damien jokingly said that “maybe we should pour one out for Steve” but some in the audience openly disagreed with that sentiment. It was an informative and fun discussion.

Fireside Chat: Access to Justice

A2J is a topic we should all know more about so I was thrilled to see some programming dedicated to it. In this session, Sheena Meade told a very personal story of how a minor bounced check infraction changed the trajectory of her life and put her on a mission to bring change to the system. This relatively small infraction impacted her ability to put a roof over her head and almost prevented her from going being admitted to college. She’s since dedicated her professional skills to The Clean Slate Initiative which helps eligible people clear their record who’ve completed their sentence and remained crime free. People’s income increases by about 25% when they are able to apply for better paying jobs as a result of having a clean slate. There are already legal processes out there but a huge lack of awareness and a resource gap that Sheena’s organization has set out to bridge.

The Intersection of Fintech and Legaltech

Tom Brown moderated a panel of Mark Dorman who’s the CEO of Elite and Dru Armstrong who’s the CEO of AffiniPay. The conversation started with Mark highlighting Elite’s on prem to cloud journey and Dru pointing out her company’s many legal brands including the recent MyCase acquisition. Tom brought up one of the things holding innovation back in legal which is the quest for firms to offset technology costs with pass through billing and how this dynamic keeps many firms “retrograde.” He’s not wrong about the under investment in technology that has plagued the industry for many years. It seems like the FUD/FOMO associated with AI might finally motivate more aggressive tech spending which would be a good thing for firms and everyone at TLTF. One very interesting thing that was discussed was legal service financing in the form of “buy now pay later” or BNPL. AffiniPay has originated over $90M in BNPL financing mostly in the area of family law. Like most people I associated BNPL with impulsive consumer purchases….not legal services.

Day 2 Keynote with Kashmir Hill

Jeff Ward interviewed Kashmir who is the author of Your Face Belongs to Us and a NYT reporter. In the conversation they discussed her journey in uncovering information about a compiled library of face pictures of private citizens by an unknown company at the time called Clearview AI. After some digging she uncovered that private companies were using the Clearview’s database in very interesting and troubling ways. Madison Square Garden, for example, used the technology to screen lawyers who worked for law firms who were suing the venue and deny them admission to events. Kashmir finally got a chance to speak with the founder of the company and was amazed at how easy he was able to cobble together the database using Google searches and GitHub. Clearview would scrape sites like Venmo for headshots to compile the database they’d then sell to clients like MSG.

Fireside Chat: The Founders

This was a collection of entrepreneurial war stories by Andrew Sieja who founded Relativity and Brian Liu who’s the co-founder and CEO of LegalZoom. The session was moderated by Haley Altman who did a great job teeing up two grizzled legal tech veterans to talk about their entrepreneurial journey and the lessons learned that founders in the audience might be able to find value in. Andrew (who could be Bill Burr’s stunt double) shared interesting lessons on accepting feedback and for founders to surround themselves with the right people to provide it. Brian talked about the importance of NPS scores as a canary in the coal mine and how important it is to choose the right financial partners whose goals align with the company’s. In a conversation Andrew had with the Eric Yuan who is the founder of Zoom and Eric made a point to talk to three Zoom clients a day in order to stay close to the customer. That’s quite an interesting goal for the CEO of a multibillion dollar company with over 8,000 employees.

From Dispute to Decision: Tech-powered Litigation

Kevin Clem from Harbor moderated a panel consisting of Darth Vaughn from Ford Motor CompanySubroto Mukerji from Integreon and Farrah Pepper from Marsh McLennan. The conversation was very data focused and the value that accurate data can provide to an in house legal team. Darth emphasized the importance of scrutinizing how data is captured and how organizations generate ROI downstream. At Ford, Darth’s team uses data to build predictive models to forecast events both good and bad that can be avoided or capitalized upon. Early legal warning signals give Ford an opportunity to proactively navigate around litigation before it happens. Farrah uses AI to analyze billing data to look for opportunities to reduce internal and external legal spend. AI turbo charges that analysis. Darth wrapped up by making the very astute observation that a lot of legal tech solutions address junior attorney problems because many start up founders are junior attorneys who leave the profession to pursue an opportunity in legal tech.


The venue, food, content, networking and weather were great. However, I wouldn’t be objective if I didn’t point out a few things that might benefit from a tweak or two. First, it might make sense to evaluate some trade offs to get the admission price down. Zach Posner and team have a tough task on their hands because you have startups who are strapped for cash on one hand and on the other end of the spectrum you have investors with a very different set of expectations. I won’t pretend to know the answer (more sponsors maybe?) but if we could lower the bar for more start ups to participate I think that would be a good thing. Another thing I’d love to see is more access to the roundtables. I was late reading my registration email and all the roundtables were full which was disappointing. There’s inherent conflict there as well because roundtables are by their nature intimate. I’m not sure how intimate you can be if they’re open to everyone. Again, I don’t think there are easy answers but there might be creative solutions out there to be had.

Those are really minor issues and Zach Posner, Nathaniel Schorr and team should be very proud for putting on a kick ass conference that I hope I get invited to again next year. I feel fortunate to have been invited to participate and hope to see everyone again next year!

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