At the Third TLTF Summit, Legal Tech Leaders Convened in Miami for Three Days of Dialogue and Serendipity

If there is a single “it” conference right now in legal tech, it is the TLTF Summit. Last week was the third annual occurrence of this invite-only event, and while organizers accepted 500 registrants – up from 150 the first year – it left another 1,000 hopefuls sitting on a waiting list.

I guess I was right when, after the first year, I predicted that when registrations opened for the second year, “it will likely be the legal tech equivalent of a Taylor Swift ticket.”

For those who did score an invite, it was well worth their time – and not just for the opportunity to visit Miami in December.  Every attendee that I had the chance to speak to described this event, without reservation, as the best legal tech conference they’d been to. Not the best legal tech conference this year, mind you, but the best ever.

If “renewal rate” is any indication, consider that of the 150 who attended the first year, 108 have attended each subsequent year. (Me among them.) Some additional number of those first-year attendees have attended at least one additional year.

In fact, being a three-peat was a badge of honor at the conference – quite literally – in that the name badges showed the years the person had attended.

After the first TLTF Summit, I described it as the Davos of legal tech, in that it brought together leaders from across disciplines to engage in open and unfettered dialogue about the state and future of legal innovation.

To encourage dialogue (and networking), the summit operates under the Chatham House Rule, by which participants are free to use the information they receive, but not reveal the identify or affiliation of any speaker or participant.

Also helping to foster dialogue is the summit’s intimacy. With just 150 participants the first year and 300 last year, some worried that this year’s jump to 500 would stifle that sense of intimacy. Thankfully, it did not.

In fact, this year’s summit was everything it had been in those prior two years, and maybe more. Among those who attended for the first time this year, the only regret I heard was that they hadn’t attended the prior two.

Thought Leaders At the Forefront

By way of background, the TLTF Summit is produced by  The LegalTech Fund, the first venture capital firm to focus exclusively on legal tech. The goal of the summit is to bring together “the most innovative thought-leaders at the forefront of the legal industry.”

It featured three days of programming along seven tracks: general, law firm, ALSP, GC/legal ops, compliance, fintech and consumer. There were 16 panels, seven roundtables, four education sessions, and four fireside chats.

Interspersed through the three days was the Startup Showcase, where pre-seed through Series A companies, selected by a panel of judges, took to the stage and presented their pitches. Twenty-four companies presented, out of 200 applicants. Five were selected by attendees to present as finalists on the last day of the summit.

(The five that attendees voted to be finalists were: Rasa, Boltive, Trustie, Skribe and Neur.on.)

Engagement and Serendipity

If you have read this far, no doubt you are wondering just what it is that makes this conference so special. As someone who has attended more than my fair share of legal tech conferences over the years, I have come to understand that the qualities that separate a great conference from a mediocre or poor one are largely intangible and therefore difficult to define. But let me try.

Without question, the defining trait of this summit is its atmosphere of engagement, discovery and serendipity.

At the opening of last year’s summit, organizer Zach Posner, cofounder and managing director of The LegalTech Fund, urged attendees to “skip a session, skip every single session,” and instead, “Take a walk with somebody.” Conjuring a concept conceived by business author Jim Collins, Posner said, “Our goal is to make ‘who luck’ happen.”

I do not know whether he again invoked “who luck” this year, as I arrived late to his opening keynote, but regardless, it was available in abundance. As noted, the conference operates under the Chatham House Rule, and attendees are encouraged to talk often and openly with one another – even better if the talk is with a stranger.

To underscore this, attendees this year were given bingo cards with which they could win prizes by identifying people who, for example, owned a working farm or had been in legal tech since the 1980s. The hallways were constantly full of people sitting and standing in pairs or groups, engaged in animated conversation, and a large room was set up as an all-day coffee shop with tables and even live music.

This isn’t networking in the traditional sense of exchanging business cards and elevator pitches. Instead, it’s an intentional cultivation of serendipitous connections.

Unique Mix of Participants

Of course, encouraging conversation would be fruitless if there were no one interesting with whom to converse.

After the conference was over, one participant – a veteran of many legal tech conferences – told me that what most impressed him was how smart the attendees were. That might sound pretentious, but it is probably also factually accurate. The people who attend this conference are the cream of the crop of those who are thinking about and working on the future of legal practice and legal technology.

Driving that is the summit’s unique mix of attendees. The summit somehow manages to draw a mix of people unlike what I see at any other legal tech conference. There are veteran founders and big-name CEOs. There are fledgling startups and late-stage enterprises. There are law firm innovation leaders and corporate operations professionals. There are practicing lawyers and legal academics. There are people from the public sector and people from “legal tech adjacent” consultancies and service providers.

Most significantly, at least to my mind, there are investors from major venture capital and financial firms, who are open and active participants. This is unlike at other conferences, where, if they attend at all, they tend to lurk in the shadows, prospecting in stealth mode.

At the TLTF Summit, a late-stage enterprise CEO might find herself in deep conversation with a pre-seed startup founder. A criminal defense lawyer could be discussing artificial intelligence with a venture capitalist. Or maybe all four of those people are sitting together over a cocktail in the balmy twilight.

Sales-Free Zone

In virtually every conversation I had, I asked people what they thought of the summit. As I already reported above, to a one they said that it was the best legal tech conference they had attended. Every time they said that, my next question was, “Why?”

Two answers came back to me over and over again.

One was what I have already described, which is the diverse mix of attendees, all thought leaders in their respective fields.

The second was the freedom from sales. Remarkably at the summit, no one was selling anything. There were no exhibit booths. Elevators did not blast advertising. Vendors’ branding did not cover every surface.

From what I heard, this was liberating for both vendors and others. Of the people I spoke to who work for legal tech companies, most of whom were top executives of those companies, their shared refrain was how freeing it felt to be at a conference where they did not have to be constantly selling. By the same token, the lawyers and other professionals I spoke to expressed how relieved they were to not constantly be the target of sales pitches.

No one comes to the summit to make sales (at least not directly). People are there to learn and share and collaborate and maybe expand their perspectives and horizons. And, honestly, that simple fact created an air of lightness at the summit that was buoying.

But Deals Do Get Done

To be clear, while no one at the summit was there to sell products, there were deals getting done. Investments were getting discussed. Acquisitions were getting germinated. Jobs were getting offered. Things happen at this conference, make no mistake about that, but they happen discretely.

In fact, Posner, in his keynote, gave some numbers about deals from the prior years’ summits – at least the deals he knows of. As a result of the 2022 and 2023 summits, there were:

• 18 rounds of funding.
• 3 M&A events.
• 20 job changes.
• 30 bizdev relationships.

Only time will tell what emerges from this year.

Other Standout Features

While those are some of the intangibles that make this summit great, there were also a number of tangible factors:

• Top-notch programming and speakers. Look, for the reasons I’ve already discussed, if you never went to a single panel during the conference, you are forgiven. But the panels provided plenty of incentive to break away from all those hallway conversations and learn from experts. Particularly thought provoking were the four fireside chats that punctuated the summit, featuring conversations with U.S. Sen. John Hickenlooper (D-CO), Carta CEO Henry Ward, criminal defense lawyers Alan Dershowitz and Alex Spiro, and legal futurist Richard Susskind.
• Picture-perfect venue. Four words: Ritz Carlton Key Biscayne. Need I say more?
• Good and seemingly limitless food. The conference served breakfast, lunch and dinner, all of which were tasty and included vegetarian and gluten-free options. In between meals were various arrays of snacks and sweets. Most meals could be taken outside or inside, and the second day’s breakfast was broken up by interest groups.
• No legal tech conference does swag like the TLTF Summit. At a designated hour, it threw open the doors to a swag room – or what you might have thought was a gold rush – as an onslaught of attendees filled swag bags with hoodies and t-shirts and hats and socks and sandals and all sorts of other paraphernalia. It was an embarrassment of riches that to some seemed over the top, even as they rifled around for a size L hoodie.

Did I Just Say ‘Chill’?

On the last day of the conference, several people asked me what my big takeaway was or what I saw as the big theme. Sure, everyone was talking about gen AI, just as they do at every other conference. But that wasn’t the takeaway.

If I haven’t by now already made it clear, for me, the theme was the value of networking, and of networking beyond your comfort zone – of letting serendipity happen, “who luck” happen. I met so many new people this week, and so many of the conversations I had with those people were not just conference chitter-chatter, but substantive and thoughtful and even challenging interactions.

A unique feature of this conference over others I’ve attended was that everyone seemed to feel free and relaxed and unburdened and open. No one was too big or important to approach, or too unapproachable because they were surrounded by their people. Everyone was on equal footing, and everyone engaged as co-equal peers.

People often refer to conferences as “shows,” and maybe that is partly because we are all expected to perform when we attend them, to be “on” and play our designated role.

Here, the pretense seemed to melt away. I found myself several times describing the conference as “chill” – which is, trust me, not a word I often use, and certainly not to describe a legal tech conference. People seemed to relax and let down their guards and thereby open themselves to truly engaging with one another.

I am leaving the TLTF Summit energized, enthusiastic, and grateful for all the “who luck” that happened for me there. And, of course, I am already looking forward to next year’s summit – provided I can score one of those coveted invites.